Enzymatic Synthesis of Homogeneous Chondroitin Sulfate Oligosaccharides

Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11784-11787. doi: 10.1002/anie.201705638. Epub 2017 Aug 17.

Abstract

Chondroitin sulfate (CS) is a sulfated polysaccharide that plays essential physiological roles. Here, we report an enzyme-based method for the synthesis of a library of 15 different CS oligosaccharides. This library covers 4-O-sulfated and 6-O-sulfated oligosaccharides ranging from trisaccharides to nonasaccharides. We also describe the synthesis of unnatural 6-O-sulfated CS pentasaccharides containing either a 6-O-sulfo-2-azidogalactosamine or a 6-O-sulfogalactosamine residue. The availability of structurally defined CS oligosaccharides offers a novel approach to investigate the biological functions of CS.

Keywords: carbohydrates; chondroitin sulfate; enzymatic synthesis; oligosaccharides; sulfotransferase.

Publication types

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

MeSH terms

  • Carbohydrate Sequence
  • Chondroitin Sulfates / chemical synthesis*
  • Chondroitin Sulfates / chemistry
  • Chromatography, High Pressure Liquid / methods
  • Magnetic Resonance Spectroscopy / methods
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Substrate Specificity
  • Sulfotransferases / chemistry*

Substances

  • Oligosaccharides
  • Chondroitin Sulfates
  • Sulfotransferases