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Unearthing the unique stability of thiophosphonium-C-terminal cysteine adducts on peptides and proteins

Spears, Richard J; Chrzastek, Alina; Yap, Steven Y; Karu, Kersti; Aliev, Abil E; Baker, James R; Chudasama, Vijay; (2022) Unearthing the unique stability of thiophosphonium-C-terminal cysteine adducts on peptides and proteins. Chemical Communication 10.1039/d2cc01090a. (In press). Green open access

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Abstract

Herein we report a fundamental discovery on the use of tris(dialkylamino)phosphine reagents for peptide and protein modification. We discovered that C-terminal thiophosphonium species, which are uniquely stable, could be selectively and rapidly generated from their disulfide counterparts. In sharp and direct contrast, internal thiophosphonium species rapidly degrade to dehydroalanine. We demonstrate this remarkable chemoselectivity on a bis-cysteine model peptide, and the formation of a stable C-terminal-thiophosphonium adduct on an antibody fragment, as well as characterise the species in various small molecule/peptide studies.

Type: Article
Title: Unearthing the unique stability of thiophosphonium-C-terminal cysteine adducts on peptides and proteins
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d2cc01090a
Publisher version: https://doi.org/10.1039/D2CC01090A
Language: English
Additional information: Open Access Article. Published on 02 April 2022. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10146675
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