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Issue 37, 2015
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The conjugates of ferrocene-1,1′-diamine and amino acids. A novel synthetic approach and conformational analysis

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Abstract

A novel synthetic approach toward a poorly explored bioorganometallic consisting of ferrocene-1,1′-diamine bearing structurally and chirally diverse amino acid sequences is reported. Until now, ferrocene-1,1′-diamine was suitable for accommodating only identical amino acid sequences at its N-termini, leading to the symmetrically disubstituted homochiral products stabilized through a 14-membered intramolecular hydrogen-bonded ring as is seen in antiparallel β-sheet peptides. The key step of the novel synthetic pathway is the transformation of Ac–Ala–Image ID:c5dt01610j-u5.gif–Fn–Image ID:c5dt01610j-u6.gifOH (5) (Fn = 1,1′-ferrocenylene) to orthogonally protected Ac–Ala–Image ID:c5dt01610j-u7.gif–Fn–Image ID:c5dt01610j-u8.gifBoc (7). The spectroscopic analysis (IR, NMR, CD) of the novel compounds, corroborated with DFT studies, suggests the interesting feature of the ferrocene-1,1′-diamine scaffold. The same hydrogen-bonding pattern, i.e. a 14-membered hydrogen-bonded ring, was determined both in solution and in the solid state, thus making them promising, yet simple scaffolds capable of mimicking β-sheet peptides. In vitro screening of potential anticancer activity in Hep G2 human liver carcinoma cells and Hs 578 T human breast cancer cells revealed a cytotoxic pattern for novel compounds (150–500 μM) with significantly decreased cell proliferation.

Graphical abstract: The conjugates of ferrocene-1,1′-diamine and amino acids. A novel synthetic approach and conformational analysis

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Publication details

The article was received on 29 Apr 2015, accepted on 11 Aug 2015 and first published on 12 Aug 2015


Article type: Paper
DOI: 10.1039/C5DT01610J
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Dalton Trans., 2015,44, 16405-16420
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    The conjugates of ferrocene-1,1′-diamine and amino acids. A novel synthetic approach and conformational analysis

    M. Kovačević, I. Kodrin, M. Cetina, I. Kmetič, T. Murati, M. Č. Semenčić, S. Roca and L. Barišić, Dalton Trans., 2015, 44, 16405
    DOI: 10.1039/C5DT01610J

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