title: Negative ion cleavages of (M-H)-anions of peptides. Part 3. Post-translational modifications.
abstract: It is now 25 years since we commenced the study of the negative-ion fragmentations of peptides and we have recently concluded this research with investigations of the negative-ion chemistry of most post-translational functional groups. Our first negative-ion peptide review (Bowie, Brinkworth, & Dua, 2002) dealt with the characteristic backbone fragmentations and side-chain cleavages from (M-H)-ions of underivatized peptides, while the second (Bilusich & Bowie, 2009) included negative-ion backbone cleavages for Ser and Cys and some initial data on some post-translational groups including disulfides. This third and final review provides a brief summary of the major backbone and side chain cleavages outlined before (Bowie, Brinkworth, & Dua, 2002) and describes the quantum mechanical hydrogen tunneling associated with some proton transfers in enolate anion/enolate systems. The review then describes, in more depth, the negative-ion cleavages of the post-translational groups Kyn, isoAsp, pyroglu, disulfides, phosphates, and sulfates. Particular emphasis is devoted to disulfides (both intra- and intermolecular) and phosphates because of the extensive and spectacular anion chemistry shown by these groups. © 2016 Wiley Periodicals, Inc. Mass Spec Rev.
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.|Genecology Research Centre, University of the Sunshine Coast, Queensland, 4556, Australia.
authors.forename: Tianfang
authors.initials: T
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.|Industrial University of Ho Chi Minh City, Ho Chi Minh City, Vietnam.
authors.forename: T T
authors.initials: TT
authors.lastname: Nha Tran
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.
authors.forename: Hayley J
authors.initials: HJ
authors.lastname: Andreazza
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.|Defence Science and Technology Organisation, Salisbury, PO Box 1500, South Australia, 5108, Australia.
authors.forename: Daniel
authors.initials: D
authors.lastname: Bilusich
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.|Defence Science and Technology Organisation, Land Division, Fishermans Bend, Victoria, 3207, Australia.
authors.forename: Craig S
authors.initials: CS
authors.lastname: Brinkworth
authors.affiliation: Department of Chemistry, The University of Adelaide, South Australia, 5005, Australia.
authors.forename: John H
authors.initials: JH
authors.lastname: Bowie
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D000838:Anions / Q000032:analysis*; D004220:Disulfides / Q000032:analysis; D006801:Humans; D026581:Isoaspartic Acid / Q000032:analysis; D007737:Kynurenine / Q000032:analysis; D010455:Peptides / Q000737:chemistry*; D010710:Phosphates / Q000032:analysis; D011499:Protein Processing, Post-Translational; D011761:Pyrrolidonecarboxylic Acid / Q000032:analysis; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013431:Sulfates / Q000032:analysis
chemical_list: D000838:Anions; D004220:Disulfides; D026581:Isoaspartic Acid; D010455:Peptides; D010710:Phosphates; D013431:Sulfates; D007737:Kynurenine; D011761:Pyrrolidonecarboxylic Acid
keywords: disulphides (both intra and intermolecular); isoAspartate (isoAsp), pyroglutamate (pyroGlu); negative-ion electrospray mass spectrometry; peptides; phosphates, and sulfates; post-translational modifications including kynurenine (Kyn); quantum mechanical hydrogen tunneling; ricin D