Formation and Dissociation of Phosphorylated Peptide Radical Cations

Kong, Ricky P.  W.; Quan, Quan; Hao, Qiang; Lai, Cheuk-Kuen; Siu, Chi-Kit; Chu, Ivan K.

doi:10.1007/s13361-012-0479-7

Formation and Dissociation of Phosphorylated Peptide Radical Cations

Journal Article · Wed Sep 12 00:00:00 EDT 2012 · Journal of the American Society for Mass Spectrometry

DOI:https://doi.org/10.1007/s13361-012-0479-7· OSTI ID:1816150

Kong, Ricky P. W. ^[1]; Quan, Quan ^[2]; Hao, Qiang ^[3]; Lai, Cheuk-Kuen ^[2]; Siu, Chi-Kit ^[4]; Chu, Ivan K. ^[2]

Univ. of Hong Kong, Hong Kong (China). Dept. of Chemistry; OSTI
Univ. of Hong Kong, Hong Kong (China). Dept. of Chemistry
Univ. of Hong Kong, Hong Kong (China). Dept. of Biology and Chemistry
Univ. of Hong Kong, Hong Kong (China). Dept. of Biology and Chemistry

In this study, we generated phosphoserine- and phosphothreonine-containing peptide radical cations through low-energy collision-induced dissociation (CID) of the ternary metal–ligand phosphorylated peptide complexes [Cu^II(terpy)_pM]^·2+ and [Co^III(salen)_pM]^·+ [_pM: phosphorylated angiotensin III derivative; terpy: 2,2':6',2''-terpyridine; salen: N,N '-ethylenebis(salicylideneiminato)]. Subsequent CID of the phosphorylated peptide radical cations (_pM^·+) revealed fascinating gas-phase radical chemistry, yielding (1) charge-directed b- and y-type product ions, (2) radical-driven product ions through cleavages of peptide backbones and side chains, and (3) different degrees of formation of [M – H₃PO₄]^·+ species through phosphate ester bond cleavage. The CID spectra of the _pM^·+ species and their non-phosphorylated analogues featured fragment ions of similar sequence, suggesting that the phosphoryl group did not play a significant role in the fragmentation of the peptide backbone or side chain. The extent of neutral H₃PO₄ loss was influenced by the peptide sequence and the initial sites of the charge and radical. A preliminary density functional theory study, at the B3LYP 6-311++G(d,p) level of theory, of the neutral loss of H₃PO₄ from a prototypical model—N-acetylphosphorylserine methylamide—revealed several factors governing the elimination of neutral phosphoryl groups through charge- and radical-induced mechanisms.

View Accepted Manuscript (DOE)

Sponsoring Organization:: Hong Kong Research Grants Council (RGC); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1816150

Journal Information:: Journal of the American Society for Mass Spectrometry, Journal Name: Journal of the American Society for Mass Spectrometry Journal Issue: 12 Vol. 23; ISSN 1044-0305

Publisher:: American Society for Mass SpectrometryCopyright Statement

Country of Publication:: United States

Language:: English

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