Design of photofunctional oligonucleotides by copolymerization of natural nucleobases with base surrogates prepared from acyclic scaffolds
We demonstrate a new methodology of DNA and RNA functionalization with a base surrogate prepared from d-threoninol. With this surrogate, we can introduce functional molecules at any position in the sequence. Our methodology is conceptually similar to copolymerization; phosphoramidite monomers of base surrogates, and natural nucleotides are ‘copolymerized’ on solid supports to prepare functional oligonucleotides. The incorporation of intercalating moieties allows for the design of four stable functional motifs: wedges, interstrand-wedges, dimers and clusters. By selecting suitable functional molecules and motifs, we can design novel photofunctional oligonucleotides.