Synthesis of the prototypical cyclopropyl dipeptide mimic and evaluation of its turn-inducing capability

Neckebroeck, A., Kelly, S. M. , Smith, B. O. and Clark, J. S. (2022) Synthesis of the prototypical cyclopropyl dipeptide mimic and evaluation of its turn-inducing capability. Journal of Organic Chemistry, 87(1), pp. 258-270. (doi: 10.1021/acs.joc.1c02344) (PMID:34913698)

Abstract

The (+) and (−) enantiomers of a new turn-inducing cyclopropyl dipeptide mimic have been synthesized and evaluated. The mimic derives its turn-inducing capabilities solely from the cyclopropyl group and without the conformational biasing that would be provided by side-chain substituents. The mimic and peptide-mimic hybrids prepared from it have been studied using a combination of spectroscopic techniques (NMR, IR, and CD). The dipeptide mimic itself displays intramolecular hydrogen bonding in organic solvents, which differs from that observed in natural peptide turns. In contrast, more elaborate peptide-mimic hybrids exhibit hydrogen bonding characteristics that vary with solvent but are consistent with structures found in the tetrapeptide portion (i → i + 3) of a native β-turn.

• Item Type: Articles
• Additional Information: The authors acknowledge the award of a studentship to A.N. by the Loudon Endowment Fund of the University of Glasgow.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Clark, Professor Stephen and Kelly, Dr Sharon and Neckebroeck, Albane and Smith, Dr Brian
• Authors: Neckebroeck, A., Kelly, S. M., Smith, B. O., and Clark, J. S.
• College/School: College of Medical Veterinary and Life Sciences > Institute of Molecular Cell and Systems Biology; College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Published Online: 16 December 2021
• Copyright Holders: Copyright © 2021 American Chemical Society
• First Published: First published in Journal of Organic Chemistry 87(1): 258-270
• Publisher Policy: Reproduced in accordance with the publisher copyright policy