Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 2, Issue 15, Pages 2165-2167Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b406926a
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A Bronsted graph with a convex break at pK(a) (Lg) = 12.58 provides compelling evidence for an intermediate in the alkaline cyclisation of uridine 3'-phosphate esters. The transient pentacoordinated oxyphosphorane dianion intermediate collapses to reactant and cyclic uridine 2', 3'-monophosphate faster than it can pseudo-rotate and isomerise to the 2'-isomer.
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