Fast atom bombardment and collision-induced dissociation of prostaglandins and thromboxanes: Some examples of charge remote fragmentation

Joseph A. Zirrolli, Enrico Davoli, Laura Bettazzoli, Michael Gross, Robert C. Murphy

Research output: Contribution to journalArticle

Abstract

The mass spectra of products found by collisional activation of selected prostaglandins and thromboxanes were studied by tandem mass spectrometry as barium carboxylate salts and as carboxylate anions. Collision-induced dissociation (CID) of these closed shell ions generated by fast atom bombardment mass spectrometry reveals a wealth of structural information for these hydroxy acids. Decomposition reactions were found to be dependent upon the eicosanoid ring structure and the type of ion being studied, either positive or negative ion. The bariated carboxylate salts undergo reactions by processes that are similar to those previously characterized as charge remote mechanisms in which neutral species are lost as in thermal and photolytic decompositions. The most abundant ion is formed by loss of water from each of the hydroxyl groups present on the prostaglandin or thromboxane structure. For these multifunctionalized eicosanoids, typical patterns of decomposition emerge as characteristic of the oxygen substituents present along the carbon chain of the eicosanoid structure. The structural information obtained from the barium salts along with those from the carboxylate anions is substantially different, yet the structural information from each process is complementary. The CIDs of positive ions (metalated salts) provide structural information concerning the substituents between the carboxyl group and C 12 of the eicosanoid structure, whereas the decompositions of the carboxylate anions (negative ion mode) provide data concerning structure alterations of the eicosanoid structure between C 15 and C 20

Original languageEnglish
Pages (from-to)325-335
Number of pages11
JournalJournal of the American Society for Mass Spectrometry
Volume1
Issue number4
DOIs
Publication statusPublished - Jul 1990

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Eicosanoids
Thromboxanes
Prostaglandins
Ions
Atoms
Salts
Decomposition
Anions
Barium
Mass spectrometry
Negative ions
Positive ions
Hydroxy Acids
Fast Atom Bombardment Mass Spectrometry
Hydroxyl Radical
Tandem Mass Spectrometry
Carbon
Chemical activation
Oxygen
Hot Temperature

ASJC Scopus subject areas

  • Spectroscopy
  • Structural Biology

Cite this

Fast atom bombardment and collision-induced dissociation of prostaglandins and thromboxanes : Some examples of charge remote fragmentation. / Zirrolli, Joseph A.; Davoli, Enrico; Bettazzoli, Laura; Gross, Michael; Murphy, Robert C.

In: Journal of the American Society for Mass Spectrometry, Vol. 1, No. 4, 07.1990, p. 325-335.

Research output: Contribution to journalArticle

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