Absolute configuration at C14 and C85 in prymnesin-2, a potent hemolytic and ichthyotoxic glycoside isolated from the red tide alga Prymnesium parvum |
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Authors: | Morohashi A Satake M Oshima Y Igarashi T Yasumoto T |
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Affiliation: | Graduate School of Agricultural Science, Tohoku University, Sendai, Japan. |
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Abstract: | 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. |
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Keywords: | prymnesin‐2 red tide toxin absolute configuration anisotropic NMR reagent fluorimetric chiral HPLC |
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