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Glycobiology Advance Access published online on December 17, 2002
Glycobiology, doi:10.1093/glycob/cwg032
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Submitted on June 10, 2002
Revised on November 18, 2002
Accepted on November 23, 2002

© 2002 Oxford University Press

ORIGINAL ARTICLES

Chemoenzymatic synthesis and application of glycopolymers containing multivalent sialyloligosaccharides with a poly(L-glutamic acid) backbone for inhibition of infection by influenza viruses

Kazuhide Totani 1, Takeshi Kubota 1, Takao Kuroda 1, Takeomi Murata 1, Kazuya I.-P. Jwa Hidari 2, Takashi Suzuki 2, Yasuo Suzuki 2, Kazukiyo Kobayashi 3, Hisashi Ashida 4, Kenji Yamamoto 4, Taichi Usui 1*

1 Department of Applied Biological Chemistry, Shizuoka University, Ohya 836, Shizuoka 422-8529, Japan
2 Department of Biochemistry, University of Shizuoka, School of Pharmaceutical Science, 52-1 Yada, Shizuoka 422-8526, Japan
3 Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan
4 Department of Applied Molecular Biology, Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan

* To whom correspondence should be addressed. E-mail: actusui{at}agr.shizuoka.ac.jp.

Abstract

Highly water-soluble glycopolymers with poly({alpha}-L-glutamic acid) (PGA) backbones carrying multivalent sialyl oligosaccharides units were chemoenzymatically synthesized as polymeric inhibitors of infection by human influenza viruses. p-Aminophenyl disaccharide glycosides were coupled with {gamma}-carboxyl groups of PGA side chains and enzymatically converted to Neu5Ac{alpha}2-3Gal{beta}1-4GlcNAc{beta}-, Neu5Ac{alpha}2-6Gal{beta}1-4GlcNAc{beta}-, Neu5Ac{alpha}2-3Gal{beta}1-3GalNAc{alpha}-, and Neu5Ac{alpha}2-3Gal{alpha}1-3GalNAc{beta}- units, respectively, by {alpha}2,3- or {alpha}2,6-sialytransferases. The glycopolymers synthesized were used for neutralization of human influenza A and B virus infection as assessed by measurement of the degree of cytopathic inhibitory effect in virus-infected MDCK cells. Among the glycopolymers tested, {alpha}2,6-sialo-PGA with a high molecular weight (260 kDa) most significantly inhibited infection by an influenza A virus strain, A/Memphis/1/71 (H3N2), which predominantly binds to {alpha}2-6 Neu5Ac residue. The {alpha}2,6-sialo-PGA also inhibited infection by an influenza B virus, B/Lee/40. The binding preference of viruses to terminal sialic acids was affected by core determinants of the sugar chain, Gal{beta}1-4GlcNAc{beta}- or Gal{beta}1-3GalNAc{alpha}/{beta}- units. Inhibition of infection by viruses was remarkably enhanced by increasing the molecular weight and sialic acid content of glycopolymers.


Key words: influenza virus, inhibition, glycopolymers, poly(L-glutamic acid), sialyloligosaccharides
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