New β-strand templates constrained by Huisgen cycloaddition

Organic Letters
Ashok D Pehere, Andrew D Abell

Abstract

New peptidic templates constrained into a β-strand geometry by linking acetylene and azide containing P(1) and P(3) residues of a tripeptide by Huisgen cycloaddition are presented. The conformations of the macrocycles are defined by NMR studies and those that best define a β-strand are shown to be potent inhibitors of the protease calpain. The β-strand templates presented and defined here are prepared under optimized conditions that should be suitable for targeting a range of proteases and other applications requiring such a geometry.

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Citations

Sep 18, 2013·Proceedings of the National Academy of Sciences of the United States of America·Kenneth V LawsonPatrick G Harran
Nov 13, 2015·ACS Combinatorial Science·Steven B CoffeyAllyn Timothy Londregan
Sep 8, 2012·The Journal of Organic Chemistry·William D Lubell
Sep 8, 2012·Organic Letters·William D Lubell
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Jul 24, 2020·Expert Opinion on Therapeutic Patents·Isaac O Donkor
Apr 23, 2013·Chemistry : a European Journal·Ashok D PehereAndrew D Abell
Jun 7, 2014·Angewandte Chemie·Krystle C H ChuaAndrew D Abell
Oct 10, 2012·Organic & Biomolecular Chemistry·Ashok D PehereAndrew D Abell
Nov 20, 2012·Chemistry & Biodiversity·Hongyuan ChenAndrew D Abell
Jun 8, 2021·Frontiers in Chemistry·Agnieszka StaśkiewiczRafal Latajka
Jul 16, 2021·RSC Medicinal Chemistry·Quynh Ngoc VuYu Heng Lau
Jun 4, 2019·Chemical Reviews·Ivan V SmolyarValentine G Nenajdenko

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