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Nucleic Acids Research, 1978, Vol. 5, No. 8 2945-2958
© 1978

Articles

Chemical synthesis of 5'-pyrophosphate and triphosphate derivatives of 3'–5' ApA, ApG, GpA and GpG. CD study of the effect of 5'-phosphate groups on the conformation of 3'–5' GpG

J. Tomasz+,*, A. Simoncsits+, M. Kajtár++, R.M. Krug{dagger} and A.J. Shatkin{dagger}{dagger}

+Inst. Biophys., Biol. Res. Cent., Hungarian Acad. Sci. H-6701 Szeged ++Inst. Org. Chem., Lóránd Eötvös Univ. H-1088 Budapest, Hungary {dagger}Memorial Sloan-Kettering Cancer Cent. New York, NY 10021 {dagger}{dagger}Roche Inst. Mol. Biol. Nutley, NJ 07110, USA

*To whom all inquiries should be addressed.

Received June 19, 1978. A simple, two-step method is described for the synthesis of the 5'-pyro- and triphosphate derivatives of 3'–5' ApA, ApG, GpA and GpG. The readily accessible 2'(3')–5' ApA, ApG, GpA and GpG were converted in one step to the corresponding 5'-phosphor-amidate derivatives which were then transformed to the 5'-pyro- and triphosphates. CD spectra of 3'–5' pn GpG (n = 0,1,2 or 3) derivatives, measured at pH 1, indicated stabilization of the (syn)G+ p(anti)G conformation by the 5'-phosphate groups.


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