Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides
Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides
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DOI：
10.1002/pola.20385
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发表时间：
2004-09
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通讯作者：
Yoshiko Miura;Natsuko Wada;Yoshihiro Nishida;Hiroshi Mori;Kazukiyo Kobayashi
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文献类型：
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作者：
Yoshiko Miura;Natsuko Wada;Yoshihiro Nishida;Hiroshi Mori;Kazukiyo Kobayashi
本文报道了含非还原性二糖[α-D-吡喃葡萄糖基-（1-1）-α-D-吡喃葡萄糖苷（海藻糖）和α-D-吡喃半乳糖基-（1-1）-α-D-吡喃葡萄糖苷（半乳糖型海藻糖）]的糖缀合物聚合物的化学酶促合成及其识别功能。脂肪酶催化的二糖与癸二酸二乙烯酯的酯化在海藻糖的主要Glc 6-OH位置和Gal型海藻糖的Gal 6-OH位置处是完全选择性的。所得乙烯基酯可聚合以产生具有聚（乙烯醇）主链的糖缀合物聚合物。由于糖簇效应，糖缀合物聚合物与凝集素（伴刀豆球蛋白A和Bandeiraera simplicifolia）的相互作用被放大。该聚合物具有与Gb 2二糖类似的立体化学结构，具有抑制滋贺毒素-1的活性。© 2004 Wiley Periodicals，Inc.聚合物科学杂志A部分：聚合物化学42：4598-4606，2004
Here we report the chemoenzymatic synthesis and recognition function of glycoconjugate polymers carrying nonreducing disaccharides [α-D-glucopyranosyl-(1-1)-α-D-glucopyranoside (trehalose) and α-D-galactopyranosyl-(1-1)-α-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 α-D-galactopyranosyl-(1-1)-α-D-glucopyranoside shows inhibition activity against Shiga toxin-1 based on a stereochemical structure similar to that of globosyl Gb2 disaccharide. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4598–4606, 2004