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Glycogen is a polymer of alpha-1,4- and alpha-1,6-linked glucose units that provides a readily available source of energy in living organisms. Glycogen synthase (GS) and glycogen phosphorylase (GP) are the two enzymes that control, respectively, the synthesis and degradation of this polysaccharide and constitute adequate pharmacological targets to modulate cellular glycogen levels, by means of inhibition of their catalytic activity. Here we report on the synthesis and biological evaluation of a selective inhibitor that consists of an azobenzene moiety glycosidically linked to the anomeric carbon of a glucose molecule. In the ground state, the more stable (E)-isomer of the azobenzene glucoside had a slight inhibitory effect on rat muscle GP (RMGP, IC50 = 4.9 mM) and Escherichia coli GS (EcGS, IC50 = 1.6 mM). After irradiation and subsequent conversion to the (Z)-form, the inhibitory potency of the azobenzene glucoside did not significantly change for RMGP (IC50 = 2.4 mM), while its effect on EcGS increased 50-fold (IC50 = 32 muM). Sucrose synthase 4 from potatoes, a glycosyltransferase that does not operate on glycogen, was only slightly inhibited by the (E)-isomer (IC50 = 0.73 mM). These findings could be rationalized on the basis of kinetic and computer-aided docking analysis, which indicated that both isomers of the azobenzene glucoside mimic the EcGS acceptor substrate and exert their inhibitory effect by binding to the glycogen subsite in the active center of the enzyme. The ability to selectively photoregulate the catalytic activity of key enzymes of glycogen metabolism may represent a new approach for the treatment of glycogen metabolism disorders.

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A new electrochemical glycosylation method is presented. According to the method cholesterol and other 3beta-hydroxy-Delta5-steroids can be selectively transformed to glycosides using non-activated sugars. The method is also useful for the synthesis of glycoconjugates with sugar linked to a steroid moiety by an ether bond.

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Syntheses of long-chain hydroxy-, methoxyalkylsilanes of the type (RSi(CH3)2OH, R(m)SiY(4-m) with R = C12H25, C18H37 and Y = OH, OMe, m = 1, 2, 3) (5, 6, 7a-c, 8a-c, 9a-c, 10a-c) and alkylsilyl glycopyranosides (13, 14, 15a-c, 16a-c) are reported. Hydroxyalkylsilanes (5, 6, 7a-c, 8a-c) were prepared by the hydrolysis of alkylchlorosilanes (1a-c, 2a-c, 3, 4) with NaHCO3-H2O in diethyl ether. Alkylchlorosilanes 1a-c and 2a-c react with KOMe in n-hexane to give methoxyalkylsilanes 9a-c and 10a-c, respectively. Alkylchlorosilanes 1a-c, 2a-c, 3 and 4react direct with 2,3,4,6-tetra-O-acetyl-alpha/beta-D-glucopyranose 12 in CH2Cl2 to give alkylsilyl glucopyranosides 13, 14, 15a-c and 16a-c, respectively.

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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals. However, they have proven to be challenging because of the mutual inactivation of both catalysts. 10343-06-3, Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, molecular formula is C14H20O10. In a Article,once mentioned of 10343-06-3, Product Details of 10343-06-3

This work aims to synthesize new trehalase inhibitors selective towards the insect trehalase versus the porcine trehalase, in view of their application as potentially non-toxic insecticides and fungicides. The synthesis of a new pseudodisaccharide mimetic 8, by means of a stereoselective alpha-glucosylation of the key pyrrolizidine intermediate 13, was accomplished. The activity of compound 8 as trehalase inhibitor towards C. riparius trehalase was evaluated and the results showed that 8 was active in the muM range and showed a good selectivity towards the insect trehalase. To reduce the overall number of synthetic steps, simpler and more flexible disaccharide mimetics 9?11 bearing a pyrrolidine nucleus instead of the pyrrolizidine core were synthesized. The biological data showed the key role of the linker chain?s length in inducing inhibitory properties, since only compounds 9 (alpha,beta-mixture), bearing a two-carbon atom linker chain, maintained activity as trehalase inhibitors. A proper change in the glucosyl donor-protecting groups allowed the stereoselective synthesis of the beta-glucoside 9beta, which was active in the low micromolar range (IC50 = 0.78 muM) and 12-fold more potent (and more selective) than 9alpha towards the insect trehalase.

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The preparation of five peracetylated a-glycosyl-H-phosphonates and their use in the straightforward preparation of phosphodiesters derivatives of 25-hydroxycholesterol is described. Examples of the extension of this process to other lipophilic alcohols are presented.

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Preparation and characterization of peripherally glucose substituted zinc(II) phthalocyanine 6, linked via the anomeric carbon through a novel glycosidation method is reported for the first time, for which classical Pc template chemistry with the unprotected phthalonitrile 4 could be used. Phthalocyanine 6 was formed in high yield and is displaying a high solubility in water as a primary condition for a potential biological application.

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Anomeric O-unprotected sugars add to 3,4,6-tri-O-benzyl-2-nitro-D-galactal to accomplish nitro group-containing 1,1-linked oligosaccharides in respectable yields with good selectivities. A 1:1 mixture of toluene and n-heptane has been found as the appropriate solvent system for these Michael-type additions. The nitro group-containing 1,1-linked oligosaccharides are easily convertible into interesting trehalosamine analogues.

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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. name: 2,3,4,6-Tetra-o-acetyl-D-glucopyranosename: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, , Name is 2,3,4,6-Tetra-o-acetyl-D-glucopyranose, molecular formula is C14H20O10. In a patent, introducing its new discovery.

3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy) ethyl 2,3,4,6-tetra-O-acetyl-beta-D-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O- acetyl-beta-D-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields. Georg Thieme Verlag Stuttgart.

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A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.

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The invention belongs to the field of chemical synthesis and relates to synthesis of glycosyl-1-monophosphate. The method disclosed by the invention comprises the following steps of 1, performing a reaction between imidazole and phosphorus trichloride to obtain phosphite tri-imidazole, performing a reaction between the phosphite tri-imidazole and an acetylated sugar raw material of which the end position is deprotected and carrying out in-situ hydrolysis to obtain corresponding glycosyl-1-hydrogen phosphite monoester; 2, carrying out silylation on the glycosyl-1-hydrogen phosphite monoester by N,O-bi(trimethylsilyl)acetamide to obtain a trialkylphosphite intermediate, carrying out oxidation on an organic alkali/iodine simple substance system and carrying out in-situ hydrolysis to obtain glycosyl-1-monophosphate protected by acetyl; 3, removing an acetyl protecting group through sodium methylate and obtaining corresponding the high-purity glycosyl-1-monophosphate through sephadex chromatographic purification and ion exchange. According to the method disclosed by the invention, the glycosyl-1-monophosphate is obtained through the three steps and the total yield can reach 75 percent to 85 percent. Loss caused by benzyl removing by hydrogenation in a conventional method is avoided. The method disclosed by the invention is particularly suitable for preparing a great amount of glycosyl-1-monophosphate.

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Tetrahydropyran – Wikipedia,
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