Synthesis of 5'-C- and 2'-O-(bromoalkyl)-substituted ribonucleoside phosphoramidites for the post-synthetic functionalization of oligonucleotides on solid support

The prepn. of building blocks for the incorporation of 6'-O-(5-bromopentyl)-substituted b-D-allofuranosylnucleosides and 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleosides into oligonucleotide sequences is presented. These reactive building blocks can be modified with a variety of soft nucleophiles while the (fully protected) sequence is still attached to the solid support. As an example of this strategy, we carried out some preliminary solid-phase substitution and conjugation reactions with DNA sequences contg. a 2'-O-[(3-bromopropoxy)methyl]-substituted ribonucleoside and detd. the pairing properties of duplexes obtained therefrom. [on SciFinder (R)]