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Pré-Publication, Document De Travail Année : 2023

Difluoroalanine: Synthesis, Incorporation in Peptides, and Hydrophobic Contribution Assessment

Résumé

The straightforward synthesis of chiral (R)- and (S)-difluoroalanine (DfAla) is reported. The key step is a Strecker-type reaction on a (R)-difluorophenethylimine followed by hydrogenolysis, Fmoc protection and acidic hydrolysis. Peptide coupling reactions at its N- and C-terminal position provide diastereomerically pure tripeptides. Based on hydrophobicity index measurements, the hydrophobic contribution of difluoroalanine in a peptide chain was found to be quite similar to that of isoleucine for a smaller van der Waals volume of the side chain.

Domaines

Chimie
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Dates et versions

hal-04249424 , version 1 (19-10-2023)

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Citer

Yazid Boutahri, Khoubaib Ben Haj Salah, Nicolas Tisserand, Nathalie Lensen, Benoit Crousse, et al.. Difluoroalanine: Synthesis, Incorporation in Peptides, and Hydrophobic Contribution Assessment. 2023. ⟨hal-04249424⟩
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