Extracurricular laboratory:new discovery of N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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HELICOBACTER PYLORI GROWTH INHIBITOR CONTAINING -N-ACETYLGLUCOSAMINYL-BINDING MONOSACCHARIDE DERIVATIVE

The present invention herein provides a proliferation inhibitor of Helicobacter pylori comprising a compound that can simply be mass-produced, can specifically inhibit the proliferation of H. pylori, which has high safety and never generates any resistant bacteria, as well as a diet of a food or beverage, and a pharmaceutical preparation containing the proliferation inhibitor of Helicobacter pylori. The proliferation inhibitor of Helicobacter pylori comprises an alpha-N-acetyl-glucosaminyl bond-containing monosaccharide derivative represented by the following chemical formula (1) ????????GlcNAc1-alpha-O-Y?????(1) (in the formula (1), Y is a straight-, branched- or cyclic- aliphatic hydrocarbon group having 1 to 27 carbon atoms or a straight-, branched- or cyclic- acyl group having 1 to 27 carbon atoms). The diet of the food, the beverage or the pharmaceutical preparation comprises the proliferation inhibitor of Helicobacter pylori.

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Tetrahydropyran – Wikipedia,
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Efficient acetylation of carbohydrates promoted by imidazole

An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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Tetrahydropyran – Wikipedia,
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Fucosylation of chitooligosaccharides by human alpha1,6-fucosyltransferase requires a nonreducing terminal chitotriose unit as a minimal structure

FUT8, a eukaryotic alpha1,6-fucosyltransferase, catalyzes the transfer of a fucosyl residue from guanine nucleotide diphosphate-beta-L-fucose to the innermost GlcNAc of an asparagine-linked oligosaccharide (N-glycan). The catalytic domain of FUT8 is structurally similar to that of NodZ, a bacterial alpha1,6-fucosyltransferase, which acts on a chitooligosaccharide in the synthesis of Nod factor. While the substrate specificities for the nucleotide sugar and the N-glycan have been determined, it is not known whether FUT8 is able to fucosylate other sugar chains such as chitooligosaccharides. The present study was conducted to investigate the action of FUT8 on chitooligosaccharides that are not generally thought to be a substrate in mammals, and the results indicate that FUT8 is able to fucosylate such structures in a manner comparable to NodZ. Surprisingly, structural analyses of the fucosylated products by high performance liquid chromatography, mass spectrometry and nuclear magnetic resonance indicated that FUT8 does not utilize the reducing terminal GlcNAc for fucose transfer but shows a preference for the third GlcNAc residue from the nonreducing terminus of the acceptor. These findings suggest that FUT8 catalyzes the fucosylation of chitooligosaccharide analogous to NodZ, but that a nonreducing terminal chitotriose structure is required for the reaction. The substrate recognition by which FUT8 selects the position to fucosylate might be distinct from that for NodZ and could be due to structural factor requirements which are inherent in FUT8. The Author 2010. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: [email protected].

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Thioglycosides Are Efficient Metabolic Decoys of Glycosylation that Reduce Selectin Dependent Leukocyte Adhesion

Small-molecule inhibitors of glycosylation can be applied in basic science studies, and clinical investigations as anti-inflammatory, anti-metastatic, and anti-viral therapies. This article demonstrates that thioglycosides represent a class of potent metabolic decoys that resist hydrolysis, and block E-selectin-dependent leukocyte adhesion in models of inflammation. Metabolic decoys are synthetic analogs of naturally occurring biosynthetic acceptors. These compounds divert cellular biosynthetic pathways by acting as artificial substrates that usurp the activity of natural enzymes. While O-linked glycosides are common, they are only partially effective even at millimolar concentrations. In contrast, we report that N-acetylglucosamine (GlcNAc) incorporated into various thioglycosides robustly truncate cell surface N- and O-linked glycan biosynthesis at 10?100 muM concentrations. The >10-fold greater inhibition is in part due to the resistance of thioglycosides to hydrolysis by intracellular hexosaminidases. The thioglycosides reduce beta-galactose incorporation into lactosamine chains, cell surface sialyl Lewis-X expression, and leukocyte rolling on selectin substrates including inflamed endothelial cells under fluid shear. Treatment of granulocytes with thioglycosides prior to infusion into mouse inhibited neutrophil homing to sites of acute inflammation and bone marrow by ?80%?90%. Overall, thioglycosides represent an easy to synthesize class of efficient metabolic inhibitors or decoys. They reduce N-/O-linked glycan biosynthesis and inflammatory leukocyte accumulation.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Selective N-deacetylation of p-nitrophenyl N,N’-diacetyl-beta-chitobioside and its use to differentiate the action of two types of chitinases

We report the synthesis of a novel compound for chitinase assays, p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranoside [GlcNGlcNAc-pNP] by selective N-deacetylation of p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranoside [(GlcNAc)2-pNP] using a purified chitin deacetylase isolated from Colletotrichum lindemuthianum ATCC 56676. FABMS, 1H NMR, and 13C NMR analyses confirmed the structure of this new compound. This disaccharide derivative can be used to distinguish special chitinases that effectively remove partially deacetylated parts of substrates within a mixture of chitinases which degrades (GlcNAc)2-pNP. Copyright (C) 1999 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
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Abberant immunoglobulin g glycosylation in rheumatoid arthritis by LTQ-ESI-MS

Aberrant glycosylation has been observed in many autoimmune diseases. For example, aberrant glycosylation of immunoglobulin G (IgG) has been implicated in rheumatoid arthritis (RA) pathogenesis. The aim of this study is to investigate IgG glycosylation and whether there is an association with rheumatoid factor levels in the serum of RA patients. We detected permethylated N-glycans of the IgG obtained in serum from 44 RA patients and 30 healthy controls using linear ion-trap electrospray ionization mass spectrometry (LTQ-ESI-MS), a highly sensitive and efficient approach in the detection and identification of N-glycans profiles. IgG N-glycosylation and rheumatoid factor levels were compared in healthy controls and RA patients. Our results suggested that total IgG purified from serum of RA patients shows significantly lower galactosylation (p = 0.0012), lower sialylation (p < 0.0001) and higher fucosylation (p = 0.0063) levels compared with healthy controls. We observed a positive correlation between aberrant N-glycosylation and rheumatoid factor level in the RA patients. In conclusion, we identified aberrant glycosylation of IgG in the serum of RA patients and its association with elevated levels of rheumatoid factor. Do you like my blog? If you like, you can also browse other articles about this kind. COA of Formula: C8H15NO6. Thanks for taking the time to read the blog about 14215-68-0

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles

Glycosyl 1,2,3-triazoles with alpha-d-gluco, beta-d-gluco, alpha-d-galacto, beta-d-galacto and beta-2-acetamido-2-deoxygluco (GlcNAc) stereochemistry were prepared by reaction of the corresponding azides with vinyl acetate under microwave irradiation. The deprotected glucosyl and galactosyl triazoles did not display inhibitory activity against the tested glycosidases at 1 mM. Of the four fungal glycosidases evaluated, GlcNAc-triazole was found to be hydrolyzed by Talaromyces flavus CCF 2686 beta-N-acetylhexosaminidase. beta-GlcNAc-triazole was furthermore established to act as a strong ligand of rat and human natural killer cell activating receptors.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Sulfonylation-induced N-to O -Acetyl migration in 2-acetamidoethanol derivatives

The first example of sulfonylation-induced N- to O-acetyl migration of 2-acetamidoethanol derivatives is described. This type of reaction could happen with any 2-acetamidoethanol derivatives under typical sulfonylation conditions (TsCl or MsCl, pyridine) and might be a common side reaction of significance. Furthermore, the results reveal that 2-acetamidoethanol derivatives with a sterically encumbered hydroxyl group result in the migration products in high yields. The mechanism of the migration reaction is discussed.

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Enzymatic synthesis and characterization of 6-O-beta-D-xylopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a structural analog of primeverose

The synthesis of the disaccharide 6-O-beta-D-xylopyranosyl-2-acetamido-2-deoxy-D-glucopyranose (N-acetylprimeverosamine), structurally related to the natural disaccharide 6-O-beta-D-xylopyranosyl-D-glucopyranose (primeverose), was obtained via a transglycosylation reaction catalyzed by a crude preparation of beta-D-xylosidase from Aspergillus niger, using p-nitrophenyl beta-D-xylopyranoside as the donor and 2-acetamido-2-deoxy-D-glucopyranose as the acceptor. The yield of the reaction was 36% on a molar basis with respect to the donor. The chemical identity of the product was assessed by HPLC, ionspray mass spectrometry and NMR spectroscopy. Copyright (C) 1998 Elsevier Science Ltd.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Synthesis of 6-, 7- and 8-carbon sugar analogues of potent anti-influenza 2,3-didehydro-2,3-dideoxy-N-acetylneuraminic acid derivatives

Analogues of the potent anti-influenza A and B compound, 4-guanidino-Neu5Ac2en, are described in which the stereochemically demanding C-6-glycerol side-chain is truncated.Syntheses of the one- and two-carbon side-chain analogues, of both 4-guanidino- and 4-amino-Neu5Ac2en, are presented, as well as the syntheses of analogues lacking any side-chain.Whilst complete removal of the C-6 side-chain abolishes activity, a stepwise increase in inhibition of influenza neuraminidase and influenza A and B in cell culture with increasing C-6 chain length is observed.The one-carbon, hydroxymethyl derivative retains significant activity to represent a suitable lead in the search for neuraminidase inhibitors of reduced stereochemical demand and synthetic complexity.

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Tetrahydropyran – Wikipedia,
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