Organometallic and Bioorganometallic Chemistry – Ferrocene Amino Acids

Kemija u Industriji

关键词: organometallic chemistry;    bioorganometallic chemistray;   

DOI  :  

来源: DOAJ

【 摘 要 】

This article is the second part of a series dealing with organometallic and bioorganometallic chemistry. In the first part of this series a short review on the history and development of these disciplines was given, emphasizing the importance and scope of bioorganometallic chemistry as a new field dealing with conjugates of organometallics and biomolecules (DNA, PNA, amino acids, peptides...).From the variety of biorganometallics, syntheses and properties of simple conjugates of ferrocene with natural amino acids/peptides were elaborated inter alia.

This material is the basis for the second part in which ferrocene amino acids are described. The introduction presents nonproteinogenicalicyclic and aromatic amino acids as the models for the title compounds.Naturally occurring amino acids labelled with ferrocene moiety mostly retain properties of the biomolecules included. Contrary to these ω-ferrocenylamino acids, one could imagine specific amino acids with inserted ferrocenecore belonging to either homo- or heterodisubstituted type. The centralpart of this article is devoted to our investigations of the second type - H₂N-(CH₂)_m-Fn-(CH₂)_n-COOH. The general rational procedure for synthesis of these compounds and oftheir N- and/or C-protected derivatives via the azide intermediates N₃-CO-(CH₂)_m- Fn-(CH₂)_n-COOMe has been described. In the solid state derivatives of ferrocene amino acids contain intermolecular hydrogen bonds giving dimeric structures, three-dimensional networks or endlesshelical chains. The solutions of homologues Ac-NH-(CH₂)_m-Fn-(CH₂)_n-COOMe in nonpolar solvents are dominated by open form conformers. Compounds containing 2–3 ferrocene cores connected by amide, imide and oxalamide spacers were prepared by oligomerization of 1'-aminoferrocene-1-carboxylic acid (Fca) or by its condensation with the appropriate reagents. Similar to natural amino acids, ferrocene amino acids are water-soluble substances with high melting points, insoluble in organic solvents.

【 授权许可】

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