Applications of Thiol-Ene Chemistry for Peptide Science

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"...

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Published inFrontiers in chemistry Vol. 8; p. 583272
Main Authors Nolan, Mark D., Scanlan, Eoin M.
Format Journal Article
LanguageEnglish
Published Frontiers Media S.A 12.11.2020
Subjects
bioconjugation
Chemistry
peptides
protein
radical
thiol (-SH)
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Summary: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.
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This article was submitted to Organic Chemistry, a section of the journal Frontiers in Chemistry
Edited by: Chun Xu, The University of Queensland, Australia
Reviewed by: Junfeng Zhao, Jiangxi Normal University, China; Mustafa O. Guler, University of Chicago, United States
ISSN:2296-2646
2296-2646
DOI:10.3389/fchem.2020.583272