Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides

Yoshiko Miura, Natsuko Wada, Yoshihiro Nishida, Hiroshi Mori, Kazukiyo Kobayashi

Research output: Contribution to journalArticle

23 Citations (Scopus)

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 languageEnglish
Pages (from-to)4598-4606
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume42
Issue number18
DOIs
Publication statusPublished - Sep 15 2004
Externally publishedYes

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Trehalose
Glycoconjugates
Disaccharides
Polymers
Shiga Toxin 1
Lipases
Esterification
Concanavalin A
Lipase
Lectins
Esters
Alcohols

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides. / Miura, Yoshiko; Wada, Natsuko; Nishida, Yoshihiro; Mori, Hiroshi; Kobayashi, Kazukiyo.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 42, No. 18, 15.09.2004, p. 4598-4606.

Research output: Contribution to journalArticle

Miura, Yoshiko ; Wada, Natsuko ; Nishida, Yoshihiro ; Mori, Hiroshi ; Kobayashi, Kazukiyo. / Chemoenzymatic synthesis of glycoconjugate polymers starting from nonreducing disaccharides. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2004 ; Vol. 42, No. 18. pp. 4598-4606.
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