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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, category: Tetrahydropyrans

(Chemical Equation Presented) Chitin synthase (CS) polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-GlcNAc), a key component of fungal cell wall biosynthesis. Little is known about the substrate specificity of chitin synthase or the scope of substrate modification the enzyme will tolerate. Following a previous report suggesting that 6-O-dansyl GlcNAc is biosynthetically incorporated into chitin, we became interested in developing an assay for CS activity based on incorporation of a fluorescent substrate. We describe the synthesis of two fluorescent UDP-GlcNAc analogues and their evaluation as chitin synthase substrates.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Green glycosylation of functionalized alcohols and alpha-amino acids, using an ionic liquid as a recyclable solvent, was performed in one step directly from the unprotected monosaccharide under scandium triflate or ferric chloride catalysis. Pure alpha- and beta-glycosides could be obtained after specific enzymatic hydrolysis.

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Tetrahydropyran – Wikipedia,
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An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (LeabetaProN3) and a library of sialyl Lewis a antigens (sLeabetaProN3) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N?-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAcbetaProN3 was synthesized using this protecting group-free method in high yield (82%). Sequential one-pot multienzyme (OPME) beta1?3-galactosylation of GlcNAcbetaProN3 followed by OPME alpha1?4-fucosylation reactions produced target LeabetaProN3 in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida alpha2?3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLeabetaProN3 containing naturally occurring or non-natural sialic acid forms in preparative scales.

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Reference:
Tetrahydropyran – Wikipedia,
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Discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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The asialoglycoprotein receptor (ASGPR) is a high-capacity galactose-binding receptor expressed on hepatocytes that binds its native substrates with low affinity. More potent ligands are of interest for hepatic delivery of therapeutic agents. We report several classes of galactosyl analogues with varied substitution at the anomeric, C2-, C5-, and C6-positions. Significant increases in binding affinity were noted for several trifluoromethylacetamide derivatives without covalent attachment to the protein. A variety of new ligands were obtained with affinity for ASGPR as good as or better than that of the parent N-acetylgalactosamine, showing that modification on either side of the key C3,C4-diol moiety is well tolerated, consistent with previous models of a shallow binding pocket. The galactosyl pyranose motif therefore offers many opportunities for the attachment of other functional units or payloads while retaining low-micromolar or better affinity for the ASGPR.

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Tetrahydropyran – Wikipedia,
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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.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, Application In Synthesis of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

Metabolic chemical reporters (MCRs) of glycosylation are analogues of monosaccharides that contain bioorthogonal functionalities and enable the direct visualization and identification of glycoproteins from living cells. Each MCR was initially thought to report on specific types of glycosylation. We and others have demonstrated that several MCRs are metabolically transformed and enter multiple glycosylation pathways. Therefore, the development of selective MCRs remains a key unmet goal. We demonstrate here that 6-azido-6-deoxy-N- acetyl-glucosamine (6AzGlcNAc) is a specific MCR for O-GlcNAcylated proteins. Biochemical analysis and comparative proteomics with 6AzGlcNAc, N-azidoacetyl-glucosamine (GlcNAz), and N-azidoacetyl-galactosamine (GalNAz) revealed that 6AzGlcNAc exclusively labels intracellular proteins, while GlcNAz and GalNAz are incorporated into a combination of intracellular and extracellular/lumenal glycoproteins. Notably, 6AzGlcNAc cannot be biosynthetically transformed into the corresponding UDP sugar-donor by the canonical salvage-pathway that requires phosphorylation at the 6-hydroxyl. In vitro experiments showed that 6AzGlcNAc can bypass this roadblock through direct phosphorylation of its 1-hydroxyl by the enzyme phosphoacetylglucosamine mutase (AGM1). Taken together, 6AzGlcNAc enables the specific analysis of O-GlcNAcylated proteins, and these results suggest that specific MCRs for other types of glycosylation can be developed. Additionally, our data demonstrate that cells are equipped with a somewhat unappreciated metabolic flexibility with important implications for the biosynthesis of natural and unnatural carbohydrates.

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Changing employment: Receptor 1 binds beta-N-acetylglucosaminyl ( beta-GlcNAc) up to 100 times more strongly than it does glucose. This synthetic lectin shows affinities similar to wheat germ agglutinin (WGA), a natural lectin used to bind GlcNAc. Remarkably, 1 is more selective than WGA. It favors especially the glycoside unit in glycopeptide 2, a model of the serine-O-GlcNAc posttranslational protein modification.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named “glycosyl Bunte salts” after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water-acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.

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The present invention provides a synthetic nutritional formulation comprising a substantially pure free N-acetyl glucosamine in concentrations effective for enhancing organ development, enhancing an immune response, or increasing tissue repair or healing in a subject. A synthetic nutritional formulation of the invention may optionally comprise one or both of substantially pure free sialic acid and/or substantially pure free fucose.

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An efficient per-O-acetylation of carbohydrates catalyzed by HClO 4-SiO2 is reported using a stoichiometric quantity of acetic anhydride avoiding the use of pyridine and excess acetic anhydride under solvent-free conditions.

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The hydroxy protons of unsaturated di-, tetra-, hexa- and octa-saccharides of hyaluronan (DeltaHA2, DeltaHA4, DeltaHA 6 and DeltaHA8) in 85% H2O/15% acetone-d 6 have been studied by NMR spectroscopy. The chemical shifts (delta), chemical shift differences (Deltadelta), temperature coefficients (ddelta/dT) and nuclear or rotating-frame Overhauser effects (NOEs or ROEs) of hydroxy protons were measured to gain insight into hydration, hydrogen bonds and flexibility of the HA structure. The NMR data give the first experimental evidence that weak hydrogen bonds exist between O(4)H of N-acetyl-D-glucosamine (GlcNAc) and O(5) of D-glucuronic acid (GlcA) across the beta(1?3) glycosidic linkage and between O(3)H of GlcA and O(5) of GlcNAc across the beta(1?4)-linkage. A chemical exchange was observed between O(4)H of GlcNAc and O(2)H of GlcA over the beta(1?3)-linkage. The interaction could be mediated through water bridge(s) and thus contribute to the water-retaining ability of hyaluronan. In this study it was also demonstrated how the chemical shifts of exchangeable hydroxy or amide proton signals can be used to describe small structural and conformational perturbations within large oligosaccharides.

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Reference:
Tetrahydropyran – Wikipedia,
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