Sulfobacins A and B, novel von Willebrand factor receptor antagonists. II. Structural elucidation

J Antibiot (Tokyo). 1995 Sep;48(9):929-36. doi: 10.7164/antibiotics.48.929.

Abstract

Sulfobacins A and B are novel von Willebrand factor (vWF) receptor antagonists produced by Chryseobacterium sp. NR 2993. The structures of sulfobacins A and B have been determined to be (2R,3R)-3-hydroxy-2-[(R)-3-hydroxy-15-methylhexadecanamido]-15- methylhexadecanesulfonic acid and (2R,3R)-3-hydroxy-15-methyl-2-[13-methyltetradecanamido]- hexadecanesulfonic acid, respectively, by various 2D NMR experiments and by methanolysis. The absolute configurations of the sulfobacins were determined by a modified MOSHER's method. The structures are related to sulfonolipids, major components of the cell envelope of gliding bacteria of the genus Cytophaga.

MeSH terms

  • Alkanesulfonic Acids / chemistry*
  • Molecular Structure
  • Platelet Membrane Glycoproteins / antagonists & inhibitors*
  • Receptors, Cell Surface / antagonists & inhibitors*
  • Stereoisomerism

Substances

  • Alkanesulfonic Acids
  • Platelet Membrane Glycoproteins
  • Receptors, Cell Surface
  • sulfobacin A
  • sulfobacin B
  • von Willebrand factor receptor