U.S. flag

An official website of the United States government

Dot gov

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Https

Secure .gov websites use HTTPS
A lock ( ) or https:// means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites.

PubAg

Main content area

You searched for: Publication year rev 7981-2019 Remove constraint Publication year rev: 7981-2019 Subject term acylation Remove constraint Subject term: acylation
Start Over

Search

131  Search Results

« Previous | 1 - 100 of 131 |
Number of results to display per page

Search Results

1. The 3′ Untranslated Region of a Plant Viral RNA Directs Efficient Cap-Independent Translation in Plant and Mammalian Systems

Author:
Jelena J. Kraft; Mariko S. Peterson; Sung Ki Cho; Zhaohui Wang; Alice Hui; Aurélie M. Rakotondrafara; Krzysztof Treder; Cathy L. Miller; W. Allen Miller
Source:
Pathogens 2019 v.8 no.1 pp. -
ISSN:
2076-0817
Subject:
Panicum; Paspalum; acylation; genome; guanosine; human cell lines; humans; messenger RNA; oats; plant viruses; plants (botany); rabbits; translation (genetics); viruses; wheat; wheat germ
Abstract:
... Many plant viral RNA genomes lack a 5′ cap, and instead are translated via a cap-independent translation element (CITE) in the 3′ untranslated region (UTR). The panicum mosaic virus-like CITE (PTE), found in many plant viral RNAs, binds and requires the cap-binding translation initiation factor eIF4E to facilitate translation. eIF4E is structurally conserved between plants and animals, ...
DOI:
10.3390/pathogens8010028
PubMed:
30823456
PubMed Central:
PMC6471432

2. Acylation of Alkenes with the Aid of AlCl₃ and 2,6-Dibromopyridine

Author:
Shinya Tanaka; Tsukasa Kunisawa; Yuji Yoshii; Tetsutaro Hattori
Source:
Organic letters 2019 v.21 no.21 pp. 8509-8513
ISSN:
1523-7052
Subject:
acylation; alkenes; aluminum chloride; chemical structure; hydrogen; organochlorine compounds; pyridines
Abstract:
... Friedel–Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl₃ and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones. ...
DOI:
10.1021/acs.orglett.9b02688

3. Acylsugar diversity in the resin glycosides from Ipomoea tricolor seeds as chemosensitizers in breast cancer cells

Author:
Jhon Castañeda-Gómez; Pedro Lavias-Hernández; Mabel Fragoso-Serrano; Argelia Lorence; Rogelio Pereda-Miranda
Source:
Phytochemistry letters 2019 v.32 pp. 77-82
ISSN:
1874-3900
Subject:
Ipomoea tricolor; acylation; breast neoplasms; esterification; glycosides; high performance liquid chromatography; humans; ions; mass spectrometry; moieties; multiple drug resistance; neoplasm cells; nuclear magnetic resonance spectroscopy; ornamental plants; seeds; sodium; sugars; vinblastine
Abstract:
... Mexican morning glory, Ipomoea tricolor Cav., is native to America and widely cultivated as an ornamental plant. High performance liquid chromatography profiling coupled with off-line electrospray mass spectrometry detection was applied to identify novel acylsugar from the CHCl3-soluble resin glycoside from seeds. Dereplication of known tricolorins A-J included the recording of mass values for ion ...
DOI:
10.1016/j.phytol.2019.05.004

4. An Aliphatic Bischler–Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

Author:
Mostafa M. Amer; Olatz Olaizola; Jennifer Carter; Hossay Abas; Jonathan Clayden
Source:
Organic letters 2019 v.22 no.1 pp. 253-256
ISSN:
1523-7052
Subject:
acylation; alanine; enantiomers; hydrolysis; moieties; organochlorine compounds; pipecolic acid; potassium iodide
Abstract:
... The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel–Crafts-type acylation that corresponds to an aliphatic Bischler ...
DOI:
10.1021/acs.orglett.9b04250

5. Antioxidant capacity and hepatoprotective activity of myristic acid acylated derivative of phloridzin

Author:
Chunli Liu; Chunlong Yuan; Hosahalli S. Ramaswamy; Yamei Ren; Xiaolin Ren
Source:
Heliyon 2019 v.5 no.5 pp. e01761
ISSN:
2405-8440
Subject:
2,2-diphenyl-1-picrylhydrazyl; acylation; antioxidant activity; antioxidants; blood serum; carbon tetrachloride; glutathione; hepatoprotective effect; hepatotoxicity; interleukin-6; liver; liver diseases; liver regeneration; malondialdehyde; moieties; myristic acid; phloridzin
Abstract:
... The antioxidant activities in vitro and hepatoprotective effects against carbon tetrachloride (CCl₄) induced acute liver injury in vivo of myristic acid acylated derivative of phloridzin (PZM) were investigated. The PZM was obtained by enzymatic acylation of myristic acid and phloridzin (PZ). The antioxidant capability of PZM in vitro was evaluated by the ferric reducing antioxidant power assay (F ...
DOI:
10.1016/j.heliyon.2019.e01761
PubMed:
31193831
PubMed Central:
PMC6543077

6. Atropselective Synthesis of N,C-Bis(diphenylphosphanes) from Bridged 2-Arylindoles Based on Effective Point-to-Axial Asymmetric Inductions after an Unusual Dilithiation⊥

Author:
Felix Bäuerle; Reinhard Brückner
Source:
Organic letters 2019 v.21 no.24 pp. 9970-9975
ISSN:
1523-7052
Subject:
acylation; anhydrides; carboxylic acids; diastereomers; indoles; lactones; methanolysis; stereospecificity
Abstract:
... An asymmetric methanolysis of glutaric anhydride and 6 ensuing steps gave veratrol-annulated dimethylcyclo-heptenone diastereomers with 99% ee; ring closures occurred by Friedel–Crafts acylations of carboxylic acids obtained by stereospecific hydrogenolyses of a pair of diastereomeric δ-lactones. The mentioned cycloheptenones and Ph−NH−NH₂ underwent Fischer indole syntheses providing the tetracycl ...
DOI:
10.1021/acs.orglett.9b03896

7. Avermectin loaded nanosphere prepared from acylated alkali lignin showed anti-photolysis property and controlled release performance

Author:
Mingsong Zhou; Dongping Wang; Dongjie Yang; Xueqing Qiu; Yingxin Li
Source:
Industrial crops and products 2019 v.137 pp. 453-459
ISSN:
0926-6690
Subject:
acylation; avermectins; encapsulation; hydrophobicity; lignin; nanospheres; organochlorine compounds; pesticides; photosensitivity; ultraviolet radiation
Abstract:
... Acetylated lignin (ACAL) and benzoylated lignin (BZAL) were obtained from the chemical modification of alkali lignin with acetyl chloride and benzoyl chloride, respectively. The results showed that the introduction of alkyl chain can increase the hydrophobicity of AL evidently. The ACAL and BZAL were used as shell materials for the preparation of nanospheres to encapsulate photosensitive pesticide ...
DOI:
10.1016/j.indcrop.2019.04.037

8. Base-Mediated One-pot Synthesis of Oxygen-Based Heterocycles from 2-Hydroxyphenyl-Substituted para-Quinone Methides

Author:
Gurdeep Singh; Suresh Kumar; Arjun Chowdhury; Ramasamy Vijaya Anand
Source:
Journal of organic chemistry 2019 v.84 no.24 pp. 15978-15989
ISSN:
1520-6904
Subject:
acylation; alkylation; chemical structure; coumarin; furans; organic chemistry; oxidation; quinones; synthesis
Abstract:
... One-pot synthesis of oxygen-containing heterocycles has been achieved through alkylation/acylation of 2-hydroxyphenyl-substituted para-quinone methides followed by an intramolecular 1,6-conjugate addition/cyclization and oxidation sequence. This protocol provides access to a wide range of oxygen-based heterocycles, such as 2,3-disubstituted benzo[b]furans, 2,3-dihydrobenzofurans and diaryl-substit ...
DOI:
10.1021/acs.joc.9b02455

9. Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose: Effects of alkyl and alkoxy side chains

Author:
Daniela C. Ferreira; Mayara L. Oliveira; Thais A. Bioni; Haq Nawaz; Alistair W.T. King; Ilkka Kilpeläinen; Michael Hummel; Herbert Sixta; Omar A. El Seoud
Source:
Carbohydrate polymers 2019 v.212 pp. 206-214
ISSN:
0144-8617
Subject:
acetates; acylation; biopolymers; cellobiose; cellulose; derivatization; dimethyl sulfoxide; hydrogen bonding; imidazoles; ionic liquids; nuclear magnetic resonance spectroscopy; oxygen; rheology
Abstract:
... The efficiency of mixtures of ionic liquids (ILs) and molecular solvents in cellulose dissolution and derivatization depends on the structures of both components. We investigated the ILs 1-(1-butyl)-3-methylimidazolium acetate (C4MeImAc) and 1-(2-methoxyethyl)-3-methylimidazolium acetate (C3OMeImAc) and their solutions in dimethyl sulfoxide, DMSO, to assess the effect of presence of an ether linka ...
DOI:
10.1016/j.carbpol.2019.02.024

10. Bioactive compounds from the seeds of Amomum tsaoko Crevost et Lemaire, a Chinese spice as inhibitors of sphingosine kinases, SPHK1/2

Author:
Seulah Lee; Joo Chan Lee; Lalita Subedi; Kyo Hee Cho; Sun Yeou Kim; Hyun-Ju Park; Ki Hyun Kim
Source:
RSC advances 2019 v.9 no.58 pp. 33957-33968
ISSN:
2046-2069
Subject:
Amomum tsao-ko; Oriental traditional medicine; acylation; bioactive compounds; bioactive properties; enantioselectivity; enzyme activity; ethanol; fatty acids; models; nuclear magnetic resonance spectroscopy; phenolic compounds; phosphotransferases (kinases); seeds; spectral analysis; sphingosine; spices; terpenoids
Abstract:
... Amomum tsaoko Crevost et Lemaire (Zingiberaceae), a traditional Chinese spice also known as “Caoguo” or “tsao-ko,” has been considered to have many health benefits. As part of our continuous efforts to screen natural resources exhibiting potential bioactivity, we examined the seeds of A. tsaoko and found that its EtOH extract inhibited sphingosine kinases 1 and 2 (SPHK1/2). Bioactivity-based analy ...
DOI:
10.1039/c9ra07988b

11. Biocatalytic Synthesis of Lipophilic Baicalin Derivatives as Antimicrobial Agents

Author:
Xuan Xin; Mengmeng Zhang; Xiao-Feng Li; Guanglei Zhao
Source:
Journal of agricultural and food chemistry 2019 v.67 no.42 pp. 11684-11693
ISSN:
1520-5118
Subject:
acylation; anti-infective agents; antimicrobial properties; baicalin; catalytic activity; esterification; fatty acids; fatty alcohols; glycosides; lipophilicity; moieties
Abstract:
... Enzymatic acylation is commonly used to increase the lipophilicity of flavonoids. However, the absence of primary hydroxyl groups makes it challenging to acylate baicalin using traditional acylation methods. In this study, an enzymatic esterification strategy was developed to introduce fatty-acid chains into baicalin at its carboxyl group, hence successfully synthesizing a new series of baicalin e ...
DOI:
10.1021/acs.jafc.9b04667

12. Biodegradation mechanism of polyesters by hydrolase from Rhodopseudomonas palustris: An in silico approach

Author:
Xiaodan Wang; Jinfeng Chen; Xiaowen Tang; Junjie Wang; Ledong Zhu; Weixin Zhang; Hui Wang; Yanwei Li; Qingzhu Zhang
Source:
Chemosphere 2019 v.231 pp. 126-133
ISSN:
0045-6535
Subject:
Rhodopseudomonas palustris; acetates; active sites; acylation; amino acids; biodegradation; catalytic activity; formates; hydrolases; hydrolysis; molecular dynamics; mutation; physicochemical properties; plastics; polyesters; polylactic acid; quantum mechanics; simulation models; surface area
Abstract:
... Massively used plastics have caused worldwide environmental concerns. Polyesters like polylactic acid (PLA) are one of the mostly used plastics due to its excellent physical and chemical properties and low-cost advantages. It is critical to develop the elimination and recycle techniques for polyesters. Experimental studies have shown that a hydrolase RPA1511 isolated from Rhodopseudomonas palustri ...
DOI:
10.1016/j.chemosphere.2019.05.112

13. Boron trifluoride etherate promoted microwave-assisted synthesis of antimalarial acridones

Author:
Papireddy Kancharla; Rozalia A. Dodean; Yuexin Li; Jane X. Kelly
Source:
RSC advances 2019 v.9 no.72 pp. 42284-42293
ISSN:
2046-2069
Subject:
acylation; antimalarials; boron; microwave treatment; multiple drug resistance; parasites
Abstract:
... A microwave-assisted, rapid and efficient method using boron trifluoride etherate (BF₃.Et₂O) for the synthesis of acridones, via an intramolecular acylation of N-phenylanthranilic acid derivatives, has been developed. The reaction proceeds under solvent-free conditions, tolerates a wide range of functional groups, and provides rapid access to a range of acridones in good to excellent yields. Sever ...
DOI:
10.1039/c9ra09478d

14. Both the mono- and di-anions of ellagic acid are effective inhibitors of the serine β-lactamase CTX-M-15

Author:
Nathan Talbot; Nicholas T. Powles; Michael I. Page
Source:
RSC advances 2019 v.9 no.53 pp. 30637-30640
ISSN:
2046-2069
Subject:
active sites; acylation; anions; beta-lactamase; ellagic acid; enzyme inhibitors; lactones; serine
Abstract:
... Ellagic acid, a δ-lactone with ionisable phenolic residues, is an efficient time-dependent inhibitor of the serine β-lactamase enzyme CTX-M-15. The pH-dependence of the rate of inhibition shows that both the mono- and di-anionic species of ellagic acid are effective inhibitors, both with second order rate constants of ∼1.5 × 10⁴ M⁻¹ s⁻¹. The structurally similar δ-lactone urolithin A, which lacks ...
DOI:
10.1039/c9ra05835d

15. Carrot anthocyanins: nutrition, diversity and genetics

Author:
P. F. Cavagnaro; F. Bannoud; M. lorizzo; D. Senalik; S. L. Ellison; P. W. Simon
Source:
Acta horticulturae 2019 v. no.1264 pp. 101-106
ISSN:
0567-7572
Subject:
acylation; anthocyanins; anti-inflammatory activity; antioxidants; biosynthesis; breeding programs; carrots; chemical structure; dietary supplements; food colorants; germplasm; glycosylation; health promotion; new variety; phytonutrients; pigmentation; plant breeding; tissues; water solubility
Abstract:
... Purple carrots represent an excellent dietary source of anthocyanins. The consumption of these water-soluble flavonoid pigments is associated with various health benefits, attributed mainly to their antioxidant and anti-inflammatory properties. Anthocyanin pigmentation varies broadly among organs and tissues of the carrot plant and among carrot genetic stocks. The chemical structure of anthocyanin ...
DOI:
10.17660/ActaHortic.2019.1264.11

16. Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates

Author:
Naoyuki Shimada; Yuki Nakamura; Takayuki Ochiai; Kazuishi Makino
Source:
Organic letters 2019 v.21 no.10 pp. 3789-3794
ISSN:
1523-7052
Subject:
Lewis bases; acylation; boronic acids; carbohydrates; catalysts; catalytic activity; glycols; moieties
Abstract:
... Site-selective acylation of unprotected carbohydrates by using stable, storable, and easily handled imidazole-containing organoboronic acid catalysts is described. This catalytic process with low catalyst loading enables the introduction of a wide variety of acyl functional groups into the equatorial position of cis-vicinal diols in unprotected hexapyranosides with excellent site selectivity. This ...
DOI:
10.1021/acs.orglett.9b01231

17. Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock

Author:
Florian Uthoff; Jana Löwe; Christina Harms; Kai Donsbach; Harald Gröger
Source:
Journal of organic chemistry 2019 v.84 no.8 pp. 4856-4866
ISSN:
1520-6904
Subject:
active pharmaceutical ingredients; acylation; amination; carboxylic ester hydrolases; chemical bonding; chemical reduction; chemical structure; drugs; feedstocks; manufacturing; naphthalene; optical isomerism; organic chemistry; sclerosis
Abstract:
... Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The to ...
DOI:
10.1021/acs.joc.8b03290

18. Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides

Author:
Ayaka Sakakura; Martin Pauze; Atsuhiro Namiki; Megumi Funakoshi-Tago; Hiroomi Tamura; Kengo Hanaya; Shuhei Higashibayashi; Takeshi Sugai
Source:
Bioscience, biotechnology, and biochemistry 2019 v.83 no.2 pp. 185-191
ISSN:
1347-6947
Subject:
Pseudozyma antarctica; acylation; biotechnology; butyrates; carboxylic ester hydrolases; chemoselectivity; fatty acids; hydroxylation; lipopolysaccharides; nitric oxide
Abstract:
... Fatty acid monoesters of hydroxytyrosol [2-(3,4-dihydroxyphenyl)ethanol] were synthesized in two steps from tyrosol (4-hydroxyphenylethanol) by successive Candida antarctica lipase B-catalyzed chemoselective acylation on the primary aliphatic hydroxy group over phenolic hydroxy group in tyrosol, and 2-iodoxybenzoic acid (IBX)-mediated hydroxylation adjacent to the remaining free phenolic hydroxy g ...
DOI:
10.1080/09168451.2018.1530970

19. Chemoproteomics Using Nucleotide Acyl Phosphates Reveals an ATP Binding Site at the Dimer Interface of Procaspase-6

Author:
Eric S. Okerberg; Kevin B. Dagbay; Jennifer L. Green; Ishankumar Soni; Arwin Aban; Tyzoon K. Nomanbhoy; Sergey N. Savinov; Jeanne A. Hardy; John W. Kozarich
Source:
Biochemistry 2019 v.58 no.52 pp. 5320-5328
ISSN:
1520-4995
Subject:
acylation; adenine; binding sites; caspase-6; in vitro studies; ligands; moieties; mutation; nucleotides; phosphates; proteins; proteolysis
Abstract:
... Acyl phosphates of ATP (ATPAc) and related nucleotides have proven to be useful for the interrogation of known nucleotide binding sites via specific acylation of conserved lysines (K). In addition, occasional K acylations are identified in proteins without such known sites. Here we present a robust and specific acylation of procaspase-6 by ATPAc at K133 in Jurkat cell lysates. The K133 acylation i ...
DOI:
10.1021/acs.biochem.9b00290
PubMed:
31095371
PubMed Central:
PMC6874883

20. Continuous Flow Synthesis of Isoxazoles via Vinyl Azides from Friedel–Crafts Acylation of Alkynes: A Modulated Troubleshooting Optimization Approach

Author:
Hyungmo Koo; Hun Young Kim; Kyungsoo Oh
Source:
Organic letters 2019 v.21 no.24 pp. 10063-10068
ISSN:
1523-7052
Subject:
acylation; alkynes; azides; chemical structure; ketones
Abstract:
... The synthesis of isoxazoles has been achieved in a continuous flow system composed of two reaction units: the Friedel–Crafts acylation of alkynes and the azide conjugate addition to the resulting β-chlorovinyl ketones followed by a photochemical–thermal reaction sequence. The salient feature of the current flow system includes the safe handling of potentially explosive organic azide species as wel ...
DOI:
10.1021/acs.orglett.9b04010

21. Continuous enantiomer‐selective acylation reaction of 1‐phenylethanamine in a magnetic fluidized bed reactor system (MFBRS)

Author:
Zhimin Ou; Jiaying Pan; Lan Tang; Hanbing Shi
Source:
Journal of chemical technology and biotechnology 2019 v.94 no.6 pp. 1951-1957
ISSN:
0268-2575
Subject:
acylation; catalysts; fluidized beds; immobilized enzymes; kinetics; magnetic fields; mixers; nanoparticles; triacylglycerol lipase
Abstract:
... BACKGROUND: Magnetic nanoparticle immobilized enzymes are attractive owing to their potential applications in many biological fields. When an alternating magnetic field is applied, the magnetic moments of the magnetic nanoparticles are apt to align in the direction of the field, and the magnetic nanoparticles experience force in the direction of the field. Thus, the magnetic nanoparticles behave l ...
DOI:
10.1002/jctb.5978

22. Convergent synthesis of diptoindonesin G

Author:
Dileep Kumar Singh; Ikyon Kim
Source:
Tetrahedron letters 2019 v.60 no.3 pp. 300-301
ISSN:
0040-4039
Subject:
Suzuki reaction; acylation; chemical structure; organic compounds
Abstract:
... A convergent and scalable synthetic route to a tetracyclic oligostilbenoid natural product, diptoindonesin G, is described where Suzuki-Miyaura cross-coupling and intramolecular Friedel-Crafts acylation were employed to construct the central C ring of diptoindonesin G. Two fragments for cross-coupling reaction were readily synthesized with similar efficiency. ...
DOI:
10.1016/j.tetlet.2018.12.036

23. Cyanobacterial peptides as a tour de force in the chemical space of antiparasitic agents

Author:
Luis Rivas; Verónica Rojas
Source:
Archives of biochemistry and biophysics 2019 v.664 pp. 24-39
ISSN:
0003-9861
Subject:
acylation; amino acid sequences; amino acids; antimicrobial peptides; antiparasitic agents; biosynthesis; cell membranes; eukaryotic cells; heterocyclic compounds; innate immunity; invertebrates; lipids; parasites; pathogens; permeability; post-translational modification; vertebrates
Abstract:
... Parasites are scarcely addressed target for antimicrobial peptides despite their big impact in health and global economy. The notion of antimicrobial peptides is frequently associated to the innate immune defense of vertebrates and invertebrate vectors, as the ultimate recipients of the parasite infection. These antiparasite peptides are produced by ribosomal synthesis, with few post-translational ...
DOI:
10.1016/j.abb.2019.01.030

24. Decanoic acid functionalized chitosan: Synthesis, characterization, and evaluation as potential wound dressing material

Author:
Qifeng Dang; Qianqian Zhang; Chengsheng Liu; Jingquan Yan; Guozhu Chang; Ying Xin; Xiaoyu Cheng; Yachan Cao; Hong Gao; Yan Liu
Source:
International journal of biological macromolecules 2019 v.139 pp. 1046-1053
ISSN:
0141-8130
Subject:
Fourier transform infrared spectroscopy; X-ray diffraction; acylation; biocompatibility; cell viability; chitosan; crystal structure; decanoic acid; hemolysis; models; moieties; nuclear magnetic resonance spectroscopy; tissue repair; titration; toxicity testing; water solubility
Abstract:
... Skin wound dressing materials, which can accelerate wound healing and have the synthetic advantages of simplicity, environmental safety, and resource abundance, are becoming a hot topic of research now. Following such a research trend, we prepared novel decanoic acid functionalized chitosan (CSDA) with good solubility by acylation via a facile one-step method. FTIR, ¹H NMR, and UV–Vis results demo ...
DOI:
10.1016/j.ijbiomac.2019.08.083

25. Degradable cellulose‐based polymer brushes with controlled grafting densities

Author:
Mateusz Olszewski; Lingchun Li; Guojun Xie; Andrew Keith; Sergei S. Sheiko; Krzysztof Matyjaszewski
Source:
Journal of polymer science 2019 v.57 no.24 pp. 2426-2435
ISSN:
0887-624X
Subject:
acylation; cellulose; cellulose acetate; esterification; glucose; lithium chloride; organobromine compounds; polymers; solvents
Abstract:
... Cellulose‐based polymer brushes with variable grafting densities and low dispersity were synthesized by grafting poly(n‐butyl acrylate) (PBA) side chains from cellulose‐derived backbones via ATRP. Esterification of commercially available cellulose acetate with 2‐bromoisobutyryl bromide (2‐BiBB) in NMP provided cellulose‐based macroinitiators averaging one initiation site per double glucose unit. A ...
DOI:
10.1002/pola.29481

26. Detection of Phenylketonuria Markers Using a ZIF-67 Encapsulated PtPd Alloy Nanoparticle (PtPd@ZIF-67)-Based Disposable Electrochemical Microsensor

Author:
Xinyue Xu; Dongqing Ji; Yuan Zhang; Xinghua Gao; Pengcheng Xu; Xinxin Li; Chung-Chiun Liu; Weijia Wen
Source:
ACS applied materials & interfaces 2019 v.11 no.23 pp. 20734-20742
ISSN:
1944-8252
Subject:
Fourier transform infrared spectroscopy; acylation; alloy nanoparticles; amino acid derivatives; amino acid metabolism; behavior disorders; behavior problems; congenital abnormalities; crystals; electrochemistry; electron transfer; encapsulation; imidazole; metabolites; nanocomposites; phenylacetic acid; phenylketonuria; phenylpyruvic acid; point-of-care systems; screening; seizures
Abstract:
... Phenylketonuria (PKU) is a common disease in congenital disorder of amino acid metabolism, which can lead to intellectual disability, seizures, behavioral problems, and mental disorders. We report herein a facile method to screen for PKU by the measurements of its metabolites (markers). In this work, a disposable electrochemical microsensor modified with a ZIF (zeolitic imidazolate framework)-base ...
DOI:
10.1021/acsami.9b05431

27. Differential occurrence of lysine 2-hydroxyisobutyrylation in psoriasis skin lesions

Author:
Huiyao Ge; Bao Li; Weiwei Chen; Qiongqiong Xu; Shirui Chen; Hui Zhang; Jing Wu; Qi Zhen; Yuwei Li; Liang Yong; Yafen Yu; Jiaqi Hong; Wenjun Wang; Jinping Gao; Huayang Tang; Xianfa Tang; Sen Yang; Liangdan Sun
Source:
Journal of proteomics 2019 v.205 pp. 103420
ISSN:
1874-3919
Subject:
acylation; bioinformatics; gene expression regulation; loci; lysine; patients; post-translational modification; proteins; proteome; psoriasis; signal transduction; skin lesions; tissues
Abstract:
... Lysine 2-hydroxyisobutyrylation is a newly discovered posttranslational modification. Although this modification is an important type of protein acylation, its role in psoriasis remains unstudied. We compared lesional and nonlesional psoriasis skin samples from 45 psoriasis patients. The result showed that this highly conserved modification was found in large quantities in both normal and diseased ...
DOI:
10.1016/j.jprot.2019.103420

28. Dihydromyricetin: A review on identification and quantification methods, biological activities, chemical stability, metabolism and approaches to enhance its bioavailability

Author:
Dan Liu; Yiqin Mao; Lijun Ding; Xin-An Zeng
Source:
Trends in food science & technology 2019 v.91 pp. 586-597
ISSN:
0924-2244
Subject:
acylation; antioxidants; bioavailability; chromatography; cyclodextrins; dietary supplements; encapsulation; flavonoids; heat; humans; laboratory animals; membrane permeability; metal ions; methylation; neuroprotective effect; pH; pharmacokinetics; phospholipids; solubility; United States
Abstract:
... Dihydromyricetin (DMY) is an important plant flavonoid, which has received great attention due to its health-benefiting activities, including antioxidant, antimicrobial, anti-inflammatory, anticancer, antidiabetic and neuroprotective activities. DMY capsules have been sold in US as a nutraceutical supplement to prevent alcoholic hangovers. The major disadvantage associated with DMY is its chemical ...
DOI:
10.1016/j.tifs.2019.07.038
PubMed:
32288229
PubMed Central:
PMC7127391

29. Direct conversion of shrimp shells to O-acylated chitin with antibacterial and anti-tumor effects by natural deep eutectic solvents

Author:
Mi Feng; Xingmei Lu; Jie Zhang; Yi Li; Chunyan Shi; Lingling Lu; Suojiang Zhang
Source:
Green chemistry 2019 v.21 no.1 pp. 87-98
ISSN:
1463-9270
Subject:
acidity; acids; acylation; alkalis; amino acids; antineoplastic activity; calcium carbonate; catalysts; chitin; choline; green chemistry; hydrogen bonding; protons; shrimp shells; solvents; spectroscopy; temperature
Abstract:
... To obtain O-acylated chitin from shrimp shells directly, the used solvent should have multiple functions to remove calcium carbonate, protein, and acylated chitin. Herein, we use the acidic natural deep eutectic solvents (NADESs) with the ability to release H⁺ and various hydrogen bonding sites to achieve the above goal. The involved NADESs with three abilities of decalcification, deproteinization ...
DOI:
10.1039/c8gc02506a

30. Diversity in flower colorations of Ranunculus asiaticus L. revealed by anthocyanin biosynthesis pathway in view of gene composition, gene expression patterns, and color phenotype

Author:
Yanfang Liu; Jianhua Zhang; Xiaohong Yang; Jiangmin Wang; Yangang Li; Peng Zhang; Jin Mao; Qingmei Huang; Hao Tang
Source:
Environmental science and pollution research international 2019 v.26 no.14 pp. 13785-13794
ISSN:
0944-1344
Subject:
Ranunculus asiaticus; acylation; anthocyanins; biosynthesis; color; cyanidin; delphinidin; flowers; gene expression regulation; glucose; glycosylation; methylation; models; pelargonidin; phenotype; transcriptomics; unigenes
Abstract:
... Anthocyanin biosynthesis is one of the best studied secondary metabolisms. However, related pathways were generally concluded based on anthocyanin components; most studies focused on the backbone forming of anthocyanidins (cyanidin, delphinidin, and pelargonidin) of model or commercial plants, while anthocyanin modification was less discussed, and non-model plants with abundant colorations were le ...
DOI:
10.1007/s11356-018-2779-3

31. ETV5 regulates GOAT/ghrelin system in an mTORC1-dependent manner

Author:
Zhuo Mao; Qing Yang; Wenzhen Yin; Wen Su; Hui Lin; Mingji Feng; Ke Pan; Yue Yin; Weizhen Zhang
Source:
Molecular and cellular endocrinology 2019 pp. -
ISSN:
0303-7207
Subject:
acylation; amino acids; biochemical pathways; energy; ghrelin; ghrelin receptors; mice; promoter regions; therapeutics; transferases
Abstract:
... Ghrelin, a 28 amino acid peptide hormone, regulates multiple important metabolic functions. Its acylation by ghrelin-O-acyl-transferase enzyme (GOAT) is required for binding to and activating its receptor, the growth hormone secretagogue receptor 1a. Mechanism underlying the regulation of GOAT and acyl ghrelin remains unclear. The present study demonstrated that ETV5 could transactivate GOAT promo ...
DOI:
10.1016/j.mce.2019.02.003

32. Effect of the inserted active-site-covering lid loop on the catalytic activity of a mutant B. subtilis γ-glutamyltransferase (GGT)

Author:
Michela Massone; Cinzia Calvio; Marco Rabuffetti; Giovanna Speranza; Carlo F. Morelli
Source:
RSC advances 2019 v.9 no.60 pp. 34699-34709
ISSN:
2046-2069
Subject:
Bacillus subtilis; Escherichia coli; acylation; bioactive properties; biocatalysts; carbon; catalytic activity; enzymatic treatment; enzyme activity; flavor enhancers; gamma-glutamyltransferase; glutamic acid; hydrolases; inheritance (genetics); mutants; peptides; sensory properties; substrate specificity; synthesis
Abstract:
... γ-Glutamylpeptides are compounds derived from the acylation of an amino acid or a short peptide by the γ-carboxyl carbon of the side chain of glutamic acid. Due to their altered chemico-physical and organoleptic properties, they may be interesting substitutes or precursors of parent compounds used in pharmaceutical, dietetic and cosmetic formulations. Some of them are naturally occurring flavor en ...
DOI:
10.1039/c9ra05941e

33. Effective MDR reversers through phytochemical study of Euphorbia boetica

Author:
Sara Neto; Noélia Duarte; Cecília Pedro; Gabriella Spengler; Joséph Molnár; Maria‐José U. Ferreira
Source:
Phytochemical analysis 2019 v.30 no.5 pp. 498-511
ISSN:
0958-0344
Subject:
Euphorbia; P-glycoproteins; acylation; chlorophyll; chromatography; derivatization; diterpenoids; doxorubicin; hydrolysis; lymphoma; methanol; mice; models; multiple drug resistance; neoplasm cells; nuclear magnetic resonance spectroscopy; phytochemicals; polyamides; polyesters; spectral analysis; therapeutics
Abstract:
... INTRODUCTION: Macrocyclic diterpenes from Euphorbia species were found to be promising modulators of multidrug resistance (MDR), a complex phenomenon that hampers the effectiveness of cancer therapy. OBJECTIVE: To find new effective MDR reversers through the phytochemical study of E. boetica, including isolation and molecular derivatisation. MATERIAL AND METHODS: The phytochemical study of E. boet ...
DOI:
10.1002/pca.2841

34. Effects of Refolding on Large-Scale RNA Structure

Author:
Elizabeth A. Dethoff; Kevin M. Weeks
Source:
Biochemistry 2019 v.58 no.28 pp. 3069-3077
ISSN:
1520-4995
Subject:
Dengue virus; RNA; acylation; denaturation; entropy; genome; heat; virion
Abstract:
... Understanding RNA-mediated functions requires a detailed characterization of the underlying RNA structure. In many cases, structure probing experiments are performed on RNA that has been “refolded” in some way, which may cause the conformation to differ from that of the native RNA. We used SHAPE−MaP (selective 2′-hydroxyl acylation analyzed by primer extension, read out by mutational profiling), t ...
DOI:
10.1021/acs.biochem.8b01219
PubMed:
31268687
PubMed Central:
PMC6687061

35. Efficient acylation of gastrodin by Aspergillus oryzae whole-cells in non-aqueous media

Author:
Xiaofeng Li; Maohua Ma; Xuan Xin; Yuqian Tang; Guanglei Zhao; Xinglong Xiao
Source:
RSC advances 2019 v.9 no.29 pp. 16701-16712
ISSN:
2046-2069
Subject:
Aspergillus oryzae; Gastrodia elata; acylation; benzyl alcohol; bioactive compounds; biocatalysis; blood plasma; brain; electrospray ionization mass spectrometry; enzymes; fatty acid esters; half life; ionic liquids; nuclear magnetic resonance spectroscopy; permeability; pyridines; tetrahydrofuran; therapeutics
Abstract:
... Gastrodin, a bioactive compound extracted from the plant source of Gastrodia elata Blume, has a wide range of therapeutic effects on central nervous system (CNS) diseases, but suffers from poor brain permeability and short half-life in plasma. In this study, fatty acid esters of gastrodin were successfully synthesized by a whole cell-based biocatalytic method. Aspergillus oryzae cells showed diffe ...
DOI:
10.1039/c9ra01605h

36. Efficient production of endotoxin depleted bioactive α-hemolysin of uropathogenic Escherichia coli

Author:
Vivek Verma; Surbhi Gupta; Parveen Kumar; Ankita Rawat; Rakesh Singh Dhanda; Manisha Yadav
Source:
Preparative biochemistry & biotechnology 2019 v.49 no.6 pp. 616-622
ISSN:
1532-2297
Subject:
acylation; biotechnology; endotoxins; hemolysis; lysine; operon; urinary tract; uropathogenic Escherichia coli; virulence
Abstract:
... Uropathogenic E. coli (UPEC), especially associated with severe urinary tract infections (UTI) pathologies, harbors an important virulence factor known as α-hemolysin (110 kDa). Hemolytic activity of α-hemolysin (HlyA) requires modification (acylation) of two lysine residues of HlyA by HlyC, part of operon hlyCABD. Most of the previous studies had used whole operon hlyCABD and gene tolC cloning fo ...
DOI:
10.1080/10826068.2019.1591993

37. Enantioenriched 1-Tetralones via Rhodium-Catalyzed Arylative Cascade Desymmetrization/Acylation of Alkynylmalonates

Author:
Aymane Selmani; Sylvain Darses
Source:
Organic letters 2019 v.21 no.19 pp. 8122-8126
ISSN:
1523-7052
Subject:
acylation; alkynes; carbon; catalytic activity; ligands; moieties; regioselectivity; rhodium
Abstract:
... An efficient atom-economic rhodium-catalyzed asymmetric arylative cyclization to access enantioenriched 1-tetralones, bearing a quaternary carbon stereocenter, is described, involving a highly regioselective alkyne insertion, a 1,4-Rh shift, and an acylation step via the desymmetrization of the malonate moiety thanks to an appropriate chiral diene ligand. ...
DOI:
10.1021/acs.orglett.9b03153

38. Enantioselective Radical Hydroacylation of Enals with α-Ketoacids Enabled by Photoredox/Amine Cocatalysis

Author:
Jia-Jia Zhao; Hong-Hao Zhang; Xu Shen; Shouyun Yu
Source:
Organic letters 2019 v.21 no.4 pp. 913-916
ISSN:
1523-7052
Subject:
acylation; chemical structure; enantioselectivity; free radicals; ions; organic compounds; redox reactions
Abstract:
... A photoredox/amine-cocatalyzed enantioselective radical hydroacylation of enals with α-ketoacids is described. Acyl radicals generated from α-ketoacids act as the acylation reagent with the iminium ions. This strategy provides an efficient way to access synthetically challenging 1,4-dicarbonyl compounds in an enantioselective manner. The reactions of various enals with α-ketoacids show the general ...
DOI:
10.1021/acs.orglett.8b03840

39. Enzymatic acylation of blackcurrant (Ribes nigrum) anthocyanins and evaluation of lipophilic properties and antioxidant capacity of derivatives

Author:
Wei Yang; Maaria Kortesniemi; Xueying Ma; Jie Zheng; Baoru Yang
Source:
Food chemistry 2019 v.281 pp. 189-196
ISSN:
0308-8146
Subject:
Ribes nigrum; absorbance; acylation; anthocyanins; antioxidant activity; black currants; dodecanoic acid; glucosides; hydrophilicity; lipid peroxidation; lipophilicity; moieties; nuclear magnetic resonance spectroscopy; rhamnose; rutin; thermal stability
Abstract:
... Anthocyanin-rich fractions isolated from blackcurrant (Ribes nigrum L.) including delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-glucoside and cyanidin-3-O-rutinoside were enzymatically acylated with lauric acid. All the four anthocyanins were successfully monoacylated, and their relative proportions did not affect the conversion yield. The acylation occurred at the 6″-OH posi ...
DOI:
10.1016/j.foodchem.2018.12.111

40. Esterification of Secondary Alcohols and Multi-hydroxyl Compounds by Candida antarctica Lipase B and Subtilisin

Author:
Hee-Jeong Cha; Jin-Byung Park; Seongsoon Park
Source:
Biotechnology and bioprocess engineering 2019 v.24 no.1 pp. 41-47
ISSN:
1226-8372
Subject:
Pseudozyma antarctica; acylation; alcohols; carbohydrates; carboxylic ester hydrolases; esterification; flavonoids; stereospecificity; subtilisin; surveys
Abstract:
... Enzyme-catalyzed esterification of secondary alcohols and multi-hydroxyl compounds is one of the most valuable reactions in organic synthesis. However, it is often difficult to achieve high reaction rates and high regio-selectivities with commonly used enzymes such as lipases and proteases. One of the reasons may include bulky substituents of the secondary alcohols and multi-hydroxyl compounds (e. ...
DOI:
10.1007/s12257-018-0379-1

41. Evaluation of astringent taste of green tea through mass spectrometry-based targeted metabolic profiling of polyphenols

Author:
Juhua Zhuang; Xinlong Dai; Mengqing Zhu; Shuxiang Zhang; Qianying Dai; Xiaolan Jiang; Yajun Liu; Liping Gao; Tao Xia
Source:
Food chemistry 2019 pp. -
ISSN:
0308-8146
Subject:
acylation; astringency; autumn; condensation reactions; flavanols; flavonols; glycosylation; green tea; hydroxylation; liquid chromatography; mass spectrometry; metabolomics; polyphenols; principal component analysis; spring
Abstract:
... The contributions of many polyphenols other than catechins and flavonols to the astringency of tea are often neglected. Here, the contributions of polyphenols were assessed through targeted metabolic profiling using liquid chromatography–mass spectrometry. A total of 86 polyphenols were identified from 47 green tea samples with varying astringency scores, of which 76 compounds were relatively quan ...
DOI:
10.1016/j.foodchem.2019.125507

42. Extraordinary solution-processability of lignin in phenol–maleic anhydride and dielectric films with controllable properties

Author:
Qi Fan; Tao Liu; Chaoqun Zhang; Zhenzhen Liu; Wenxu Zheng; Rongxian Ou; Qingwen Wang
Source:
Journal of materials chemistry A 2019 v.7 no.40 pp. 23162-23172
ISSN:
2050-7496
Subject:
acylation; ambient temperature; cost effectiveness; crosslinking; dielectric properties; electronics; hydrogen bonding; lignin; maleic anhydrides; mechanical properties; phenol; solvents; value added
Abstract:
... Highly efficient and cost-competitive dissolution of lignin is vital to value-added utilization of lignin waste streams. Here, a novel and cost-efficient supramolecular eutectic liquid (phenol-MAH) comprising phenol and maleic anhydride was developed, which can rapidly dissolve lignin with ultrahigh-solid loading (>50 wt%) at room temperature. About 70 wt% lignin loading in phenol-MAH leads to a h ...
DOI:
10.1039/c9ta06665a

43. Fabrication of Stable and Self-Assembling Rapeseed Protein Nanogel for Hydrophobic Curcumin Delivery

Author:
Zhigao Wang; Rui Xue Zhang; Cheng Zhang; Caixia Dai; Xingrong Ju; Rong He
Source:
Journal of agricultural and food chemistry 2019 v.67 no.3 pp. 887-894
ISSN:
1520-5118
Subject:
acylation; antineoplastic activity; biopolymers; cell lines; crosslinking; curcumin; disulfide bonds; drug delivery systems; encapsulation; freeze drying; functional foods; heat; heat treatment; hydrophilicity; hydrophobicity; ionic strength; moieties; nanoparticles; neoplasm cells; neoplasms; pH; protein denaturation; protein isolates; rapeseed protein; temperature
Abstract:
... Food-dervied biopolymer nanogels have recently received considerable attention as favorable carrier systems for nutraceuticals and drugs. In the present study, new biocompatible and self-assembled acylated rapeseed protein isolate (ARPI)-based nanogels were fabricated for potential hydrophobic drug delivery by chemical acylation and heat-induced protein denaturation. The effects of the ARPI concen ...
DOI:
10.1021/acs.jafc.8b05572

44. Formal [4 + 2] Cycloadditions of Anhydrides and α,β-Unsaturated N-Tosyl Ketimines

Author:
Noah P. Burlow; Sara Y. Howard; Carla M. Saunders; James C. Fettinger; Dean J. Tantillo; Jared T. Shaw
Source:
Organic letters 2019 v.21 no.4 pp. 1046-1049
ISSN:
1523-7052
Subject:
acylation; anhydrides; chemical structure; cycloaddition reactions; diastereoselective synthesis; esterification; ketimines; ketones
Abstract:
... A method for the diastereoselective synthesis of highly substituted β-enamino ketones from anhydrides and ketone-derived imines is reported. Cyclic, enolizable anhydrides undergo a base-promoted conjugate addition reaction with α,β-unsaturated N-tosyl ketimines, followed by an intramolecular acylation to give formal [4 + 2] cycloaddition products. The carboxylic acid-containing products are formed ...
DOI:
10.1021/acs.orglett.8b04091

45. Formation, Tentative Mass Spectrometric Identification, and Color Stability of Acetaldehyde-Catalyzed Condensation of Red Radish (Raphanus sativus) Anthocyanins and (+) Catechin

Author:
Nathan B. Stebbins; Luke R. Howard; Ronald L. Prior; Cindi Brownmiller; Rohana Liyanage; Jackson O. Lay
Source:
Beverages 2019 v.5 no.4 pp. -
ISSN:
2306-5710
Subject:
Raphanus sativus; Zymomonas mobilis; acetaldehyde; acylation; ambient temperature; anthocyanins; catechin; cocoa powder; color; food colorants; mass spectrometry; phenolic acids; radishes
Abstract:
... Red radish anthocyanins are relatively stable due to the acylation of anthocyanins with organic and phenolic acid moieties. The objective of this study was to create and identify a novel ethyl-bridged acylated anthocyanin with a stable violet color from red radishes in the presence of acetaldehyde and catechin. After incubation at ambient temperature for one week at 21 °C the reaction mixture with ...
DOI:
10.3390/beverages5040064

46. Genome-wide analysis and functional characterization of Acyl-CoA:diacylglycerol acyltransferase from soybean identify GmDGAT1A and 1B roles in oil synthesis in Arabidopsis seeds

Author:
Jiangzhe Zhao; Rongrong Bi; Shuxiang Li; Dan Zhou; Yang Bai; Guangqin Jing; Kewei Zhang; Wenhua Zhang
Source:
Journal of plant physiology 2019 pp. -
ISSN:
0176-1617
Subject:
Arabidopsis; Glycine max; acylation; catalytic activity; diacylglycerol acyltransferase; gene expression; genes; genome-wide association study; leaves; lipid content; mutants; protein content; seed oils; seeds; soybeans; transgenic plants; triacylglycerols; yeasts
Abstract:
... Acyl-CoA:diacylglycerol acyltransferase (DGAT) is a key enzyme in the Kennedy pathway of triacylglycerol (TAG) synthesis. It catalyzes the acyl-CoA-dependent acylation of sn-1, 2-diacylglycerol to form TAG. DGATs in soybean (Glycine max) have been reported, but their functions are largely unclear. Here we cloned three members of DGAT1 and four members of DGAT2 family from soybean, named GmDGAT1A t ...
DOI:
10.1016/j.jplph.2019.153019

47. Heteropoly acids-functionalized Janus particles as catalytic emulsifier for heterogeneous acylation in flow ionic liquid-in-oil Pickering emulsion

Author:
Xiuping Tang; Yu Hou; Qing Bo Meng; Guolin Zhang; Fuxin Liang; Xi-Ming Song
Source:
Colloids and surfaces 2019 v.570 pp. 191-198
ISSN:
0927-7757
Subject:
acylation; catalysts; catalytic activity; emulsifiers; emulsifying; emulsions; ionic liquids; moieties; nanoparticles; silica; toluene
Abstract:
... In this work, we developed a continuous non-aqueous flow Pickering emulsion interface catalysis (FPIC) system for heterogeneous acylation. Poly (1-vinyl-3-ethylimidazolium bromide) (PILs) functionalized silica@PS/PDVB Janus particles (JPs) were synthesized. The catalyst H3PW12O40 (PA) was then immobilized on PIL-modified JPs by anion-exchanging. The PIL grafted on the silica side and the inherent ...
DOI:
10.1016/j.colsurfa.2019.02.066

48. High flux reverse osmosis membranes fabricated with hyperbranched polymers via novel twice-crosslinked interfacial polymerization method

Author:
Hao Wu; Xiao Zhang; Xue-Ting Zhao; Ke Li; Chun-Yang Yu; Li-Fen Liu; Yong-Feng Zhou; Cong-Jie Gao
Source:
Journal of membrane science 2019 pp. -
ISSN:
0376-7388
Subject:
acylation; crosslinking; hydrophilicity; manganese; moieties; organochlorine compounds; polyamides; polyesters; polymerization; reverse osmosis; thin film composite membranes; trimesoyl chloride
Abstract:
... In this study, two kinds of carboxyl-terminated hyperbranched polyesters (HBPs) with special three-dimensional structure were proposed to act as the substrates to synthesize two new kinds of acyl chloride-terminated hyperbranched polyesters (HBPACs) that were used as the key functional materials to participate in the interfacial polymerization reaction to fabricate the novel thin film composite me ...
DOI:
10.1016/j.memsci.2019.117480

49. Highly chemoselective, sterically sensitive NHC-catalysed amine acylation with pyridil

Author:
Amy C. Maguire; Vikas Kumar; Stephen J. Connon
Source:
Chemical communications 2019 v.55 no.90 pp. 13526-13529
ISSN:
1364-548X
Subject:
acylation; amides; amines; carbenes; catalytic activity; chemoselectivity; heterocyclic nitrogen compounds; hydrolysis
Abstract:
... A new strategy for the protection of amines has been developed involving reaction with pyridil under the influence of N-heterocyclic carbene catalysis. The methodology is capable of distinguishing between two amines characterised by small differences in steric bulk and the resulting pyridoyl amides can be cleaved without requiring either strongly acidic or basic hydrolysis. ...
DOI:
10.1039/c9cc06937b

50. Homogeneous acylation of Cellulose diacetate: Towards bioplastics with tuneable thermal and water transport properties

Author:
Manon Boulven; Guilhem Quintard; Amandine Cottaz; Catherine Joly; Aurélia Charlot; Etienne Fleury
Source:
Carbohydrate polymers 2019 v.206 pp. 674-684
ISSN:
0144-8617
Subject:
acylation; bioplastics; cellulose; esters; glass; moieties; solvents; temperature; water solubility
Abstract:
... In this study, we report a simple, non-degrading and efficient homogeneous acylation of cellulose diacetate (CDA) by using a large panel of commercially available acylating aliphatic moieties, differing in their structure (fatty, ramified, bulky, cycloaliphatic, aromatic, more or less spaced from the cellulose backbone), in view of generating a library of well-defined cellulose mixed esters with e ...
DOI:
10.1016/j.carbpol.2018.11.030

51. Hydrophobized laminarans as new biocompatible anti-oomycete compounds for grapevine protection

Author:
Franck Paris; Sophie Trouvelot; Manon Jubien; Grégory Lecollinet; Jean-Marie Joubert; Annick Chiltz; Marie-Claire Héloir; Jonathan Negrel; Marielle Adrian; Laurent Legentil; Xavier Daire; Vincent Ferrières
Source:
Carbohydrate polymers 2019 v.225 pp. 115224
ISSN:
0144-8617
Subject:
Laminaria digitata; Plasmopara viticola; Vitis; acylation; anti-infective agents; antimicrobial properties; disease control; downy mildew; elicitors; glucans; grapes; vineyards
Abstract:
... Laminaran, a β-(1→3)-glucan extracted from Laminaria digitata, is a known elicitor of plant defenses, but provides only low level of disease control in vineyard trials. In this context, laminaran was partly hydrophobized by grafting from 1.6 to 7.6 lauryl chains to the native saccharidic chain and the impact of sulfation of the hydrophobized glucans was studied. The activity of the different synth ...
DOI:
10.1016/j.carbpol.2019.115224

52. Identification and Characterization of Two New 1-O-Acyl-glucose-ester Forming Glucosyltransferases from Erigeron breviscapus

Author:
Yan Yang; Minzhi Liu; Wenxuan Zhang; Yunsong Cao; Changkun Li; Wei Wang
Source:
Journal of agricultural and food chemistry 2019 v.67 no.10 pp. 2848-2855
ISSN:
1520-5118
Subject:
Erigeron; Escherichia coli; Malus; acylation; anthocyanins; cinnamates; glucose; glucosides; glucosylation; glucosyltransferases; phylogeny; sequence analysis; substrate specificity; vanillic acid
Abstract:
... Two versatile UDP-glucosyltransferases, UGT75L25 and UGT75X1, were isolated from Erigeron breviscapus. The enzymes display high sequence identity to flavonoid 7-O-glucosyltransferase from Malus species and cluster to the phylogenetic group L of plant glucosyltransferases, also involved in the formation of hydroxycinnamoyl glucose esters, which are used as bifunctional donors in the glucosylation o ...
DOI:
10.1021/acs.jafc.8b07215

53. Immobilized feruloyl esterase from Humicola insolens catalyzes the synthesis of feruloylated oligosaccharides

Author:
Juan Tamayo-Cabezas; Salwa Karboune
Source:
Process biochemistry 2019 v.79 pp. 81-90
ISSN:
1359-5113
Subject:
Humicola insolens; acylation; catalytic activity; emulsions; epoxides; ferulic acid; feruloyl esterase; magnetism; microparticles; nanoparticles; raffinose; substrate specificity
Abstract:
... Ferulic acid acylation of oligosaccharides catalyzed by feruloyl esterases (FAE) is a promising route to produce feruloylated oligosaccharides. However, modulation of FAE synthetic properties is a key step to improve the acylation. The efficiency of H. insolens FAE to catalyze the feruloylation in six different surfactantless microemulsions reaction systems was evaluated. The highest yield (57%) w ...
DOI:
10.1016/j.procbio.2018.12.013

54. Insights into the Autoproteolytic Processing and Catalytic Mechanism of the Chlamydia trachomatis Virulence-Associated Protease CPAF

Author:
Brianne M. Dudiak; Kenneth R. Maksimchuk; Maria M. Bednar; Christopher J. Podracky; Jonathan M. Burg; Tri M. Nguyen; Felix O. Nwogbo; Raphael H. Valdivia; Dewey G. McCafferty
Source:
Biochemistry 2019 v.58 no.33 pp. 3527-3536
ISSN:
1520-4995
Subject:
Chlamydia trachomatis; Lewis bases; acylation; assays; classification; cytoskeleton; cytosol; design; deuterium; infection; inflammation; isotopes; kinetics; liquids; mutagenesis; neutrophils; peptides; protons; serine proteinases; solvents
Abstract:
... CPAF (chlamydial protease-like activity factor) is a Chlamydia trachomatis protease that is translocated into the host cytosol during infection. CPAF activity results in dampened host inflammation signaling, cytoskeletal remodeling, and suppressed neutrophil activation. Although CPAF is an emerging antivirulence target, its catalytic mechanism has been unexplored to date. Steady state kinetic para ...
DOI:
10.1021/acs.biochem.9b00522

55. Interaction of DGAT1 and PDAT1 to enhance TAG assembly in Arabidopsis

Author:
Hong Gil Lee; Pil Joon Seo
Source:
Plant signaling & behavior 2019 v.14 no.1 pp. 1554467
ISSN:
1559-2324
Subject:
Arabidopsis; PDAT (acyltransferase); acylation; biosynthesis; carbon; catalytic activity; energy; metabolic engineering; oils; seed maturation; seeds; transcription (genetics); transcription factors; triacylglycerols
Abstract:
... Seeds contain a large quantity of oils, which are mainly constituted of triacylglycerol (TAG), a fundamental source of carbon and energy. TAG biosynthesis is catalyzed by a series of multiple enzymes. In particular, two key enzymes catalyzing the last acylation step for TAG production, acyl-CoA:diacylglycerol acyltransferase 1 (DGAT1) and phospholipid:diacylglycerol acyltransferase 1 (PDAT1), are ...
DOI:
10.1080/15592324.2018.1554467
PubMed:
30537885
PubMed Central:
PMC6351085

56. Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids

Author:
Xiu-Zhi Wang; Cheng-Chu Zeng
Source:
Tetrahedron 2019 v.75 no.10 pp. 1425-1430
ISSN:
0040-4020
Subject:
acylation; catalysts; chemical structure; iron; keto acids; protocols; silver
Abstract:
... An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N ...
DOI:
10.1016/j.tet.2019.01.060

57. Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling

Author:
Claudia Bonfio; Cécile Caumes; Colm D. Duffy; Bhavesh H. Patel; Claudia Percivalle; Maria Tsanakopoulou; John D. Sutherland
Source:
Journal of the American Chemical Society 2019 v.141 no.9 pp. 3934-3939
ISSN:
1520-5126
Subject:
acylation; carboxylic acids; hydrolysis; oligonucleotides; phospholipids; prebiotics
Abstract:
... The main aim of origins of life research is to find a plausible sequence of transitions from prebiotic chemistry to nascent biology. In this context, understanding how and when phospholipid membranes appeared on early Earth is critical to elucidating the prebiotic pathways that led to the emergence of primitive cells. Here we show that exposing glycerol-2-phosphate to acylating agents leads to the ...
DOI:
10.1021/jacs.8b12331
PubMed:
30767518
PubMed Central:
PMC6506141

58. Metabolic stress leads to divergent changes in the ghrelinergic system in goldfish (Carassius auratus) gonads

Author:
Jithine Jayakumar Rajeswari; Azadeh Hatef; Mahdi Golshan; Sayyed Mohammad Hadi Alavi; Suraj Unniappan
Source:
Comparative biochemistry and physiology 2019 v.235 pp. 112-120
ISSN:
1095-6433
Subject:
Carassius auratus; Western blotting; acylation; animal ovaries; energy; fasting; females; gene expression; ghrelin; ghrelin receptors; goldfish; homeostasis; hypothalamus; males; mammals; messenger RNA; metabolism; oocytes; quantitative polymerase chain reaction; reproduction; reverse transcriptase polymerase chain reaction; testes
Abstract:
... Various endocrine factors that regulate energy homeostasis are also implicated in the reproductive physiology of mammals. However, the hormonal link between metabolism and reproduction in fish is poorly understood. Ghrelin is a multifunctional hormone with both metabolic and reproductive roles in vertebrates. Post-translational acylation by ghrelin-O-acyltransferase (GOAT) is critical for its biol ...
DOI:
10.1016/j.cbpa.2019.05.027

59. Metal-, Photocatalyst-, and Light-Free Direct C–H Acylation and Carbamoylation of Heterocycles

Author:
Matthew T. Westwood; Claire J. C. Lamb; Daniel R. Sutherland; Ai-Lan Lee
Source:
Organic letters 2019 v.21 no.17 pp. 7119-7123
ISSN:
1523-7052
Subject:
acylation; catalytic activity; chemical structure; drugs; heterocyclic compounds; photocatalysts; toxicity; wastes
Abstract:
... Direct C–H acylations and carbamoylations of heterocycles can now be readily achieved without requiring any conventional metal, photocatalyst, electrocatalysis, or light activation, thus significantly improving on sustainability, costs, toxicity, waste, and simplicity of the operational procedure. These mild conditions are also suitable for gram-scale reactions and late-stage functionalizations of ...
DOI:
10.1021/acs.orglett.9b02679

60. Modular photoinduced grafting onto approach by ketene chemistry

Author:
Yonca Alkan Goksu; Volkan Kumbaraci; Yusuf Yagci
Source:
Journal of polymer science 2019 v.57 no.3 pp. 274-280
ISSN:
0887-624X
Subject:
acylation; composite polymers; esterification; fluorescence; methanol; methylene chloride; models; nuclear magnetic resonance spectroscopy; polyethylene glycol; polymerization; ultraviolet radiation
Abstract:
... A modular approach for the synthesis of graft copolymers by the combination of reversible addition–fragmentation chain‐transfer (RAFT) polymerization and photoinduced acylation processes is described. In the two‐step approach, first the copolymers of benzodioxinone containing monomer, namely, 4‐oxo‐2,2‐diphenyl‐4H‐benzo[d][1,3]dioxin‐7‐yl methacrylate (BDMA) and methyl methacrylate (MMA) in differ ...
DOI:
10.1002/pola.29045

61. Molar absorptivities (ε) and spectral and colorimetric characteristics of purple sweet potato anthocyanins

Author:
Gregory T. Sigurdson; Rebecca J. Robbins; Thomas M. Collins; M. Mónica Giusti
Source:
Food chemistry 2019 v.271 pp. 497-504
ISSN:
0308-8146
Subject:
acylation; anthocyanins; aqueous solutions; color; colorimetry; cyanidin; food colorants; high performance liquid chromatography; hydrochloric acid; isomers; methanol; pH; sweet potatoes
Abstract:
... Purple sweet potato, a source of acylated cyanidin and peonidin derivatives, is commercially available as a food colorant. Our objectives were to determine molar absorptivities (ε), spectral and colorimetric properties of purple sweet potato anthocyanins. Anthocyanins were isolated by semi-preparative HPLC, weighed, dried, and redissolved in acidic methanol or water. Anthocyanins were diluted in p ...
DOI:
10.1016/j.foodchem.2018.07.096

62. NHC-Catalyzed Atroposelective Acylation of Phenols: Access to Enantiopure NOBIN Analogs by Desymmetrization

Author:
Shenci Lu; Si Bei Poh; Zi-Qiang Rong; Yu Zhao
Source:
Organic letters 2019 v.21 no.15 pp. 6169-6172
ISSN:
1523-7052
Subject:
acylation; catalytic activity; enantiomers; enantioselectivity; phenols
Abstract:
... Herein we present a highly efficient N-heterocyclic-carbene (NHC)-catalyzed atroposelective acylation of amino bisphenols to provide access to a wide range of 1,1′-biaryl-2,2′-amino alcohols (NOBIN analogs) in high yield and with uniformly excellent enantioselectivity. This catalytic system is shown to proceed through a combination of desymmetrization and secondary kinetic resolution to produce th ...
DOI:
10.1021/acs.orglett.9b02425

63. New Conformations of Acylation Adducts of Inhibitors of β-Lactamase from Mycobacterium tuberculosis

Author:
Raffaella Tassoni; Anneloes Blok; Navraj S. Pannu; Marcellus Ubbink
Source:
Biochemistry 2019 v.58 no.7 pp. 997-1009
ISSN:
1520-4995
Subject:
Mycobacterium tuberculosis; X-ray diffraction; active sites; acylation; alanine; beta-lactamase; crystal structure; crystallography; cysteine; enzyme inhibitors; lysine; mutation; nuclear magnetic resonance spectroscopy; serine; sulbactam; tuberculosis
Abstract:
... Mycobacterium tuberculosis (Mtb), the main causative agent of tuberculosis (TB), is naturally resistant to β-lactam antibiotics due to the production of the extended spectrum β-lactamase BlaC. β-Lactam/β-lactamase inhibitor combination therapies can circumvent the BlaC-mediated resistance of Mtb and are promising treatment options against TB. However, still little is known of the exact mechanism o ...
DOI:
10.1021/acs.biochem.8b01085
PubMed:
30632739
PubMed Central:
PMC6383187

64. New facile synthesis of furan-2(3H)-ones and 2,3,5-trisubstituted furans via intramolecular Wittig reaction of acid anhydride

Author:
Mei Sun; Qin Wan; Ming-Wu Ding
Source:
Tetrahedron 2019 v.75 no.25 pp. 3441-3447
ISSN:
0040-4020
Subject:
acylation; anhydrides; chemical structure; furans; organochlorine compounds; triethylamine
Abstract:
... A new facile preparation of furan-2(3H)-ones and 2,3,5-trisubstituted furans by a sequential O-acylation/Wittig(/O-acylation) reaction has been developed. The easily accessible 2-(triphenylphosphoranylidene)-succinic acid 1-ester 3 reacted with acid chloride produced furan-2(3H)-ones 4 in good yields in the presence of DMAP via sequential O-acylation and intramolecular Wittig reaction of acid anhy ...
DOI:
10.1016/j.tet.2019.04.074

65. Novel Sustainable Superabsorbents: A One-Pot Method for Functionalization of Side-Stream Potato Proteins

Author:
Antonio J. Capezza; David Glad; Hüsamettin Deniz Özeren; William R. Newson; Richard T. Olsson; Eva Johansson; Mikael S. Hedenqvist
Source:
ACS sustainable chemistry & engineering 2019 v.7 no.21 pp. 17845-17854
ISSN:
2168-0485
Subject:
absorbents; absorption; acylation; anhydrides; blood; centrifugation; hydrolysis; potato protein; potato protein concentrate; potatoes; powders; swelling (materials); temperature
Abstract:
... The functionalization of inexpensive potato protein concentrate (PPC) is presented as a simple and easily scalable method to produce bio-based superabsorbent powders. Five nontoxic acylating agents were evaluated at different reaction temperatures for solvent-free acylation of the protein. The best results were obtained for succinic anhydride (SA) and a reaction temperature of 140 °C. These condit ...
DOI:
10.1021/acssuschemeng.9b04352

66. One-Pot Synthesis of π-Extended Fluorenone-Fused Subphthalocyanines

Author:
Lara Tejerina; M. Victoria Martínez-Díaz; Tomás Torres
Source:
Organic letters 2019 v.21 no.8 pp. 2908-2912
ISSN:
1523-7052
Subject:
absorption; acylation; chemical structure; organic compounds; synthesis
Abstract:
... A family of inherently chiral nonplanar aromatic chromophores, comprising Subphthalocyanines bearing fluorenone-fused units (SubFcs), have been prepared by an innovative one-pot synthesis, which relies on the standard cross-cyclotrimerization of phthalonitriles followed by intramolecular Friedel–Crafts acylation. Their Q-band absorption experiences a ca. 20 nm red shift per fused fluorenone as a c ...
DOI:
10.1021/acs.orglett.9b00944

67. One-Step Activation and Surface Fatty Acylation of Cellulose Fibers in a Solvent-Free Condition

Author:
Lang Huang; Qiong Wu; Qingwen Wang; Michael Wolcott
Source:
ACS sustainable chemistry & engineering 2019 v.7 no.19 pp. 15920-15927
ISSN:
2168-0485
Subject:
acetic anhydride; acylation; catalysts; cellulose; cellulosic fibers; esterification; esters; mechanochemistry; oleic acid; powders; thermal stability
Abstract:
... Fatty acid cellulose esters with excellent water repellency and improved processability have gained a lot of attention in varied applications. In this study, a “green” synthetic route employing mechanochemical reaction methods was developed to prepare long-chain cellulose esters from cellulose fibers. Specifically, cellulose fibers were ball-milled to prepare activated cellulose particles; asymmet ...
DOI:
10.1021/acssuschemeng.9b01974

68. Palladium(0)-Catalyzed Carbonylative Synthesis of N-Acylsulfonamides via Regioselective Acylation

Author:
Luke S. Schembri; Jonas Eriksson; Luke R. Odell
Source:
Journal of organic chemistry 2019 v.84 no.11 pp. 6970-6981
ISSN:
1520-6904
Subject:
Lewis bases; acylation; azides; biological assessment; carboxylic acids; chemical structure; hydrogen bonding; in vivo studies; organic chemistry; palladium; positron-emission tomography; pyrroles; regioselectivity; temperature
Abstract:
... N-Acylsulfonamides represent an important bioisostere of carboxylic acids that allow for greater molecular elaboration and enhanced hydrogen bonding capabilities. Herein, we present a mild and convenient palladium(0)-catalyzed synthesis of N-acylsulfonamides via the carbonylative coupling of sulfonyl azides and electron-rich heterocycles. The reaction proceeds via in situ generation of a sulfonyl ...
DOI:
10.1021/acs.joc.9b00740

69. Palladium-Catalyzed Acylation of Terminal Alkynes toward 3-Ynone-Linked Chlorophyll-a Derivatives and Their Optical Properties

Author:
Takeo Nakano; Hitoshi Tamiaki
Source:
Journal of organic chemistry 2019 v.84 no.24 pp. 16116-16123
ISSN:
1520-6904
Subject:
absorption; acylation; alkynes; anhydrides; catalytic activity; chlorophyll; fluorescence; moieties; optical properties; organic chemistry; organochlorine compounds; palladium
Abstract:
... The Pd-catalyzed acylation reactions of terminal 3-ethynyl moieties of chlorophyll-a (Chl-a) derivatives are described herein. Both acyl chlorides and acid anhydrides were valuable reagents for the coupling, resulting in the formation of π-conjugation extended Chl-a derivatives possessing a carbonyl-ethynyl group at the C3-position. The ultraviolet–visible absorption and fluorescence emission data ...
DOI:
10.1021/acs.joc.9b02607

70. Palladium-Catalyzed C8-H Acylation of 1-Naphthylamines with Acyl Chlorides

Author:
Xiaomeng Yu; Fan Yang; Yusheng Wu; Yangjie Wu
Source:
Organic letters 2019 v.21 no.6 pp. 1726-1729
ISSN:
1523-7052
Subject:
acylation; amines; catalytic activity; moieties; organochlorine compounds; palladium; regioselectivity
Abstract:
... A facile and efficient protocol for palladium-catalyzed regioselective C8-H acylation of 1-naphthylamine derivatives with acyl chlorides has been developed. The reaction exhibits broad functional group tolerance, and both aromatic and α,β-unsaturated acyl chlorides can be effectively coupled with 1-naphthylamines. Moreover, the picolinamide moiety as a bidentate directing likely plays a key role i ...
DOI:
10.1021/acs.orglett.9b00283

71. Palladium-catalyzed intramolecular CH acylation of indoles with thioester

Author:
Min Liu; Yu-Wen Liu; Hui Xu; Hui-Xiong Dai
Source:
Tetrahedron letters 2019 pp. -
ISSN:
0040-4039
Subject:
acylation; catalytic activity; chemical structure; cross-coupling reactions; indoles; organic halogen compounds; palladium; thioesters
Abstract:
... A palladium-catalyzed intramolecular CH acylation of indole with thioester is described, providing a direct and effective approach for the synthesis of the biologically active indole-indolone scaffolds. The method obviates the need for the prefunctionalized starting materials including organometallic reagents, alkyl halides, and NHP esters in previous metal-catalyzed cross-coupling reaction with t ...
DOI:
10.1016/j.tetlet.2019.151061

72. Pantheric Acids A–C from a Poisonous Mushroom, Amanita pantherina, Promote Lipid Accumulation in Adipocytes

Author:
Seoung Rak Lee; Sang Ah Yi; Ki Hong Nam; Rhim Ryoo; Jaecheol Lee; Ki Hyun Kim
Source:
Journal of natural products 2019 v.82 no.12 pp. 3489-3493
ISSN:
1520-6025
Subject:
Amanita pantherina; acylation; adipocytes; adverse effects; droplets; enantioselectivity; fatty acids; fruiting bodies; lipogenesis; lipolysis; muscles; mushrooms; nuclear magnetic resonance spectroscopy; poisonous fungi; tandem mass spectrometry
Abstract:
... Amanita pantherina is a poisonous mushroom that causes muscle cramps, insanity, and audiovisual disorders. As part of our systematic study on Korean mushrooms, a chemical investigation of A. pantherina fruiting bodies resulted in the isolation and structural identification of three new fatty acid derivatives, pantheric acids A–C (1–3), and a known compound, 1,10-dimethyl ester-2-decenedioic acid ( ...
DOI:
10.1021/acs.jnatprod.9b00782

73. Photocatalytic 1,1-Hydrofluoroalkylation of Alkynes with a Concurrent Vicinal Acylation: An Access to Fluoroalkylated Cyclic Ketones

Author:
Yimei Wan; Tianbo Shang; Zenghui Lu; Gangguo Zhu
Source:
Organic letters 2019 v.21 no.11 pp. 4187-4191
ISSN:
1523-7052
Subject:
acylation; alkynes; chemical structure; hydrogen; indans; ketones; photocatalysis; tetrahydrofuran
Abstract:
... A visible-light-induced 1,1-hydrofluoroalkylation of alkynes with a concomitant vicinal acylation is developed using tetrahydrofuran (THF) as the hydrogen atom source. Various fluoroalkylated cyclic ketones, such as indanones, chroman-4-ones, 2,3-dihydroquinolin-4(1H)-ones, and 3,4-dihydronaphthalen-1(2H)-ones, can be efficiently synthesized with excellent trans-diastereoselectivity. The reaction ...
DOI:
10.1021/acs.orglett.9b01366

74. Photogenerated acyl/alkoxycarbonyl/carbamoyl radicals for sustainable synthesis

Author:
Carlotta Raviola; Stefano Protti; Davide Ravelli; Maurizio Fagnoni
Source:
Green chemistry 2019 v.21 no.4 pp. 748-764
ISSN:
1463-9270
Subject:
acylation; alkynes; ambient temperature; aromatic compounds; free radicals; green chemistry; ketones; moieties; photochemistry; solar radiation
Abstract:
... Acylation reactions are of crucial importance in synthesis since they provide access to ketones or related derivatives. The well known acylations of aromatics (the Friedel–Crafts reaction) or olefins are commonly carried out under harsh and/or non-sustainable conditions. An alternative approach consists in the use of acyl (or related) radicals as acylating agents. Recently, the photochemical appro ...
DOI:
10.1039/c8gc03810d

75. Photoinduced Divergent Alkylation/Acylation of Pyridine N-Oxides with Alkynes under Anaerobic and Aerobic Conditions

Author:
Jin-hui Xu; Wen-bin Wu; Jie Wu
Source:
Organic letters 2019 v.21 no.13 pp. 5321-5325
ISSN:
1523-7052
Subject:
acylation; aerobic conditions; alkylation; alkynes; chemical structure; nitrogen oxides; pyridines; regioselectivity
Abstract:
... Ortho-alkylated and ortho-acylated pyridines have been conveniently synthesized from pyridine N-oxides and alkynes under visible-light-mediation in a metal-free manner. The alkynes served as both alkylating and acylating agents via switching between anaerobic and aerobic conditions. The overall strategy accommodates a broad scope of substituted pyridine N-oxides and alkynes, with excellent regiose ...
DOI:
10.1021/acs.orglett.9b01940

76. Polyacetate and Polycarbonate RNA: Acylating Reagents and Properties

Author:
Maryam Habibian; Willem A. Velema; Anna M. Kietrys; Yoshiyuki Onishi; Eric T. Kool
Source:
Organic letters 2019 v.21 no.14 pp. 5413-5416
ISSN:
1523-7052
Subject:
RNA; RNA-directed DNA polymerase; acylation; melting; moieties; organic compounds
Abstract:
... Acylation of RNA at 2′-OH groups is widely applied in mapping RNA structure and recently for controlling RNA function. Reactions are described that install the smallest 2-carbon acyl groups on RNA—namely, 2′-O-acetyl and 2′-O-carbonate groups. Hybridization and thermal melting experiments are performed to assess the effects of the acyl groups on duplex formation. Both reagents can be employed at l ...
DOI:
10.1021/acs.orglett.9b01526
PubMed:
31268332
PubMed Central:
PMC6775763

77. Prenylated Acylphloroglucinols from Hypericum faberi

Author:
Xin-Wen Zhang; Shao-Qiang Fan; Fan Xia; Yan-Song Ye; Xing-Wei Yang; Xian-Wen Yang; Gang Xu
Source:
Journal of natural products 2019 v.82 no.5 pp. 1367-1371
ISSN:
1520-6025
Subject:
Hypericum; acylation; cell lines; cytotoxicity; inhibitory concentration 50; nuclear magnetic resonance spectroscopy; styrene
Abstract:
... The isolation and structure elucidation of six new prenylated acylphloroglucinols, faberiones A–F, from the whole plant of Hypericum faberi is reported. Faberiones A–D (1–4) share a rare styrene substituent and may be biosynthetically generated via further acylation of the acylphloroglucinols. By analyzing the MS and NMR data, the structures of the new isolates were established. Faberiones B (2) a ...
DOI:
10.1021/acs.jnatprod.8b01006

78. Preparation and Characterization of Acylcaramel

Author:
Yichao Geng; Yulin Ning; Qiang Shao; Yaozhong Lv; Xianfu Wei; Yujie Dai; Shiru Jia; Cheng Zhong; Shuli Man; Liming Zhang; Xiuli Zhang
Source:
Journal of agricultural and food chemistry 2019 v.67 no.19 pp. 5614-5620
ISSN:
1520-5118
Subject:
Fourier transform infrared spectroscopy; acylation; color; corn oil; lipids; organochlorine compounds; raw materials; scanning electron microscopy; thermal analysis; titration; water solubility; weight loss
Abstract:
... Caramel is a widely used water-soluble food pigment. The acylation of caramel was conducted by aliphatic acyl chlorides with different chain lengths. Acetyl, butyryl, octyl, lauryl, palmityl, and stearyl caramels were prepared with the ratio of acyl chloride/caramel of 6. The formation of acylated caramel was confirmed by Fourier transform infrared spectra, and the acyl mass fraction in acylcarame ...
DOI:
10.1021/acs.jafc.8b07148

79. Prospects for economical natural colorants: insights from maize

Author:
Laura A. Chatham; Michael Paulsmeyer; John A. Juvik
Source:
Theoretical and applied genetics 2019 v.132 no.11 pp. 2927-2946
ISSN:
0040-5752
Subject:
acylation; anthocyanins; biosynthesis; color; corn; flavanols; methylation; polymerization
Abstract:
... KEY MESSAGE: Anthocyanin pigments from maize offer a natural yet economical alternative to artificial dyes. Breeding for optimal colorant production requires understanding and integrating all facets of anthocyanin chemistry and genetics research. Replacing artificial dyes with natural colorants is becoming increasingly popular in foods and beverages. However, natural colorants are often expensive, ...
DOI:
10.1007/s00122-019-03414-0

80. Quantitation of Reactive Acyl-CoA Species Mediated Protein Acylation by HPLC–MS/MS

Author:
Tim Baldensperger; Simone Di Sanzo; Alessandro Ori; Marcus A. Glomb
Source:
Analytical chemistry 2019 v.91 no.19 pp. 12336-12343
ISSN:
1520-6882
Subject:
Western blotting; acyl coenzyme A; acylation; brain; epigenetics; fractionation; heart; high performance liquid chromatography; kidneys; liver; lysine; mass spectrometry; metabolism; mice; proteomics
Abstract:
... Recently discovered acylation by reactive acyl-CoA species is considered a novel regulatory mechanism in epigenetics and metabolism. Established analytical methods like Western blotting and proteomics fail to detect the plethora of acylation structures in a single analysis and lack the ability of absolute quantitation. In this paper, we developed an HPLC–MS/MS method for the simultaneous detection ...
DOI:
10.1021/acs.analchem.9b02656

81. Quantum Mechanics/Molecular Mechanics (QM/MM) Calculations Support a Concerted Reaction Mechanism for the Zika Virus NS2B/NS3 Serine Protease with Its Substrate

Author:
Bodee Nutho; Adrian J. Mulholland; Thanyada Rungrotmongkol
Source:
Journal of physical chemistry 2019 v.123 no.13 pp. 2889-2903
ISSN:
1520-5207
Subject:
Aedes; Lewis bases; Zika virus; acylation; adults; humans; molecular dynamics; neonates; peptides; polyproteins; potential energy; quantum mechanics; reaction mechanisms; serine proteinases; simulation models; vaccines
Abstract:
... Zika virus (ZIKV) is mainly transmitted to humans by Aedes species mosquitoes and is associated with serious pathological disorders including microcephaly in newborns and Guillain–Barré syndrome in adults. Currently, there is no vaccine or anti-ZIKV drug available for preventing or controlling ZIKV infection. An attractive drug target for ZIKV treatment is a two-compartment (NS2B/NS3) serine prot ...
DOI:
10.1021/acs.jpcb.9b02157

82. Radical Addition to N-Tosylimines via C–H Activation Induced by Decatungstate Photocatalyst

Author:
Vyacheslav I. Supranovich; Vitalij V. Levin; Alexander D. Dilman
Source:
Organic letters 2019 v.21 no.11 pp. 4271-4274
ISSN:
1523-7052
Subject:
acylation; aldehydes; alkylation; carbon-hydrogen bond activation; chemical structure; dimethylformamide; ethers; irradiation; light emitting diodes; photocatalysts; tetrabutylammonium compounds
Abstract:
... A method for the radical addition toward N-tosylimines based on light promoted C–H activation by tetrabutylammonium decatungstate is described. The reaction proceeds under irradiation using 400 nm light emitting diodes in conventional glassware. The method can be applied for alkylations (cycloalkanes, ethers, dimethylformamide) and acylation (primary aliphatic aldehydes) of both aromatic and aliph ...
DOI:
10.1021/acs.orglett.9b01450

83. Regiospecific methylation of all the hydroxyls in (+)‐catechin by a stepwise differentiation strategy

Author:
Shan Hong; Shanshan Wang; He Cai; Songbai Liu
Source:
Journal of the science of food and agriculture 2019 v.99 no.8 pp. 3785-3791
ISSN:
0022-5142
Subject:
acylation; anti-allergic agents; antioxidant activity; flavanols; methylation; moieties; regioselectivity
Abstract:
... BACKGROUND: Methylated derivatives of catechins have received great attention for health beneficial effects, especially antiallergic activity. However, the scarce natural abundance of methylated catechins limits further bioactive studies. The objective of this work was to investigate regiospecific methylation of the hydroxyls of (+)‐catechin through a stepwise differentiation strategy based on ele ...
DOI:
10.1002/jsfa.9594

84. Repurposing an Ancient Protein Core Structure: Structural Studies on FmtA, a Novel Esterase of Staphylococcus aureus

Author:
Vikram Dalal; Pramod Kumar; Gaddy Rakhaminov; Aneela Qamar; Xin Fan; Howard Hunter; Shailly Tomar; Dasantila Golemi-Kotra; Pravindra Kumar
Source:
Journal of molecular biology 2019 v.431 no.17 pp. 3107-3123
ISSN:
0022-2836
Subject:
Lewis bases; Staphylococcus aureus; active sites; acylation; antibiotic resistance; catalytic activity; cell walls; crystal structure; drug therapy; enzyme activity; esterases; hydrolysis; lysine; mutagenesis; pathogenesis; polymers; serine; teichoic acids; tyrosine
Abstract:
... FmtA is a penicillin-recognizing protein (PRP) with novel hydrolytic activity toward the ester bond between d-Ala and the backbone of teichoic acids. Teichoic acids are polyol-phosphate polymers found in the Staphylococcus aureus cell wall, and they play important roles in antibiotic resistance and pathogenesis. Two of the PRPs conserved motifs, namely, SXXK and Y(S)XN, are involved in the hydroly ...
DOI:
10.1016/j.jmb.2019.06.019

85. Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow

Author:
Benjamin Heinz; Dimitrije Djukanovic; Maximilian A. Ganiek; Benjamin Martin; Berthold Schenkel; Paul Knochel
Source:
Organic letters 2019 v.22 no.2 pp. 493-496
ISSN:
1523-7052
Subject:
acylation; aromatic compounds; chemical structure; esters; ketones; temperature
Abstract:
... A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/ ...
DOI:
10.1021/acs.orglett.9b04254

86. Selective C–H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis

Author:
Jitan Zhang; Manyi Wu; Jian Fan; Qiaoqiao Xu; Meihua Xie
Source:
Chemical communications 2019 v.55 no.56 pp. 8102-8105
ISSN:
1364-548X
Subject:
acylation; antineoplastic activity; carbon-hydrogen bond activation; carboxylic acids; catalytic activity; decarboxylation; free radicals; indoles; moieties; palladium; regioselectivity; tubulin
Abstract:
... The first Pd-catalyzed direct C–H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K₂S₂O₈ promoted decar ...
DOI:
10.1039/c9cc03893k

87. Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach

Author:
D. M. M. Mevan Dissanayake; Aaron K. Vannucci
Source:
Organic letters 2019 v.21 no.2 pp. 457-460
ISSN:
1523-7052
Subject:
acylation; anhydrides; anions; batteries; benzimidazoles; chemical structure; electrochemistry; electrosynthesis; hydrogen; indoles
Abstract:
... An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This “anion pool” approach electrochemically reduces indazole molecules generating indazole anions and H₂. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles a ...
DOI:
10.1021/acs.orglett.8b03683

88. Selectivity of pigments extraction from grapes and their partial retention in the pomace during red-winemaking

Author:
Guzmán Favre; Isidro Hermosín-Gutiérrez; Diego Piccardo; Sergio Gómez-Alonso; Gustavo González-Neves
Source:
Food chemistry 2019 v.277 pp. 391-397
ISSN:
0308-8146
Subject:
Vitis vinifera; acylation; anthocyanins; ferulic acid; grapes; malvidin; pomace; winemaking; wines
Abstract:
... The purpose of this investigation was to assess the grape pigment extraction during red-winemaking. The pigment content and profile of skin, wines and pomace of Vitis vinifera grapes with different pigment profiles Syrah, Marselan and Tannat was thoroughly studied. The p-coumaroylated anthocyanin proportions were 37% in pomace, compared to 19% in skins and just 5% in wines, highlighting their poor ...
DOI:
10.1016/j.foodchem.2018.10.085

89. Simple alkanoyl acylating agents for reversible RNA functionalization and control

Author:
Hyun Shin Park; Anna M. Kietrys; Eric T. Kool
Source:
Chemical communications 2019 v.55 no.35 pp. 5135-5138
ISSN:
1364-548X
Subject:
RNA; acylation; imidazoles; moieties
Abstract:
... We describe the synthesis and RNA acylation activity of a series of minimalist azidoalkanoyl imidazole reagents, with the aim of functionalizing RNA at 2′-hydroxyl groups at stoichiometric to superstoichiometric levels. We find marked effects of small structural changes on their ability to acylate and be reductively removed, and identify reagents and methods that enable efficient RNA functionaliza ...
DOI:
10.1039/c9cc01598a
PubMed:
30977472
PubMed Central:
PMC6541391

90. Site-Selective Esterifications of Polyol β-Hydroxyamides and Applications to Serine-Selective Glycopeptide Modifications

Author:
Kohei Takemoto; Yasuhiro Nishikawa; Shohei Moriguchi; Yuna Hori; Yuki Kamezawa; Takami Matsui; Osamu Hara
Source:
Organic letters 2019 v.21 no.18 pp. 7534-7538
ISSN:
1523-7052
Subject:
acylation; esters; glycopeptides; moieties; polyols; pyridines; sugars
Abstract:
... The site-selective acylations of β-hydroxyamides in the presence of other hydroxyl groups are described. Central to the success of this modification is the metal-template-driven acylation using pyridine ketoxime esters as acylating reagents in combination with CuOTf. This strategy enables β-hydroxyl groups to be site-selectively acylated in various derivatives, including sterically hindered second ...
DOI:
10.1021/acs.orglett.9b02809

91. Spermine and oxacillin stress response on the cell wall synthesis and the global gene expression analysis in Methicillin-resistance Staphylococcus aureus

Author:
Shrikant Pawar; Xiangyu Yao; Chung-Dar Lu
Source:
Genes & genomics 2019 v.41 no.1 pp. 43-59
ISSN:
1976-9571
Subject:
Escherichia coli; Salmonella enterica; acylation; antibiotic resistance; bacteria; biochemical pathways; cell walls; crosslinking; dose response; gene expression; gene expression regulation; iron; methicillin; methicillin-resistant Staphylococcus aureus; mutation; operon; oxacillin; potassium; potassium channels; regulon; serotypes; spermine; stress response; therapeutics; transcriptomics; trypsin
Abstract:
... Methicillin-resistant Staphylococcus aureus (MRSA) is a rapidly emerging bacteria causing infection, which has developed resistance to most of the beta-lactam antibiotics because of newly acquired low-affinity penicillin-binding protein (PBP2a), which can continue to build the cell wall when beta-lactams block other PBPs. Exogenous spermine exerts a dose-dependent inhibition effect on the growth o ...
DOI:
10.1007/s13258-018-0735-8

92. Strongly Lewis Acidic Metal–Organic Frameworks for Continuous Flow Catalysis

Author:
Pengfei Ji; Xuanyu Feng; Pau Oliveres; Zhe Li; Akiko Murakami; Cheng Wang; Wenbin Lin
Source:
Journal of the American Chemical Society 2019 v.141 no.37 pp. 14878-14888
ISSN:
1520-5126
Subject:
Lewis acids; acidity; acylation; catalysts; catalytic activity; coordination compounds; cycloaddition reactions; electron paramagnetic resonance spectroscopy; energy; fluorescence emission spectroscopy; formates; hydrochloric acid; organosilicon compounds; quantitative analysis; silica; spectral analysis; zirconium
Abstract:
... The synthesis of highly acidic metal–organic frameworks (MOFs) has attracted significant research interest in recent years. We report here the design of a strongly Lewis acidic MOF, ZrOTf-BTC, through two-step transformation of MOF-808 (Zr-BTC) secondary building units (SBUs). Zr-BTC was first treated with 1 M hydrochloric acid solution to afford ZrOH-BTC by replacing each bridging formate group w ...
DOI:
10.1021/jacs.9b07891

93. Structural and Morphological Transformations of Lignin Macromolecules during Bio-Based Deep Eutectic Solvent (DES) Pretreatment

Author:
Xiao-Jun Shen; Tianying Chen; Han-Min Wang; Qingqing Mei; Fengxia Yue; Shaoni Sun; Jia-Long Wen; Tong-Qi Yuan; Run-Cang Sun
Source:
ACS sustainable chemistry & engineering 2019 v.8 no.5 pp. 2130-2137
ISSN:
2168-0485
Subject:
Eucalyptus; acylation; aromatic compounds; biorefining; carbon; dissociation; gas chromatography-mass spectrometry; gel chromatography; lactic acid; lignin; moieties; nanoparticles; nuclear magnetic resonance spectroscopy; phosphorus; scanning electron microscopy; solvents; stable isotopes; temperature
Abstract:
... Elucidating the structural characteristics and changes of lignin during biorefining is considerably important for lignin valorization. To examine the structural transformations of lignin under deep eutectic solvent (DES) pretreatments, the double enzymatic lignin (DEL) isolated from Eucalyptus was pretreated with DES (ChCl/lactic acid, 1:10) under the conditions of 60–140 °C for 6 h. The structura ...
DOI:
10.1021/acssuschemeng.9b05106

94. Structure and Activity of the Camellia oleifera Sapogenin Derivatives on Growth and Biofilm Inhibition of Staphylococcus aureus and Escherichia coli

Author:
Chunfang Zhu; Meng Zhang; Qiaoling Tang; Qian Yang; Jing Li; Xuan He; Yong Ye
Source:
Journal of agricultural and food chemistry 2019 v.67 no.51 pp. 14143-14151
ISSN:
1520-5118
Subject:
Camellia oleifera; Escherichia coli; Staphylococcus aureus; acylation; antibacterial properties; antibiotics; aromatic compounds; bacteria; biofilm; heterocyclic compounds; moieties; quantitative structure-activity relationships; saponins
Abstract:
... Sapogenin is the main block of Camellia oleifera saponin, which was purified and structurally modified by the C₂₈ acylation reaction to synthesize 19 new derivatives. The growth and biofilm inhibition of Staphylococcus aureus and Escherichia coli was measured to evaluate their antibacterial effects. A three-dimensional quantitative structure–activity relationship (3D-QSAR) assay indicated that the ...
DOI:
10.1021/acs.jafc.9b03577

95. Studies About the Acylation of Starch in Dipolar Aprotic Solvents

Author:
Sascha Blohm; Thomas Heinze
Source:
Stärke = 2019 v.71 no.9-10 pp. e1900053
ISSN:
0038-9056
Subject:
Fourier transform infrared spectroscopy; acetates; acylation; dimethylformamide; lithium chloride; moieties; nuclear magnetic resonance spectroscopy; organochlorine compounds; polymerization; pyridines; solvents; starch; triethylamine
Abstract:
... Starch laurates with average degrees of substitution (DS) from 0.63 to 2.52 are obtained applying three equivalents lauroyl chloride per anhydroglucose unit (AGU). Different solvents, that is, N,N‐dimethylacetamide (DMAc), DMAc/LiCl, and N,N‐dimethylformamide (DMF)/LiCl are studied as reaction medium without and with a base. In the presence of pyridine, products of highest DS and degree of polymer ...
DOI:
10.1002/star.201900053

96. Succinylation Is a Gain-of-Function Modification in Human Lens αB-Crystallin

Author:
Sandip K. Nandi; Stefan Rakete; Rooban B. Nahomi; Cole Michel; Alexandra Dunbar; Kristofer S. Fritz; Ram H. Nagaraj
Source:
Biochemistry 2019 v.58 no.9 pp. 1260-1274
ISSN:
1520-4995
Subject:
Western blotting; acylation; crystallins; epithelium; fiber cells; gain-of-function mutation; humans; immunohistochemistry; liquid chromatography; lysine; post-translational modification; precipitin tests; tandem mass spectrometry
Abstract:
... Acylation of lysine residues is a common post-translational modification of cellular proteins. Here, we show that lysine succinylation, a type of acylation, occurs in human lens proteins. All of the major crystallins exhibited Nᵋ-succinyllysine (SuccK) residues. Quantification of SuccK in human lens proteins (from donors between the ages of 20 and 73 years) by LC–MS/MS showed a range between 1.2 a ...
DOI:
10.1021/acs.biochem.8b01053
PubMed:
30758948
PubMed Central:
PMC6662615

97. Surface hemocompatible modification of polysulfone membrane via covalently grafting acrylic acid and sulfonated hydroxypropyl chitosan

Author:
Ming-Ming Tu; Jing-Jie Xu; Yun-Ren Qiu
Source:
RSC advances 2019 v.9 no.11 pp. 6254-6266
ISSN:
2046-2069
Subject:
Fourier transform infrared spectroscopy; X-ray photoelectron spectroscopy; acrylic acid; acylation; adhesion; adsorption; anticoagulant activity; biocompatibility; blood platelets; cell adhesion; chemical bonding; chitosan; moieties; prothrombin; thrombin; thromboplastin
Abstract:
... In this study, acrylic acid (AA) and sulfonated hydroxypropyl chitosan (SHPCS) were covalently grafted on the PSf membrane surface to improve its hemocompatibility. First, the modified AA-PSf membrane was obtained through the Friedel–Craft reaction between acrylic acid and the PSf membrane surface. Then, the modified SHPCS-AA-PSf membrane was prepared by grafting SHPCS onto the AA-PSf membrane sur ...
DOI:
10.1039/c8ra10573a

98. Synthesis and Properties of 1-Acyl Triazenes

Author:
Iris R. Landman; Emilio Acuña-Bolomey; Rosario Scopelliti; Farzaneh Fadaei-Tirani; Kay Severin
Source:
Organic letters 2019 v.21 no.16 pp. 6408-6412
ISSN:
1523-7052
Subject:
acylation; catalytic activity; gold; hydrolysis; moieties; organic compounds; oxidation; thermal stability
Abstract:
... 1-Acyl triazenes can be prepared by acid-catalyzed hydration, gold/iodine-catalyzed oxidation, or oxyhalogenation of 1-alkynyl triazenes. Crystallographic analyses reveal a pronounced effect of the acyl group on the electronic structure of the triazene function. 1-Acyl triazenes display high thermal stability, and only moderate sensitivity toward hydrolysis. They are compatible with basic and oxid ...
DOI:
10.1021/acs.orglett.9b02248

99. Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Author:
Thidarat Chalothorn; Vatcharin Rukachaisirikul; Souwalak Phongpaichit; Sakawrat Pannara; Chittreeya Tansakul
Source:
Tetrahedron letters 2019 pp. -
ISSN:
0040-4039
Subject:
acylation; ammonium salts; antibacterial properties; antibiotic resistance; bromine; chlorine; cytotoxicity; emodin; iodine; methicillin; methicillin-resistant Staphylococcus aureus; moieties; quaternary ammonium compounds; structure-activity relationships
Abstract:
... Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cell ...
DOI:
10.1016/j.tetlet.2019.151004

100. Synthesis of 1,3-Diketones and β-Keto Thioesters via Soft Enolization

Author:
Sabrina O. Aderibigbe; Don M. Coltart
Source:
Journal of organic chemistry 2019 v.84 no.15 pp. 9770-9777
ISSN:
1520-6904
Subject:
acylation; chemical structure; cost effectiveness; ketones; organic chemistry; organochlorine compounds; thioesters
Abstract:
... Ketones and thioesters undergo soft enolization and acylation using crude acid chlorides on treatment with MgBr₂·OEt₂ and i-Pr₂NEt to give 1,3-diketones and β-keto thioesters, respectively. The use of crude acid chlorides adds efficiency and cost reduction by avoiding the need to purify and/or purchase them. The process is conducted in a direct fashion that does not require prior enolate formation ...
DOI:
10.1021/acs.joc.9b00397