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Nucleic Acids Research, 1984, Vol. 12, No. 22 8525-8538
© 1984

CHEMISTRY

Cylci diacyl groups for protection of the N6-amino group of deoxyadenosine in oligodeoxynucleotide synthesis

Akiko Kume, Reiko Iwase, Mitsuo Sekine and Tsujiaki Hata

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

Received October 2, 1984. Accepted October 29, 1984.

Three kinds of substituted phthaloyl groups and a succinyl group were introduced onto the N6-amino function of deoxyadenosine derivatives. Among them, the succinyl group was found to be the most effective for prevention of depurination upon detritylation in acidic media and the most stable in basic media. Protection of the N6-amino function of 5'-O-dimethoxytrityldeoxy-adenosine and introduction of a succinate linker into the 3'-hydroxyl were achieved simultaneously by a one-step reaction with succinic anhydride. A tetradeoxyribonucleotide, dTpTpTpA containing a 3'-terminal deoxyadenosine was successfully synthesized on a polystyrene support via the phosphotriester method.


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