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Characterization of Z‐blocked isomeric dipeptides by fast atom bombardment tandem mass spectrometry and kinetic energy release measurements
Author(s) -
Mammoliti Ezio,
Sindona Giovanni,
Uccella Nicola
Publication year - 1992
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210270422
Subject(s) - chemistry , kinetic energy , protonation , decarboxylation , mass spectrometry , tandem mass spectrometry , fast atom bombardment , tandem , activation energy , stereochemistry , ion , medicinal chemistry , analytical chemistry (journal) , computational chemistry , organic chemistry , chromatography , catalysis , physics , materials science , quantum mechanics , composite material
Abstract Fast‐ and slow‐reacting, protonated, Z‐blocked (Z = benzyloxycarbonyl) phenylalanylphenylalanine and alanylpbenylalanyl 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 2 elimination allows the distinction of the S , S from the R , S isomers by moss‐analysed ion kinetic‐energy experiments.