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Structural confirmation of ostreocin‐D by application of negative‐ion fast‐atom bombardment collision‐induced dissociation tandem mass spectrometric methods
Author(s) -
Ukena Takanori,
Satake Masayuki,
Usami Masaya,
Oshima Yasukatsu,
Fujita Tsuyoshi,
Naoki Hideo,
Yasumoto Takeshi
Publication year - 2002
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.867
Subject(s) - chemistry , tandem mass spectrometry , collision induced dissociation , fast atom bombardment , palytoxin , ion , tandem , dissociation (chemistry) , mass spectrometry , analytical chemistry (journal) , chromatography , organic chemistry , biochemistry , composite material , toxin , materials science
Abstract Negative‐ion fast‐atom bombardment collision‐induced dissociation tandem mass spectrometric (FAB‐CID‐MS/MS) methodology was successfully applied to verify the highly complex structure of ostreocin‐D (MW 2633), a new palytoxin analog isolated from the marine dinoflagellate Ostreopsis siamensis and proposed to be 42‐hydroxy‐3,26‐didemethyl‐19,44‐dideoxypalytoxin based on NMR data. The charge‐remote fragmentations were facilitated by a negative charge introduced to a terminal amino group or to a hydroxyl group at the other terminus by a reaction with 2‐sulfobenzoic acid cyclic anhydride. Product ions generated from the [M − H] − ions provided information on the structural details of ostreocin‐D. Comparisons between the spectral data for ostreocin‐D and palytoxin also provided a rational basis for the assignments of product ions. Copyright © 2002 John Wiley & Sons, Ltd.