Enantiopure 5-CF 3 –Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry
Overview & Synopsis
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 trans to cis amide bond isomerization energy and an increase of the cis conformer population.
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hal.science)
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Document Information
| Document Title | Enantiopure 5-CF 3 –Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry |
|---|---|
| Author / Organization | Thierry Brigaud, Clément A Sanchez, Charlène Gadais, Grégory Chaume, Sylvaine Girard, Evelyne Chelain |
| Subject & Discipline | Multidisciplinary Academic Open Research |
| Categories | Science & Mathematics |
| Publication Year | 2021 |
| License / Rights | Open Access / Creative Commons |
| Resource Verification | Listed PDF (Verification Pending) |
| Original Host Website |
HAL Open Science
(hal.science)
|
| File Format | application/pdf (Portable Document Format) |
| Language | EN |
| Catalog ID | DOC-224147 |
| Original Source Link | Visit Source Page on hal.science » |