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; T. Brigaud

doi:10.1039/C9CC05771D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

N. Malquin,^a K. Rahgoshay,^a N. Lensen,

*^a G. Chaume,

*^a E. Miclet

^b and T. Brigaud

*^a

Author affiliations

* Corresponding authors

^a Laboratory of Chemical Biology (LCB, EA 4505), Université de Cergy-Pontoise, 5 Mail Gay-Lussac, 95000 Cergy-Pontoise, France
E-mail: nathalie.lensen@u-cergy.fr, gregory.chaume@u-cergy.fr, thierry.brigaud@u-cergy.fr

^b Sorbonne Université, École Normale Supérieure, PSL University, CNRS, Laboratoire des Biomolécules, 75005 Paris, France

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.

Download options Please wait...

Supplementary files

Supplementary information PDF (8807K)

Article information

DOI: https://doi.org/10.1039/C9CC05771D
Article type: Communication
Submitted: 25 Jul 2019
Accepted: 23 Sep 2019
First published: 23 Sep 2019

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications