Compelling Evidence for a Stepwise Mechanism of the Alkaline Cyclisation of Uridine 3'-phosphate Esters

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2004 Jul 29

PMID 15280948

Citations 15

Authors

Harri Lonnberg

Roger Stromberg

Andrew Williams

Affiliations

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Abstract

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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