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Jelena J. Kraft; Mariko S. Peterson; Sung Ki Cho; Zhaohui Wang; Alice Hui; Aurélie M. Rakotondrafara; Krzysztof Treder; Cathy L. Miller; W. Allen Miller
... 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, ...
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 ...