Duprey, Jean-Louis Henry Alan
(2011).
Studies on Anthracene Tagged Oligonucleotides.
University of Birmingham.
Ph.D.
Abstract
This thesis describes the synthesis, characterization and study of a range of oligonucleotides that were modified by the inclusion of a non-nucleosidic anthracene unit. This involved the synthesis of different stereoisomers of a non-nucleosidic backbone attached to DNA via a carbon chain linker. These monomers were then coupled to short (15-mer) oligonucleotide chains using solid state DNA synthesis and purified using RP-HPLC. Two systems were studied: a duplex with anthracene functioning as a non-bonding base opposite of a natural nucleobase and a wedge type system. The probes were then examined by a variety of physical techniques that included UV melting point studies, fluorescence and CD spectroscopy in order to understand the effect of varying base pairs and introducing mismatches. Certain duplexes were then studied in greater depth using transient absorption spectroscopy, to probe the formation of electron transfer intermediates and by high field NMR to look at the effect of intercalation between base pairs. In order to aid explanation of the acquired data, molecular modeling studies were undertaken using AMBER and the University of Birmingham Bluebear cluster to produce solvated, molecular dynamics optimized structures. The formation of excimers in bis-anthracene systems as potential precursors to photo-ligated DNA duplexes was also studied.
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