A facile enzymatic synthesis of cellooligosaccharide derivatives using β-lactosyl fluoride

Shin ichiro Shoda, Tatsuya Kawasaki, Kei Obata, Shiro Kobayashi

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

A convenient method for the preparation of cellooligosaccharide derivatives has been developed that uses β-lactosyl fluoride as the glycosyl donor. The reaction consists of the following enzymatic processes; (1) a cellulase-catalyzed regio- and stereo-selective lactosylation of a β-cellobioside as the glycosyl acceptor, utilizing the transglycosylating ability of an enzyme-substrate complex formed from β-lactosyl fluoride and cellulase; (2) β-d-galactosidase-catalyzed regioselective cleavage of the terminal d-galactose unit from the lactosylated product, giving rise to a β-cellotrioside derivative. A cellotetraoside derivative has successfully been prepared in a stereo- and regio-selective manner by repeating these enzymatic reactions and using the resulting β-cellotrioside as starting material.

Original languageEnglish
Pages (from-to)127-137
Number of pages11
JournalCarbohydrate Research
Volume249
Issue number1
DOIs
Publication statusPublished - 1993 Oct 18

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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