Issue 2, 2018

Expedient on-resin modification of a peptide C-terminus through a benzotriazole linker

Abstract

A convenient and efficient chemical toolbox was developed for the on-resin C-terminal functionalization of various peptides. By transforming resin-bound 3,4-diaminobenzoic acid species with isoamyl nitrite, the resulting resin-bound benzotriazole entity can be efficiently displaced by nucleophiles during cleavage of the peptide–resin connection in a short reaction time. The resin cleavage step allowed for the use of various nucleophiles including water, EtOH, amines, thiol, and G5 poly(amidoamino) dendrimers with yields ranging from 66% to 82% within 5 h. This method was successfully applied to prepare the elastin sequence (VPGVG)4 through on-resin ligation in 77% yield in one day and a head-to-tail cyclic peptide, sunflower trypsin inhibitor-1, in 42% yield.

Graphical abstract: Expedient on-resin modification of a peptide C-terminus through a benzotriazole linker

Supplementary files

Article information

Article type
Edge Article
Submitted
24 jul 2017
Accepted
29 out 2017
First published
30 out 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 345-349

Expedient on-resin modification of a peptide C-terminus through a benzotriazole linker

A. Selvaraj, H. Chen, A. Ya-Ting Huang and C. Kao, Chem. Sci., 2018, 9, 345 DOI: 10.1039/C7SC03229C

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