A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of Sialyl Lewisx mimics

Yoshihiro Nishida, Hirotaka Uzawa, Tadashi Toba, Kenji Sasaki, Hirosato Kondo, Kazukiyo Kobayashi

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

A highly practical synthetic approach is described for artificial L- and P-selectin blockers. The synthesis involves radical bi- and terpolymerizations of p-(N-acrylamido)phenyl 3- or/and 6-sulfo-β-D-galactoside with allyl α-L-fucoside in the presence of acrylamide. Each of the two glycosyl monomers constructs a key carbohydrate module responsible for selectins/sulfated sialyl Lewisx (sLex) bindings. Whereas an acrylamide copolymer carrying 3-sulfo-galactoside showed no activity for any selectins, the fucosylated terpolymer showed a potent activity to block both of P- and L-selectins/sLex binding at a concentration of a few micrograms per milliliter. The enhanced activity is apparently ascribed to the cooperative binding effects of the fucoside and the 3-sulfo-galactoside residues.

Original languageEnglish
Pages (from-to)68-74
Number of pages7
JournalBiomacromolecules
Volume1
Issue number1
Publication statusPublished - Mar 1 2000
Externally publishedYes

Fingerprint

L-Selectin
Galactosides
P-Selectin
Carbohydrates
Copolymerization
Selectins
Acrylamide
Monomers
Terpolymerization
Terpolymers
Copolymers

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Polymers and Plastics
  • Materials Chemistry

Cite this

A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of Sialyl Lewisx mimics. / Nishida, Yoshihiro; Uzawa, Hirotaka; Toba, Tadashi; Sasaki, Kenji; Kondo, Hirosato; Kobayashi, Kazukiyo.

In: Biomacromolecules, Vol. 1, No. 1, 01.03.2000, p. 68-74.

Research output: Contribution to journalArticle

Nishida, Yoshihiro ; Uzawa, Hirotaka ; Toba, Tadashi ; Sasaki, Kenji ; Kondo, Hirosato ; Kobayashi, Kazukiyo. / A facile synthetic approach to L- and P-selectin blockers via copolymerization of vinyl monomers constructing the key carbohydrate modules of Sialyl Lewisx mimics. In: Biomacromolecules. 2000 ; Vol. 1, No. 1. pp. 68-74.
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