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Fluoro-Aryl Substituted ?,?2,3-Peptides in the Development of Foldameric Antiparallel ?-Sheets: A Conformational Study.

ABSTRACT: ?,?2,3-Disteroisomeric foldamers of general formula Boc(S-Ala-?-2R,3R-Fpg)nOMe or Boc(S-Ala-?-2S,3S-Fpg)nOMe were prepared from both enantiomers of syn H-2-(2-F-Phe)-h-PheGly-OH (named ?-Fpg) and S-alanine. Our peptides show two appealing features for biomedical applications: the presence of fluorine, attractive for non-covalent interactions, and aryl groups, crucial for ?-stacking. A conformational study was performed, using IR, NMR and computational studies of diastereoisomeric tetra- and hexapeptides containing the ?2,3-amino acid in the R,R- and S,S-stereochemistry, respectively. We found that the stability of peptide conformation is dependent on the stereochemistry of the ?-amino acid. Combining S-Ala with ?-2R,3R-Fpg, a stable extended ?-strand conformation was obtained. Furthermore, ?-2R,3R-Fpg containing hexapeptide self-assembles to form antiparallel ?-sheet structure stabilized by intermolecular H-bonds and ?,?-interactions. These features make peptides containing the ?2,3-fluoro amino acid very appealing for the development of bioactive proteolytically stable foldameric ?-sheets as modulators of protein-protein interaction (PPI).

SUBMITTER: Bucci R 

PROVIDER: S-EPMC6454073 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Fluoro-Aryl Substituted α,β<sup>2,3</sup>-Peptides in the Development of Foldameric Antiparallel β-Sheets: A Conformational Study.

Bucci Raffaella R   Contini Alessandro A   Clerici Francesca F   Beccalli Egle Maria EM   Formaggio Fernando F   Maffucci Irene I   Pellegrino Sara S   Gelmi Maria Luisa ML  

Frontiers in chemistry 20190402

α,β<sup>2,3</sup>-Disteroisomeric foldamers of general formula Boc(<i>S-</i>Ala-β-2<i>R</i>,3<i>R-</i>Fpg)<sub>n</sub>OMe or Boc(<i>S-</i>Ala-β-2<i>S</i>,3<i>S-</i>Fpg)<sub>n</sub>OMe were prepared from both enantiomers of <i>syn</i> H-2-(2-F-Phe)-h-PheGly-OH (named β-Fpg) and <i>S-</i>alanine. Our peptides show two appealing features for biomedical applications: the presence of fluorine, attractive for non-covalent interactions, and aryl groups, crucial for π-stacking. A conformational study wa  ...[more]

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