Synthesis and study of (Z)-3-chlorophosphoenolpyruvate.
(Z)-3-Chlorophosphoenolpyruvate has been synthesized by the reaction of 3,3-dichloropyruvic acid with trimethylphosphite, followed by deesterification. This compound is a competitive inhibitor of pyruvate kinase and phosphoenolpyruvate carboxylase. Pyruvate kinase is not inactivated upon prolonged incubation with the compound, but phosphoenolpyruvate carboxylase is slowly inactivated (t1/2 = 5 h). The compound is a substrate for both enzymes, being acted upon by pyruvate kinase approximately 0.1% as rapidly as phosphoenolpyruvate itself. In the case of phosphoenolpyruvate carboxylase, the compound is converted into a 3:1 mixture of chloropyruvate and chlorooxalacetate, at an overall rate that is about 25% the carboxylation rate for phosphoenolpyruvate.
Liu
J
J
Department of Chemistry, University of Wisconsin, Madison 53706.
Peliska
J A
JA
O'Leary
M H
MH
D001667:Binding, Competitive; D002262:Carboxy-Lyases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D007536:Isomerism; D010728:Phosphoenolpyruvate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010730:Phosphoenolpyruvate Carboxylase / Q000037:antagonists & inhibitors*; D011770:Pyruvate Kinase / Q000037:antagonists & inhibitors*; D013379:Substrate Specificity
D007202:Indicators and Reagents; C063016:phosphoenol-3-chloropyruvate; D010728:Phosphoenolpyruvate; D011770:Pyruvate Kinase; D002262:Carboxy-Lyases; D010730:Phosphoenolpyruvate Carboxylase