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Characterization of Z-blocked isomeric dipeptides by fast atom bombardment tandem mass spectrometry and kinetic energy release measurements

✍ Scribed by Ezio Mammoliti; Giovanni Sindona; Nicola Uccella

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 551 KB
Volume: 27
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210270422

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✦ Synopsis

Fast-and slow-reacting, protonated, Z-blocked (Z = benzyloxycarbonyl) phenylalanylphenylalanine and alanylphenylalanyl diasteromeric dipeptides undergo decarboxylation through two competing pathways assisted by the migration of the urethane benzyl group either to the terminal or to the amidic nitrogens. The reaction mechanism has been proved by tandem mass spectrometric experiments. The different kinetic energy released associated with CO, elimination allows the distinction of the S,S from the R,S isomers by mass-analysed ion kinetic-energy experiments.

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