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Issue 38, 2020
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Copper-mediated peptide arylation selective for the N-terminus

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Abstract

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

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Supplementary files

Article information


Submitted
23 May 2020
Accepted
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

Chem. Sci., 2020,11, 10501-10505
Article type
Edge Article

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

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    [Original citation] - Published by The Royal Society of Chemistry.

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