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Nucleic Acids Research, 1984, Vol. 12, No. 12 5025-5036
© 1984

CHEMISTRY

Chemical synthesis of 5-azacytidlne nucleotides and preparation of tRNAs containing 5-azacytidine in its 3'-terminus

Wojciech S. Zidinski* and Mathias Sprinzl

Department of Biochemistry, University of Bayreuth PO Box 3008, D-8580 Bayreuth, FRG

Received May 2, 1984. Revised June 1, 1984. Accepted June 1, 1984.

5-azacytidine-5'-triphosphate prepared from 5-azacytidine by chemical phosphorylation is a substrate for AMP(CMP)tRNA nucleo-tidyl transferase from yeast. tRNAsphe from yeast containing 5-azacytidine in their 3'-termini were prepared enzymatically. tRNAphe-Cpn5 CpA and tRNAphe -nSCpn5CpA can be aminoacylated by phenylalanyl-tRNA synthetase from yeast and they are active in the poly(U)-dependent synthesis of poly(Phe) on E. coli ribosomes.

The decomposition of 5-azacytidine via hydrolysis of the tri-azine ring is significantly accelerated by a phosphate group on the 5'-position of the nucleotide. After the incorporation of 5-azacytidine-5'-phosphate into a polynucleotide chain the rate of hydrolysis of the triazine ring decreases considerably.

*Present address: The Salk Institute, PO Box 85 800, San Diego, CA 92138, USA


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