Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines

Xinyue Fang, Yong Zeng, Yawen Huang, Zile Zhu, Shengsheng Lin, Wenyan Xu, Chengwei Zheng, Xinwei Hu (), Youai Qiu () and Zhixiong Ruan ()
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Xinyue Fang: Guangzhou Medical University
Yong Zeng: Guangzhou Medical University
Yawen Huang: Guangzhou Medical University
Zile Zhu: Nankai University
Shengsheng Lin: Guangzhou Medical University
Wenyan Xu: Guangzhou Medical University
Chengwei Zheng: Guangzhou Medical University
Xinwei Hu: Guangzhou Medical University
Youai Qiu: Nankai University
Zhixiong Ruan: Guangzhou Medical University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Peptide aldehydes are crucial biomolecules essential to various biological systems, driving a continuous demand for efficient synthesis methods. Herein, we develop a metal-free, facile, and biocompatible strategy for direct electrochemical synthesis of unnatural peptide aldehydes. This electro-oxidative approach enabled a step- and atom-economical ring-opening via C‒N bond cleavage, allowing for homoproline-specific peptide diversification and expansion of substrate scope to include amides, esters, and cyclic amines of various sizes. The remarkable efficacy of the electro-synthetic protocol set the stage for the efficient modification and assembly of linear and macrocyclic peptides using a concise synthetic sequence with racemization-free conditions. Moreover, the combination of experiments and density functional theory (DFT) calculations indicates that different N-acyl groups play a decisive role in the reaction activity.

Date: 2024
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DOI: 10.1038/s41467-024-49223-y

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