Backbone fragmentations of [M–H]– anions from peptides. Reinvestigation of the mechanism of the beta prime cleavage

Tianfang Wang; T T Nha Tran; A N Calabrese; J H Bowie

doi:10.1002/rcm.6297

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Backbone fragmentations of [M–H]– anions from peptides. Reinvestigation of the mechanism of the beta prime cleavage

Tianfang Wang, T T Nha Tran, A N Calabrese and J H Bowie

Rapid Communications in Mass Spectrometry, Vol.26(16), pp.1832-1840

2012

DOI: https://doi.org/10.1002/rcm.6297

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Abstract

RATIONALE: In experimental study has shown that the structure of a β' ion proposed earlier is incorrect. Backbone cleavage β' anions have structures R(NH-) from systems [[RNHCH(X)CONHCH(Y)CO2H (or C-terminal CONH2) - H]- (where R is the rest of the peptide molecule and X and Y represent the α side chains of the individual amino acid residues). METHODS: Ab initio calculations were carried out at the CAM-B3LYP/6-311++g(d,p) level of theory. CONCLUSIONS: The calculations suggest that RNH- ions are formed by Sni cyclisation processes involving either (i) the C-terminal CO2- or C-terminal [CONH]- as appropriate, or (ii) an enolate ion [-NHC-(Y)-] cyclising at the backbone CH of the -CH(X)- group. Concomitant C-N bond cleavage then liberates an RNH- ion, processes which can occur along the peptide backbone.

Details

Title: Backbone fragmentations of [M–H]– anions from peptides. Reinvestigation of the mechanism of the beta prime cleavage
Authors: Tianfang Wang (Author) - University of Adelaide
T T Nha Tran (Author) - University of Adelaide
A N Calabrese (Author) - University of Adelaide
J H Bowie (Author) - University of Adelaide
Publication details: Rapid Communications in Mass Spectrometry, Vol.26(16), pp.1832-1840
Publisher: John Wiley & Sons Ltd.
Date published: 2012
DOI: 10.1002/rcm.6297
ISSN: 0951-4198
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
Language: English
Record Identifier: 99450499702621
Output Type: Journal article

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