The Best Chemistry compound: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Various 2-pyridyl 1-thioglycosides, important synthetic intermediates and enzyme inhibitors in sugar chemistry, have been synthesized directly from the corresponding unprotected sugars in good yields by using 2-chloro-1,3- dimethylimidazolinium chloride (DMC) as dehydrative condensing agent. The reaction proceeds in aqueous media without using any protecting groups, affording 2-pyridyl 1-thioglycosides with beta-configuration selectively. According to the present method, not only unprotected monosaccharides but also unprotected oligosaccharides, such as cello-oligosaccharides, chito-oligo-saccharides, malto-oligosaccharides, and glucosamine oligomers, can be converted to the corresponding 2-pyridylthio derivatives, which would greatly expand the utility of aryl 1-thioglycosides in sugar chemistry.

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The synthesis of a library of nucleoside triphoshate mimetics is described where the Mg2+ chelated triphosphate sidechain is replaced by an uncharged methylene-triazole linked monosaccharide sidechain. The compounds have been evaluated as inhibitors of Bacillus anthracis pantothenate kinase and a competitive inhibitor has been identified with a Ki that is 3-fold lower than the Km value of ATP.

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The initial transfer of a complex glycan in protein N-glycosylation is catalyzed by oligosaccharyltransferase (OST), which is generally a multisubunit membrane protein complex in the endoplasmic reticulum but a single-subunit enzyme (ssOST) in some protists. To investigate the reaction mechanism of ssOST, we recombinantly expressed, purified and characterized the STT3A protein from Trypanosoma brucei (TbSTT3A). We analyzed the in vitro activity of TbSTT3A by synthesizing fluorescently labeled acceptor peptides as well as lipid-linked oligosaccharide (LLO) analogs containing a chitobiose moiety coupled to oligoprenyl carriers of distinct lengths (C10, C15, C20 and C25) and with different double bond stereochemistry. We found that in addition to proline, charged residues at the +1 position of the sequon inhibited glycan transfer. An acidic residue at the -2 position significantly increased catalytic turnover but was not essential, in contrast to the bacterial OST. While all synthetic LLO analogs were processed by TbSTT3A, the length of the polyprenyl tail, but not the stereochemistry of the double bonds, determined their apparent affinity. We also synthesized phosphonate analogs of the LLOs, which were found to be competitive inhibitors of the reaction, although with lower apparent affinity to TbSTT3A than the active pyrophosphate analogs.

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Our Top Choice Compound: C8H15NO6

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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., name: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

Two novel oligosaccharides were isolated from yak milk. The milk was processed by the method of Kobata and Ginsberg involving deproteination, centrifugation and lyophilization followed by gel filtrate chromatography acetylation and silica gel column chromatography of derivatized oligosaccharides while their homogeneity was confirmed by HPLC. The structures of these isolated oligosaccharides were elucidated by chemical transformation, chemical degradation, 1H, 13C NMR, 2D NMR (COSY, TOCSY and HSQC) and mass spectrometry. The geometry of compound A (Bosiose) and B (Bovisose) have been optimized at B3LYP method and 6-311 + G(d,p) basis set. The difference between the energies of A and B is 1.269 a.u. or 796.309 kcal/mol.

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Our Top Choice Compound: 14215-68-0

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Chemistry, like all the natural sciences, begins with the direct observation of nature— in this case, of matter. 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, Computed Properties of C8H15NO6

Carbohydrate esters are biodegradable, and the degraded adducts are naturally occurring carbohydrates and fatty acids which are environmentally friendly and non-toxic to human. A simple one-step regioselective acylation of mono-carbohydrates has been developed that leads to the synthesis of a wide range of carbohydrate esters. Screening of these acylated carbohydrates revealed that several compounds were active against a panel of bacteria and fungi, including Staphylococcus aureus, methicillin-resistant S. aureus (MRSA), Candida albicans, Cryptococcus neoformans, Aspergillus flavus and Fusarium graminearum. Unlike prior studies on carbohydrate esters that focus only on antibacterial applications, our compounds are found to be active against both bacteria and fungi. Furthermore, the synthetic methodology is suitable to scale-up production for a variety of acylated carbohydrates. The identified lead compound, MAN014, can be used as an antimicrobial in applications such as food processing and preservation and for treatment of bacterial and fungal diseases in animals and plants.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Our Top Choice Compound: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

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Benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (5) was synthesized by the treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (3) with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl bromide in the presence of silver trifluoromethanesulfonate and s-collidine.O-Deacetylation, followed by oxidation with acetic anhydride-dimethyl sulfoxide, and stereoselective reduction with sodium borohydride, converted 5 into benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-beta-D-mannopyranosyl)-alpha-D-glucopyranoside (8).Catalytic hydrogenation of 8 gave 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucopyranose, which was converted into 2-methyl-<3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-mannopyranosyl)-alpha-D-glucopyrano>–<2,1-d>-2-oxazoline (13), by treatment with hydrogen chloride-acetyl chloride, followed by chloride-ion catalysis.Condensation of 13 with 3 gave the trisaccharide, benzyl O-(2,3,4,6-tetra-O-acetyl-beta-D-mannopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside (14).Removal of the O-acetyl and O-benzyl groups from 14 gave the title compound.

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Our Top Choice Compound: 14215-68-0

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The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline.

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The synthesis of sialic acids and their analogs was accomplished based on substrate-controlled asymmetric aldol reactions between sterically complicated aldehydes easily prepared from commercially available carbohydrates and a novel pyruvic acid oxabicyclo[2.2.2]octyl orthoester. Systematic aldol reaction studies using chiral aldehydes revealed that alpha,beta,gamma-benzyloxy-substituted aldehydes with an alpha,beta-anti relative configuration preferentially provided the Felkin products with the 4,5-anti configuration with high diastereoselectivity. The relative beta,gamma-configuration in alpha,beta,gamma-benzyloxy-substituted aldehydes with an alpha,beta-syn arrangement exerted a secondary effect on the diastereoselectivity of the stereogenic center formed in aldol reactions, and alpha,beta-syn-beta,gamma-anti benzyloxyaldehyde exhibited superior diastereoselectivity to alpha,beta-syn-beta,gamma-syn benzyloxyaldehyde to yield the Felkin products.

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Chemical Properties and Facts of C8H15NO6

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category: Tetrahydropyrans. Chemistry graduates have much scope to use their knowledge in a range of research sectors, including roles within chemical engineering, chemical and related industries, healthcare and more. Like 14215-68-0, Name is N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide. In a document type is Patent, introducing its new discovery.

This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising alpha-D-Gal(1?3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of alpha-D-galactopyranosyl-(1?3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R3 is methoxy or methyl; R1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl. 1

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Chemistry is traditionally divided into organic and inorganic chemistry. The former is the study of compounds containing at least one carbon-hydrogen bonds. In an article, published in an article, once mentioned the application of 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, is a conventional compound. this article was the specific content is as follows.Product Details of 14215-68-0

Hyaluronan (HA) is well known to reside in the extracellular matrix as a water-sorbed macromolecule. The aims of this study were twofold: to investigate the regulation of HA synthesis in keratinocytes, and to develop a method to modulate this regulatory process. We found that N-acetylglucosamine (NAG) increased the production of HA by cultured keratinocytes dose dependently, but had no effect on the production by skin fibroblasts. The effect of NAG in keratinocytes was found to be specific for HA production, as there was no change in sulfated glycosaminoglycan formation. The copresence of NAG with either of two retinoids, retinoic acid (RA) or retinol, exerted a synergistic effect on HA production. To investigate whether human HA synthase (HAS) genes were regulated by NAG or retinoids, total RNA extracted from cells treated with these agents was subjected to Northern blot analysis. We observed that RA and retinol markedly induced the expression of HA synthase-3 (HAS3) mRNA. Moreover, beta-carotene, a provitamin A, influenced HA production and HAS3 gene expression in a manner similar to the retinoids. Conversely, NAG had no effect on the expression of HAS3 transcripts. Pretreatment of cells with RA stimulated the activity of membrane-associated HAS, whereas pretreatment with NAG did not. These results suggest that HA production is regulated by at least two pathways: one involving the regulation of HAS gene expression, and the other independent of such a regulatory effect. Taken together, our findings suggest that NAG is a new modulator of HA synthesis. Copyright

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Tetrahydropyran – Wikipedia,
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