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Issue 15, 2004
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Compelling evidence for a stepwise mechanism of the alkaline cyclisation of uridine 3′-phosphate esters

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Abstract

A Brønsted graph with a convex break at pKa (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.

Graphical abstract: Compelling evidence for a stepwise mechanism of the alkaline cyclisation of uridine 3′-phosphate esters

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Publication details

The article was received on 07 May 2004, accepted on 15 Jun 2004 and first published on 05 Jul 2004


Article type: Communication
DOI: 10.1039/B406926A
Citation: Org. Biomol. Chem., 2004,2, 2165-2167
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    Compelling evidence for a stepwise mechanism of the alkaline cyclisation of uridine 3′-phosphate esters

    H. Lönnberg, R. Strömberg and A. Williams, Org. Biomol. Chem., 2004, 2, 2165
    DOI: 10.1039/B406926A

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