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Ferrocene-dipeptide conjugates derived from aminoferrocene and 1-acetyl-1′-aminoferrocene: synthesis and conformational studies
Authors:Veronika Kovač  Mojca Čakić Semenčić  Ivan Kodrin  Sunčica Roca  Vladimir Rapić
Institution:1. Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, 10000 Zagreb, Croatia;2. Department of Chemistry, Faculty of Science, Horvatovac 102a, 10000 Zagreb, Croatia;3. Ru?er Boškovi? Institute, NMR center, Bijeni?ka 54, 10000 Zagreb, Croatia
Abstract: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.
Keywords:Ferrocene peptide  Conformational analysis  Hydrogen bonds  Induced circular dichroism  DFT calculations
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