A new strategy for liquid-phase synthesis of disaccharides based on the use of glycosidases

被引：8

作者：

Corrales, G ^{[1
]}

Fernández-Mayoralas, A ^{[1
]}

García-Junceda, E ^{[1
]}

Rodríguez, Y ^{[1
]}

机构：

[1] CSIC, Inst Quim Organ Gen, Dept Quim Organ Biol, E-28006 Madrid, Spain

来源：

BIOCATALYSIS AND BIOTRANSFORMATION | 2000年 / 18卷 / 04期

关键词：

glycosidases; enzymatic synthesis; polymer-supported synthesis; liquid-phase synthesis; polyethylene glycol monomethylether;

D O I：

10.3109/10242420009015250

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：

A new strategy for the glycosidase-catalyzed liquid-phase synthesis of oligosaccharides, which facilitates the purification of the products, is described. This strategy is based on the use of glycosidases in two key steps: (i) glycosidation of a sugar bound to a soluble-support, and (ii) specific removal of the unreacted monosaccharide acceptor. Glucose is attached to the MPEG support through a linker derived from valeric acid. The introduction of the linker moiety was performed by an O-anomeric alkylation reaction. The galactosylation of the glucose-bound to the soluble-support using beta-galactosidase gave, after removal of by-products by precipitation and filtration of the support, galactosyl-glucose disaccharides bound to MPEG. Finally the alkylated disaccharides were released from the MPEG by ethanolysis. Unreacted glucose could be removed from the support by hydrolysis using glucosidases.

引用

页码：271 / 281

页数：11

共 9 条

[1] SOLID-PHASE SYNTHESIS OF OLIGOSACCHARIDES .5. PREPARATION OF AN INORGANIC SUPPORT [J].

EBY, R ;

SCHUERCH, C .

CARBOHYDRATE RESEARCH, 1975, 39 (01) :151-155

[2]

FernandezMayoralas A, 1997, TOP CURR CHEM, V186, P1

[3] Organic chemistry on solid supports [J].

Fruchtel, JS ;

Jung, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42

[4] Synthesis on soluble polymers: new reactions and the construction of small molecules [J].

Gravert, DJ ;

Janda, KD .

CURRENT OPINION IN CHEMICAL BIOLOGY, 1997, 1 (01) :107-113

[5] ENZYME-CATALYZED OLIGOSACCHARIDE SYNTHESIS [J].

ICHIKAWA, Y ;

LOOK, GC ;

WONG, CH .

ANALYTICAL BIOCHEMISTRY, 1992, 202 (02) :215-238

[6]

KREPINSKY JJ, 1996, MODERN METHODS CARBO, P194

[7] Stereoselectivity control in anomeric O-alkylation. Application to the synthesis of C-2 symmetric glycoconjugates. [J].

Lubineau, A ;

Escher, S ;

Alais, J ;

Bonnaffe, D .

TETRAHEDRON LETTERS, 1997, 38 (23) :4087-4090

[8] SOLID-PHASE CHEMICAL-ENZYMATIC SYNTHESIS OF GLYCOPEPTIDES AND OLIGOSACCHARIDES [J].

SCHUSTER, M ;

WANG, P ;

PAULSON, JC ;

WONG, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1135-1136

[9] An efficient synthesis of sialoglycoconjugates on a peptidase-sensitive polymer support [J].

Yamada, K ;

Nishimura, SI .

TETRAHEDRON LETTERS, 1995, 36 (52) :9493-9496

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