title: 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 compound to thiopyruvate, which is a substrate for lactate dehydrogenase. Phosphoenolpyruvate carboxylase is slowly inactivated by phosphoenolthiopyruvate.
authors.affiliation: Department of Chemistry, University of Wisconsin--Madison 53706.
authors.forename: K D
authors.initials: KD
authors.lastname: Sikkema
authors.forename: M H
authors.initials: MH
authors.lastname: O'Leary
mesh_terms: D000469:Alkaline Phosphatase / Q000378:metabolism*; D002262:Carboxy-Lyases / Q000378:metabolism*; D007202:Indicators and Reagents; D007700:Kinetics; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D010728:Phosphoenolpyruvate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D010730:Phosphoenolpyruvate Carboxylase / Q000378:metabolism*; D011770:Pyruvate Kinase / Q000378:metabolism*; D013055:Spectrophotometry, Infrared; D013379:Substrate Specificity
chemical_list: D007202:Indicators and Reagents; C055833:phosphoenolthiopyruvate; D010728:Phosphoenolpyruvate; D007770:L-Lactate Dehydrogenase; D011770:Pyruvate Kinase; D000469:Alkaline Phosphatase; D002262:Carboxy-Lyases; D010730:Phosphoenolpyruvate Carboxylase