Issue 38, 2020

Copper-mediated peptide arylation selective for the N-terminus


Polypeptides present remarkable selectivity challenges for chemical methods. Amino groups are ubiquitous in polypeptide structure, yet few paradigms exist for reactivity and selectivity in arylation of amine groups. This communication describes the utilization of boronic acid reagents bearing certain o-electron withdrawing groups for copper-mediated amine arylation of the N-terminus under mild conditions and primarily aqueous solvent. The method adds to the toolkit of boronic acid reagents for polypeptide modification under mild conditions in water that shows complete selectivity for the N-terminus in the presence of lysine side chains.

Graphical abstract: Copper-mediated peptide arylation selective for the N-terminus

Supplementary files

Article information

Article type
Edge Article
23 May 2020
11 Sep 2020
First published
14 Sep 2020
This article is Open Access

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

Chem. Sci., 2020,11, 10501-10505

Copper-mediated peptide arylation selective for the N-terminus

M. K. Miller, H. Wang, K. Hanaya, O. Zhang, A. Berlaga and Z. T. Ball, Chem. Sci., 2020, 11, 10501 DOI: 10.1039/D0SC02933E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity