title: Stable analogs of acyl adenylates. Inhibition of acetyl- and acyl-CoA synthetase by adenosine 5'-alkylphosphates.
abstract: Adenosine 5'-alkylphosphates are potent inhibitors of acetyl- and acyl-CoA synthetase. In each case, the most effective inhibitor in the series is homologous with the tightly bound acyl adenylate intermediate. Adenosine 5'-ethylphosphate (Ki = 33 nM) is 88-fold more potent than adenosine 5'-methylphosphate (Ki = 2900 nM) as a competitive inhibitor of acetyl-CoA synthetase; the contribution of a single carbon to the observed binding energy (-11 kJ/mol) is much larger than is typically observed.
mesh_terms: D000106:Acetate-CoA Ligase / Q000037:antagonists & inhibitors*; D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D001665:Binding Sites; D001667:Binding, Competitive; D003066:Coenzyme A Ligases / Q000037:antagonists & inhibitors*; D007700:Kinetics; D011550:Pseudomonas aeruginosa / Q000201:enzymology; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D012995:Solubility; D013816:Thermodynamics
chemical_list: D000249:Adenosine Monophosphate; D003066:Coenzyme A Ligases; D000106:Acetate-CoA Ligase