Journal article
Diagnostic di- and triphosphate cyclisation in the negative ion electrospray mass spectra of phosphoSer peptides
Rapid Communications in Mass Spectrometry, Vol.25(18), pp.2649-2656
2011
Abstract
It has been shown previously that [M-H]- anions of small peptides containing two phosphate residues undergo cyclisation of the phosphate groups, following collision-induced dissociation (CID), to form a characteristic singly charged anion A (H3P2O7-, m/z 177). In the present study it is shown that the precursor anions derived from the diphosphopeptides of caerin 1.1 [GLLSVLGSVAKHVLPHVVPVIAEHL(NH2)] and frenatin 3 [GLMSVLGHAVGNVLGGLFKPKS(OH)] also form the characteristic product anion A (m/z 177). Both of the precursor peptides show random structures in water, but partial helices in membrane-mimicking solvents [e.g. in d3-trifluoroethanol/water (1:1)]. In both cases the diphosphopeptide precursor anions must have flexible conformations in order to allow approach of the phosphate groups with consequent formation of A: for example, the two pSer groups of 4,22-diphosphofrenatin 3 are seventeen residues apart. Finally, CID tandem mass spectrometric (MS/MS) data from the [M-H]- anion of the model triphosphoSer-containing peptide GpSGLGpSGLGpSGL(OH) show the presence of both product anions A (m/z 177) and D (m/z 257, H4P3O10-). Ab initio calculations at the HF/6-31+G(d)//AM1 level of theory suggest that cyclisation of the three phosphate groups occurs by a stepwise cascade mechanism in an energetically favourable reaction (ΔG = -245 kJ mol-1) with a maximum barrier of +123 kJ mol-1.
Details
- Title
- Diagnostic di- and triphosphate cyclisation in the negative ion electrospray mass spectra of phosphoSer peptides
- Authors
- Tianfang Wang (Author) - University of AdelaideT T Nha Tran (Author) - University of AdelaideD Scanlon (Author) - University of AdelaideH J Andreazza (Author) - University of AdelaideA D Abell (Author) - University of AdelaideJ H Bowie (Author) - University of Adelaide
- Publication details
- Rapid Communications in Mass Spectrometry, Vol.25(18), pp.2649-2656
- Publisher
- John Wiley & Sons Ltd.
- Date published
- 2011
- DOI
- 10.1002/rcm.5171
- 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
- 99450150002621
- Output Type
- Journal article
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