SULFOBACIN-A AND SULFOBACIN-B, NOVEL VON-WILLEBRAND-FACTOR RECEPTOR ANTAGONISTS .2. STRUCTURAL ELUCIDATION

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.