Fine-tuning of the substrate binding mode to enhance the catalytic efficiency of an ortho-haloacetophenone-specific carbonyl reductase was written by Li, Aipeng;Li, Xue;Pang, Wei;Tian, Qing;Wang, Ting;Zhang, Lianbing. And the article was included in Catalysis Science & Technology in 2020.Application of 171032-87-4 This article mentions the following:
Carbonyl reductase BaSDR1 has been identified as a potential ortho-haloacetophenone-specific biocatalyst for the synthesis of chiral 1-(2-halophenyl)ethanols due to its excellent stereoselectivity. However, the catalytic efficiency of BaSDR1 is far below the required level for practical applications. Thus, fine-tuning of the substrate binding mode, which aimed at maximum preservation of the pos. factors for substrate specificity and stereoselectivity, was proposed as a tentative strategy for enhancing its catalytic efficiency. The designed mutants Q139S, D253Y and Q139S/D253Y showed significantly enhanced catalytic efficiency. Remarkably, the variants Q139S and Q139S/D253Y exhibited a more than 9-fold improvement in catalytic efficiency (kcat/Km) toward substrates 6a and 11a, resp. More importantly, none of the variants caused activity-stereoselectivity trade-off and all variants exhibited excellent stereoselectivity (99% ee). Anal. of variant-substrate complexes showed that the mutations indeed enable the fine-tuning of the substrate binding mode. New strengthening factors for consolidating the productive conformation were introduced while the original pos. factors were preserved. Furthermore, at a substrate concentration of 100 mM, recombinant E. coli whole cells expressing the BaSDR1 mutants were successfully applied to the synthesis of several key intermediates of chiral pharmaceuticals, including (S)-1-(2-chlorophenyl)ethanol, (S)-1-(2,4-difluorophenyl)ethanol and (S)-1-(2,6-difluorophenyl)ethanol, with 99% enantiomeric excess, and the conversion reached over 95% in a certain period of time. These results demonstrated the effectiveness of the strategy involving the fine-tuning of the substrate binding mode and the applicability of the designed mutants in efficient reduction of ortho-haloacetophenones. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Application of 171032-87-4).
(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Application of 171032-87-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts