Issue 10, 2022

Umpolung strategies for the functionalization of peptides and proteins

Abstract

Umpolung strategies, defined as synthetic approaches which reverse commonly accepted reactivity patterns, are broadly recognized as enabling tools for small molecule synthesis and catalysis. However, methods which exploit this logic for peptide and protein functionalizations are comparatively rare, with the overwhelming majority of existing bioconjugation approaches relying on the well-established reactivity profiles of a handful of amino acids. This perspective serves to highlight a small but growing body of recent work that masterfully capitalizes on the concept of polarity reversal for the selective modification of proteinogenic functionalities. Current applications of umpolung chemistry in organic synthesis and chemical biology as well as the vast potential for further innovations in peptide and protein modification will be discussed.

Graphical abstract: Umpolung strategies for the functionalization of peptides and proteins

Article information

Article type
Perspective
Submitted
05 nov 2021
Accepted
04 jan 2022
First published
02 feb 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 2809-2823

Umpolung strategies for the functionalization of peptides and proteins

A. M. White, I. R. Palombi and L. R. Malins, Chem. Sci., 2022, 13, 2809 DOI: 10.1039/D1SC06133J

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