Characterization of the physiological substrate for lipopolysaccharide heptosyltransferases I and II

J Endotoxin Res. 2001;7(4):263-70.


L-Glycero-D-manno-heptopyranose is a characteristic compound of many lipopolysaccharide (LPS) core structures of Gram-negative bacteria. In Escherichia coli two heptosyltransferases, namely WaaC and WaaF, are known to transfer L-glycero-D-manno-heptopyranose to Re-LPS and Rd(2)-LPS, respectively. It had been proposed that both reactions involve ADPL-glycero-D-manno-heptose as a sugar donor; however, the structure of this nucleotide sugar had never been completely elucidated. In the present study, ADPL-glycero-D-manno-heptose was isolated from a heptosyltransferase-deficient E. coli mutant, and its structure was determined by nuclear magnetic resonance spectroscopy and matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry as ADPL-glycero-beta-D-manno-heptopyranose. This compound represented the sole constituent of the bacterial extract that was accepted as a sugar donor by heptosyltransferases I and II in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Diphosphate Sugars / metabolism
  • Escherichia coli / enzymology
  • Glycosyltransferases / metabolism*
  • Heptoses / chemistry
  • Heptoses / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Substrate Specificity / physiology


  • Adenosine Diphosphate Sugars
  • Heptoses
  • glycero-alpha-manno-heptopyranose
  • glycero-manno-heptose
  • Glycosyltransferases
  • heptosyltransferase
  • lipooligosaccharide 1,5-heptosyltransferase