Synthesis and study of phosphoenolthiopyruvate.
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.
Sikkema
K D
KD
Department of Chemistry, University of Wisconsin--Madison 53706.
O'Leary
M H
MH
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
D007202:Indicators and Reagents; C055833:phosphoenolthiopyruvate; D010728:Phosphoenolpyruvate; D007770:L-Lactate Dehydrogenase; D011770:Pyruvate Kinase; D000469:Alkaline Phosphatase; D002262:Carboxy-Lyases; D010730:Phosphoenolpyruvate Carboxylase