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Nucleic Acids Research, 1981, Vol. 9, No. 8 2003-2020
© 1981

CHEMISTRY

Synthesis and properties of 5'-triphosphoryl 2'-5' oligoadenylates (2-5A), and a general method for synthesis of 3', 5'-bisphosphorylated oligonucleotides

M. Ikehara, K. Oshie, A. Hasegawa and E. Ohtsuka

Faculty of Pharmaceutical Sciences, Osaka University Suita, Osaka 565, Japan

Received February 4, 1981. 2'-5'-Linked oligoadenylic acid 5'-triphosphates (2-5A) having chain lengths of 2–4 have been synthesized by polymerization of 3'-O-(o-nitrobenzyl)-N-benzoyladenosine 5'-phosphate followed by 5T-triphosphorylation via the imidazolidates. A large scale preparation of 5'-O-phosphoryladenylyl-(2'-5')-adenylyl-(2'-5')-adenosine was performed by the phosphotriester method using 5'-O-monomethoxytrityl-3'-O-(o-nitrobenzyl)-N-benzoyladenosine 2'-O-p-chlorophenylphosphate and 5'-O-phosphorodianilido-3'-O-(o-nitrobenzyl)-N-benzoyladenosine 2'-O-p-chlorophenyl phosphate as intermediates. The trimer was also triphosphorylated by the imidazolide method. CD spectra for 5'-mono and triphosphorylated 2'-5' adenylates were measured as well as their UV hypochromicities.

This triester method was also applied to the synthesis of 3',5'-bisphosphorylated protected oligoadenylic acids with natural 3'-5' linkages, which could be used for further condensations to yield 5'-phosphorylated polynucleotides.


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