Proton Mobility in b2 Ion Formation and Fragmentation Reactions of Histidine-Containing Peptides

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• 作者：Carissa R. Nelson ; Maha T. Abutokaikah…
• 关键词：b2 and a2 Ion fragmentation ; Energy ; resolved studies ; Oxazolone structure ; Diketopiperazine structure ; Lactam structure
• 刊名：Journal of The American Society for Mass Spectrometry
• 出版年：2016
• 出版时间：March 2016
• 年：2016
• 卷：27
• 期：3
• 页码：487-497
• 全文大小：2,323 KB
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• 作者单位：Carissa R. Nelson (1)
  Maha T. Abutokaikah (1)
  Alex G. Harrison (2)
  Benjamin J. Bythell (1)
  
  1. Department of Chemistry and Biochemistry, University of Missouri, St. Louis, MO, 63121, USA
  2. Department of Chemistry, University of Toronto, Toronto, ON, M5S 1A1, Canada
  
• 刊物主题：Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
• 出版者：Springer US
• ISSN：1879-1123

文摘

A detailed energy-resolved study of the fragmentation reactions of protonated histidine-containing peptides and their b₂ ions has been undertaken. Density functional theory calculations were utilized to predict how the fragmentation reactions occur so that we might discern why the mass spectra demonstrated particular energy dependencies. We compare our results to the current literature and to synthetic b₂ ion standards. We show that the position of the His residue does affect the identity of the subsequent b₂ ion (diketopiperazine versus oxazolone versus lactam) and that energy-resolved CID can distinguish these isomeric products based on their fragmentation energetics. The histidine side chain facilitates every major transformation except trans-cis isomerization of the first amide bond, a necessary prerequisite to diketopiperazine b₂ ion formation. Despite this lack of catalyzation, trans-cis isomerization is predicted to be facile. Concomitantly, the subsequent amide bond cleavage reaction is rate-limiting.