Enzymatic polymerization to novel polysaccharides having a glucose-N-acetylglucosamine repeating unit, a cellulose - Chitin hybrid polysaccharide

Shiro Kobayashi, Akira Makino, Hironori Matsumoto, Shigeru Kunii, Masashi Ohmae, Toshitsugu Kiyosada, Ken Makiguchi, Akira Matsumoto, Michinobu Horie, Shin Ichiro Shoda

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48 Citations (Scopus)

Abstract

A cellulose-chitin hybrid polysaccharide having alternatingly β(1→4)-linked D-glucose (Glc) and N-acetyl-D-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazoline monomer of Glcβ(1→4)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitin hybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecular weight (Mn) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer of GlcNAcβ(1→4)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzyme catalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselective manner. Mn of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealed that these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnatural hybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils.

Original languageEnglish
Pages (from-to)1644-1656
Number of pages13
JournalBiomacromolecules
Volume7
Issue number5
DOIs
Publication statusPublished - 2006 May 1

ASJC Scopus subject areas

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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    Kobayashi, S., Makino, A., Matsumoto, H., Kunii, S., Ohmae, M., Kiyosada, T., Makiguchi, K., Matsumoto, A., Horie, M., & Shoda, S. I. (2006). Enzymatic polymerization to novel polysaccharides having a glucose-N-acetylglucosamine repeating unit, a cellulose - Chitin hybrid polysaccharide. Biomacromolecules, 7(5), 1644-1656. https://doi.org/10.1021/bm060094q