title: Synthesis of labeled 1-amino-2-methylenecyclopropane-1-carboxylic acid, an inactivator of 1-aminocyclopropane-1-carboxylate deaminase.
abstract: 1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.
authors.affiliation: Division of Medicinal Chemistry, College of Pharmacy, University of Texas, Austin, TX 78712, USA.
authors.forename: Zongbao
authors.initials: Z
authors.lastname: Zhao
authors.forename: Hung-wen
authors.initials: HW
authors.lastname: Liu
mesh_terms: D000598:Amino Acids, Cyclic / Q000737:chemistry; D000641:Ammonia / Q000378:metabolism; D001665:Binding Sites; D002087:Butyrates / Q000378:metabolism; D019755:Carbon-Carbon Lyases / Q000037:antagonists & inhibitors* / Q000302:isolation & purification; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002855:Chromatography, Thin Layer; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011549:Pseudomonas / Q000201:enzymology* / Q000235:genetics*; D017386:Sequence Homology, Amino Acid; D013045:Species Specificity; D014316:Tritium
chemical_list: C461921:1-amino-2-methylenecyclopropane-1-carboxylic acid; D000598:Amino Acids, Cyclic; D002087:Butyrates; D002264:Carboxylic Acids; D003521:Cyclopropanes; D004791:Enzyme Inhibitors; D014316:Tritium; C023863:1-aminocyclopropane-1-carboxylic acid; C005087:alpha-ketobutyric acid; D000641:Ammonia; C033634:1-aminocyclopropane-1-carboxylate deaminase; D019755:Carbon-Carbon Lyases