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Nucleic Acids Research, 1990, Vol. 18, No. 15 4439-4446
© 1990

CHEMISTRY

Chemical synthesis and biological activities of analogues of 2',5'-oligoadenylates containing 8-substituted adenosine derivatives

Masayasu Kanou, Hisanori Ohomori, Hiroshi Takaku*, Shigeyuki Yokoyama1, Gota Kawai1,+, Robert.J. Suhadolnik2 and Robert Sobol, Jr2

Department of Industrial Chemistry, Chiba Institute of Technology Tsudanuma, Narashino, Chiba 275

*To whom correspondence should be addressed

Received May 16, 1990. Revised June 19, 1990. Accepted June 19, 1990.

The synthesis of sequence-specific 2'–5' oligonucleotides and analogues of 2'-5' linked oligoadenylates containing 8-substituted adenosine derivatives [8-hydroxypropyladenosine (AHPr) and 8-hydroxyadenosine (A0H)] is reported. The reaction of 5'-phosphoroimidazolidate of 8-substituted adenosines under conditions of lead ion catalyst did not give the corresponding 2'–5' oligoadenylates containing pAHPr and pA0H. When these reactions were carried out in the presence of uranyl ion (UO2 2+) in place of lead ion as a catalyst, the desired 2'–5' oligoadenylates were obtained. The p5'AHPr2'p5'AHPr2'p5'AHPr and p5'AOH2'p5'AOH2'p5'AOH, p5'A2'p5'A2'pAOH were slightly resistant to snake venom phosphodiesterase. The both circular dichroism and 1H-NMR spectra studies were used to characterize the modified 2'–5 oligoadenylates. Further, the biological activity evaluations of 8-substituted analogues of 2–5A are also described.

+Present address: Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240, Japan

1department of Biophysics and Biochemistry, Faculty of Science, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan

2department of Biochemistry, Temple University School of Medicine, Philadelphia, PA 19140, USA


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