Novel mass spectral fragmentation of heptafluorobutyryl derivatives of acyl analogues of platelet-activating factor

Susan T. Weintraub, R. Neal Pinckard, Timothy G. Heath, Douglas A. Gage

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Direct derivatization of the acyl analogue of platelet-activating factor (acyl.PAF) with heptafluorobutyric anhydride results in replacement of the phosphocholine moiety with a heptafluorobutyryl (HFB) group. Electron capture (EC) mass spectrometric analysis of this compound that makes use of negative ion detection along with subsequent accurate mass measurement and tandem mass spectrometry studies revealed that in addition to expected fragmentation due to losses of elements of HF, ketene, and/or acetic acid, there is a rearrangement reaction between the HFB group and the subsequent on carbon-2 of the glycerol backbone. For 2-acetyl isomers, this fragmentation yields a characteristic ion at m/z 237; for 1-acetyl isomers, the analogous ion is observed at [M-135]-, along with a corresponding carboxylate anion. The use of the HFB derivative is invaluable for analysis of PAF homologues and analogues because it provides detailed structural information in combination with the high sensitivity of a gas chromatography combined with EC-mass spectrometry assay.

Original languageEnglish (US)
Pages (from-to)476-482
Number of pages7
JournalJournal of the American Society for Mass Spectrometry
Volume2
Issue number6
DOIs
StatePublished - Dec 1991

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

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