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

Clément A. Sanchez | Zendy; Charlène Gadais | Zendy; Grégory Chaume | Zendy; Sylvain Girard | Zendy; Évelyne Chelain | Zendy; Thierry Brigaud | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

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

Author(s) -

Clément A. Sanchez,

Charlène Gadais,

Grégory Chaume,

Sylvain Girard,

Évelyne Chelain,

Thierry Brigaud

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03880

Subject(s) - enantiopure drug , chemistry , pyroglutamic acid , peptide bond , conformational isomerism , peptide synthesis , proline , reagent , isomerization , peptide , stereochemistry , amino acid , combinatorial chemistry , amide , organic chemistry , molecule , enantioselective synthesis , catalysis , biochemistry

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 CF 3 group provides a decrease of the rans o cis amide bond isomerization energy and an increase of the cis conformer population.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research