具有N-乙酰乳糖胺核心的唾液酸化和岩藻糖基化寡糖的化学酶法合成。

Chemoenzymic synthesis of sialylated and fucosylated oligosaccharides having an N-acetyllactosaminyl core.

作者信息

Kashem M A, Wlasichuk K B, Gregson J M, Venot A P

机构信息

Alberta Research Council, Carbohydrate Research Program, Edmonton, Canada.

出版信息

Carbohydr Res. 1993 Dec 16;250(1):129-44. doi: 10.1016/0008-6215(93)84161-x.

DOI:10.1016/0008-6215(93)84161-x

PMID:8143287

Abstract

Several sialylated and fucosylated oligosaccharides, based upon the N-acetyllactosaminyl core structure, have been synthesized from a single trisaccharide glycoside, beta-D-GlcNAc-(1-->3)-beta-D-Gal-(1-->4)-beta-D-GlcNAc-OCH2(CH2)++ +7CO2CH3, by the sequential use of several glycosyltransferases and one sialidase. In these chemoenzymic syntheses, selective internal monofucosylation of a dimeric N-acetyl-lactosaminyl tetrasaccharide is achieved via two routes. It is demonstrated that the pentasaccharide beta-D-Gal-(1-->4)-beta-D-GlcNAc-(1-->3)-beta-D-Gal-(1-->4)-[alpha- L-Fuc-(1-->3)]-beta-D-GlcNAc-OCH2(CH2)7-CO2CH3 is an acceptor for the rat liver beta-D-Gal-(1-->3/4)-D-Glc-NAc alpha 2,3- and beta-D-Gal-(1-->4)-D-GlcNAc alpha 2,6-sialyltransferases. Among the structures obtained is the terminal hexasaccharide of the CD-65/VIM-2 epitope.

摘要

基于N-乙酰乳糖胺核心结构，通过依次使用几种糖基转移酶和一种唾液酸酶，已从单一三糖糖苷β-D-葡萄糖胺-(1→3)-β-D-半乳糖-(1→4)-β-D-葡萄糖胺-OCH2(CH2)7CO2CH3合成了几种唾液酸化和岩藻糖基化的寡糖。在这些化学酶促合成中，通过两条途径实现了二聚N-乙酰乳糖胺基四糖的选择性内部单岩藻糖基化。结果表明，五糖β-D-半乳糖-(1→4)-β-D-葡萄糖胺-(1→3)-β-D-半乳糖-(1→4)-[α-L-岩藻糖-(1→3)]-β-D-葡萄糖胺-OCH2(CH2)7-CO2CH3是大鼠肝脏β-D-半乳糖-(1→3/4)-D-葡萄糖胺α2,3-和β-D-半乳糖-(1→4)-D-葡萄糖胺α2,6-唾液酸转移酶的受体。所获得的结构中包括CD-65/VIM-2表位的末端六糖。