SELECTIVE LIPASE-CATALYZED ESTERIFICATION OF ALKYL GLYCOSIDES

被引：23

作者：

DEGOEDE, ATJW ^{[1
]}

VANOOSTEROM, M ^{[1
]}

VANDEURZEN, MPJ ^{[1
]}

SHELDON, RA ^{[1
]}

VANBEKKUM, H ^{[1
]}

VANRANTWIJK, F ^{[1
]}

机构：

[1] DELFT UNIV TECHNOL,ORGAN CHEM & CATALYSIS LAB,JULIANALAAN 136,2628 BL DELFT,NETHERLANDS

来源：

BIOCATALYSIS | 1994年 / 9卷 / 1-4期

关键词：

LIPASE; ALKYL GLYCOSIDE; ALKYL FRUCTOSIDE; TRANSESTERIFICATION; ZEOLITE; WATER ACTIVITY;

D O I：

10.3109/10242429408992116

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：

Alkyl derivatives of glucose, galactose and fructose were acylated by lipase-catalyzed transesterification with alkanoic esters. The best results were obtained with immobilized lipases of the Candida antarctica type. Primary alcohol functions were acylated first, followed by secondary ones depending on the structure of the glycoside. The water activity in the reaction medium had a striking effect on both the rate and the selectivity of the process. The size and orientation of the alkyl substituent and the structure of the acyl acceptor were also found to exert a profound influence on the course of the reaction.

引用

页码：145 / 155

页数：11

共 24 条

[1] A SERINE PROTEASE TRIAD FORMS THE CATALYTIC CENTER OF A TRIACYLGLYCEROL LIPASE [J].

BRADY, L ;

BRZOZOWSKI, AM ;

DEREWENDA, ZS ;

DODSON, E ;

DODSON, G ;

TOLLEY, S ;

TURKENBURG, JP ;

CHRISTIANSEN, L ;

HUGEJENSEN, B ;

NORSKOV, L ;

THIM, L ;

MENGE, U .

NATURE, 1990, 343 (6260) :767-770

[2] A MODEL FOR INTERFACIAL ACTIVATION IN LIPASES FROM THE STRUCTURE OF A FUNGAL LIPASE-INHIBITOR COMPLEX [J].

BRZOZOWSKI, AM ;

DEREWENDA, U ;

DEREWENDA, ZS ;

DODSON, GG ;

LAWSON, DM ;

TURKENBURG, JP ;

BJORKLING, F ;

HUGEJENSEN, B ;

PATKAR, SA ;

THIM, L .

NATURE, 1991, 351 (6326) :491-494

[3] REGIOSELECTIVE ACYLATION OF 6-DEOXY-L-HEXOSIDES AND 6-DEOXY-D-HEXOSIDES THROUGH LIPASE-CATALYZED TRANSESTERIFICATION - ENHANCED REACTIVITY OF THE 4-OH FUNCTION IN THE L SERIES [J].

CIUFFREDA, P ;

COLOMBO, D ;

RONCHETTI, F ;

TOMA, L .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4187-4190

[4] ACYLATION OF 6-DEOXY-L-HEXOSES - REGIOSELECTIVITY IN THE ENZYMATIC TRANSESTERIFICATION AS COMPARED TO CHEMICAL ESTERIFICATION [J].

CIUFFREDA, P ;

RONCHETTI, F ;

TOMA, L .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (01) :125-129

[5] ENZYMATIC ACYLATION OF METHYL D-GLUCOPYRANOSIDES AND L-GLUCOPYRANOSIDES AND 6-DEOXY-GLUCOPYRANOSIDES [J].

COLOMBO, D ;

RONCHETTI, F ;

SCALA, A ;

TOMA, L .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (01) :89-94

[6] ENZYMATIC ACYLATION OF SUGARS - RATIONALE OF THE REGIOSELECTIVE BUTYRYLATION OF SECONDARY HYDROXY-GROUPS OF D-GALACTO AND L-GALACTO AND MANNOPYRANOSIDES [J].

COLOMBO, D ;

RONCHETTI, F ;

TOMA, L .

TETRAHEDRON, 1991, 47 (01) :103-110

[7]

DEGOEDE ATJ, 1993, IN PRESS RECL TRAV C

[8]

DENIJS MP, 1990, RECL TRAV CHIM PAY B, V109, P429

[9] THE CRYSTAL AND MOLECULAR-STRUCTURE OF THE RHIZOMUCOR-MIEHEI TRIACYLGLYCERIDE LIPASE AT 1.9-ANGSTROM RESOLUTION [J].

DEREWENDA, ZS ;

DEREWENDA, U ;

DODSON, GG .

JOURNAL OF MOLECULAR BIOLOGY, 1992, 227 (03) :818-839

[10] NEW IDEAS ABOUT ENZYME-REACTIONS [J].

DEWAR, MJS .

ENZYME, 1986, 36 (1-2) :8-20

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