Diastereoselective resolution of 6-substituted glycosides via enzymatic hydrolysis

被引：11

作者：

Grabowska, U

MacManus, DA

Biggadike, K

Bird, MI

Davies, S

Gallagher, T

Hall, LD

Vulfson, EN

机构：

[1] Food Res Inst, Food Macromol Sci Dept, Reading RG6 6BZ, Berks, England

[2] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

[3] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[4] Univ Bristol, Sch Chem, Xray Crystallog Unit, Bristol BS8 1TS, Avon, England

来源：

CARBOHYDRATE RESEARCH | 1997年 / 305卷 / 3-4期

关键词：

enzymes; glycosidase; diastereoselectivity; resolution; transglycosylation; unnatural glycosides;

D O I：

10.1016/S0008-6215(97)00246-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The diastereoselectivity of the enzymatic hydrolyses of 4-nitrophenyl 6-deoxy-6-methyl-(R)- and (S)-sulfinyl-beta-D-galactopyranoside (la,b), 4-nitrophenyl 7-deoxy-D- and L-glycero-beta-D-galacto-heptopyranoside ide (2a,b) and 4-nitrophenyl 6,7-anhydro-D- and L-glycero-beta-D-galacto-heptopyranoside (3a,b) was investigated using a range of crude glycosidase preparations. It was shown that the enzymes display a high degree of discrimination between diastereomers thereby demonstrating the utility of glycosidases for the diastereomeric resolution of unnatural 6-substituted monosaccharide derivatives. (C) 1998 Elsevier Science Ltd.

引用

页码：351 / 361

页数：11

共 17 条

[1]

BJORKLING F, 1988, TETRAHEDRON, V44, P2957

[2] ENZYMATIC-SYNTHESIS OF GLYCOSIDES USING THE BETA-GALACTOSIDASE OF ESCHERICHIA-COLI - REGIOCHEMICAL AND STEREOCHEMICAL STUDIES [J].