Norbornene probes for the study of cysteine oxidation

Lisa Alcock, Kyle Farrell, Mawey Akol, Gregory Jones, Matthew Tierney, Holger Kramer, Tara Pukala, Goncalo Bernardes, Michael Perkins, Justin Chalker

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)1220-1228
    Number of pages9
    JournalTetrahedron
    Volume74
    Issue number12
    Early online date2018
    DOIs
    Publication statusPublished - 22 Mar 2018

    Keywords

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

    Fingerprint Dive into the research topics of 'Norbornene probes for the study of cysteine oxidation'. Together they form a unique fingerprint.

    Cite this