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CC BY-NC-ND 4.0 · Synthesis 2022; 54(06): 1518-1526
DOI: 10.1055/s-0040-1719862
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
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).
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)Publikationsverlauf
Eingereicht: 23. Juli 2021
Angenommen nach Revision: 17. September 2021
Artikel online veröffentlicht:
05. Januar 2022
© 2022. The Author(s). 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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