Naslov
Ferrocene-dipeptide conjugates derived from aminoferrocene and 1-acetyl-1′-aminoferrocene: synthesis and conformational studies

Autori
Kovač, Veronika ; Čakić Semenčić, Mojca ; Kodrin, Ivan ; Roca, Sunčica ; Rapić, Vladimir

Izvornik
Tetrahedron (0040-4020) 69 (2013), 48; 10497-10506

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ferrocene peptide ; conformational analysis ; hydrogen bonds ; induced circular dichroism ; DFT calculations

Sažetak
In this study we present the synthesis and conformational analysis of mono- and disubstituted ferrocene bioconjugates bearing dipeptide chains (Boc-AA-AA-Fn-X, AA=Gly, l-Ala, l-Val). The conformational preferences of novel aminoferrocene derived conjugates with X=H, as well as their 1-acetyl analogues (X=COMe), were investigated by spectroscopic techniques (IR, NMR and CD) and corroborated by DFT calculations. Chirally organized structures, stabilized through intrachain hydrogen bonds, prevail in solution when X=H. The resulting 10-membered hydrogen-bond ring is destabilized by heteroannular introduction of an acetyl group when X=COMe.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA