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Issue 15, 2007
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Reactions of phosphate and phosphorothiolate diesters with nucleophiles: comparison of transition state structures

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Abstract

A series of methyl aryl phosphorothiolate esters (SP) were synthesized and their reactions with pyridine derivatives were compared to those for methyl aryl phosphate esters (OP). Results show that SP esters react with pyridine nucleophiles via a concerted SN2(P) mechanism. Brønsted analysis suggests that reactions of both SP and OP esters proceed via transition states with dissociative character. The overall similarity of the transition state structures supports the use of phosphorothiolates as substrate analogues to probe mechanisms of enzyme-catalyzed phosphoryl transfer reactions.

Graphical abstract: Reactions of phosphate and phosphorothiolate diesters with nucleophiles: comparison of transition state structures

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Publication details

The article was received on 14 May 2007, accepted on 08 Jun 2007 and first published on 29 Jun 2007


Article type: Paper
DOI: 10.1039/B707205H
Citation: Org. Biomol. Chem., 2007,5, 2491-2497
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    Reactions of phosphate and phosphorothiolate diesters with nucleophiles: comparison of transition state structures

    J. Ye, C. D. Barth, P. S. R. Anjaneyulu, T. Tuschl and J. A. Piccirilli, Org. Biomol. Chem., 2007, 5, 2491
    DOI: 10.1039/B707205H

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