Sallustrau, Antoine
(2014).
Synthesis of ferrocenyl derivatives as novel nucleic analogue monomers.
University of Birmingham.
Ph.D.
Abstract
Bioorganometallic chemistry is a growing field of research in which organometallic chemistry is combined with biology to achieve novel molecules with novel properties at the biological level. In this area, the tagging of DNA with bioorganometallic molecules such as ferrocene has been the object of much attention over the past few decades. In recent years, a novel approach has been developed consisting of replacing parts of nucleic acids with organic groups including metal-binding ligands. Considering this approach, it was decided to investigate the replacement of DNA dinucleotides with a tetra-substituted ferrocenyl monomer containing nucleobases, leading to the formation of a novel nucleic acid analogue called ferrocene nucleic acid (FcNA). The synthesis of several monomers containing adenine and uracil has been the subject of this thesis. Coupling nucleobases to form bis-substituted ferrocenes was first investigated as a model for the subsequent synthesis of tetra-substituted ferrocenyl monomers with high chiral purity. The compounds were characterised using a range of spectroscopic and analytical techniques, including Xray crystallography. The influence of the nucleobases and the nature of the linker to the ferrocenyl group have also been investigated using electrochemistry.
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