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CC BY-NC-ND 4.0 · Synthesis 2022; 54(06): 1518-1526
DOI: 10.1055/s-0040-1719862
short review

N-Amino-imidazol-2-one (Nai) Residues as Tools for Peptide Mimicry: Synthesis, Conformational Analysis and Biomedical Applications

Yousra Hamdane 
,
Julien Poupart
,
William D. Lubell∗
This work was funded by the Natural Sciences and Engineering Research Council of Canada (NSERC), Discovery Research Project (Grant no. 04079), NSERC/Canadian Institutes of Health Research (CIHR), Collaborative Health Research Projects ‘Treatment of Age-Related Macular Degeneration with CD36 Receptor Modulators’ (Grant no. 315878) and ‘Azacyclopeptide Modulators of Immuno-metabolism to Treat Age-Related Macular Degeneration’ (Grant no. 163973), NuChem Therapeutics, Inc., Mperia Therapeutics, Inc. and the Fonds de Recherche Nature et Technologie Québec for the Centre in Green Chemistry and Catalysis (CCVC).
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In memory of Professor Robin E. Offord (1940–2021), inspirational scholar, peptide scientist, humanitarian and mentor dedicated to the empowerment of young investigators.

Abstract

N-Amino-imidazol-2-one (Nai) residues are tools for studying peptide-backbone and side-chain conformation and function. Recent methods for substituted Nai residue synthesis, conformational analysis by X-ray crystallography and computation, and biomedical applications are reviewed, demonstrating the utility of this constrained residue to favor biologically active turn conformers with defined χ-dihedral angle orientations.

1 Introduction

2 Synthetic Methods

3 Conformational Analysis

4 Biomedical Applications

5 Conclusions

Key words

N-aminoimidazol-2-one - Nai residue - peptide mimicry - 5-endo-dig cyclization - β-turn - organocatalysis - cluster of differentiation-36 (CD36)


Publication History

Received: 23 July 2021

Accepted after revision: 17 September 2021

Article published online:
05 January 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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