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Nucleic Acids Research, 1990, Vol. 18, No. 11 3327-3331
© 1990

CHEMISTRY

Use of new phosphonylating and coupling agents in the synthesis of oligodeoxyribonucleotides via the H-phosphonate approach

Osamu Sakatsume, Hiroshi Yamane, Hiroshi Takaku* and Naoki Yamamoto1

Laboratory of Bioorganic Chemistry, Department of Industrial Chemistry, Chiba Institute of Technology Tsudanuma, Narashino, Chiba 275 1Department of Virology and Parasitology, Yamaguchi University of Medicine Ube 755, Japan

*To whom correspondence should be addressed

Received January 31, 1990. Accepted April 19, 1990.

New phosphonylating and coupling agents for the synthesis of oligodeoxyribonucleotides via Hphosphonate approach have been developed. Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite, prepared by the reaction of lithium salt of 1,1,1,3,3,3-hexafluoro-2-propoxide with PCI3, reacts with deoxyribonucleosides in the presence of a catalytic amount of triethylamine to produce in the high yield the corresponding deoxyribonucleoside 3'- phosphonate units. The use of a new coupling reagent, 1,3-dimethyl-2-chloro-imidazolinium chloride (DMCI) for the internucleotidic H-phosphonate bond formation via the H-phosphonate approach is also discussed in detail.


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