ArticleJournal of the American Society for Mass Spectrometry2009
Deciphering the peptide iodination code: influence on subsequent gas-phase radical generation with photodissociation ESI-MS.
Article in Journal of the American Society for Mass Spectrometry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 41 citations in OpenAlex.
- Comprehensive Proteomics and Machine Learning Analysis to Distinguish Follicular Adenoma and Follicular Thyroid Carcinoma from Indeterminate Thyroid Nodules.Endocrinology and metabolism (Seoul, Korea) · 2025Article
- Late-stage labeling of diverse peptides and proteins with iodine-125.Journal of pharmaceutical analysis · 2025Review
- The Antioxidant Properties of Selected Varieties of Pumpkin Fortified with Iodine in the Form of Potassium Iodide and Potassium Iodate.Foods (Basel, Switzerland) · 2023Article
- Ultraviolet Photodissociation Mass Spectrometry for Analysis of Biological Molecules.Chemical reviews · 2020Review
- Article
- SITS Derivatization of Peptides to Enhance 266 nm Ultraviolet Photodissociation (UVPD).Journal of the American Society for Mass Spectrometry · 2017Article
- Exploitation of the Ornithine Effect Enhances Characterization of Stapled and Cyclic Peptides.Journal of the American Society for Mass Spectrometry · 2016Article
- Comparison of Ultraviolet Photodissociation and Collision Induced Dissociation of Adrenocorticotropic Hormone Peptides.Journal of the American Society for Mass Spectrometry · 2015Article
- Photodissociation mass spectrometry: new tools for characterization of biological molecules.Chemical Society reviews · 2014Review
- UV photodissociation action spectroscopy of haloanilinium ions in a linear quadrupole ion trap mass spectrometer.Journal of the American Society for Mass Spectrometry · 2013Article
- Structure and reactivity of the distonic and aromatic radical cations of tryptophan.Journal of the American Society for Mass Spectrometry · 2013Article
- Electron capture dissociation of hydrogen-deficient peptide radical cations.Journal of the American Society for Mass Spectrometry · 2012Article
- Tyrosine deprotonation yields abundant and selective backbone cleavage in peptide anions upon negative electron transfer dissociation and ultraviolet photodissociation.Journal of the American Chemical Society · 2012Article
- Structure and reactivity of the N-acetyl-cysteine radical cation and anion: does radical migration occur?Journal of the American Society for Mass Spectrometry · 2011Article
- Shedding light on the frontier of photodissociation.Journal of the American Society for Mass Spectrometry · 2011Article
- Oxidative protein labeling in mass-spectrometry-based proteomics.Analytical and bioanalytical chemistry · 2010Review
- Mobile protons versus mobile radicals: gas-phase unimolecular chemistry of radical cations of cysteine-containing peptides.Journal of the American Society for Mass Spectrometry · 2010Article
- Radical directed dissociation for facile identification of iodotyrosine residues using electrospray ionization mass spectrometry.Analytical chemistry · 2010Article
- Comparative dissociation of peptide polyanions by electron impact and photo-induced electron detachment.Journal of the American Society for Mass Spectrometry · 2010Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Iodination of tyrosine was recently discovered as a useful method for generating radical peptides via photodissociation of carbon-iodine bonds by an ultraviolet photon in the gas phase. The subsequent fragmentation behavior of the resulting odd-electron peptides is largely controlled by the radical. Although previous experiments have focused on mono-iodination of tyrosine, peptides and proteins can also be multiply iodinated. Tyrosine and, to a lesser extent, histidine can both be iodinated or doubly iodinated. The behavior of doubly iodinated residues is explored under conditions where the sites of iodination are carefully controlled. It is found that radical peptides generated by the loss of a single iodine from doubly iodinated tyrosine behave effectively identically to singly iodinated peptides. This suggests that the remaining iodine does not interfere with radical directed dissociation pathways. In contrast, the concerted loss of two iodines from doubly iodinated peptides yields substantially different results that suggest that radical recombination can occur. However, sequential activation can be used to generate multiple usable radicals in different steps of an MS(n) experiment. Furthermore, it is demonstrated that in actual peptides, the rate of iodination for tyrosine versus mono-iodotyrosine cannot be predicted easily a priori. In other words, previous assumptions that mono-iodination of tyrosine is the rate-limiting step to the formation of doubly iodinated tyrosine are incorrect.
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