Premium
Absolute configuration at C14 and C85 in prymnesin‐2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga Prymnesium parvum
Author(s) -
Morohashi Akio,
Satake Masayuki,
Oshima Yasukatsu,
Igarashi Tomoji,
Yasumoto Takeshi
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.1184
Subject(s) - chemistry , absolute configuration , chirality (physics) , stereochemistry , reagent , glycoside , ether , chiral column chromatography , red tide , organic chemistry , enantiomer , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark , ecology , biology
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. Chirality 13:601–605, 2001. © 2001 Wiley‐Liss, Inc.