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Issue 83, 2019
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CF2H as a hydrogen bond donor group for the fine tuning of peptide bond geometry with difluoromethylated pseudoprolines

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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

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Publication details

The article was received on 25 Jul 2019, accepted on 23 Sep 2019 and first published on 23 Sep 2019


Article type: Communication
DOI: 10.1039/C9CC05771D
Chem. Commun., 2019,55, 12487-12490

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    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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