β-galactosidase-catalyzed intramolecular transglycosylation

被引：11

作者：

Komba, S ^{[1
]}

Ito, Y ^{[1
]}

机构：

[1] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 48期

关键词：

galactosidase; intramolecular transglycosylation; N-acetyllactosamine; sialyltransferase;

D O I：

10.1016/S0040-4039(01)01826-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel transglycosylation strategy for efficient preparation of N-acetyllactosamine (Gal beta1 --> 4GlcNAc, LacNAc) and sialyl LacNAc was developed using beta -galactosidase from Bacillus circulans. In order to minimize the competing hydrolysis by forcing the enzymatic transglycosylation to proceed in an intramolecular manner, a novel substrate 9 carrying the donor (galactose) and the acceptor (N-acetylglucosamine) components linked via a 2-hydroxy-5-nitro-benzylalcohol derived tether was prepared. Treatment with beta -galactosidase from B. circulans afforded the transglycosylation product 11 in 26% yield. Furthermore, addition of sialyltransferase and CMP-sialic acid to this system gave sialyl LacNAc 18 in 39% yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8501 / 8505

页数：5

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