![]() ![]() αGA1 was successfully conjugated with alkynes attached to different functional groups, including aryl, ether, amine, amide, ester, alcohol, and flavone via copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry reactions. The pNPGlc and azide reaction product was purified by Sephadex LH-20 column chromatography to yield 280 mg of pure αGA1 (68% yield). Thermoanaerobacterium xylanolyticus glucosyl hydrolase 116 β-glucosidase ( TxGH116) E441G nucleophile mutant catalyzed synthesis of αGA1 from sodium azide and pNP-β- d-glucoside ( pNPGlc) or cellobiose in aqueous medium at 45 ☌. Glycosynthase enzymes, made by nucleophile mutations of retaining β-glucosidases, produce αGA1 in chemical rescue experiments. Α-Glucosyl triazoles have rarely been tested as α-glucosidase inhibitors, partly due to inefficient synthesis of their precursor α- d-glucosylazide ( αGA1).
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