title: Irreversible inhibition of aldolase by a phosphorylated alpha-dicarbonyl compound.
abstract: The preparation of a phosphorylated alpha-dicarbonyl compound designed to specifically react with arginine residues of enzymes accepting phosphorylated compounds as effectors is reported, and shown to inhibit rabbit muscle aldolase in a time-dependent and irreversible manner. This irreversible inhibition occured in a buffer devoid of borate ions, suggesting that the presence of the phosphate moiety contributes in the stabilization of the adduct formed with arginine residues. Under the same conditions, the metalloenzyme iron superoxide dismutase, in which an arginine is known to be critical for the catalytic function, is not significantly inhibited.
authors.affiliation: Groupe de Chimie Organique Biologique, Laboratoire LSPCMIB - UMR 5068 CNRS, Université Paul Sabatier, Toulouse cedex 9, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Chabot
authors.forename: Virginie
authors.initials: V
authors.lastname: Vinatier
authors.forename: Thierry
authors.initials: T
authors.lastname: Gefflaut
authors.forename: Cecile
authors.initials: C
authors.lastname: Baudoin
authors.forename: Frederic
authors.initials: F
authors.lastname: Rodriguez
authors.forename: Casimir
authors.initials: C
authors.lastname: Blonski
authors.forename: Pascal
authors.initials: P
authors.lastname: Hoffmann
mesh_terms: D000818:Animals; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004926:Escherichia coli / Q000201:enzymology*; D005634:Fructose-Bisphosphate Aldolase / Q000037:antagonists & inhibitors*; D054354:Iron Carbonyl Compounds / Q000494:pharmacology*; D007659:Ketones / Q000494:pharmacology; D007700:Kinetics; D007783:Lactones / Q000494:pharmacology; D010766:Phosphorylation; D011817:Rabbits; D013482:Superoxide Dismutase / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D007659:Ketones; D007783:Lactones; C004773:diketene; D054354:Iron Carbonyl Compounds; D013482:Superoxide Dismutase; D005634:Fructose-Bisphosphate Aldolase