title: Selective inhibition of lignoceroyl-CoA synthetase by adenosine 5'-alkylphosphates.
abstract: Structural analogs of adenosine 5'-acylphosphates, which are intermediates of the reaction catalyzed by acyl-CoA synthetases, were synthesized by condensing primary alcohols with AMP to examine the inhibitory effects on the lignoceroyl-CoA and palmitoyl-CoA synthetase activities. Hexadecyl, octadecyl, eicosyl, docosyl and tetracosyl esters of AMP were remarkably potent inhibitors of the lignoceroyl-CoA formation. On the other hand, the eicosyl, docosyl or tetracosyl esters of AMP did not behave as significant inhibitors of the palmitoyl-CoA formation at the concentration at which the two other shorter chain analogs were effective. Namely, these longer alkyl esters of AMP have selective inhibitory effects on the lignoceroyl-CoA synthetase activity. The Ki value of adenosine 5'-tetracosylphosphate, the most potent inhibitor, was about one tenth lower than the Km value for the substrate lignoceric acid. Furthermore, the results support the notion that lignoceroyl-CoA synthetase is distinct from palmitoyl-CoA synthetase.
authors.affiliation: Laboratory of Health Chemistry, Niigata College of Pharmacy, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Shiraishi
authors.forename: K
authors.initials: K
authors.lastname: Tezuka
authors.forename: Y
authors.initials: Y
authors.lastname: Uda
mesh_terms: D000249:Adenosine Monophosphate / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D002645:Chickens; D003066:Coenzyme A Ligases / Q000037:antagonists & inhibitors* / Q000302:isolation & purification; D007202:Indicators and Reagents; D007700:Kinetics; D008862:Microsomes, Liver / Q000201:enzymology; D051381:Rats; D017208:Rats, Wistar; D013329:Structure-Activity Relationship
chemical_list: D007202:Indicators and Reagents; D000249:Adenosine Monophosphate; D003066:Coenzyme A Ligases; C044125:lignoceroyl-CoA ligase