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Facile method for the synthesis of triazole- and tetrazole-containing peptoids on a solid support

Author:
Lee, Yen Jea, Kang, Dahyun, Seo, Jiwon
Source:
Tetrahedron letters 2018
ISSN:
0040-4039
Subject:
Lewis bases, N-substituted glycines, azides, biomimetics, chemical bonding, chemical reactions, cyanides, moieties, triazoles
Abstract:
The late-stage functionalization of a biomimetic foldamer such as a peptoid is a useful tool to achieve structural diversity. Herein, a facile method for the synthesis of triazole- or tetrazole-containing peptoids using post-synthetic modifications has been reported. On a resin-bound peptoid with a chloroalkyl side chain(s), substitution with nucleophiles (azide or cyanide) and the subsequent [3 + 2]-cycloaddition reaction were optimized. Peptoids with azide, triazole, and tetrazole functional groups could be readily synthesized and could potentially be utilized further for orthogonal bioconjugation or metal recognition.
Agid:
6097707