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

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Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus

Two oligosaccharides, alpha-D-Manp-(1?2)-alpha-D-Manp-(1?2)- alpha-D-Manp-(1?6)-alpha-D-Manp-(1?4)-alpha-D-GlcpNAc (I) and alpha-D-Manp-(1?3)-alpha-D-Manp-(1?2)-alpha-D-Manp-(1?2) -alpha-D-Manp-(1?6)-alpha-D-Manp-(1?4)-alpha-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-alpha-D-mannopyranosyl-(1?4)-2- acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1?2)-3,4, 6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl- alpha-D-mannopyranosyl-(1?2)-3,4,6-tri-O-benzoyl-alpha-D- mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl- (1?3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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An expeditious route to N-Acetyl-D-galactosamine from N-Acetyl-D- glucosamine based on the selective protection of hydroxy groups

GalNAc (1) was straightforwardly prepared from GlcNAc (2a) in six steps. Selective protection of the hydroxy groups on the C-1, C-3, and C-6 positions at the same time was performed by the treatment of TBDPS chloride (5.5 eq.) in DMF in 70% yield. The nucleophilic attack with CsOAc or KOBz on the chloromethylsulfonyloxy group at C-4 worked well (69-77% yield), accompanied by an unexpected rearrangement, to give the furanose products (6). The deprotection of all silyl and acyl groups under acidic conditions and the re-acetylation provided GalNAc (1) in 51% yield.

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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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Chitosan as an adhesive

Chitosan is a well-known polysaccharide abundantly published during the last decades. This heteropolymer, composed of 2-acetamido-2-deoxy-d-glucopyranose and 2-amino-2-deoxy-d-glucopyranose, is obtained after alkaline deacetylation of chitin from crustaceans, fungi and other non-vegetable organisms. Soluble only at acidic pH, it is the unique polycationic polysaccharide extracted from bioresources. This characteristic gives to it original and specific properties finding some applications in several industrial fields but especially in the biomedical one because of its biocompatibility and its non-toxicity. Besides these traditional applications other ones begin actually to appear in the literature. They focus on the development of chitosan-based adhesives, binders or films. This review synthetizes the state of the art on this domain, but also deals with the assessment of chitosan environmental impact.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Some scientific research about N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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THE FIRST MOENOMYCIN ANTIBIOTIC WITHOUT THE METHYL-BRANCHED URONIC ACID CONSTITUENT. – UNEXPECTED STRUCTURE ACTIVITY RELATIONS

Isolation and structure elucidation of a new moenomycin antibiotic (C1, 1e) that lacks the branching methyl group in the 4-position of unit F are reported.The smallest antibiotically active degradation product of 1e is the trisaccharide derivative 3.This observation is in contrast to structure activity relations in the moenomycin A series where it was found that disaccharide 4a is fully active.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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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

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

Quantitative production of 2-acetamido-2-deoxy-D-glucose from crystalline chitin by bacterial chitinase

Finely powdered alpha- and beta-chitin can be completely hydrolyzed with chitinase (EC 3.2.1.14) and beta-N-acetylhexosaminidase (EC 3.2.1.52) for the production of 2-acetamido-2-deoxy-D-glucose (GlcNAc). Crude chitinase from Burkholderia cepacia TU09 and Bacillus licheniformis SK-1 were used to digest alpha- and beta-chitin powder. Chitinase from B. cepacia TU09 produced GlcNAc in greater than 85% yield from beta- and alpha-chitin within 1 and 7 days, respectively. B. licheniformis SK-1 chitinase completely hydrolyzed beta-chitin within 6 days, giving a final GlcNAc yield of 75%, along with 20% of chitobiose. However, only a 41% yield of GlcNAc was achieved from digesting alpha-chitin with B. licheniformis SK-1 chitinase.

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

Can You Really Do Chemisty Experiments About N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis

The N,O-dimethyloxyamine-N-glycosides are introducedas anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these Nglycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Glycosyl azides – An alternative way to disaccharides

Glycosyl azides are shown to be efficient donors for beta-galactosidases, beta-glucosidases and alpha mannosidases. Only alpha-galactosidases do not cleave the respective glycosyl azide 1 and, moreover, they exhibit competitive inhibition (especially alpha-galactosidase from Talaromyces flavus). High water solubility and ready synthesis of glycosyl azides enable transglycosylation reactions even with difficult acceptors like N-acetyl-D-mannosamine in good yields. The versatility of glycosyl azides was demonstrated in the synthesis of five disaccharides – two of them are described for the first time. All the reactions were highly regioselective, yielding beta(1?6) isomers. beta Galactosidase from E. coli proved to have the best synthetic capabilities. The present study shows that glycosyl azides are a valuable alternative to common p-nitrophenyl glycoside donors and in many synthetic reactions.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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

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Synthesis of antimitotic thioglycosides: In vitro and in vivo evaluation of their anticancer activity

The synthesis and biological activity of oleylN-acetyl-alpha- and beta-d-glucosaminides (1 and 2, respectively) and their thioglycosyl analogues (3 and 4, respectively) are reported. The compounds exhibited antimitotic activity on rat glioma (C6) and human lung carcinoma (A549) cell cultures in the micromolar range. Analysis of cell extracts using ultra performance liquid chromatography-mass spectrometry showed that the synthetic glycosides produce alterations in glycosphingolipid metabolism, with variable effect on the level of glucosylceramide depending on the configuration of the antimitotic used. In vivo experiments in nude mice bearing an implanted C6 glioma showed that the alpha-thioglycoside 3 reduced tumor volume, while the O-glycosyl derivative was inactive, highlighting the importance of using enzyme resistant glycosides.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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LC-MS-based metabolomics reveals metabolic signatures related to glioma stem-like cell self-renewal and differentiation

Gliomas are the most common and lethal primary malignant brain tumors. Recent studies implicate an important role for a rare population of glioma stem cells (GSCs) in glioma maintenance and recurrence. New therapeutic strategies are desperately needed requiring insights into the biological and molecular mechanisms underlying the self-renewal and differentiation of GSCs. We now investigate the metabolic signatures of three glioma cell lines with different stemness using a liquid chromatography-mass spectrometry (LC-MS)-based metabolomics approach. Cellular metabolites differentially expressed in U87MG stem-like cells (SLCs) relative to U87 malignant glioma cells (GCs) and U87MG stem-like cell differentiation cells (SLCDCs) were identified. The specific and significant alterations including nucleotide metabolism, glycerophospholipid metabolism, glutathione metabolism, carnitine metabolism and tryptophan metabolism were characterized. Cell function assays were further used to evaluate the self-renewal ability of SLCs treated with differential metabolites, indicating that these metabolites are involved in the maintenance of stemness. The results provide valuable information on the association of the significantly altered metabolites and metabolic pathways with SLC self-renewal and differentiation.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics