AbstractsChemistry

Three activated modified dimers 9, 21 and 35, which contain a dialkyl sulfide backbone, have been synthesized. These dimers, as well as dimer A, have been incorporated into DNA strands by solid-phase techniques. The number of these dimers being incorporated varied from 1-3.$ sp*$ Thermal studies have shown that the oligomers containing modified dimers indeed bind to their complementary DNA or RNA, except for two oliglomers in which dimer 9 or 21 was incorporated three times. They only bind relatively poorly to complementary RNA, but not at all to DNA. The incorporation of 35 into DNA oligomers showed good binding to its complementary RNA, but not DNA. All sulfide-containing oligomers have been oxidized to sulfone-containing oligomers using oxone. In thermal studies, hybrids of the sulfone-containing oligomers with their complementary DNA and RNA showed much poorer binding properties than the corresponding sulfide-containing oligomers. The synthesis of nucleoside 28, the upper half of dimer 21, as well as an improved procedure for the preparation of 2$ sp prime$-O-methyluridine, are described. ftn$ sp*$Please refer to the dissertation for diagrams.