Fluorescent nucleosides as probes for DNA structure and recognition

This thesis focuses on the development of fluorescent probes for incorporation into DNA. The first chapter is an overview of the properties and the utility of fluorescent nucleosides that have been developed to date. The following chapters introduce new fluorescent nucleosides designed to act as reporter probes when incorporated into DNA. The second chapter focuses on a uracil analog, dUphen, which is conjugated to 1,10-phenanthroline at the 5 position of the base through an ethynl linkage. This modified nucleoside was incorporated into DNA and can be used to distinguish between perfect and mismatched complementary oligonucleotides. The third chapter presents an isomorphic, fluorescent guanosine analog, furo[3,2-D]pyrimidine. Although this nucleoside has not been incorporated into DNA, it served as a useful model for the development of related nucleosides. The last chapter discusses the development of thieno[3,2-D]pyrimidine as a fluorescent purine analog. This modified nucleoside was incorporated into DNA its photophysical properties were evaluated.