Issue 83, 2019

CF2H as a hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines

Abstract

CF2H-Pseudoprolines obtained from difluoroacetaldehyde hemiacetal and serine are stable proline surrogates. The consequence of the incorporation of the CF2H group is an important decrease of the trans to cis amide bond isomerization energy and a remarkable stabilisation of the cis conformer by an hydrogen bond.

Graphical abstract: CF2H as a hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines

Supplementary files

Article information

Article type
Communication
Submitted
25 Jul 2019
Accepted
23 Sep 2019
First published
23 Sep 2019

Chem. Commun., 2019,55, 12487-12490

CF2H as a hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines

N. Malquin, K. Rahgoshay, N. Lensen, G. Chaume, E. Miclet and T. Brigaud, Chem. Commun., 2019, 55, 12487 DOI: 10.1039/C9CC05771D

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