Chemoenzymatic synthesis of glycoconjugate polymers: Greening the synthesis of biomaterials

Yoshiko Miura, Takayasu Ikeda, Natsuko Wada, Hajime Sato, Kazukiyo Kobayashi

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Glycoconjugate polymers with biodegradable poly(viny) alcohol) (PVA) were synthesized via lipase-catalyzed transesterification of sugar alcohols (maltitol and lactitol) with divinyl dicarboxylates and subsequent radical polymerization. The conversion and chemoselectivity in transesterification were dependent on the lipases, the sugar alcohols, and the alkyl chain length of the dicarboxylates. Chemoselective esterification was attained in the presence of lipase from Candida antarctica (lipase CA) to give maltitol 6-vinyl sebacate, lactitol 6-vinyl sebacate, and lactitol 6-vinyl adipate in high yields. Polymerization of these vinyl esters with hydrogen peroxide/ascorbic acid as initiator gave glycoconjugate polymers. These polymers were suggested to take micellar conformations in water and to bind strongly to specific lectins (concanavalin A or RCA120). The biodegradabilities of these polymers were modest but higher than PVA. This simple synthesis will be useful to develop various glycoconjugate polymers with high biological activities due to the multivalent glyco-cluster effect and biodegradability due to their PVA backbone and ester linkage.

Original languageEnglish
Pages (from-to)610-614
Number of pages5
JournalGreen Chemistry
Volume5
Issue number5
DOIs
Publication statusPublished - Oct 1 2003

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Glycoconjugates
Biocompatible Materials
Biomaterials
Polymers
polymer
Lipases
Lipase
Sugar Alcohols
alcohol
Biodegradability
Transesterification
polymerization
ester
sugar
Esters
Candida
Ascorbic acid
Esterification
ascorbic acid
Concanavalin A

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

Cite this

Chemoenzymatic synthesis of glycoconjugate polymers : Greening the synthesis of biomaterials. / Miura, Yoshiko; Ikeda, Takayasu; Wada, Natsuko; Sato, Hajime; Kobayashi, Kazukiyo.

In: Green Chemistry, Vol. 5, No. 5, 01.10.2003, p. 610-614.

Research output: Contribution to journalArticle

Miura, Yoshiko ; Ikeda, Takayasu ; Wada, Natsuko ; Sato, Hajime ; Kobayashi, Kazukiyo. / Chemoenzymatic synthesis of glycoconjugate polymers : Greening the synthesis of biomaterials. In: Green Chemistry. 2003 ; Vol. 5, No. 5. pp. 610-614.
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