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Issue 2, 2018
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Expedient on-resin modification of a peptide C-terminus through a benzotriazole linker

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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

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Supplementary files

Article information


Submitted
24 Jul 2017
Accepted
29 Oct 2017
First published
30 Oct 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 345-349
Article type
Edge Article

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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