Norbornene probes for the study of cysteine oxidation

TETRAHEDRON

卷:74

Article

Alcock, Lisa J.¹  Farrell, Kyle D.¹  Akol, Mawey T.¹  Jones, Gregory H.²  Tierney, Matthew M.³  Kramer, Holger B.⁴  Pukala, Tara L.⁵  Bernardes, Goncalo J. L.^6,7  Perkins, Michael V.¹  Chalker, Justin M.¹ 

[1] Flinders Univ S Australia, Coll Sci & Engn, Sturt Rd, Bedford Pk, SA 5042, Australia

[2] CALTECH, Div Chem & Chem Engn, 1200 East Calif Blvd, Pasadena, CA 91125 USA

[3] Univ North Carolina Chapel Hill, Dept Chem, Chapel Hill, NC 27599 USA

[4] Imperial Coll London, MRC London Inst Med Sci, Hammersmith Hosp Campus,Du Cane Rd, London W12 0NN, England

[5] Univ Adelaide, Sch Phys Sci, Adelaide, SA 5005, Australia

[6] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[7] Univ Lisbon, Fac Med, Inst Med Mol, Ave Prof Egas Moniz, P-1649028 Lisbon, Portugal

关键词: Cysteine;    Cysteine sulfenic acid;    Norbornene;    Oxidative stress;    Chemical biology;   

DOI  :  10.1016/j.tet.2017.11.011

来源: Elsevier

【 摘 要 】

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. (C) 2017 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.orgilicensesiby/4.0/).

【 授权许可】

Free