NDLI: Collision-Induced Dissociation of Diazirine-Labeled Peptide Ions. Evidence for Brønsted-Acid Assisted Elimination of Nitrogen

Content Provider	Springer Nature Link
Author	Marek, Aleš Tureček, František
Copyright Year	2014
Abstract	Gas-phase dissociations were investigated for several peptide ions containing the Gly-Leu* N-terminal motif where Leu* was a modified norleucine residue containing the photolabile diazirine ring. Collisional activation of gas-phase peptide cations resulted in facile N$_{2}$ elimination that competed with backbone dissociations. A free lysine ammonium group can act as a Brønsted acid to facilitate N$_{2}$ elimination. This dissociation was accompanied by insertion of a lysine proton in the side chain of the photoleucine residue, as established by deuterium labeling and gas-phase sequencing of the products. Electron structure calculations were used to provide structures and energies of reactants, intermediates, and transition states for Gly-Leu*-Gly-Gly-Lys amide ions that were combined with RRKM calculations of unimolecular rate constants. The calculations indicated that Brønsted acid-catalyzed eliminations were kinetically preferred over direct loss of N$_{2}$ from the diazirine ring. Mechanisms are proposed to explain the proton-initiated reactions and discuss the reaction products. The non-catalyzed diazirine ring cleavage and N$_{2}$ loss is proposed as a thermometer dissociation for peptide ion dissociations. Fig. a ᅟ
Starting Page	778
Ending Page	789
Page Count	12
File Format	PDF
ISSN	10440305
Journal	Journal of The American Society for Mass Spectrometry
Volume Number	25
Issue Number	5
e-ISSN	18791123
Language	English
Publisher	Springer US
Publisher Date	2014-02-19
Publisher Institution	The American Society for Mass Spectrometry
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Diazirine-labeled peptides Collision-induced dissociation Nitrogen elimination Ion structures Dissociation mechanisms Analytical Chemistry Biotechnology Organic Chemistry Proteomics Bioinformatics
Content Type	Text
Resource Type	Article
Subject	Spectroscopy Structural Biology

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