Solid-phase synthesis of oligodeoxynucleotides containing N 4-[2-(t-butyldisulfanyl)ethyl]-5-methylcytosine moieties

Abstract

An efficient route for the synthesis of the phosphoramidite derivative of 5- methylcytosine bearing a tert-butylsulfanyl group protected thiol is described. This building block is used for the preparation of oligonucleotides carrying a thiol group at the nucleobase at the internal position of a DNA sequence. The resulting thiolated oligonucleotides are useful intermediates to generate oligonucleotide conjugates carrying molecules of interest at internal positions of a DNA sequence. © 2010 by the authors.