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Norbornene probes for the study of cysteine oxidation |
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| Authors: | Lisa J. Alcock Kyle D. Farrell Mawey T. Akol Gregory H. Jones Matthew M. Tierney Holger B. Kramer Tara L. Pukala Gonçalo J.L. Bernardes Michael V. Perkins Justin M. Chalker |
| Affiliation: | 1. Flinders University, College of Science and Engineering, Sturt Road, Bedford Park, South Australia, 5042, Australia;2. California Institute of Technology, Division of Chemistry and Chemical Engineering, 1200 East California Boulevard, Pasadena, CA, 91125, USA;3. The University of North Carolina at Chapel Hill, Department of Chemistry, Chapel Hill, NC, 27599, USA;4. Imperial College London, MRC London Institute of Medical Sciences, Hammersmith Hospital Campus, Du Cane Road, London, W12 0NN, UK;5. The University of Adelaide, School of Physical Sciences, Adelaide, South Australia, 5005, Australia;6. University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, UK;g. Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Avenida Professor Egas Moniz, 1649-028, Lisboa, Portugal |
| Abstract: | Cysteine residues on proteins can react with cellular oxidants such as hydrogen peroxide. While this process is important for scavenging excess reactive oxygen species, the products of this oxidation may also mediate cell signalling. To understand the role of cysteine oxidation in biology, selective probes are required to detect and quantify its occurrence. Cysteine oxidation products such as sulfenic acids are sometimes unstable and therefore short-lived. If such cysteine derivatives are to be analysed, rapid reaction with the probe is required. Here we introduce norbornene derivatives as probes for cysteine oxidation, and demonstrate their ability to trap sulfenic acids. The synthesis of norbornene derivatives containing alkyne or biotin affinity tags are also reported to facilitate the use of these probes in chemical biology and proteomics. |
| Keywords: | Cysteine Cysteine sulfenic acid Norbornene Oxidative stress Chemical biology |
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