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

ABSTRACT: α,β^2,3-Disteroisomeric foldamers of general formula Boc(S-Ala-β-2R,3R-Fpg)_nOMe or Boc(S-Ala-β-2S,3S-Fpg)_nOMe were prepared from both enantiomers of syn H-2-(2-F-Phe)-h-PheGly-OH (named β-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 π-stacking. A conformational study was performed, using IR, NMR and computational studies of diastereoisomeric tetra- and hexapeptides containing the β^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

SUBMITTER: Bucci R 

PROVIDER: S-EPMC6454073 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature