REGIOSELECTIVE ACYLATION OF SECONDARY HYDROXYL-GROUPS IN SUGARS CATALYZED BY LIPASES IN ORGANIC-SOLVENTS
REGIOSELECTIVE ACYLATION OF SECONDARY HYDROXYL-GROUPS IN SUGARS CATALYZED BY LIPASES IN ORGANIC-SOLVENTS
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DOI：
10.1021/ja00247a024
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发表时间：
1987-06-24
影响因子：
15
通讯作者：
KLIBANOV, AM
中科院分区：
文献类型：
--
作者：
THERISOD, M;KLIBANOV, AM
Several unrelated, commercially available lipases (porcine pancreatic, bacterial, yeast, and fungal) can catalyze transesterification reactions between trichloroethyl butyrate and monosaccharides with blocked C-6 hydroxyl groups (enzymatically acylated or chemically alkylated) in dry organic solvents. Lipases exhibit a remarkable regioselectivity by discriminating among the four available secondary hydroxyl groups in C-6 protected glucose, galactose, and mannose. While some lipases exclusively acylate the C-3 hydroxyl group, others display an overwhelming preference toward the C-2 hydroxyl group. This positional specificity of lipases was used for the preparation of various sugar diesters and, consequently, for either fully enzymatic or chemicoenzymatic preparative synthesis of C-2 or C-3 monoesters of glucose.
