engleski

New types of heteroannularly substituted ferrocene peptides

Among artificial peptide building blocks the 1, 1'-disubstituted ferrocene scaffold has attracted particular interest because of its unique properties and potential usage in biomedical, nano- and material sciences. Herein we report the synthesis and characterization of unsymmetrical disubstituted ferrocene peptides type I (NOH(CH3)C-Fn-CO-AA-OCH3) and II (NOH(CH3)C-Fn-NH-AA-Boc) with oxime subunit on 1’-cyclopentadienyl ring as potential hydrogen donor/acceptor of hydrogen bond. Prepared bioconjugates I and II were characterized by FTIR, NMR and CD spectroscopy. Conformational analysis of prepared unsymmetrically substituted ferrocene compounds type I and II has shown presence of week to medium intramolecular hydrogen bonds. Positive Cotton effects have been associated with P-helical ferrocene units while negative Cotton effects are considered to be indicative of M-helical ferrocene chromophores which suggest that in this case compounds I form predominantly P-helical conformations while compounds II form M-helical conformations.

ferrocene; peptides; oxime; IHB; synthesis; conformational analysis; spectroscopy

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