Synthesis of 3'-Deoxy-3'-C-Hydroxymethyl-aldopentopyranosyl Nucleosides and their Incorporation in Oligonucleotides. Part II.

Article abstract of DOI:10.1016/0040-4020(95)00777-6

The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described.This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and quanine nucleosides.Dependent on the configuration (β-D-erythro or α-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for α-D-erythro and equatorial adenine base for α-L-threo nucleosides) which could be explained by the gauche effect.Oligonucleotides built up to 2',3'-dideoxy-3'-C-hydroxymethyl-α-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA.