Peptide Elongation Using α-NCAs Both as Nucleophiles and Electrophiles

Key words

α-amino acid N-carboxy anhydrides - three-component coupling - continuous flow - column-chromatography-free synthesis

Significance

Peptides are one of the most useful compounds as drugs. However, conventional methods for peptide synthesis require deprotection steps and cumbersome purification. The authors have developed a rapid and column-chromato­graphy-free three-component peptide-coupling reaction using α-amino acid N-carboxy anhydrides (α-NCAs) both as nucleophiles and electrophiles.

Comment

First, the nitrogen of the α-NCAs ­reacts with amino acid chloride as a nucleophile. Subsequently, a reaction occurs between the acid anhydride moiety of α-NCAs as an electrophile and the amino group of the amino ester, resulting in a formation of various peptides.

Publication History

Article published online:
16 August 2023