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Updated: Jun 3, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
(E)-alkene Peptide bond isosteres by cuprate opening of vinyl aziridines
1Department of Chemistry, University of Pittsburgh, Pittsburgh, PA.
Abstract:
Alkene isosteres are important nonhydrolyzable and rigidified analogs of peptide bonds. The (E-alkene effectively mimics the three-dimensional structure of the amide bond, especially the C(α)( n )-C(α)( n+1 ) distance (Fig. 1). The incorporation of an alkene isostere into a biologically active peptide provides a peptidomimetic that should have improved resistance to proteolysis and similar conformational preferences. The low polarity of the alkene is useful in increasing lipophilicity, but hydrogen bonding or dipolar interactions are generally not possible. Fig. 1. Geometry of peptide bond and alkene isostere.
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