Abstract
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.
Original language | English |
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Pages (from-to) | 4598-4606 |
Number of pages | 9 |
Journal | Journal of Polymer Science, Part A: Polymer Chemistry |
Volume | 42 |
Issue number | 18 |
DOIs | |
Publication status | Published - Sep 15 2004 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Polymers and Plastics
- Organic Chemistry
- Materials Chemistry