A Unique Collision-Induced Dissociation Reaction of Cholamine Derivatives of Certain Prostaglandins

Journal of the American Society for Mass Spectrometry
Dong SunJingkai Gu

Abstract

Prostaglandins (PGs) are biologically active metabolites of arachidonic acid containing 20 carbon atoms, a cyclic moiety, and two side chains (A and B) in common. The bioassay of PGs requires high sensitivity because of their low concentration in tissues and blood and has usually been carried out by electrospray ionization tandem mass spectrometry (ESI-MS/MS) in the negative ion mode. Chemical derivatization of PG carboxylic acid groups to introduce positive charge-carrying groups is an established strategy to improve the sensitivity and selectivity of such assays. In this study, we exploited this approach for structural identification of a series of PGs using cholamine derivatization through an amidation reaction. However, we observed that collision-induced dissociation of these derivatives gave rise to unexpected product ions that we postulated were formed by unique long-range intramolecular reactions resulting in dehydration of the B chain accompanied by fragmentation of the A chain through an unusual Hofmann rearrangement. Evidence for the proposed mechanism is presented based on ESI-MS/MS and high resolution mass spectrometry studies of cholamine derivatives of PGE1, PGE2, PGD2, PGI2, and C-17 methyl deuterium-labeled lima...Continue Reading

References

Jun 18, 2005·Analytical Biochemistry·Robert C MurphySimona Zarini
Aug 14, 2010·Analytical Chemistry·James G BollingerMichael H Gelb
Dec 24, 2010·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·A KretschmerW M A Niessen
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Mar 26, 2013·Drug Discoveries & Therapeutics·T Santa

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Citations

Feb 6, 2020·Rapid Communications in Mass Spectrometry : RCM·Venkateswara R NarreddulaStephen J Blanksby

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