1,142
Views
61
CrossRef citations to date
0
Altmetric
Review Article

Biological chemistry and functionality of protein sulfenic acids and related thiol modifications

, &
Pages 172-194 | Received 03 Jul 2015, Accepted 31 Aug 2015, Published online: 11 Nov 2015

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (2)

Kei Goto, Tsukasa Sano, Ryosuke Masuda, Shotaro Otaka, Ryutaro Kimura, Shohei Sase & Satoru Kuwano. (2023) Stable cysteine sulfenic acid: synthesis by direct oxidation of a thiol, crystallographic analysis, and elucidation of reactivities. Phosphorus, Sulfur, and Silicon and the Related Elements 198:6, pages 466-470.
Read now
Rafael Radi & Madia Trujillo. (2016) Special issue on “Free Radical and Redox Biochemistry of Thiols”. Free Radical Research 50:2, pages 123-125.
Read now

Articles from other publishers (59)

Anthony E. Postiglione, Laquaundra L. Adams, Ese S. Ekhator, Anuoluwapo E. Odelade, Supriya Patwardhan, Meenal Chaudhari, Avery S. Pardue, Anjali Kumari, William A. LeFever, Olivia P. Tornow, Tamer S. Kaoud, Johnathan Neiswinger, Jun Seop Jeong, Derek Parsonage, Kimberly J. Nelson, Dukka B. Kc, Cristina M. Furdui, Heng Zhu, Andrew J. Wommack, Kevin N. Dalby, Ming Dong, Leslie B. Poole, Jeremiah D. Keyes & Robert H. Newman. (2023) Hydrogen peroxide-dependent oxidation of ERK2 within its D-recruitment site alters its substrate selection. iScience 26:10, pages 107817.
Crossref
Lucia Coppo, Simona ScheggiGraziella DeMontisRaffaella PrioraSimona FrosaliAntonio MargaritisDomenico SummaDanila Di GiuseppeMonica UlivelliPaolo Di Simplicio. (2023) Does Risk of Hyperhomocysteinemia Depend on Thiol-Disulfide Exchange Reactions of Albumin and Homocysteine?. Antioxidants & Redox Signaling.
Crossref
Man Li, Zhiyi Cai, Mengzhao Li, Linfeng Chen, Weili Zeng, Hong Yuan & Chunrong Liu. (2023) The dual detection of formaldehydes and sulfenic acids with a reactivity fluorescent probe in cells and in plants. Analytica Chimica Acta 1239, pages 340734.
Crossref
Jean-Valery Guillaubez, Delphine Pitrat, Yann Bretonnière, Jérôme Lemoine & Marion Girod. (2022) Relative quantification of sulfenic acids in plasma proteins using differential labelling and mass spectrometry coupled with 473 nm photo-dissociation analysis: A multiplexed approach applied to an Alzheimer's disease cohort. Talanta 250, pages 123745.
Crossref
Oscar N. Ventura, Marc Segovia, Mauricio Vega-Teijido, Aline Katz, Martina Kieninger, Nicola Tasinato & Zoi Salta. (2022) Correcting the Experimental Enthalpies of Formation of Some Members of the Biologically Significant Sulfenic Acids Family. The Journal of Physical Chemistry A 126:36, pages 6091-6109.
Crossref
Mariia Khamina, Karla Martinez Pomier, Madoka Akimoto, Bryan VanSchouwen & Giuseppe Melacini. (2022) Non-Canonical Allostery in Cyclic Nucleotide Dependent Kinases. Journal of Molecular Biology 434:17, pages 167584.
Crossref
Pablo Andrei Nogara, Marco Bortoli, Laura Orian & João Batista T. Rocha. (2022) Biological Activity of Synthetic Organoselenium Compounds: What do we Know about the Mechanism?. Current Chemical Biology 16:1, pages 12-24.
Crossref
Man Li, Bing Wang, Mengzhao Li, Xiang Li, Li Wang, Na Li, Li Rao, Cuihong Wan, Changlin Liu & Chunrong Liu. (2022) A reactivity-based probe for off-on fluorescent detection, labeling, and profiling of protein S-sulfenylation in cells. Sensors and Actuators B: Chemical 354, pages 131235.
Crossref
Kiran Kumar Solingapuram Sai, Xiaofei Chen, Zhe Li, Caigang Zhu, Kirtikar Shukla, Tom E. Forshaw, Hanzhi Wu, Stephen A. Vance, Buddhika Liyana Pathirannahel, Megan Madonna, Mark W. Dewhirst, Allen W. Tsang, Leslie B. Poole, Nimmi Ramanujam, S. Bruce King & Cristina M. Furdui. (2022) [18F]Fluoro-DCP, a first generation PET radiotracer for monitoring protein sulfenylation in vivo. Redox Biology 49, pages 102218.
Crossref
Sebastián Carballal & Ruma Banerjee. 2022. Redox Chemistry and Biology of Thiols. Redox Chemistry and Biology of Thiols 423 450 .
Pablo A. Nogara, Cláudia S. Oliveira, Meire E. Pereira, Marco Bortoli, Laura Orian, Michael Aschner & João B.T. Rocha. 2022. Redox Chemistry and Biology of Thiols. Redox Chemistry and Biology of Thiols 643 677 .
Elena Hipper, Michaela Blech, Dariush Hinderberger, Patrick Garidel & Wolfgang Kaiser. (2021) Photo-Oxidation of Therapeutic Protein Formulations: From Radical Formation to Analytical Techniques. Pharmaceutics 14:1, pages 72.
Crossref
Nathan A. Snyder & Gustavo M. Silva. (2021) Deubiquitinating enzymes (DUBs): Regulation, homeostasis, and oxidative stress response. Journal of Biological Chemistry 297:3, pages 101077.
Crossref
Shuwen Jiang, Luke Carroll, Michele Mariotti, Per Hägglund & Michael J. Davies. (2021) Formation of protein cross-links by singlet oxygen-mediated disulfide oxidation. Redox Biology 41, pages 101874.
Crossref
Nicholas J. Day, Matthew J. Gaffrey & Wei-Jun Qian. (2021) Stoichiometric Thiol Redox Proteomics for Quantifying Cellular Responses to Perturbations. Antioxidants 10:3, pages 499.
Crossref
Tsukasa Sano, Ryosuke Masuda, Shohei Sase & Kei Goto. (2021) Isolable small-molecule cysteine sulfenic acid. Chemical Communications 57:20, pages 2479-2482.
Crossref
Susanne Schipper, Hanzhi Wu, Cristina M. Furdui, Leslie B. Poole, Claire M. Delahunty, Robin Park, John R. YatesIIIIII, Katja Becker & Jude M. Przyborski. (2021) Identification of sulfenylation patterns in trophozoite stage Plasmodium falciparum using a non-dimedone based probe. Molecular and Biochemical Parasitology 242, pages 111362.
Crossref
Lucía Turell, Martina Steglich, Maria J. Torres, Matías Deambrosi, Laura Antmann, Cristina M. Furdui, Francisco J. Schopfer & Beatriz Alvarez. (2021) Sulfenic acid in human serum albumin: Reaction with thiols, oxidation and spontaneous decay. Free Radical Biology and Medicine 165, pages 254-264.
Crossref
Jean-Valery Guillaubez, Delphine Pitrat, Yann Bretonnière, Jérôme Lemoine & Marion Girod. (2021) Unbiased Detection of Cysteine Sulfenic Acid by 473 nm Photodissociation Mass Spectrometry: Toward Facile In Vivo Oxidative Status of Plasma Proteins . Analytical Chemistry 93:5, pages 2907-2915.
Crossref
Yew Mun Lee, Weifeng He & Yih-Cherng Liou. (2021) The redox language in neurodegenerative diseases: oxidative post-translational modifications by hydrogen peroxide. Cell Death & Disease 12:1.
Crossref
Giona Sonego, Truong‐Thien Melvin Le, David Crettaz, Mélanie Abonnenc, Jean‐Daniel Tissot & Michel Prudent. (2021) Sulfenylome analysis of pathogen‐inactivated platelets reveals the presence of cysteine oxidation in integrin signaling pathway and cytoskeleton regulation. Journal of Thrombosis and Haemostasis 19:1, pages 233-247.
Crossref
Reetta Holmila, Hanzhi Wu, Jingyun Lee, Allen W. Tsang, Ravi Singh & Cristina M. Furdui. (2021) Integrated Redox Proteomic Analysis Highlights New Mechanisms of Sensitivity to Silver Nanoparticles. Molecular & Cellular Proteomics 20, pages 100073.
Crossref
Camilo López-Alarcón, Eduardo Fuentes-Lemus, Juan David Figueroa, Eva Dorta, Christian Schöneich & Michael J. Davies. (2020) Azocompounds as generators of defined radical species: Contributions and challenges for free radical research. Free Radical Biology and Medicine 160, pages 78-91.
Crossref
John T. PetroffIIII, Sara M. Omlid, Nandan Haloi, Louis Sith, Shaquina Johnson & Ryan D. McCulla. (2020) Reactions of sulfenic acids with amines, thiols, and thiolates studied by quantum chemical calculations. Computational and Theoretical Chemistry 1189, pages 112979.
Crossref
Lucia Turell, Ari Zeida & Madia Trujillo. (2020) Mechanisms and consequences of protein cysteine oxidation: the role of the initial short-lived intermediates. Essays in Biochemistry 64:1, pages 55-66.
Crossref
Leslie B. Poole, Cristina M. FurduiS. Bruce King. (2020) Introduction to approaches and tools for the evaluation of protein cysteine oxidation. Essays in Biochemistry 64:1, pages 1-17.
Crossref
Shyamal K. Goswami. 2020. Models, Molecules and Mechanisms in Biogerontology. Models, Molecules and Mechanisms in Biogerontology 199 212 .
Clare L. Hawkins & Michael J. Davies. (2019) Detection, identification, and quantification of oxidative protein modifications. Journal of Biological Chemistry 294:51, pages 19683-19708.
Crossref
Reetta J. Holmila, Stephen A. Vance, S. Bruce King, Allen W. Tsang, Ravi Singh & Cristina M. Furdui. (2019) Silver Nanoparticles Induce Mitochondrial Protein Oxidation in Lung Cells Impacting Cell Cycle and Proliferation. Antioxidants 8:11, pages 552.
Crossref
Xixi Zhou, Xiaofeng Ding, Jiangang Shen, Dan Yang, Laurie G. Hudson & Ke Jian Liu. (2019) Peroxynitrite contributes to arsenic-induced PARP-1 inhibition through ROS/RNS generation. Toxicology and Applied Pharmacology 378, pages 114602.
Crossref
Ines Batinic-Haberle & Margaret E. Tome. (2019) Thiol regulation by Mn porphyrins, commonly known as SOD mimics. Redox Biology 25, pages 101139.
Crossref
Guang Yang, Yue Lu, Hunter N. Bomba & Zhen Gu. (2019) Cysteine-rich Proteins for Drug Delivery and Diagnosis. Current Medicinal Chemistry 26:8, pages 1377-1388.
Crossref
Matthew E. Albertolle, Sarah M. Glass, Elijah Trefts & F. Peter Guengerich. (2019) Isotopic tagging of oxidized and reduced cysteines (iTORC) for detecting and quantifying sulfenic acids, disulfides, and free thiols in cells. Journal of Biological Chemistry 294:16, pages 6522-6530.
Crossref
Zhe Li, Tom E. Forshaw, Reetta J. Holmila, Stephen A. Vance, Hanzhi Wu, Leslie B. Poole, Cristina M. Furdui & S. Bruce King. (2019) Triphenylphosphonium-Derived Protein Sulfenic Acid Trapping Agents: Synthesis, Reactivity, and Effect on Mitochondrial Function. Chemical Research in Toxicology 32:3, pages 526-534.
Crossref
Matthew E. Albertolle, Hyun D. Song, Clayton J. Wilkey, Jere P. Segrest & F. Peter Guengerich. (2019) Glutamine-451 Confers Sensitivity to Oxidative Inhibition and Heme-Thiolate Sulfenylation of Cytochrome P450 4B1. Chemical Research in Toxicology 32:3, pages 484-492.
Crossref
Tom E. Forshaw, Reetta Holmila, Kimberly J. Nelson, Joshua E. Lewis, Melissa L. Kemp, Allen W. Tsang, Leslie B. Poole, W. Todd Lowther & Cristina M. Furdui. (2019) Peroxiredoxins in Cancer and Response to Radiation Therapies. Antioxidants 8:1, pages 11.
Crossref
Shyamal K. Goswami. 2019. Modulation of Oxidative Stress in Heart Disease. Modulation of Oxidative Stress in Heart Disease 403 418 .
Xiaofei Chen, Jingyun Lee, Hanzhi Wu, Allen W. Tsang & Cristina M. Furdui. 2019. Advancements of Mass Spectrometry in Biomedical Research. Advancements of Mass Spectrometry in Biomedical Research 327 358 .
Xiaofei ChenJade MimsXiumei HuangNaveen SinghEdward MoteaSarah M. PlanchonMuhammad BegAllen W. TsangMercedes PorosnicuMelissa L. KempDavid A. BoothmanCristina M. Furdui. (2018) Modulators of Redox Metabolism in Head and Neck Cancer. Antioxidants & Redox Signaling 29:16, pages 1660-1690.
Crossref
Kimberly J. Nelson, Jesalyn A. Bolduc, Hanzhi Wu, John A. Collins, Elizabeth A. Burke, Julie A. Reisz, Chananat Klomsiri, Scott T. Wood, Raghunatha R. Yammani, Leslie B. Poole, Cristina M. Furdui & Richard F. Loeser. (2018) H2O2 oxidation of cysteine residues in c-Jun N-terminal kinase 2 (JNK2) contributes to redox regulation in human articular chondrocytes. Journal of Biological Chemistry 293:42, pages 16376-16389.
Crossref
Saba Parvez, Marcus J. C. Long, Jesse R. Poganik & Yimon Aye. (2018) Redox Signaling by Reactive Electrophiles and Oxidants. Chemical Reviews 118:18, pages 8798-8888.
Crossref
Matthew E. Albertolle, Thanh T.N. Phan, Ambra Pozzi & F. Peter Guengerich. (2018) Sulfenylation of Human Liver and Kidney Microsomal Cytochromes P450 and Other Drug-Metabolizing Enzymes as a Response to Redox Alteration. Molecular & Cellular Proteomics 17:5, pages 889-900.
Crossref
Seema Irani, Nathchar Naowarojna, Yang Tang, Karan R. Kathuria, Shu Wang, Anxhela Dhembi, Norman Lee, Wupeng Yan, Huijue Lyu, Catherine E. Costello, Pinghua Liu & Yan Jessie Zhang. (2018) Snapshots of C-S Cleavage in Egt2 Reveals Substrate Specificity and Reaction Mechanism. Cell Chemical Biology 25:5, pages 519-529.e4.
Crossref
Jesse R. Poganik, Marcus J. C. Long & Yimon Aye. (2018) Getting the Message? Native Reactive Electrophiles Pass Two Out of Three Thresholds to be Bona Fide Signaling Mediators. BioEssays 40:5, pages 1700240.
Crossref
Vehary Sakanyan. (2018) Reactive Chemicals and Electrophilic Stress in Cancer: A Minireview. High-Throughput 7:2, pages 12.
Crossref
Reetta J. Holmila, Stephen A. Vance, Xiaofei Chen, Hanzhi Wu, Kirtikar Shukla, Manish S. Bharadwaj, Jade Mims, Zack Wary, Glen Marrs, Ravi Singh, Anthony J. Molina, Leslie B. Poole, S. Bruce King & Cristina M. Furdui. (2018) Mitochondria-targeted Probes for Imaging Protein Sulfenylation. Scientific Reports 8:1.
Crossref
Milos R. Filipovic, Jasmina Zivanovic, Beatriz Alvarez & Ruma Banerjee. (2017) Chemical Biology of H 2 S Signaling through Persulfidation . Chemical Reviews 118:3, pages 1253-1337.
Crossref
Jeremiah D. Keyes, Derek Parsonage, Rama D. Yammani, LeAnn C. Rogers, Chelsea Kesty, Cristina M. Furdui, Kimberly J. Nelson & Leslie B. Poole. (2017) Endogenous, regulatory cysteine sulfenylation of ERK kinases in response to proliferative signals. Free Radical Biology and Medicine 112, pages 534-543.
Crossref
Kate Samardzic & Kenneth J. Rodgers. (2017) Oxidised protein metabolism: recent insights. Biological Chemistry 398:11, pages 1165-1175.
Crossref
David Long, Hanzhi Wu, Allen W. Tsang, Leslie B. Poole, Barbara K. Yoza, Xianfeng Wang, Vidula Vachharajani, Cristina M. Furdui & Charles E. McCall. (2017) The Oxidative State of Cysteine Thiol 144 Regulates the SIRT6 Glucose Homeostat. Scientific Reports 7:1.
Crossref
Xiaofei Chen, Hanzhi Wu, Chung-Min Park, Thomas H. Poole, Gizem Keceli, Nelmi O. Devarie-Baez, Allen W. Tsang, W. Todd Lowther, Leslie B. Poole, S. Bruce King, Ming Xian & Cristina M. Furdui. (2017) Discovery of Heteroaromatic Sulfones As a New Class of Biologically Compatible Thiol-Selective Reagents. ACS Chemical Biology 12:8, pages 2201-2208.
Crossref
Matthew E. Albertolle, Donghak Kim, Leslie D. Nagy, Chul-Ho Yun, Ambra Pozzi, Üzen Savas, Eric F. Johnson & F. Peter Guengerich. (2017) Heme–thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition. Journal of Biological Chemistry 292:27, pages 11230-11242.
Crossref
Antoine Bersweiler, Benoît D'Autréaux, Hortense Mazon, Alexandre Kriznik, Gemma Belli, Agnès Delaunay-Moisan, Michel B Toledano & Sophie Rahuel-Clermont. (2017) A scaffold protein that chaperones a cysteine-sulfenic acid in H2O2 signaling. Nature Chemical Biology 13:8, pages 909-915.
Crossref
Murugaeson R. Kumar & Patrick J. Farmer. (2016) Trapping Reactions of the Sulfenyl and Sulfinyl Tautomers of Sulfenic Acids. ACS Chemical Biology 12:2, pages 474-478.
Crossref
Anna Bogdanova, Irina Y. Petrushanko, Pablo Hernansanz-Agustín & Antonio Martínez-Ruiz. (2016) “Oxygen Sensing” by Na,K-ATPase: These Miraculous Thiols. Frontiers in Physiology 7.
Crossref
Anna C. Krämer, Peter W. Thulstrup, Marianne N. Lund & Michael J. Davies. (2016) Key role of cysteine residues and sulfenic acids in thermal- and H2O2-mediated modification of β-lactoglobulin. Free Radical Biology and Medicine 97, pages 544-555.
Crossref
Vinayak Gupta, Hanumantharao Paritala & Kate S. Carroll. (2016) Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes. Bioconjugate Chemistry 27:5, pages 1411-1418.
Crossref
Paul K. Witting. (2016) Measuring redox-active species in cells and tissues . Focus on “A case of mistaken identity: are reactive oxygen species actually reactive sulfide species?” . American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 310:7, pages R547-R548.
Crossref
Jie Wang & Carolyn S. Sevier. (2016) Formation and Reversibility of BiP Protein Cysteine Oxidation Facilitate Cell Survival during and post Oxidative Stress. Journal of Biological Chemistry 291:14, pages 7541-7557.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.