Issue 31, 2022

Peptide macrocyclisation via late-stage reductive amination

Abstract

A two-component reductive amination approach to the synthesis of peptide macrocycles is reported which leverages the inherent reactivity of proteinogenic amine nucleophiles. Unprotected peptides bearing α-amine and side chain amine motifs undergo two-fold reductive amination reactions with 2,6-pyridinedialdehyde linkers in aqueous media to afford macrocyclic peptide products with backbone embedded pyridine motifs. Dialdehyde staples bearing valuable azide and alkyne handles also enable the post-cyclisation modification of peptides using copper-catalysed azide–alkyne cycloaddition (CuAAC) chemistry.

Graphical abstract: Peptide macrocyclisation via late-stage reductive amination

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
26 avr. 2022
Accepted
24 mai 2022
First published
27 mai 2022

Org. Biomol. Chem., 2022,20, 6250-6256

Peptide macrocyclisation via late-stage reductive amination

H. J. Bell and L. R. Malins, Org. Biomol. Chem., 2022, 20, 6250 DOI: 10.1039/D2OB00782G

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