Chemoenzymatic synthesis of lacto-N-tetrasaccharide and sialyl lacto-N-tetrasaccharides

Carbohydr Res. 2015 Jan 12:401:5-10. doi: 10.1016/j.carres.2014.10.017. Epub 2014 Oct 29.

Abstract

A concise and practical chemoenzymatic synthesis of lacto-N-tetraose, a major component and one of the most common core structures of human milk oligosaccharides (HMOs) was reported. This convergent synthesis relies on the glycosylation of a readily available lactoside acceptor with a lacto-N-biose donor generated from a highly efficient one-pot two-enzyme synthesis.

Keywords: Chemoenzymatic synthesis; Glycosylation; Lacto-N-tetrasaccharide; Sialyl lacto-N-tetrasaccharide; Sialylation.

Publication types

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

MeSH terms

  • Acetylglucosamine / chemistry
  • Bifidobacterium / enzymology
  • Chemistry Techniques, Synthetic
  • Escherichia coli K12 / enzymology
  • Galactokinase / metabolism*
  • Glycosylation
  • Humans
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Phosphorylases / metabolism*

Substances

  • Oligosaccharides
  • lacto-N-neotetraose
  • Phosphorylases
  • Galactokinase
  • Acetylglucosamine