S-acetonyl-CoA. A nonreactive analog of acetyl-CoA.
We have synthesized S-acetonyl-CoA from CoASH and 1-bromoacetone. This thioether-containing structural analogue of acetyl-CoA is a potent competitive inhibitor, with respect to acetyl-CoA, of citrate synthase, phosphotransacetylase, and carnitine acetyltransferase. This analog will not activate Escherichia coli phosphoenolpyruvate carboxylase or rat liver pyruvate carboxylase, two enzymes which require acetyl-CoA as an obligate activator. Furthermore, acetonyl-CoA will not compete with acetyl-CoA for binding to these enzymes showing the apparent absolute requirement of these two enzymes for a thioester group on the activating ligand. S-Acetonyl-CoA should be a useful reagent in the investigation of acetyl-CoA-requiring processes.
D000818:Animals; D002332:Carnitine O-Acetyltransferase / Q000037:antagonists & inhibitors; D002950:Citrate (si)-Synthase / Q000037:antagonists & inhibitors; D003065:Coenzyme A / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004789:Enzyme Activation / Q000187:drug effects; D004926:Escherichia coli / Q000201:enzymology; D008099:Liver / Q000201:enzymology; D010709:Phosphate Acetyltransferase / Q000037:antagonists & inhibitors; D010730:Phosphoenolpyruvate Carboxylase / Q000037:antagonists & inhibitors; D011766:Pyruvate Carboxylase / Q000037:antagonists & inhibitors*; D051381:Rats
C026513:acetonyl-coenzyme A; D002332:Carnitine O-Acetyltransferase; D010709:Phosphate Acetyltransferase; D002950:Citrate (si)-Synthase; D010730:Phosphoenolpyruvate Carboxylase; D011766:Pyruvate Carboxylase; D003065:Coenzyme A