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| Origine | Fichiers produits par l'(les) auteur(s) |
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