Sulfobacins A and B, novel von Willebrand factor receptor antagonists. II. 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.
Kamiyama
T
T
Nippon Roche Research Center, Kamakura, Japan.
Umino
T
T
Itezono
Y
Y
Nakamura
Y
Y
Satoh
T
T
Yokose
K
K
D017738:Alkanesulfonic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010980:Platelet Membrane Glycoproteins / Q000037:antagonists & inhibitors*; D011956:Receptors, Cell Surface / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D017738:Alkanesulfonic Acids; D010980:Platelet Membrane Glycoproteins; D011956:Receptors, Cell Surface; C096615:sulfobacin A; C096616:sulfobacin B; C028254:von Willebrand factor receptor