Studies of 1-Amino-2,2-difluorocyclopropane-1-carboxylic Acid: Mechanism of Decomposition and Inhibition of 1-Aminocyclopropane-1-carboxylic Acid Deaminase

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• 作者：Cheng-Hao Liu ; Shao-An Wang ; Mark W. Ruszczycky ; Huawei Chen ; Keqiang Li ; Kazuo Murakami ; Hung-wen Liu
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：July 2, 2015
• 年：2015
• 卷：17
• 期：13
• 页码：3342-3345
• 全文大小：277K
• ISSN：1523-7052

文摘

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 卤 0.01 min^鈥?. Upon incubation with ACC deaminase, DFACC is found to be a slow-dissociating inhibitor of ACC deaminase with submicromolar affinity.