Absolute configuration at C14 and C85 in prymnesin-2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga Prymnesium parvum.
Prymnesin-2 is a potent red tide toxin characterized by a highly oxidized C(90) carbon chain and multiple functional groups. Succeeding the assignment of the relative stereochemistry in the polycyclic-ether segment, the absolute configurations of two chiral centers in linear chain parts were elucidated. The configuration at C14 bearing an amino group was determined to be S by using a chiral anisotropic reagent and that at chlorinated C85 to be S by fluorimetric chiral HPLC comparison between a degradation product and synthetic references.
Morohashi
A
A
Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.
Satake
M
M
Oshima
Y
Y
Igarashi
T
T
Yasumoto
T
T
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004141:Dinoflagellida / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry*; D008968:Molecular Conformation; D061065:Polyketides; D011714:Pyrans / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D006027:Glycosides; D008387:Marine Toxins; D061065:Polyketides; D011714:Pyrans; C440216:prymnesin 1; C440215:prymnesin 2