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

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METHOD FOR PRODUCTION OF SUGAR OXAZOLINE DERIVATIVE

Disclosed is a process for producing an oxazoline derivative from a non-protected sugar in a simple manner. Also disclosed is a process for producing a glycoside by utilizing the product of the aforementioned process. A sugar oxazoline derivative is synthesized in one step in an aqueous solution from a sugar having a free hemiacetalic hydroxy group and an amido group by using a haloformamidinium derivative as a dehydrating agent. A glycoside compound is produced by using the oxazoline derivative as a sugar donor and also using a sugar dehydrogenase. The method can be applied to the production of a compound having a long sugar chain, and is therefore useful for the production of a physiologically active oligosaccharide, a carrier for a drug delivery system, a surfactant, a carbohydrate-based drug, a glycopeptide, a glycoprotein, a carbohydrate polymer or the like.

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Tetrahydropyran – Wikipedia,
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Synthesis and properties of alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

A class of novel sugar-based surfactants named alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosides were constructed by the introduction of oxyethene fragment (-OCH2CH2-) in the traditional alkyl glycoside structure. Such alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranosides with different length of alkyl chain were synthesized, and their single configurations were confirmed to be alpha-anomer by 1H NMR and HRMS analysis. Their water solubility, surface tension, emulsification, foaming and thermal stability were investigated, and the effect of alkyl chain length on their surface property was also compared. The water solubility of alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside was significantly superior to that of alkyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside without an oxyethene fragment. Their dissolution process was an endothermic process and was driven by entropy increment as well. Alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside was disclosed to reduce significantly the surface tension of water. For both of CMC and gammaCMC, there was a decreasing trend with increasing of alkyl chain length. As increasing of alkyl chain length, the maximum surface adsorption (Gammamax) increased and the molecular cross-sectional area (Amin) decreased. They adsorbed preferentially on the solution surface and then formed spontaneously micelles in solution by the hydrophobic effect. Nonyloxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside had the best foaming and emulsifying properties. All glycosides are thermally stable below 270?C. In view of the improvement of the water solubility and maintainance of surface activity with the introduction of the hydrophilic spacer, the novel alkoxyethyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside should be expected to develop further its multiple applications as a class of novel water-soluble sugar-based surfactants in the future.

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Synthesis of new sugar derivatives and evaluation of their antibacterial activities against Mycobacterium tuberculosis

A series of sugar derivatives (1-13) were synthesized and evaluated for antibacterial activity against Mycobacterium tuberculosis (MTB), especially multi-drug resistant (MDR) MTB, and the structure-activity relationships of these compounds were studied. The results showed that the compound OCT313 (2-acetamido-2deoxy-beta-d-glucopyranosyl N,N-dimethyldithiocarbamate) (4) exhibited significant in vitro bactericidal activity, and that the dithiocarbamate group at C-1 position of the glucopyranoside ring was requisite for the antibacterial activity.

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Tetrahydropyran – Wikipedia,
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Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

Abstract: A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity?a prerequisite for the flow experiments?no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.

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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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Conversion of glucosamine to galactosamine and allosamine derivatives: Control of inversions of stereochemistry at C-3 and C-4

The reactions of sodium benzoate with a series of trimesylates derived from glucosamine have been examined in an attempt to gain facile access to galactosamine analogues. Trimesylate 17, in which the amino group was protected as a phthalimide, underwent double displacement at positions 4 and 6 to give the dibenzoate 18 with the desired galactosamine configuration. In contrast, trimesylates 21 and 27, in which the amino groups were protected as acetamides, unexpectedly underwent double displacement at positions 3 and 6, giving products 22 and 28, respectively, with allosamine configurations.

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Recognition of poly-N-acetyllactosaminyl saccharide chains on iron-oxidized erythrocytes by human monocytic leukemia cell line THP-1 differentiated into macrophages

The cells of the human monocytic leukemia cell line THP-1 differentiated into macrophages bound to human erythrocytes oxidized with adenosine 5?-diphosphate (ADP)-Fe3+ chelate (ADP/Fe3+) in the absence of serum. The binding was prevented when the cells were treated with ADP/Fe3+ in the presence of antioxidants, indicating that oxidation of the cells is responsible for the increased susceptibility to the THP-1 cell binding. Galactose, fucose, mannose and mannan partially inhibited the binding. Glycoproteins containing poly-N-acetyllactosaminyl saccharide chains such as band 3 glycoprotein isolated from human erythrocyte membrane and lactoferrin, and their oligosaccharides, strongly inhibited the binding. On the other hand, glycoproteins with non-poly-N-acctyl-lactosaminyl saccharide chains such as glycophorin A isolated from the erythrocyte membrane, fetuin and alpha1-acid glycoprotein, little or partially inhibited the binding. The inhibitory activity of band 3 oligosaccharides and lactoferrin oligosaccharides was little affected by treatment with endo-beta-galactosidase, which specifically cleaves poly-N-acetyllactosamine to shorter oligosaccharides. Removal of the nonreducing terminal region of the saccharide chains of band 3 on the eythrocyte surface by treatment of the cells with endo-beta-galactosidase resulted in a decrease in the susceptibility of the cells to the THP-1 cell binding. These results suggest that THP-1 cells which have been differentiated into macrophages bind the oxidized erythrocytes primarily through the recognition of poly-N-acetyllactosaminyl saccharide chains of band 3, and the site of the recognition exists in the nonreducing terminal region of the saccharide chains. Clustering of band 3 molecules is proposed as a possible alteration of oxidized erythrocyte membrane which promotes the interaction of the saccharide receptor on THP-1 cells with the saccharide chains of band 3 on erythrocytes.

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Highly efficient enzymatic synthesis of Galbeta-(1?3)-GalNAc and Galbeta-(1?3)-GlcNAc in ionic liquids

Ionic liquids (ILs) have emerged as an alternative to conventional organic media due to their high thermal and chemical stability, negligible vapour pressure, non-flammability and easy recycling. In this context, this work assesses the catalytic activity of a beta-galactosidase from Bacillus circulans ATCC 31382 (beta-Gal-3-NTag) in the synthesis of beta-(1?3)-galactosides using different ILs. A noticeably increase in activity, retaining total regioselectivity was found in the synthetic behaviour of B. circulans beta-galactosidase in ILs as co-solvents and using a 1:5 molar ratio of donor (pNP-beta-Gal):acceptor (GlcNAc or GalNac). Yields up to 97% of beta-(1?3) with different ILs were found. These reactions take place without noticeable hydrolytic activity and with total regioselectivity, representing a considerable improvement over the use of aqueous buffer or conventional organic solvents. Furthermore, reaction scaling up and IL recovery and recycling are feasible without losing catalytic action. Molecular modelling studies performed predict a three-dimensional interaction at the active centre between the acceptor and the water-IL mixture, which could explain the results obtained.

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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 Patent£¬once mentioned of 14215-68-0, Recommanded Product: N-((2S,3R,4R,5R,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES

The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.

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Tetrahydropyran – Wikipedia,
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Structure and activity of the streptomyces coelicolor A3(2) beta-N-acetylhexosaminidase provides further insight into GH20 family catalysis and inhibition

beta-N-acetylhexosaminidases (HEX) are glycosidases that catalyze the glycosidic linkage hydrolysis of gluco- and galacto-configured N-acetyl-beta-d-hexosaminides. These enzymes are important in human physiology and are candidates for the biocatalytic production of carbohydrates and glycomimetics. In this study, the three-dimensional structure of the wild-type and catalytically impaired E302Q HEX variant from the soil bacterium Streptomyces coelicolor A3(2) (ScHEX) were solved in ligand-free forms and in the presence of 6-acetamido-6-deoxy-castanospermine (6-Ac-Cas). The E302Q variant was also trapped as an intermediate with oxazoline bound to the active center. Crystallographic evidence highlights structural variations in the loop 3 environment, suggesting conformational heterogeneity for important active-site residues of this GH20 family member. The enzyme was investigated for its beta-N-acetylhexosaminidase activity toward chitooligomers and pNP-acetyl gluco- and galacto-configured N-acetyl hexosaminides. Kinetic analyses confirm the beta(1-4) glycosidic linkage substrate preference, and HPLC profiles support an exoglycosidase mechanism, where the enzyme cleaves sugars from the nonreducing end of substrates. ScHEX possesses significant activity toward chitooligosaccharides of varying degrees of polymerization, and the final hydrolytic reaction yielded pure GlcNAc without any byproduct, promising high applicability for the enzymatic production of this highly valued chemical. Thermostability and activation assays further suggest efficient conditions applicable to the enzymatic production of GlcNAc from chitooligomers.

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Synthesis and Biological Evaluation of Novel Carbohydrate-Derived Derivatives of Erlotinib

(Table presented.). A series of novel carbohydrate-derived Erlotinib derivatives were prepared by the copper-catalyzed cycloaddition reaction of erlotinib with various azido-sugars. The structures of the newly synthesized compounds were characterized and their cytostatic effects evaluated in vitro on human cancer cell lines MDA-MB-231, HEPG-2, A549, and MCF-7 using an MTS assay. The novel erlotinib derivatives had the expected inhibitory effects on MDA-MB-231 and HEPG-2 cell llines. Among the compounds evaluated the carbohydrate-derived compounds 5b, 5d, 6a, and 6c had more potent activities against MDA-MB-231 or HEPG-2 than Erlotinib. Drug Dev Res, 2016.

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Tetrahydropyran – Wikipedia,
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