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Nucleic Acids Research, 1989, Vol. 17, No. 21 8581-8593
© 1989

CHEMISTRY

Reinvestigation of deoxyribonucleoside phosphorothioites: synthesis and properties of deoxyribonudeoside-3' dimethyl phosphites

Hajime Nagai, Toshiki Fujiwara, Mitsuo Fujii, Sekine Fujii and Tsujiaki Hata*

Department of Life Chemistry, Tokyo Institute of Technology Nagatsuta, Midoriku, Yokohama 227, Japan

*To whom correspondence should be addressed

Received July 11, 1989. Revised September 22, 1989. Accepted September 22, 1989.

Further investigation of the synthesis of deoxyribonucleoside-3' (t-butyl) O-(2-cyanoethyl) phosphorothioites as monomer building units for the phosphorothioite approach has led us to conclude that internucleotidic bond formation proceeded via bis(deoxyribonucleoside-3') (2-cyanoethyl) phosphite intermediates, which proved to be activated by iodine, rather than the mechanism previously reported. In connection with this study, deoxyribonucleoside-3' dimethyl phosphites were synthesized and detailed properties of them are also described.


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