Enzymatic synthesis of vancomycin derivatives using galactosyltransferase and sialyltransferase

J Antibiot (Tokyo). 2011 Jan;64(1):103-9. doi: 10.1038/ja.2010.131. Epub 2010 Dec 1.

Abstract

Analogs of vancomycin and pseudo-vancomycin with new sugar attachments in mono- and di-saccharide form have been enzymatically synthesized by glycosylation with overexpressed glycosyltransferases, β1,4-galactosyltransferase and α2,3-sialyl transferases. All four analogs, including galactose-containing derivatives (6 and 8) and galactose- and sialic acid-containing derivatives (7 and 9) were prepared and characterized by HPLC, LC-MS, NMR and MIC test.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Chromatography, Liquid
  • Galactose / analogs & derivatives
  • Galactose / chemistry
  • Galactose / metabolism
  • Galactose / pharmacology
  • Galactosyltransferases / metabolism*
  • Glycosylation
  • Glycosyltransferases / metabolism*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • N-Acetylneuraminic Acid / analogs & derivatives
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / metabolism
  • N-Acetylneuraminic Acid / pharmacology
  • Vancomycin / analogs & derivatives*
  • Vancomycin / biosynthesis*
  • Vancomycin / chemistry
  • Vancomycin / pharmacology

Substances

  • Anti-Bacterial Agents
  • Vancomycin
  • Glycosyltransferases
  • Galactosyltransferases
  • N-Acetylneuraminic Acid
  • Galactose