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Treatment of unprotected methyl-alpha-D-glucopyranoside, N-acetyl-glucosamine and maltose with methacrylic acid, 1-adamantanecarboxylic acid, 2′,7′-dichlorofluorescein or phenol in the presence of triphenylphosphine and diethylazodicarboxylate gave C-6 (or C-6′ for maltose) esterified sugars in acceptable yields.

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Insect chitinolytic beta-N-acetylhexosaminidase OfHex1, from the agricultural pest Ostrinia furnacalis (Guenee), is considered as a potential target for green pesticide design. In this study, rational molecular design and optimization led to the synthesis of compounds 15r (Ki = 5.3 muM) and 15y (Ki = 2.7 muM) that had superior activity against OfHex1 than previously reported lead compounds. Both compounds 15r and 15y had high selectivity toward OfHex1 over human beta-N-acetylhexosaminidase B (HsHexB) and human O-GlcNAcase (hOGA). In addition, to investigate the basis for the potency of glycosylated naphthalimides against OfHex1, molecular docking and molecular dynamics simulations were performed to study possible binding modes. Furthermore, the in vivo biological activity of target compounds with efficient OfHex1 inhibitory potency was assayed against Myzus persicae, Plutella xylostella, and O. furnacalis. This present work indicates that glycosylated naphthalimides can be further developed as potential pest control and management agents targeting OfHex1.

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Glucose metabolism is essential for survival of bloodstream form Trypanosoma brucei subspecies which cause human African trypanosomiasis (sleeping sickness). Hexose analogues may represent good compounds to inhibit glucose metabolism in these cells. Delivery of such compounds to the parasite is a major consideration in drug development. A series of D-glucose and D-fructose analogues were developed to explore the limits of the structure-activity relationship of the THT1 hexose transporter of bloodstream form African trypanosomes, a portal that might be exploited for drug uptake. D-Glucose analogues with substituents at the C2 and C6 position continued to interact with the exofacial hexose binding site of the transporter. There was a limit to the size at C6 which still permitted recognition, although compounds carrying large groups at position C2 were still recognised. However, radiolabelled N-acetyl-D-[1-14C] glucosamine was not internalised by trypanosomes, in spite of the ability of this compound to inhibit glucose uptake, indicating that there is a limit to the size of C2 substituent that allows translocation. Addition of an alkylating group (bromoacetyl) at position C2 in the D-glucose series and at position 6 in the D-fructose set, created two analogues which interact with the transporter and kill trypanosomes in vitro. This indicates that inhibition of the transporter may be a good means of killing trypanosomes.

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A methanol extract of the dried leaves of Lansium domesticum showed antimutagenic effects against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) and 2-amino-1-methyl-6-phenylimidazo[4,5-bI]pyridine (PhIP) using the Ames assay. Nine new onoceranoid-type triterpenoids, lansium acids I-IX (1-9), and nine known compounds (10-16) were isolated from the extract. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. The absolute stereostructures of the new compounds were determined via their electronic circular dichroism spectra. Several isolated onoceranoid-type triterpeneoids showed antimutagenic effects in an in vitro Ames assay. Moreover, oral intake of a major constituent, lansionic acid (10), showed antimutagenic effects against PhIP in an in vivo micronucleus test.

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The reaction of a partially protected 1-hydroxy derivative of N-acetyl-d-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali metal cation constituent of a transient ion pair. The substitution of the Li+ cation for K + or complexation with a crown ether allowed the steric outcome to be shifted from beta- to alpha-selectivity.

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N-Acetyllactosamine 5 is obtained by transglycoslyation between p-nitrophenyl beta-D-galactopyranoside 3 and N-acetyl-D-glucosamine 4 by using the beta-galactosidase from Bacillus circulans as the biocatalyst. Sodium salts of beta-Gal(6-SO4)-(1?4)-GlcNAc 1 and beta-Gal-(1?4)-GlcNAc(6-SO4) 2 have been prepared from N-acetyllactosamine 5 in five and three steps respectively. beta-D-GlcNAc-(1?4)-D-GlcNAc(6-SO4) (di-N-acetylchitobiose 6-sulfate) 10 is synthesised from chitin in three steps. The products have been tested as fucosyl acceptors in reactions catalysed by recombinant human fucosyltransferases III to VII.

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Recombinant N-acetylglucosamine kinase, pyruvate kinase, N-acetylglucosamine phosphate mutase, uridine 5?-diphosphate N-acetylglucosamine pyrophosphorylase, and inorganic pyrophosphatase were overexpressed in E. coli and co-immobilized on agarose beads for the practical synthesis of uridine 5?-diphosphate N-acetylglucosamine.

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We found that a chitin deacetylase from Colletotrichum lindemuthianum could acetylate free amino sugar residues into N-acetylated forms in the presence of 3.0 M sodium acetate. The result was analyzed using a beta-N-acetylhexosaminidase-coupled assay system with p-nitrophenyl 2-amino-2-deoxy-beta-D-glucopyranosyl-(1?4)-2-acetamido-2-deoxy-beta-D-glucopyranoside as the substrate, and the liberation of p-nitrophenol was observed as a consequence of enzymatic N-acetylation of the glucosamine residue at the nonreducing end of the substrate. The chitin deacetylase also acetylated chitobiose and chitotetraose as substrates, which was evidenced by the decrease in the amount of free amino sugar residues in the chitooligosaccharides. The reaction product of chitobiose after the acetylation reaction was exclusively 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1?4)-2-amino-2-deoxy-D-glucose [GlcNAcGlcN], the structure of which was determined by FABMS and NMR analyses. This study offers a novel method for enzymatic N-acetylation of amino sugars, and especially with chitobiose as substrate, a selectively N-acetylated product, GlcNAcGlcN, can be synthesized. Copyright (C) 1999 Elsevier Science Ltd.

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A method is provided for treating a dermatological condition in a patient. The method includes (a) measuring the intracellular water content of the patient to provide an initial intracellular water content measurement; (b) administering to the patient at least one active agent; (c) re-measuring the intracellular water content of the patient to provide a post-treatment intracellular water content measurement; and (d) repeating steps (b) and (c) until the post-treatment intracellular water content measurement is greater than the initial intracellular water content measurement. A method is also provided for treating other health-related conditions in a patient.

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[A] producing an un hydro amino sugar derivatives by a simple method. [Solution] amino derivative in an organic solvent by heating, and the furanose sugar derivative un hydro amino-hexose-simultaneously. [16 a][Drawing] no (by machine translation)

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