Botanical Institute and Botanic Gardens, Kiel University, D-24098, Kiel, Germany.
Anal Bioanal Chem. 2024 Dec;416(29):7085-7098. doi: 10.1007/s00216-024-05613-1. Epub 2024 Oct 23.
Acetohydroxyacid synthase (AHAS, EC 2.2.1.6) catalyzes the first step in the synthesis of the branched-chain amino acids valine, leucine, and isoleucine, pathways being present in plants and microorganisms, but not in animals. Thus, AHAS is an important target for numerous herbicides and, more recently, for the development of antimicrobial agents. The need to develop new and optimized herbicides and pharmaceuticals requires a detailed understanding of the biochemistry of AHAS. AHAS transfers an activated two-carbon moiety derived from pyruvate to either pyruvate or 2-oxobutyrate as acceptor substrates, forming 2-acetolactate or 2-acetohydroxy-2-butyrate, respectively. Various methods have been described in the literature to biochemically characterize AHAS with respect to substrate preferences, substrate specificity, or kinetic parameters. However, the simultaneous detection and quantification of substrates and unstable products of the AHAS-catalyzed reaction have always been a challenge. Using AHAS isoform II from Escherichia coli, we have developed a sensitive assay for AHAS-catalyzed reactions that uses derivatization with ethyl chloroformate to stabilize and volatilize all reactants in the aqueous solution and detect them by gas chromatography coupled to flame ionization detection or mass spectrometry. This assay allows us to characterize the product formation in reactions in single and dual substrate reactions and the substrate specificity of AHAS, and to reinterpret previous biochemical observations. This assay is not limited to the AHAS-catalyzed reactions, but should be applicable to studies of many metabolic pathways.
乙酰羟酸合酶 (AHAS, EC 2.2.1.6) 催化支链氨基酸缬氨酸、亮氨酸和异亮氨酸合成的第一步,该途径存在于植物和微生物中,但不存在于动物中。因此,AHAS 是许多除草剂的重要靶标,最近也是抗菌剂开发的靶标。开发新的和优化的除草剂和药物的需求需要对 AHAS 的生物化学有详细的了解。AHAS 将来自丙酮酸的激活的两个碳部分转移到丙酮酸或 2-氧代丁酸作为接受体底物,分别形成 2-乙酰乳酸或 2-乙酰羟丁酸。文献中已经描述了各种方法来从生化方面表征 AHAS 对底物偏好、底物特异性或动力学参数的影响。然而,同时检测和定量 AHAS 催化反应的底物和不稳定产物一直是一个挑战。我们使用来自大肠杆菌的 AHAS 同工型 II 开发了一种灵敏的 AHAS 催化反应测定法,该方法使用氯甲酸乙酯进行衍生化,以稳定和挥发水溶液中的所有反应物,并通过气相色谱法与火焰离子化检测或质谱法进行检测。该测定法使我们能够在单底物和双底物反应中表征产物形成以及 AHAS 的底物特异性,并重新解释以前的生化观察结果。该测定法不仅限于 AHAS 催化的反应,而应该适用于许多代谢途径的研究。