Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.