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Nucleic Acids Research, 1977, Vol. 4, No. 8 2843-2853
© 1977

Articles

Formation of ribonucleotide 2', 3'-cyclic carbonates during conversion of ribonucleoside 5'-phosphates to diphosphates and triphosphates by the phosphorimidazolidate procedure

Mitsuaki Maeda, Arvind D. Patel and Alexander Hampton*

The Institute for Cancer Research, The Fox Chase Cancer Center Philadelphia, PA 19111, USA

* To whom correspondence should be addressed

Received May 25, 1977. Ribo- and 2'-deoxyribonucleoside 5'-di- or triphosphates are commonly synthesized by reaction of inorganic phosphate or pyrophosphate with phosphorimidazolidates obtained by reaction of nucleoside 5'-phosphates with 1,1'-carbonyldiimidazole. The latter reaction, however, converted UMP, CMP, IMP, GMP, and AMP in high yield to the 2',3'-cyclic carbonate derivatives of their phosphorimidazolidates. Acidic treatment of the product from AMP gave AMP 2',3'-cyclic carbonate dihydrate; this was characterized by its uv, ir, and pmr spectra and by its conversion to adenosine 2',3'-cyclic carbonate by acid phosphatase and to AMP by basic hydrolysis. ADP or ATP synthesized by the phosphorimidazolidate method contained equal or greater amounts of their respective 2',3'-cyclic carbonates. The latter could be quantitatively converted to ADP and ATP, respectively, by 4-hr hydrolysis at pH 10.5, 22°. ADP or ATP can be synthesized without concomitant 2',3'-cyclic carbonate formation by reaction of AMP with phosphorimidazolidates of inorganic phosphate or pyrophosphate.


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