Chitinase-Catalyzed Synthesis of Alternatingly N-Deacetylated Chitin:  A Chitin−Chitosan Hybrid Polysaccharide

Akira Makino, Kazuhiro Kurosaki, Masashi Ohmae, and Shiro Kobayashi*†
Department of Materials Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
Biomacromolecules, 2006, 7 (3), pp 950–957
DOI: 10.1021/bm050895d
Publication Date (Web): February 16, 2006
Copyright © 2006 American Chemical Society
*

 To whom correspondence should be addressed. E-mail:  kobayash@ kit.ac.jp. Tel/Fax:  +81-75-724-7688.

,
†

 Present address:  R&D Center for Bio-based Materials, Kyoto Institute of Technology, Kyoto 606-8585, Japan

Abstract

Abstract Image

A chitin−chitosan hybrid polysaccharide (2) having a β(1→4)-linked alternating structure of an N-acetyl-d-glucosamine (GlcNAc) unit and a d-glucosamine (GlcN) unit was synthesized via chitinase-catalyzed polymerization of an oxazoline derivative of a GlcNβ(1→4)GlcNAc monomer (1). Monomer 1 was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis, which belongs to the glycoside hydrolase family 18. Monomer 1 was effectively polymerized by the catalysis of enzymes from Bacillus sp., Serratia marcescens and Streptomyces griseus, under weak alkaline conditions, giving rise to a water-soluble hybrid polysaccharide (2) in good yields. Molecular weights of 2 reached 2020 with using chitinase from Serratia marcescens, which corresponds to 10−12 saccharide units.

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History

  • Published In Issue March 13, 2006
  • Received November 24, 2005
    Revised Manuscript Received January 9, 2006

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