Do amines react with protonated peptides in the gas phase via transacylation reactions to induce peptide bond cleavage?
Details
Publication Year 2000, Volume 14, Issue #18, Page 1707-1716
Journal Title
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
Publication Type
Journal Article
Abstract
The proposal that protonated peptides react with NH3 in the gas phase via transacylation reactions (Tabet at at, Spectros, Int. J, 5: 253 1987) has been investigated by studying the reactions of the fixed charge derivatives [RC(O)NMe2CH2CO2H](+) (R=Me and Ph) with pyridine and triethylamine and the reactions of protonated glycine oligomers and leucine enkenphalin with butylamine, Under the near thermal conditions of the quadrupole ion trap, both the fixed charge derivatives as well as the protonated peptides react with the amines via either proton transfer or proton bound dimer formation, Collision induced dissociation of protonated peptides in the presence of butylamine yields b(n) and y(n) sequence ions as well as [b(n) + BuNH2](+) and [y(n)+BuNH2](+) ions. MS3 experiments reveal that a major route to these [b(n) + BuNH2](+) and [y(n) + BuNH2](+) ions involves ion-molecule reactions between the b(n) and y(n) sequence ions and butylamine, MS4 experiments, carried out to determine the nature of the [b(n) + BuNH2](+) ions, reveal that they correspond to a mixture of hydrogen bonded (i.e. proton bound dimer) and covalent amide bond structures, Copyright (C) 2000 John Wiley & Sons, Ltd.
Publisher
JOHN WILEY & SONS LTD
Keywords
ION-MOLECULE REACTIONS; TANDEM MASS-SPECTROMETRY; GLYCINE OLIGOMERS; H/D EXCHANGE; AB-INITIO; BASICITIES; FRAGMENTATION; DISSOCIATION; AFFINITIES; SPECTRA
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Creation Date: 2000-01-01 12:00:00
Last Modified: 0001-01-01 12:00:00
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