Synthesis and study of phosphoenolthiopyruvate

Abstract
Phosphoenolthiopyruvate, the analogue of phosphoenolpyruvate in which the bridging oxygen of the phosphate ester is replaced by sulfur, has been synthesized from methyl acrylate and dimethyl (chlorothio)phosphonate. The compound is a substrate for alkaline phosphatase, pyruvate kinase, enolase, and phosphoenolpyruvate carboxylase. Both pyruvate kinase and phosphoenolpyruvate carboxylase convert the compoundto thiopyruvate, which is a substrate for lactate dehydrogenase. Phosphoenolpyruvate carboxylase is slowly inactivated by phosphoenolthiopyruvate.

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