Applications of Thiol-Ene Chemistry for Peptide Science

Abstract

Radical thiol-ene chemistry has been demonstrated for a range of applications in peptide science, including macrocyclization, glycosylation and lipidation amongst a myriad of others. The thiol-ene reaction offers a number of advantages in this area, primarily those characteristic of “click” reactions. This provides a chemical approach to peptide modification that is compatible with aqueous conditions with high orthogonality and functional group tolerance. Additionally, the use of a chemical approach for peptide modification affords homogeneous peptides, compared to heterogeneous mixtures often obtained through biological methods. In addition to peptide modification, thiol-ene chemistry has been applied in novel approaches to biological studies through synthesis of mimetics and use in development of probes. This review will cover the range of applications of the radical-mediated thiol-ene reaction in peptide and protein science.

Radical-mediated thiol–ene ‘click’ reactions in deep eutectic solvents for bioconjugation

“…Radical thiol–ene chemistry in traditional solvents has found significant application in synthetic chemistry, 30 including in carbohydrate 31 and peptide science. 32,33 The ‘click’ characteristics of the radical thiol–ene reaction, 34 together with excellent atom economy, complement the development of ‘green’ syntheses, in particular bioconjugation reactions (Fig. 1).…”

A biohybrid strategy for enabling photoredox catalysis with low-energy light

“…We first investigated the effectiveness of RPE- (Ru) n in the thiol-ene reaction, a widely adopted bioconjugation strategy extended to photoredox catalysis by Yoon and coworkers. 71,73,74 ll reports 74 ). To demonstrate the generality of the observed enhancement, four additional substrates (4-7) were evaluated.…”

Catch, Modify and Analyze: Methods of Chemoselective Modification of Cysteine-Containing Peptides

“…Due to the importance of cysteine-containing peptides, resulting from their role in biological systems, different strategies for their enrichment (catching) and modification have been developed [ 10 , 11 , 12 , 13 , 14 ]. In general, methods of cysteine-containing peptide enrichment can be divided into enrichment in solution, or on solid supports.…”