Oxygen chiral phosphodiesters—8 : Stereochemical course of the base-catalyzed hydrolysis of cyclic 2'-deoxyadenosine 3',5'-[17O, 18O]monophosphate

Add time:09/06/2019    Source:sciencedirect.com

At 100° and in 0.2 M Ba(OH)2 the Rp diastereomer of cyclic 2'-deoxyadenosine 3',5' -[17O, 18O]monophosphate is hydrolyzed to a 4:1 mixture of the Sp diastereomer of 3' -[16O, 17O, 18O]dAMP and the Rp diastereomer of 5' -[16O, 17O, 18O]dAMP, respectively, demonstrating that the hydrolysis reaction is accompanied by complete inversion of configuration at phosphorus. This finding establishes that pseudorotation of pentacoordinate reaction intermediates is unimportant in this chemical hydrolysis reaction.

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