Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells

Lisa J Alcock; Bruno L Oliveira; Michael J Deery; Tara L Pukala; Michael V Perkins; Gonçalo J L Bernardes; Justin M Chalker

doi:10.1021/acschembio.8b01104

Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells

ACS Chem Biol. 2019 Apr 19;14(4):594-598. doi: 10.1021/acschembio.8b01104. Epub 2019 Mar 26.

Authors

Lisa J Alcock^{1

2}, Bruno L Oliveira³, Michael J Deery⁴, Tara L Pukala⁵, Michael V Perkins¹, Gonçalo J L Bernardes^{3

6}, Justin M Chalker^{1

2}

Affiliations

¹ Flinders University , College of Science and Engineering , Sturt Road , Bedford Park , South Australia 5042 , Australia.
² Flinders University , Institute for NanoScale Science and Technology , Sturt Road , Bedford Park , South Australia 5042 , Australia.
³ Department of Chemistry , University of Cambridge , Lensfield Road , Cambridge CB2 1EW , United Kingdom.
⁴ Cambridge Centre for Proteomics, Cambridge Systems Biology Centre, Department of Biochemistry , University of Cambridge , Tennis Court Road , Cambridge CB2 1QW , United Kingdom.
⁵ The University of Adelaide , School of Physical Sciences , Adelaide , South Australia 5005 , Australia.
⁶ Instituto de Medicina Molecular, Faculdade de Medicina , Universidade de Lisboa , Avenida Professor Egas Moniz , 1649-028 , Lisboa , Portugal.

PMID: 30893551
DOI: 10.1021/acschembio.8b01104

Abstract

Norbornene derivatives were validated as probes for cysteine sulfenic acid on proteins and in live cells. Trapping sulfenic acids with norbornene probes is highly selective and revealed a different reactivity profile than the traditional dimedone reagent. The norbornene probe also revealed a superior chemoselectivity when compared to a commonly used dimedone probe. Together, these results advance the study of cysteine oxidation in biological systems.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cysteine / analogs & derivatives*
Cysteine / analysis
Molecular Probes / chemistry*
Norbornanes / chemistry*
Oxidation-Reduction
Sulfenic Acids / analysis*

Substances

Molecular Probes
Norbornanes
Sulfenic Acids
2-norbornene
cysteinesulfenic acid
Cysteine