ArticleJournal of the American Society for Mass Spectrometry2011
Effects of peptide backbone amide-to-ester bond substitution on the cleavage frequency in electron capture dissociation and collision-activated dissociation.
Article in Journal of the American Society for Mass Spectrometry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Chryseochelins-structural characterization of novel citrate-based siderophores produced by plant protecting Chryseobacterium spp.Metallomics : integrated biometal science · 2023Article
- Toward Microbial Recycling and Upcycling of Plastics: Prospects and Challenges.Frontiers in microbiology · 2022Review
- Surveying the sequence diversity of model prebiotic peptides by mass spectrometry.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Investigation of the Mechanism of Electron Capture and Electron Transfer Dissociation of Peptides with a Covalently Attached Free Radical Hydrogen Atom Scavenger.International journal of mass spectrometry · 2015Article
- Electron transfer dissociation of photolabeled peptides. Backbone cleavages compete with diazirine ring rearrangements.Journal of the American Society for Mass Spectrometry · 2013Article
- Electron transfer dissociation reveals changes in the cleavage frequencies of backbone bonds distant to amide-to-ester substitutions in polypeptides.Journal of the American Society for Mass Spectrometry · 2011Article
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Authors and funding
2 authors.
Funding
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Abstract
Probing the mechanism of electron capture dissociation on variously modified model peptide polycations has resulted in discovering many ways to prevent or reduce N-Cα bond fragmentation. Here we report on a rare finding of how to increase the backbone bond dissociation rate. In a number of model peptides, amide-to-ester backbone bond substitution increased the frequency of O-Cα bond cleavage (an analogue of N-Cα bonds in normal peptides) by several times, at the expense of reduced frequency of cleavages of the neighboring N-Cα bonds. In contrast, the ester linkage was only marginally broken in collisional dissociation. These results further highlight the complementarity of the reaction mechanisms in electron capture dissociation (ECD) and collision-activated dissociation (CAD). It is proposed that the effects of amide-to-ester bond substitution on fragmentation are mainly due to the differences in product ion stability (ECD, CAD) as well as proton affinity (CAD). This proposal is substantiated by calculations using density functional theory. The implications of these results in relation to the current understanding of the mechanisms of electron capture dissociation and electron transfer dissociation are discussed.
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