New types of heteroannularly substituted ferrocene peptides (CROSBI ID 374986)
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Bilić, Josipa
Djaković, Senka
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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02.07.2012.
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