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. 2021 Jan 15;23(2):382-387.
doi: 10.1021/acs.orglett.0c03880. Epub 2020 Dec 28.

Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry

Clément A Sanchez  1   2 , Charlène Gadais  1   2 , Grégory Chaume  1   2 , Sylvaine Girard  1   2 , Evelyne Chelain  1   2 , Thierry Brigaud  1   2
Affiliations

Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry

Clément A Sanchez et al. Org Lett. .

Abstract

The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.

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