Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms

Chem Commun (Camb). 2015 Jun 28;51(51):10310-3. doi: 10.1039/c5cc03746h.

Abstract

Galacto-N-biose (GNB) derivatives were efficiently synthesized from galactose derivatives via a one-pot two-enzyme system containing two promiscuous enzymes from Bifidobacterium infantis: a galactokinase (BiGalK) and a d-galactosyl-β1-3-N-acetyl-d-hexosamine phosphorylase (BiGalHexNAcP). Mono-sialyl and di-sialyl galacto-N-biose derivatives were then prepared using a one-pot two-enzyme system containing a CMP-sialic acid synthetase and an α2-3-sialyltransferase or an α2-6-sialyltransferase.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bifidobacterium / enzymology
  • Disaccharides / chemical synthesis*
  • Galactans / chemical synthesis*
  • Galactokinase / chemistry
  • Galactokinase / metabolism
  • Galactosyltransferases / chemistry
  • Galactosyltransferases / metabolism
  • N-Acylneuraminate Cytidylyltransferase / chemistry
  • N-Acylneuraminate Cytidylyltransferase / metabolism
  • Sialic Acids / chemical synthesis*
  • Sialyltransferases / chemistry
  • Sialyltransferases / metabolism
  • beta-D-Galactoside alpha 2-6-Sialyltransferase
  • beta-Galactoside alpha-2,3-Sialyltransferase

Substances

  • Disaccharides
  • Galactans
  • Sialic Acids
  • Galactosyltransferases
  • beta-1,3-galactosyl-N-acetylhexosamine phosphorylase
  • Sialyltransferases
  • Galactokinase
  • N-Acylneuraminate Cytidylyltransferase
  • beta-D-Galactoside alpha 2-6-Sialyltransferase
  • beta-Galactoside alpha-2,3-Sialyltransferase