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Issue 35, 2021

Oxidative peptide bond formation of glycine–amino acid using 2-(aminomethyl)malononitrile as a glycine unit

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Abstract

Amide linkage of glycine–amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O2 in an aqueous solution. This is a coupling reagent-free and catalyst-free peptide synthesis via oxidative amide bond formation. Various tripeptides and tetrapeptides were synthesized efficiently and the sulfide moiety is inert even under an oxygen atmosphere.

Graphical abstract: Oxidative peptide bond formation of glycine–amino acid using 2-(aminomethyl)malononitrile as a glycine unit

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Article information


Submitted
08 Jan 2021
Accepted
22 Mar 2021
First published
23 Mar 2021

Chem. Commun., 2021,57, 4283-4286
Article type
Communication

Oxidative peptide bond formation of glycine–amino acid using 2-(aminomethyl)malononitrile as a glycine unit

X. Wang, J. Li and Y. Hayashi, Chem. Commun., 2021, 57, 4283 DOI: 10.1039/D1CC00130B

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