Acetoacetyl-CoA reductase PhaB as an excellent anti-Prelog biocatalyst for the synthesis of chiral β-hydroxyl ester and the molecular basis of its catalytic performance was written by Wang, Ting;Yang, Ke;Tian, Qing;Han, Ruiting;Zhang, Xuanshuo;Li, Aipeng;Zhang, Lianbing. And the article was included in Molecular Catalysis in 2021.Synthetic Route of C6H9ClO3 The following contents are mentioned in the article:
Acetoacetyl-CoA reductase PhaB turned out to be capable of catalyzing the anti-Prelog asym. reduction of various β-ketoesters (1a-12a) and aromatic ketones (13a-29a). Particularly, PhaB showed high specific activity and excellent stereoselectivity (93.0%-99.8% eep) toward β-ketoesters. The specific activity of PhaB toward Et 4-chloroacetoacetate 11a was up to 1302.2 mU/mg. The mol. basis anal. showed the rotatable single bonds in β-ketoesters endow them with a high degree of structural flexibility and adaptability. Thus, β-ketoesters could quickly adjust their conformation and further form a productive conformation in the narrow substrate-binding pocket of the enzyme. In contrast, PhaB exhibited low specific activity and stereoselectivity toward the majority of aromatic ketones. The large steric hindrance and rigid structure resulted from aromatic rings made the aromatic ketones impossible to adjust their conformation as conveniently as β-ketoesters. Furthermore, it was found the halogen bond was the major driven force of the high specific activity of PhaB toward chlorinated β-ketoesters (10a and 11a), while the distribution of enzyme-substrate interactions was an important factor determining the enzyme activity besides the steric hindrance. Moreover, the geometric configuration of the substrate and the enzyme substrate-binding pocket played critical roles in determining the substrate binding mode and the enzyme stereoselectivity. This study involved multiple reactions and reactants, such as Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3Synthetic Route of C6H9ClO3).
Ethyl 4-chloro-3-oxobutanoate (cas: 638-07-3) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.Synthetic Route of C6H9ClO3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics