Norbornene probes for the study of cysteine oxidation

Thumbnail Image
Date
2017-11-04
Authors
Alcock, Lisa J
Farrell, Kyle D
Akol, Mawey T
Jones, Gregory H
Tierney, Matthew M
Kramer, Holger B
Pukala, Tara L
Bernardes, Goncalo J L
Perkins, Michael Victor
Chalker, Justin M
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
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.
Description
© 2017 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license http://creativecommons.org/licenses/by/4.0/).
Keywords
Cysteine, Cysteine sulfenic acid, Norbornene, Oxidative stress, Chemical biology
Citation
Alcock, L. J., Farrell, K. D., Akol, M. T., Jones, G. H., Tierney, M. M., Kramer, H. B., … Chalker, J. M. (2018). Norbornene probes for the study of cysteine oxidation. Tetrahedron, 74(12), 1220–1228. https://doi.org/10.1016/j.tet.2017.11.011