title: Studies of 1-Amino-2,2-difluorocyclopropane-1-carboxylic Acid: Mechanism of Decomposition and Inhibition of 1-Aminocyclopropane-1-carboxylic Acid Deaminase.
abstract: 1-Amino-2,2-difluorocyclopropane-1-carboxylic acid (DFACC) is of interest in the study of 1-aminocyclopropane-1-carboxylic acid (ACC) deaminase due to the increased reactivity of its cyclopropyl functionality. It is shown that DFACC is unstable under near-physiological conditions where it primarily decomposes via specific-base catalysis to 3-fluoro-2-oxobut-3-enoic acid with a rate constant of 0.18 ± 0.01 min(-1). Upon incubation with ACC deaminase, DFACC is found to be a slow-dissociating inhibitor of ACC deaminase with submicromolar affinity.
authors.forename: Cheng-Hao
authors.initials: CH
authors.lastname: Liu
authors.forename: Shao-An
authors.initials: SA
authors.lastname: Wang
authors.forename: Mark W
authors.initials: MW
authors.lastname: Ruszczycky
authors.affiliation: §Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
authors.forename: Huawei
authors.initials: H
authors.lastname: Chen
authors.affiliation: §Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
authors.forename: Keqiang
authors.initials: K
authors.lastname: Li
authors.affiliation: §Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Murakami
authors.affiliation: §Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States.
authors.forename: Hung-wen
authors.initials: HW
authors.lastname: Liu
mesh_terms: D000598:Amino Acids, Cyclic / Q000737:chemistry*; D019755:Carbon-Carbon Lyases / Q000037:antagonists & inhibitors*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure
chemical_list: C000602574:1-amino-2,2-difluorocyclopropane-1-carboxylic acid; D000598:Amino Acids, Cyclic; D002264:Carboxylic Acids; C023863:1-aminocyclopropane-1-carboxylic acid; C033634:1-aminocyclopropane-1-carboxylate deaminase; D019755:Carbon-Carbon Lyases