ArticleThe journal of physical chemistry. B2011
Reversible hydrogen transfer reactions of cysteine thiyl radicals in peptides: the conversion of cysteine into dehydroalanine and alanine, and of alanine into dehydroalanine.
Article in The journal of physical chemistry. B, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 36 citations in OpenAlex.
- The Chemical Reactivity of Membrane Lipids.Chemical reviews · 2024Review
- Oxidative Crosslinking of Peptides and Proteins: Mechanisms of Formation, Detection, Characterization and Quantification.Molecules (Basel, Switzerland) · 2021Review
- Thiyl Radical Reactions in the Chemical Degradation of Pharmaceutical Proteins.Molecules (Basel, Switzerland) · 2019Review
- Identification of D-Amino Acids in Light Exposed mAb Formulations.Pharmaceutical research · 2018Article
- Light-Induced Covalent Buffer Adducts to Histidine in a Model Protein.Pharmaceutical research · 2018Article
- Photodegradation Pathways of Protein Disulfides: Human Growth Hormone.Pharmaceutical research · 2017Article
- Sulfheme formation during homocysteine S-oxygenation by catalase in cancers and neurodegenerative diseases.Nature communications · 2016Article
- Protein oxidation and peroxidation.The Biochemical journal · 2016Review
- Thiyl radicals and induction of protein degradation.Free radical research · 2016Review
- Protein thiyl radical reactions and product formation: a kinetic simulation.Free radical biology & medicine · 2015Review
- Peroxiredoxin-2 recycling is inhibited during erythrocyte storage.Antioxidants & redox signaling · 2015Article
- Effects of ionizing radiation on biological molecules--mechanisms of damage and emerging methods of detection.Antioxidants & redox signaling · 2014Review
- UV photodegradation of murine growth hormone: chemical analysis and immunogenicity consequences.European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V · 2014Article
- Intramolecular hydrogen transfer reactions of thiyl radicals from glutathione: formation of carbon-centered radical at Glu, Cys, and Gly.Chemical research in toxicology · 2012Article
- Reversible hydrogen transfer reactions in thiyl radicals from cysteine and related molecules: absolute kinetics and equilibrium constants determined by pulse radiolysis.The journal of physical chemistry. B · 2012Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
The photodissociation of disulfide bonds in model peptides containing Ala and Ala-d(3) generates a series of photoproducts following the generation of a CysS(•) thiyl radical pair. These photoproducts include transformations of Cys to dehydroalanine (Dha) and Ala, as well as Ala to Dha. Intramolecular Michael addition of an intact Cys with a photolytically generated Dha results in the formation of cyclic thioethers. The conversion of Cys into Dha likely involves a 1,3-H-shift from the Cys (α)C-H bond to the thiyl radical, followed by elimination of HS(•). The conversion of Dha into Ala most likely involves hydrated electrons, which are generated through the photolysis of Cys, the photoproduct of disulfide photolysis. Prior to stable product formation, CysS(•) radicals engage in reversible hydrogen transfer reactions with (α)C-H and (β)C-H bonds of the surrounding amino acids. Especially for the (β)C-H bonds of Ala, such hydrogen transfer reactions are unexpected on the basis of thermodynamic grounds; however, the replacement of deuterons in Ala-d(3) by hydrogens in H(2)O provides strong experimental evidence for such reactions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.