Phenyl-n-butylborinic acid is a potent transition state analog inhibitor of lipolytic enzymes.
The cholesterol esterase and lipoprotein lipase catalyzed hydrolyses of the water-soluble substrate p-nitrophenyl butyrate are competitively inhibited by butaneboronic acid and phenylboronic acid. Phenyl-n-butylborinic acid has been synthesized and characterized as an ultrapotent transition state analog inhibitor: Ki = 2.9 +/- 0.6 nM and 1.7 +/- 0.3 microM for the cholesterol esterase and lipoprotein lipase reactions, respectively. These results are interpreted in terms of transition state structure and stabilization.
D000818:Animals; D001889:Borinic Acids / Q000494:pharmacology*; D001896:Boron Compounds; D001897:Boronic Acids / Q000494:pharmacology; D002087:Butyrates / Q000494:pharmacology; D007700:Kinetics; D008066:Lipolysis / Q000187:drug effects*; D008071:Lipoprotein Lipase / Q000378:metabolism; D008433:Mathematics; D002787:Sterol Esterase / Q000378:metabolism; D013552:Swine
D001889:Borinic Acids; D001896:Boron Compounds; D001897:Boronic Acids; D002087:Butyrates; C047177:phenyl-n-butylborinic acid; C033592:4-nitrophenyl butyrate; C030433:n-butylboronic acid; D002787:Sterol Esterase; D008071:Lipoprotein Lipase; C010686:benzeneboronic acid