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.HPLC of Formula: 120121-01-9 This article mentions the following:
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. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9HPLC of Formula: 120121-01-9).
(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.HPLC of Formula: 120121-01-9
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts