Chemo-enzymatic synthesis of novel oligo-N-acetyllactosamine derivatives having a β(1-4)-β(1-6) repeating unit by using transition sttate analogue substrate

Shin Ichiro Shoda, Yoshinori Misawa, Yousuke Nishijima, Yukiko Tawata, Tomohiko Kotake, Masato Noguchi, Atsushi Kobayashi, Takeshi Watanabe

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Chitinase-catalyzed hydrolytic and transglycosylating behavior of 1,2-oxazoline derivative of N-acetyllactosamine (LacNAc-oxa) 1 has been investigated. An extremely rapi d hydrolysis (ring-opening of the oxazoline moiety) could be observed, suggesting that 1 behaves as a transition state analogue substrate for chitinase A1 (Bacillus circulans WL-12). This disaccharide monomer 1 was found to polymerize under basic conditions, giving rise to novel oligosaccharides having a β(1-4)-β(1-6) repeating unit in the main chain. The degree of polymerization of the resulting oligosaccharides was up to 5. This is the first example of enzymatic glycosylation reaction forming a β(1-6) bond catalyzed by chitinase.

Original languageEnglish
Pages (from-to)477-484
Number of pages8
JournalCellulose
Volume13
Issue number4
DOIs
Publication statusPublished - 2006 Aug 1

Keywords

  • 1,2-Oxazoline derivative
  • Chitinase
  • Enzymatic polyaddition
  • N-acetyllactosamine
  • Oligo-N-acetyllactosaminoglycan

ASJC Scopus subject areas

  • Polymers and Plastics

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