Issue 2, 2021
From the journal:

RSC Chemical Biology

Identifying cysteine residues susceptible to oxidation by photoactivatable atomic oxygen precursors using a proteome-wide analysis†

Ankita Isor,a   Benjamin V. Chartier,b   Masahiro Abo,b   Emily R. Currens,a   Eranthie Weerapanab  and  Ryan D. McCulla ORCID logo *a  

* Corresponding authors

a Department of Chemistry, Saint Louis University, 3501 Laclede Ave, Saint Louis, MO 63103, USA
E-mail: ryan.mcculla@slu.edu

b Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA

Abstract

The reactivity profile of atomic oxygen [O(3P)] in the condensed phase has shown a preference for the thiol group of cysteines. In this work, water-soluble O(3P)-precursors were synthesized by adding aromatic burdens and water-soluble sulphonic acid groups to the core structure of dibenzothiophene-S-oxide (DBTO) to study O(3P) reactivity in cell lysates and live cells. The photodeoxygenation of these compounds was investigated using common intermediates, which revealed that an increase in aromatic burdens to the DBTO core structure decreases the total oxidation yield due to competitive photodeoxygenation mechanisms. These derivatives were then tested in cell lysates and live cells to profile changes in cysteine reactivity using the isoTOP-ABPP chemoproteomics platform. The results from this analysis indicated that O(3P) significantly affects cysteine reactivity in the cell. Additionally, O(3P) was found to oxidize cysteines within peptide sequences with leucine and serine conserved at the sites surrounding the oxidized cysteine. O(3P) was also found to least likely oxidize cysteines among membrane proteins.

Graphical abstract: Identifying cysteine residues susceptible to oxidation by photoactivatable atomic oxygen precursors using a proteome-wide analysis

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Article information

DOI
https://doi.org/10.1039/D0CB00200C
Article type
Paper
Submitted
10 Nov 2020
Accepted
03 Jan 2021
First published
19 Jan 2021
This article is Open Access
Creative Commons BY-NC license

RSC Chem. Biol., 2021,2, 577-591

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Identifying cysteine residues susceptible to oxidation by photoactivatable atomic oxygen precursors using a proteome-wide analysis

A. Isor, B. V. Chartier, M. Abo, E. R. Currens, E. Weerapana and R. D. McCulla, RSC Chem. Biol., 2021, 2, 577 DOI: 10.1039/D0CB00200C

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