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Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
Published on: July 6, 2016
Stereocontrolled synthesis of H-phosphonate DNA
Naoki Iwamoto1, Terutoshi Sato, Natsuhisa Oka
1Development of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Building 702, Kashiwa, Chiba 277-8562, Japan.
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.
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