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- W2013988350 abstract "Abstract Hydrolysis of six methyl O ‐benzoyl‐pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C‐6. The rate of reaction was dependent on pyranoside structure, reaction temperature and scale, dioxane concentration and agitation speed. Starting from their C‐6 O ‐benzoyl precursors, the methyl 2,3,4‐tri‐ O ‐benzoyl‐pyranosides of α‐ D ‐galactose, β‐ D ‐galactose, α‐ D ‐glucose, and methyl 2,3‐di‐ O ‐benzoyl‐α‐ D ‐galactopyranoside could be isolated in 85–96 % yield. In hydrolysis of methyl 2,3,4,6‐tetra‐ O ‐benzoyl‐α‐ D ‐glucopyranoside and methyl 2,3,4,6‐tetra‐ O ‐benzoyl‐β‐ D ‐galactopyranoside substrate inhibition were observed, which in part could be overcome by increasing the reaction volume. Methyl 2,3,4,6‐tetra‐ O ‐benzoyl‐β‐ D ‐glucopyranoside and methyl 2,3,4,6‐tetra‐ O ‐benzoyl‐α‐ D ‐mannopyranoside were poor substrates for Candida rugosa lipase and low degree of conversion towards products were obtained under all conditions. No acyl migration was detected in any of the products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)" @default.
- W2013988350 created "2016-06-24" @default.
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- W2013988350 date "2009-03-13" @default.
- W2013988350 modified "2023-10-14" @default.
- W2013988350 title "Regioselective C-6 Hydrolysis of Methyl<i>O</i>-Benzoyl-pyranosides Catalysed by<i>Candida Rugosa</i>Lipase" @default.
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- W2013988350 doi "https://doi.org/10.1002/ejoc.200801268" @default.
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