Synthesis and binding properties of oligodeoxynucleotides containing phenylphosphon(othio)ate linkages

• Published in: Bioorganic & medicinal chemistry 1997-12, Vol.5 (12), p.2213-2220
• Main Authors: Mag, Matthias, Muth, Jochen, Jahn, Kerstin, Peyman, Anusch, Kretzschmar, Gerhard, Engels, Joachim W., Uhlmann, Eugen
• Format: Article
• Language: English
• Subjects: antisense; Chromatography, High Pressure Liquid; hybridization; Magnetic Resonance Spectroscopy; Models, Chemical; Oligodeoxyribonucleotides - chemical synthesis; Oligodeoxyribonucleotides - metabolism; oligonucleotide; Organothiophosphorus Compounds - chemical synthesis; Organothiophosphorus Compounds - metabolism; phenylphosphon(othio)ate; solid-phase synthesis; Spectrometry, Mass, Fast Atom Bombardment
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/S0968-0896(97)00164-8

A method for the synthesis of chimeric oligodeoxynucleotides comprised of phosphodiester and phenylphosphonate [3′-O-P(=O)(C 6H 5)-O-5′] or phenylphosphono-thioate [3′-O-P(=S)(C 6H 5)-O-5′] linkages has been developed. Synthesis was performed using suitably protected nucleoside phenylphosphonamidites as building blocks following an adjusted solid-phase phosphoramidite synthesis protocol. The new oligodeoxy-nucleotide analogues were characterized by electrospray ionization- and matrix-assisted laser desorption mass spectrometry, as well as by 31P NMR spectroscopy. Additionally, their binding properties to complementary oligodeoxynucleotides has been studied. Novel oligodeoxynucleotides containing phenylphosphonate and phenylphosphonothioate linkages, and their synthesis and binding properties to complementary nucleic acids are described.