SELECTED ASPECTS OF THE CHEMISTRY AND BIOCHEMISTRY OF SULFUR-CONTAINING NUCLEOSIDES

Synthetic nucleoside 5'-(alpha-halo)thioethers and derived 5'-halo(met hylene) compounds function as potent mechanism-based inhibitors of S-a denosyl-L-homocysteine hydrolase. Nucleoside 5'-carboxaldehydes have b een converted into 6'-tosyl(vinyl) derivatives, Radical-mediated stann yldesulfonylation of these homonucleoside vinyl sulfones gave 8-stanny l(vinyl) derivatives. Stereoselective halodestannylation with electrop hiles gave the 6-halo(homovinyl)nucleoside analogues. Some of these nu cleoside analogue types have inhibitory activity against enzymes in th e nucleic acid biochemical manifold and these effects correlate with i n vitro anticancer and antiviral activities in certain cases.