Research Paper on Bis-Ferrocenyl End-Capped Peptides: Helical versus Flat: The Effect of the Molecular Skeleton on Redox Properties

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Title: Bis-Ferrocenyl End-Capped Peptides: Helical versus Flat: The Effect of the Molecular Skeleton on Redox Properties

Abstract: Bis-ferrocenyl end-capped peptides are infrequently synthesized, despite the fact that peptide conjugates with a pendant ferrocenyl (Fc) have been extensively studied. In order to gain insight into the effects of the amino acids amino isobutyric (Aib), 2,3-diamino propionic (Dap), and C, -didehydroalanine (DAla) on the peptide secondary structure and on the ferrocene redox properties, we report a comparison of the three series of bis-ferrocenyl homopeptides synthesized up to this point. 310-helical or fully extended (2.05-helix) structures are formed depending on the nature of the amino acid, according to the results of 2D NMR analysis and X-ray crystal structures, which are further supported by electrochemical data. As the peptide chain lengthens, oxidation of the Fc moieties occurs more or less readily depending on the orientation of the macrodipole moment due to the orientation of the carbonyl groups in these foldamers, which produce a macrodipole with the positive pole on the N-terminal amino acid and the negative pole on the C-terminal amino acid. In contrast, neither a macrodipole nor Fc oxidation are impacted by the fully extended conformation used by DAla flat peptides. The two terminal Fc groups of the L-Dap(Boc) series can be used as electrochemical and optical (Circular Dichroism) probes to study the end-to-end effects of the positive charges produced by single and double oxidations, and to demonstrate the presence of “exciton-coupled” CD among the two intramolecularly interacting Fc groups.

Keywords: helical peptides; ferrocene; -amino isobutyric acid; 2,3-diamino propionic acid; C,-didehydroalanine; macrodipole; electrochemistry; exciton-coupled Circular Dichroism

Paper Quality: SCOPUS / Web of Science Level Research Paper

Subject: Chemistry

Writer Experience: 20+ Years

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