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Norbornene probes for the study of cysteine oxidation

Published version
Peer-reviewed

Type

Article

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Authors

Alcock, LJ 
Farrell, KD 
Akol, MT 
Jones, GH 
Tierney, MM 

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 occurence. 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

Keywords

Cysteine, Cysteine sulfenic acid, Norbornene, Oxidative stress, Chemical biology

Journal Title

Tetrahedron

Conference Name

Journal ISSN

0040-4020
1464-5416

Volume Title

74

Publisher

Elsevier BV
Sponsorship
Engineering and Physical Sciences Research Council (EP/M003647/1)
The Royal Society (uf110046)
European Research Council (676832)
European Commission (EC) (852985)