Turker, Sarah Didem (2010)
M.Res. thesis, University of Birmingham.
Non-nucleosidic anthracene-functionalised phosphoramidites 5a and 5b have been synthesised. 5b has been incorporated into oligonucleotide sequences (PrA, PrB, PrC, PrD, PrE, PrF and PrG) as a DNA base analogue using automated synthesis. Melting temperature (T\(_m\)) studies of double-stranded 15-mer / 14-mer deletion sequences compared to 15-mer / 15-mer analogues demonstrated that the incorporation of anthracene serves to stabilise the duplexes by improved intercalation in the former case. PrA, was used as a probe for detection of base pair mismatches in target DNA sequences using fluorescence spectroscopy. Titration of PrA versus a range of matched target oligonucleotides (TarAx where x = 1 - 5) demonstrated an enhancement in anthracene fluorescence when adenine was positioned adjacent to the anthracene tag on the opposite strand for 15-mer / 15-mer duplexes. Titration of PrA versus a range of mismatched target oligonucleotide sequences (TarBx, TarCx, TarDx, TarEx, TarFx and TarGx where x = 1 - 2) demonstrated enhancements in emission for C-A, C-T and CC mismatches, which were dependent on mismatch position (5’ or 3’) in the target strand. The latter effect is possibly due to the chiral nature of 5b. Probes such as PrA show potential for use as sensors for single nucleotide polymorphisms (SNPs) in DNA sequences.
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