Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system was written by Yang, Zeyu;Fu, Hengwei;Ye, Wenjie;Xie, Youyu;Liu, Qinghai;Wang, Hualei;Wei, Dongzhi. And the article was included in Catalysis Science & Technology in 2020.Quality Control of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:
Alc. dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asym. synthesis of chiral alcs.; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the byproduct, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technol. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, volume/volume) concentration Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the byproduct acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcs. are synthesized at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) Et acetoacetate is completely converted into Et (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Mol. dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcs. on an industrial scale. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Quality Control of (R)-1-(3-Chlorophenyl)ethanol).
(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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Quality Control of (R)-1-(3-Chlorophenyl)ethanol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts