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Synthesis of N-acetyl-D-lactosamine (Gal-beta[1?4]GlcNAc, LacNAc) catalyzed by beta-galactosidase from Thermus thermophilus (TTP0042) is affected by side reactions that give as result very low yields (about 20%) of LAcNAc when the reaction is performed in buffer. The process is improved (up to 91% of disaccharide yield) when the reaction takes place in the presence of solvents from biomass (bio-solvents) at 2.0 M concentration. Most of the solvents tested increased the LacNAc synthesis and reduced the undesired side reactions. In order to understand the possible effects of these solvents over the enzyme regioselectivity, we developed a conformational study of the enzyme structure in the presence of a selected bio-solvent by circular dichroism and fluorescence. According to this study, we were able to conclude that the presence of bio-solvents in the reaction media modifies the enzyme secondary and tertiary structure and this may be the cause of the regioselectivity changes observed in the transglycosylation reaction.

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Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.

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The chelating properties of the common aldohexoses d-glucose, d-mannose, and d-galactose are characteristically modified in 2-substituted derivatives. The 2-amino-2-deoxy-aldohexoses provide mono- and bis-metallisable anionic ligands after their reaction with metal probes of the PdIIN 2 type (N2 = bidentate nitrogen ligand). The 2-amino function reliably participates in metal binding of the, mostly pyranoidic, carbohydrate chelators. Acetylation of the amino function yields the biologically important 2-N-acetylamino-2-deoxy-hexoses (GlcNAc, ManNAc, and GalNAc). On reaction with the palladium probe, the metal-binding properties of the deprotonated acetylamino function depends on the steric requirements introduced by the acetyl residue which is forced into a coplanar arrangement with the chelate ring. In the two 2-deoxy-aldohexoses, 2-deoxy-arabino-d-hexose (the 2-deoxy derivative of both d-glucose and d-mannose, ‘2-deoxy-glucose’) and 2-deoxy-lyxo-d-hexose (‘2-deoxy galactose’), the 2-position cannot contribute to metal binding. As a result, furanose-1,3 chelation becomes an important metal-binding mode. Due to the decreased acidity of the 2-deoxy-glycose’s 1-hydroxy function, monometallation also takes place at the pyranose’s 3,4-site.

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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals. However, they have proven to be challenging because of the mutual inactivation of both catalysts. 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide, molecular formula is C8H15NO6. In a Patent,once mentioned of 14215-68-0, Electric Literature of 14215-68-0

A composition useful for cosmetic treatment of the skin containing N-acetylglucosamine and an alkaline metal sulphate in equivalent mass ratios between 1:0.5 and 1:3, optionally in association with hyaluronic acid or a salt thereof.

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We found that a chitin deacetylase from Colletotrichum lindemuthianum could acetylate free amino sugar residues into N-acetylated forms in the presence of 3.0 M sodium acetate. The result was analyzed using a beta-N-acetylhexosaminidase-coupled assay system with p-nitrophenyl 2-amino-2-deoxy-beta-D-glucopyranosyl-(1?4)-2-acetamido-2-deoxy-beta-D-glucopyranoside as the substrate, and the liberation of p-nitrophenol was observed as a consequence of enzymatic N-acetylation of the glucosamine residue at the nonreducing end of the substrate. The chitin deacetylase also acetylated chitobiose and chitotetraose as substrates, which was evidenced by the decrease in the amount of free amino sugar residues in the chitooligosaccharides. The reaction product of chitobiose after the acetylation reaction was exclusively 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1?4)-2-amino-2-deoxy-D-glucose [GlcNAcGlcN], the structure of which was determined by FABMS and NMR analyses. This study offers a novel method for enzymatic N-acetylation of amino sugars, and especially with chitobiose as substrate, a selectively N-acetylated product, GlcNAcGlcN, can be synthesized. Copyright (C) 1999 Elsevier Science Ltd.

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In the nematode model organisms Caenorhabditis elegans and Pristionchus pacificus, a new class of natural products based on modular assembly of primary-metabolism-derived building blocks control organismal development and behavior. We report identification and biological activities of the first pentamodular metabolite, pasa#9, and the 8-oxoadenine-containing npar#3 from P. pacificus. These structures suggest co-option of nucleoside and tryptophan metabolic pathways for the biosynthesis of endogenous metabolite libraries that transcend the dichotomy between primary and secondary metabolism.

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Eight diversely substituted delta-allenic alcohols have been synthesized by using three different methods for the formation of the allenic linkage.When treated with silver nitrate or mercuric salts, these alcohols are transformed in fairly good yields into alpha-alkenyl-2 tetrahydropyrans.In addition to its regioselectivity in the formation of the heterocycle this reaction shows in certain cases a high stereoselectivity.Alcohols monosubstituted on the thermal allenic carbon lead to more than 90percent of the E product whereas the 2,4 or 2,6 disubstituted tetrahydropyrans are obtained in predominantly the Z configuration.

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Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In homogeneous catalysis, catalysts are in the same phase as the reactants.14215-68-0, C8H15NO6. A document type is Article, introducing its new discovery., Quality Control of: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

The syntheses of four analogues of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine are described. Activated carboxylic acids were reacted with 2-acetamido-2-deoxy-beta-D-glucopyranosylamine. n-Butyric anhydride gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-n-butyramide. 3-Chloropropionic anhydride was synthesized from 3-chloropropionic acid and gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3-chloropropionamide. Equilibration of the latter with ammonium bicarbonate gave N1-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-3- aminopropionamide. Succinimidyl isovalerate was synthesized and gave N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)isovaleramide.

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Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme. Irreversible inhibitors are therefore the equivalent of poisons in heterogeneous catalysis. 14215-68-0, C8H15NO6. A document type is Article, introducing its new discovery., Computed Properties of C8H15NO6

Truncated aminoglycoside-coenzyme A bisubstrate analogues were efficiently prepared using a convergent approach where the amine and the thiol are coupled in one pot with the addition of a linker, without the need for protecting groups. These derivatives were tested for their effect on the activity of the resistance-causing enzyme aminoglycoside 6?-N-acetyltransferase Ii, and key structure-activity relationships are reported. Moreover, one of the inhibitors is able to block aminoglycoside resistance in cells expressing this enzyme.

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Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, causing turnover rates to depend strongly on interfacial structure and composition. 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide, molecular formula is C8H15NO6. In a Article,once mentioned of 14215-68-0, Electric Literature of 14215-68-0

To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.

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