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Highly efficient chemoenzymatic synthesis and facile purification of alpha-Gal pentasaccharyl ceramide Galalpha3nLc4betaCer

A highly efficient chemoenzymatic method for synthesizing glycosphingolipids using alpha-Gal pentasaccharyl ceramide as an example is reported here. Enzymatic extension of the chemically synthesized lactosyl sphingosine using efficient sequential one-pot multienzyme (OPME) reactions allowed glycosylation to be carried out in aqueous solutions. Facile C18 cartridge-based quick (<30 minutes) purification protocols were established using minimal amounts of green solvents (CH3CN and H2O). Simple acylation in the last step led to the formation of the target glycosyl ceramide in 4 steps with an overall yield of 57%. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Safety of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide. In my other articles, you can also check out more blogs about 14215-68-0

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Novel O-acetylated decasaccharides

The present invention relates to diversely acetylated decasaccharides of formula (I) representative of two repeating units of Shigella flexneri serotype 2a O-antigen, conjugates and method of preparation thereof. These compounds exhibit antigenic properties and are particularly useful for the diagnosis of Shigella infection. wherein R1 and R2 are as defined in claim 1.

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Tetrahydropyran – Wikipedia,
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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, belongs to Tetrahydropyrans compound, is a common compound. In a patnet, once mentioned the new application about 14215-68-0, Product Details of 14215-68-0

Synthesis of artificial N-glycopolypeptides carrying N-acetyllactosamine and related compounds and their specific interactions with lectins.

Artificial N-glycopolypeptides carrying N-acetyllactosamine (LacNAc) or related compounds were synthesized. First, sugars were converted into their corresponding beta-glycosylamines with ammonium hydrogen carbonate. Then, the beta-glycosylamines were condensated with the carboxyl groups of poly(L-glutamic acid). N-Glycopolypeptides with different degrees of substitution of sugars were isolated by passage through a column of Sephadex G-25. These synthetic polymers were used as model compounds in the analysis of oligosaccharide-lectin interactions. Interactions with some lectins were investigated by agar-gel double-diffusion tests and in terms of inhibition of hemagglutination. A glycopolypeptide substituted with LacNAc reacted with Erythrina cristagalli agglutinin (ECA), peanut (Arachis hypogaea) agglutinin (PNA), Ricinus communis agglutinin-120 (RCA120), wheat germ (Triticum vulgaris) agglutinin (WGA) lectins, which recognize either galactosyl or N-acetylglucosamine (GlcNAc) residues. Other synthetic glycopolymers carrying N-acetylisolactosamine, GlcNAc, N,N’-diacetylchitobiose, or N,N’, N”-triacetylchitotriose also reacted with WGA, and these last two polymers inhibited hemagglutination most. Of these five glycopolypeptides, only the one substituted with LacNAc reacted with ECA. These sugar-substituted glycopolypeptides interacted specifically with the corresponding lectins, no matter how much shorter the sugar side chains of the glycopolymers were than those of natural glycoproteins.

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Tetrahydropyran – Wikipedia,
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Enzymatic Discrimination of 2-Acetamido-2-deoxy-D-mannopyranose-Containing Disaccharides Using beta-N-Acetylhexosaminidases

beta-N-Acetylhexosaminidase from Aspergillus oryzae selectively discriminates mixture of the disaccharides GlcNAcbeta(1?4)GlcNAc (1) and GlcNAcbeta(1?4)ManNAc (2). N,N?-Diacetylchitobiose (1) was selectively hydrolyzed by beta-N-acetylhexosaminidase, whereas its C-2 epimer (2) was completely resistant to the enzyme hydrolysis. Analogous discrimination was observed also with GalNAcbeta(1?4)GlcNAc (3) and GalNAcbeta(1? 4)ManNAc (4). beta-N-Acetylhexosaminidases from A. terreus, A. flavus, bovine kidney and bovine epididymis displayed the same selectivity, whereas the enzymes from A. sojae, A. tamarii, Penicillium brasilianum, P. oxalicum, P. funiculosum, P. multicolor, Talaromyces flavus and jack beans hydrolyzed both types of disaccharides. Molecular modelling of beta-N-acetylhexosaminidase from A. oryzae CCF 1066 and docking experiments with both types of disaccharides revealed that the ManNAc residue causes distortion of disaccharide molecule resulting in a steric conflict with a Trp482 that causes diminished stabilization of the oxazolinium transition state by extending the distance of Asp345 in the active site. Both ManNAc-containing disaccharides 2 and 4 dock with similar steric energies into the active site but without cleaving and also without notable inhibition. This novel phenomenon enables also the preparative production of both disaccharides 2 and 4 starting from N, N?-diacetylchitobiose (1) or GalNAcbeta(1? 4)GlcNAc (3) followed by Lobry de Bruyn-Albreda van Ekenstein C-2 epimerization catalyzed by Ca(OH)2. The resultant mixture of the respective epimers 1, 2 or 3, 4 that is hardly separable by, e.g., analytical HPLC can be treated with the beta-N-acetylhexosaminidase from A. oryzae and the mixture of monosaccharides and target disaccharide can be easily separated using gel filtration.

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Tetrahydropyran – Wikipedia,
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Regioselective Reductive Ring Opening of 4-Methoxybenzylidene Acetals of Hexopyranosides. Access to a Novel Protective Group Strategy

Reduction of fully protected 4,6-O-(4-methoxybenzylidene)hexopyranosides with sodium cyanoborohydride-trifluoroacetic acid in N,N-dimethylformamide, or with trimethylsilyl chloride in acetonitrile, gives the 6- and 4-O-(4-methoxybenzyl) ethers, respectively, in good yields and with good regioselectivity; the 4-methoxybenzyl ether linkage in products containing benzyl ethers or other protective groups is selectively cleaved upon treatment with cerium(IV) ammonium nitrate in aqueous acetonitrile.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 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, SDS of cas: 14215-68-0

An efficient synthesis of N-allylglycosylamides from unprotected carbohydrates

Synthetic, multivalent, carbohydrato assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N-allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N-allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis(x) and sulfo Lewis(X) have been derivatized by this process.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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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, belongs to Tetrahydropyrans compound, is a common compound. In a patnet, once mentioned the new application about 14215-68-0, category: Tetrahydropyrans

ENZYMIC SYNTHESIS OF DISACCHARIDES BY USE OF THE REVERSED HYDROLYSIS ACTIVITY OF beta-D-GALACTOSIDASES

D-Galactosyl disaccharides have been synthesized by utilizing the reversed hydrolysis activity of beta-D-galactosidases from E. coli and from A. oryzae, respectively.In order to shift the equilibrium towards the formation of disaccharide, solutions of monosaccharides were circulated through columns of immobilized beta-D-galactosidase and activated carbon in series.After 24 h, the disaccharides were eluted with aqueous 50 percent ethanol from the column of activated carbon and analyzed by h.p.l.c. and 13C-n.m.r. spectroscopy.In this way, beta-D-galactosyl-D-glucose, beta-D-galactosyl-2-acetamido-2-deoxy-D-glucose, and beta-D-galactosyl-D-fructose were produced in yields of 6.0, 16.0, and 11.3 percent, respectively, when the immobilized beta-D-galactosidase from E. coli was used.The possible mechanism of the synthesis of the disaccharides is discussed.

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DENTAL COMPOSITION

The present invention relates to a dental composition comprising (i) an acidic polymerizable compound of the following formula (la), (lb) (Ic) wherein X, Y, Y’, Z, L, R2, R3 and R4 are as defined in claim 1; and (ii) an initiator system. Furthermore, the present invention relates to the use of the polymerizable compound of formula (I) for the preparation of a dental composition.

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Chemo-enzymatic approach to access diastereopure alpha-substituted GlcNAc derivatives

The formation of diastereopure alpha-substituted GlcNAc derivatives in a simple and straightforward way is a challenging task. Herein, we report the chemical synthesis of diastereomeric alpha/beta-substituted GlcNAc derivatives under non-anhydrous atmosphere using unprotected GlcNAc, followed by a selective enzymatic hydrolysis step using a bacterial N-acetyl-hexosaminidase to provide only alpha-substituted GlcNAc. This enzyme proved to selectively hydrolyze the beta-anomeric GlcNAc derivatives, while the alpha-anomeric GlcNAc derivatives remained unreacted. The released GlcNAc (and therefore the alpha/beta ratios) could be quantified using a coupled enzymatic assay consisting of GlcNAc 2-epimerase and N-acetyl- mannosamine dehydrogenase in a simple and accurate way.

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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, belongs to Tetrahydropyrans compound, is a common compound. In a patnet, once mentioned the new application about 14215-68-0, name: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives

We report herein a bacterial N-acetylhexosamine kinase, NahK, with broad substrate specificity towards structurally modified GalNAc analogues, and the production of a GalNAc-1-phosphate library using this kinase.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics