Hydrolysis of Esters of Monoribonucleotides

Abstract

CONSIDERABLE attention has been paid in recent years to the hydrolysis of ribonucleic acids to mononucleotides. It was shown1,2 that alkyl esters of the 2′- and 3′-monoribonucleotides (partial formula I ; R = alkyl) provided simple model substances which could be used for a more precise study of the mechanism of hydrolysis. The overall process, effected by acid or by alkali, results in a conversion of (I) to a mixture of (III) and (IV). Both procedures involve the unstable cyclic ester intermediate (II), which is then hydrolysed to the isomeric mononucleotides (III) and (V). Since the conversion of (I) → (II) is formally a trans-esterification3, it seemed possible that the analogous process (I) → (V), that is, migration of the alkyl phosphate residue without loss of R, might also occur simultaneously.

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BROWN, D., MAGRATH, D., NEILSON, A. et al. Hydrolysis of Esters of Monoribonucleotides. Nature 177, 1124–1125 (1956). https://doi.org/10.1038/1771124a0

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