Dinucleoside (5′ → 3′)-O,S-Phosphorodithioates - New Class of Dinucleotide Analogues

Abstract

Nucleoside 3′-0- and 5′-O-phosphorodithioates have been recently described by Caruthers et al.¹ as a new type of nucleotide analogues. These compounds have also been obtained in our Laboratory by one-pot dithiaphospholane approach.² We now report on the transformation of some of these derivatives into new class of dinucleotide analogues. We have found that nucleoside 3′-O-phosphorodithioates (1) react in DMF solution with 5′-bromo-5′-deoxythymidine to give in high yield corresponding dinucleoside (5′→3′)-O,S-phosphorodithioates (2) - first examples of a new class of dinucleotide analogues possessing the internucleotide phosphorothioate linkage with one of the sulfur atoms in a 3′-bridging position.