An official website of the United States government
Here’s how you know
Official websites use .gov
A .gov website belongs to an official government organization in the United States.
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.
acylation; chemical structure; esterification; metabolites; organic chemistry; organic compounds
Abstract:
... A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A–D were synthesized for the first time. The key steps in this approach included esterification, Friedel–Crafts acylation, and ring-closing metathesis (or cross metathesis). ...
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. ...
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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
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
... 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 ...
... 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 ...
... 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 ...
... 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 ...
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 ...
... 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 ...
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 ...
... 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 ...
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 ...
... 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 ...
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
... 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 ...
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 ...
... 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 ...
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. ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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. ...
... 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 ...
... 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 ...
... 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. ...
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 ...
... 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 ...
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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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 ...
... 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. ...
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 ...