Hydrolysis of Esters of Monoribonucleotides


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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