Stereocontrolled synthesis of H-phosphonate DNA.
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.
Iwamoto
Naoki
N
Development of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.
Sato
Terutoshi
T
Oka
Natsuhisa
N
Wada
Takeshi
T
D004247:DNA / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry; D013237:Stereoisomerism
D003853:Deoxyribonucleosides; D009838:Oligodeoxyribonucleotides; D063065:Organophosphonates; D004247:DNA