title: Stereocontrolled synthesis of H-phosphonate DNA.
abstract: Stereocontrolled synthesis of H-phosphonate DNA by an oxazaphospholidine approach is described. Diastereopure 2'-deoxynucleoside 3'-oxazaphospholidine monomers having two substituents at the 5-position of the oxazaphospholidine ring were allowed to condense with the 5'-hydroxy group of nucleosides in the presence of a less-nucleophilic acidic activator to afford the diastereopure dinucleoside phosphite intermediates. Upon treatment with an anhydrous acid, the phosphite intermediates were stereospecifically converted into the diastereopure dinucleoside H-phosphonates. The method was applied to the solid-phase synthesis of stereoregulated H-phosphonate DNA oligomers containing four kinds of nucleobases.
authors.affiliation: Development of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Iwamoto
authors.forename: Terutoshi
authors.initials: T
authors.lastname: Sato
authors.forename: Natsuhisa
authors.initials: N
authors.lastname: Oka
authors.forename: Takeshi
authors.initials: T
authors.lastname: Wada
mesh_terms: D004247:DNA / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003853:Deoxyribonucleosides; D009838:Oligodeoxyribonucleotides; D063065:Organophosphonates; D004247:DNA