Chemo-enzymatic synthesis of Lacto-N-biose I catalyzed by β-1,3-galactosidase from Bacillus circulans using 4,6-dimethoxy-1,3,5-triazin-2-yl β-galactopyranoside as a glycosyl donor

Biosci Biotechnol Biochem. 2021 Jun 24;85(7):1716-1719. doi: 10.1093/bbb/zbab071.

Abstract

Chemo-enzymatic synthesis of lacto-N-biose I (LNB) catalyzed by β-1,3-galactosidase from Bacillus circulans (BgaC) has been developed using 4,6-dimethoxy-1,3,5-triazin-2-yl β-galactopyranoside (DMT-β-Gal) and GlcNAc as the donor and acceptor substrates, respectively. BgaC transferred the Gal moiety to the acceptor, giving rise to LNB. The maximum yield of LNB was obtained at the acceptor : donor substrate ratio of 1:30.

Keywords: lacto-N-biose I; transglycosylation; triazinyl glycoside; β-1,3-galactosidase.

MeSH terms

  • Acetylglucosamine / analogs & derivatives
  • Acetylglucosamine / metabolism
  • Bacillus / enzymology*
  • Catalysis
  • Glycosylation
  • Kinetics
  • Stereoisomerism
  • Substrate Specificity
  • beta-Galactosidase / metabolism*

Substances

  • galactosyl-1,3-N-acetylglucosamine
  • beta-Galactosidase
  • Acetylglucosamine

Supplementary concepts

  • Bacillus circulans