Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides

被引：24

作者：

Miura, Y

Wada, N

Nishida, Y

Mori, H

Kobayashi, K ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Gifu Pharmaceut Univ, Dept Publ Hlth Pharm, Gifu 5028585, Japan

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2004年 / 42卷 / 18期

关键词：

chemoenzymatic synthesis; glycoconjugate polymers; nonreducing disaccharides; biomaterials; functionalization of polymers; sensors;

D O I：

10.1002/pola.20385

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Here we report the chemoenzymatic synthesis and recognition function of glycoconjugate polymers carrying nonreducing disaccharides [alpha-D-glucopyranosyl-(1-1)alpha-D-glucopyranoside (trehalose) and alpha-D-galactopyranosyl-(1-1)-alpha-D-glucopyranoside (Gal-type trehalose)]. The lipase-catalyzed esterification of the disaccharides with divinyl sebacate is completely selective at the primary Glc 6-OH position of trehalose and at the Gal 6-OH position of Gal-type trehalose. The resultant vinyl esters can be polymerized to yield glycoconjugate polymers with poly(vinyl alcohol) backbones. The interactions of the glycoconjugate polymers with lectins (concanavalin A and Bandeiraera simplicifolia) are amplified because of the glycocluster effect. The polymer carrying pendant alpha-D-galactopyranosyl-(1-1)-alpha-D-glucopyranoside shows inhibition activity against Shiga toxin-1 based on a stereochemical structure similar to that of globosyl Gb2 disaccharide. (C) 2004 Wiley Periodicals, Inc.

引用

页码：4598 / 4606

页数：9

共 32 条

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