Efficient synthesis of thymidine boranophosphoramidates conjugated with amino acids.

An efficient synthesis of a thymidine boranophosphoramidate prodrug was accomplished using a phosphoramidite approach in high yield. This new class of compounds is designed to have improved antiviral and anticancer advantages conferred by combining the boranophosphate and normal nucleoside amino acid phosphoramidate. Compounds were characterized by MS and 31P NMR.

Synthesis of 5-ethynyl-2'-deoxyuridine-5'-boranomono phosphate as a potential thymidylate synthase inhibitor.

The 5-ethynyl-2'-deoxyuridine nucleoside and the 5'-boranomonophosphate nucleotide were synthesized as analogs of 5-fluoro-2'-deoxyuridine monophosphate (5-FdUMP), a widely used mechanism-based inhibitor of thymidylate synthase. Synthesis was carried out from protected 5-iodo-2'-deoxyuridine and trimethylsilylacetylene by Sonogashira palladium-catalyzed cross coupling reaction followed by selective phosphorylation and finally boronation.

Solid-Phase Synthesis and Photophysical Properties of DNA Labeled at the Nucleobase with Ru(bpy)(2)(4-m-4'-pa-bpy)(2+).

A facile procedure for incorporating a Ru(diimine)(3)(2+) complex at the nucleobase in an oligonucleotide is reported that combines the advantages of Pd(0) cross-coupling and solid-phase DNA chemistries. These ruthenium-modified oligonucleotides form stable duplexes, and the favorable photophysical properties associated with the Ru(diimine)(3)(2+) complex are retained after site-specific covalent attachment.