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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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Publication details

The article was received on 24 Jul 2017, accepted on 29 Oct 2017 and first published on 30 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC03229C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C7SC03229C

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