Synthesis of a nucleoside phosphorodithioate analogue responsive to microenvironmental changes through chiral induction

We have synthesized a 2′-aminomethyl branched-chain sugar nucleoside phosphorodithioate from 2,2′-anhydro uridine and subjected the material to a subsequent cyclization reaction under aqueous conditions using bi-functional linkers. The rate of the cyclization reaction was dependent on the leaving group on the bi-functional linkers. The generation of a chiral phosphorous peak from the achiral precursor, as indicated by 31P NMR, was identified as a good indicator for potentially probing the local and global features of the DNA structure.