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Barišić, Lidija; Kovačević, Monika; Mamić, Marija; Kodrin, Ivan; Mihalić, Zlatko; Rapić, Vladimir
European journal of inorganic chemistry, April 2012, Volume: 2012, Issue: 11Journal Article
Structurally different ferrocene peptides I–VI exhibit considerable conformational differences. This study has explored the structural properties of VII Y‐AA‐Fca‐OMe; Y = di‐tert‐butyl dicarbonate (Boc), acetyl (Ac); AA = L‐Ala, D‐Ala; Fca = 1′‐aminoferrocene‐1‐carboxylic acid with an exchanged sequence of constituent amino acids relative to VI (Y‐Fca‐AA‐OMe; Y = Boc, Ac; AA = L‐Ala, D‐Ala). The ferrocene peptides VII were obtained by coupling C‐protected Fca with Boc‐L‐Ala‐OH and Boc‐D‐Ala‐OH, respectively. The Boc protecting groups of the obtained conjugates Boc‐AA‐Fca‐OMe (2a, AA = L‐Ala; 2b, AA = D‐Ala) were converted to sterically less demanding Ac groups to give Ac‐AA‐Fca‐OMe (3a, AA = L‐Ala; 3b, AA = D‐Ala). In order to examine their conformational properties, peptides VII were subjected to spectroscopic analysis (IR, 1H NMR, CD) and molecular modeling (DFT). The alteration of peptides VI into VII significantly influenced their conformational properties. Conjugates VI were stabilized through interchain hydrogen bonding, whereas inter‐ and intrachain hydrogen bonds were established in their constitutional isomers VII. The replacement of the bulky Boc group with an Ac group did not cause major conformational changes, and the absolute configuration of the alanine chiral centers did not affect the conformational properties. It was determined by IR and NMR spectroscopy and DFT calculations that ferrocene peptides adopt several conformations stabilized through intra‐ and interchain hydrogen bonds. The protecting groups and absolute configuration of the alanine chiral centers do not significantly affect their conformational properties.
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