Metabolism of 1-aminoethylphosphinate generates acetylphosphinate, a potent inhibitor of pyruvate dehydrogenase.
The alanine analogue 1-aminoethylphosphinate [H3C-CH(NH2)-PO2H2] effectively inhibited anthocyanin synthesis in buckwheat hypocotyls and caused an increase in the concentrations of alanine and alanine-derived metabolites. Aminotransferase inhibitors partially alleviated the effects of the analogue. 1-Aminoethylphosphinate did not affect the growth of Klebsiella pneumoniae under anaerobic conditions, but under aerobic conditions it inhibited growth and caused the massive excretion of pyruvate. The analogue inhibited the pyruvate dehydrogenase complex in vitro in the presence of an aminotransferase activity. The transamination product of 1-aminoethylphosphinate, acetylphosphinate (H3C-CO-PO2H2), was found to inhibit the pyruvate dehydrogenase complex in a time-dependent reaction that followed first-order and saturation kinetics and required the presence of thiamin pyrophosphate.
Laber
B
B
Lehrstuhl für Pflanzenphysiologie, Ruhr-Universität Bochum, Federal Republic of Germany.
Amrhein
N
N
D000872:Anthocyanins / Q000037:antagonists & inhibitors; D007700:Kinetics; D007711:Klebsiella pneumoniae / Q000187:drug effects / Q000378:metabolism; D008968:Molecular Conformation; D009943:Organophosphorus Compounds / Q000378:metabolism* / Q000494:pharmacology; D010721:Phosphinic Acids; D010944:Plants / Q000187:drug effects / Q000378:metabolism; D011767:Pyruvate Decarboxylase / Q000037:antagonists & inhibitors; D011768:Pyruvate Dehydrogenase Complex / Q000037:antagonists & inhibitors*; D011773:Pyruvates / Q000378:metabolism; D019289:Pyruvic Acid; D000637:Transaminases / Q000037:antagonists & inhibitors
D000872:Anthocyanins; D009943:Organophosphorus Compounds; D010721:Phosphinic Acids; D011768:Pyruvate Dehydrogenase Complex; D011773:Pyruvates; C054773:acetylphosphinic acid; C054771:1-aminoethylphosphinic acid; D019289:Pyruvic Acid; D000637:Transaminases; D011767:Pyruvate Decarboxylase