CUED Publications database

Site-Selective Modification of Proteins with Oxetanes

Boutureira, O and Martínez-Sáez, N and Brindle, KM and Neves, AA and Corzana, F and Lopes Bernardes, GJ (2017) Site-Selective Modification of Proteins with Oxetanes. Chemistry - A European Journal, 23. pp. 6483-6489. (Unpublished)

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Oxetanes are four-membered ring oxygen heterocycles that are advantageously used in medicinal chemistry as modulators of physicochemical properties of small molecules. Herein, we present a simple method for the incorporation of oxetanes into proteins through chemoselective alkylation of cysteine. We demonstrate a broad substrate scope by reacting proteins used as apoptotic markers and in drug formulation, and a therapeutic antibody with a series of 3-oxetane bromides, enabling the identification of novel handles (S-to-S/N rigid, non-aromatic, and soluble linker) and reactivity modes (temporary cysteine protecting group), while maintaining their intrinsic activity. The possibility to conjugate oxetane motifs into full-length proteins has potential to identify novel drug candidates as the next-generation of peptide/protein therapeutics with improved physicochemical and biological properties.

Item Type: Article
Uncontrolled Keywords: antibodies oxetanes protein modifications small oxygen heterocycles sulfur
Depositing User: Cron Job
Date Deposited: 25 Jun 2019 02:49
Last Modified: 13 Apr 2021 08:54
DOI: 10.1002/chem.201700745