ENZYMATIC GLUCOSYLATION OF HYDROPHOBIC ALCOHOLS IN ORGANIC MEDIUM BY THE REVERSE HYDROLYSIS REACTION USING ALMOND-BETA-D-GLUCOSIDASE

被引：55

作者：

VIC, G

BITON, J

LEBELLER, D

MICHEL, JM

THOMAS, D

机构：

[1] UNIV TECHNOL COMPIEGNE,TECHNOL ENZYMAT LAB,CNRS,URA 1442,F-60206 COMPIEGNE,FRANCE

[2] ROUSSEL UCLAF ZAC MERCIERES,DEPT BIOTECHNOL,ENZYMOL RES UNIT,F-60200 COMPIEGNE,FRANCE

来源：

BIOTECHNOLOGY AND BIOENGINEERING | 1995年 / 46卷 / 02期

关键词：

GLUCOSYLATION; ALCOHOL; HYDROLYSIS; REVERSE; GALACTOSIDE;

D O I：

10.1002/bit.260460204

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Alkyl beta-D-glucosides were synthesized from D-glucose and alcohols by reverse hydrolysis using the commercially available almond beta-D-glucosidase in 9:1 (v/v) acetonitrile-water medium. The main characteristics of this enzyme-catalyzed glucosylation were established by using 2-hydroxybenzyl alcohol. The reaction is entirely regio- and stereoselective. The solvent plays a fundamental role because, by decreasing the water concentration in the medium, the shift of the reaction equilibrium toward synthesis is realized without using an excessive amount of alcohol. Nevertheless, a minimum amount of water is necessary to maintain the enzyme activity. In contrast to the use of the enzyme in aqueous medium, the pH of the added water in acetonitrile did not influence the synthesis. Using this procedure, we have conducted systematic glucosylation of numerous alcohols and we have investigated enzyme specificity and alcohol reactivity. The enzyme has a pronounced affinity for the alcohols containing a phenyl group, and enantioselectivity for the aglycon is obtained with 1-phenylethyl alcohol. Moreover, by using almond beta-D-glucosidase it was also possible to synthesize alkyl beta-D-galactosides. (C) 1995 John Wiley and Sons, Inc.

引用

页码：109 / 116

页数：8

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