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Question

The 2', 3'-cyclic phosphodiester that is formed when RNA is hydrolyzed reacts with water, forming a mixture of nucleotide 2' - and 3'-phosphates. Propose a mechanism for this reaction.

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The mechanism for the hydrolysis of a 2',3'-cyclic phosphodiester that is formed when RNA is cleaved is shown in the figure below. The reaction forms a mixture of a nucleotide 2'- and 3'-phosphates.

The first step includes nucleophilic attack of water. The water attacks the phosphorus of a cyclic diester. Consequently the π\pi bond between phosphorus and oxygen breaks. In the second step, the cyclic diester can break in two ways, and therefore two products are formed.

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