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Studies of 1-Amino-2,2-difluorocyclopropane-1-carboxylic Acid: Mechanism of Decomposition and Inhibition of 1-Aminocyclopropane-1-carboxylic Acid Deaminase
Organic Letters ( IF 4.9 ) Pub Date : 2015-06-23 00:00:00 , DOI: 10.1021/acs.orglett.5b01570
Cheng-Hao Liu , Shao-An Wang , Mark W Ruszczycky , Huawei Chen 1 , Keqiang Li 1 , Kazuo Murakami 1 , Hung-wen Liu 1
Affiliation  

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.

中文翻译:


1-氨基-2,2-二氟环丙烷-1-甲酸的研究:1-氨基环丙烷-1-甲酸脱氨酶的分解和抑制机制



1-氨基-2,2-二氟环丙烷-1-羧酸 (DFACC) 由于其环丙基官能团的反应性增加,在 1-氨基环丙烷-1-羧酸 (ACC) 脱氨酶的研究中受到关注。结果表明,DFACC 在接近生理条件下不稳定,主要通过特定碱催化分解为 3-氟-2-氧代丁-3-烯酸,速率常数为 0.18 ± 0.01 min –1 。与 ACC 脱氨酶一起孵育后,发现 DFACC 是 ACC 脱氨酶的缓慢解离抑制剂,具有亚微摩尔亲和力。
更新日期:2015-06-23
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