Configuration of the psymberin amide side chain.
[structure: see text] The structure of the amide side chain of psymberin, a potent and selective cytotoxin, is proposed. Syn and anti models of the amide side chain were prepared, and the structural assignment was confirmed by X-ray crystallographic analysis of the anti isomer. Comparison of (1)H and (13)C NMR data establishes homology between the natural product and the synthetic model compound of anti configuration and not the corresponding syn isomer.
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, 08854, USA.
Sezgin
S
Kiren
Lawrence J
LJ
Williams
D000577:Amides / Q000737:chemistry; D000818:Animals; D003374:Coumarins; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D003374:Coumarins; D011714:Pyrans; D011753:Pyrones; C498383:psymberin