ArticleRapid communications in mass spectrometry : RCM2010
Desulfurization of cysteine-containing peptides resulting from sample preparation for protein characterization by mass spectrometry.
Article in Rapid communications in mass spectrometry : RCM, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 90 citations in OpenAlex.
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- Cysteine metabolic engineering and selective disulfide reduction produce superior antibody-drug-conjugates.Scientific reports · 2022Article
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- Compactness of Protein Folds Alters Disulfide-Bond Reducibility by Three Orders of Magnitude: A Comprehensive Kinetic Case Study on the Reduction of Differently Sized Tryptophan Cage Model Proteins.Chembiochem : a European journal of chemical biology · 2020Article
- Thiyl Radical Reactions in the Chemical Degradation of Pharmaceutical Proteins.Molecules (Basel, Switzerland) · 2019Review
- Effect of Reducing Agent TCEP on Translational Diffusion and Supramolecular Assembly in Aqueous Solutions of α-Casein.The journal of physical chemistry. B · 2019Article
- Traceless β-mercaptan-assisted activation of valinyl benzimidazolinones in peptide ligations.Chemical science · 2018Article
- Photodegradation Pathways of Protein Disulfides: Human Growth Hormone.Pharmaceutical research · 2017Article
- Adductomics Pipeline for Untargeted Analysis of Modifications to Cys34 of Human Serum Albumin.Analytical chemistry · 2016Article
- Comparison of Protein N-Homocysteinylation in Rat Plasma under Elevated Homocysteine Using a Specific Chemical Labeling Method.Molecules (Basel, Switzerland) · 2016Article
- Nickel-pincer cofactor biosynthesis involves LarB-catalyzed pyridinium carboxylation and LarE-dependent sacrificial sulfur insertion.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Mildly acidic conditions eliminate deamidation artifact during proteolysis: digestion with endoprotease Glu-C at pH 4.5.Amino acids · 2016Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
In this study, we have examined two cysteine modifications resulting from sample preparation for protein characterization by mass spectrometry (MS): (1) a previously observed conversion of cysteine into dehydroalanine, now found in the case of disulfide mapping and (2) a novel modification corresponding to conversion of cysteine into alanine. Using model peptides, the conversion of cysteine into dehydroalanine via beta-elimination of a disulfide bond was seen to result from the conditions of typical tryptic digestion (37 degrees C, pH 7.0-9.0) without disulfide reduction and alkylation. Furthermore, the surprising conversion of cysteine into alanine was shown to occur by heating cysteine-containing peptides in the presence of a phosphine (tris(2-carboxyethyl)phosphine hydrochloride (TCEP)). The formation of alanine from cysteine, investigated by performing experiments in H(2)O or D(2)O, suggested a radical-based desulfurization mechanism unrelated to beta-elimination. Importantly, an understanding of the mechanism and conditions favorable for cysteine desulfurization provides insight for the establishment of improved sample preparation procedures of protein analysis.
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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.