Discovery of a Switch Between Prelog and Anti-Prelog Reduction toward Halogen-Substituted Acetophenones in Short-Chain Dehydrogenase/Reductases was written by Qin, Fengyu;Qin, Bin;Zhang, Wenhe;Liu, Yalin;Su, Xin;Zhu, Tianhui;Ouyang, Jingping;Guo, Jiyang;Li, Yuxin;Zhang, Feiting;Tang, Jun;Jia, Xian;You, Song. And the article was included in ACS Catalysis in 2018.Reference of 171032-87-4 This article mentions the following:
The application of ketoreductases based biocatalytic reduction to access optically pure Prelog or anti-Prelog alcs. offers a valuable approach for asym. synthesis. Despite this, control the stereopreferences of ketoreductases as desired remains challenging since natural ketoreductases usually display Prelog preference and it is difficult to transfer the knowledge from engineered anti-Prelog ketoreductases to the others. Here, we present the discovery of a switch between Prelog and anti-Prelog reduction toward halogen-substituted acetophenones in six short-chain dehydrogenase/reductases (SDRs). Through carefully analyzing the structural information and multiple-sequence alignment of several reported SDRs with Prelog or anti-Prelog stereopreference, the key residues that might control their stereopreferences were identified using Lactobacillus fermentum short-chain dehydrogenase/reductase 1 (LfSDR1) as the starting enzyme. Protein engineering at these positions of LfSDR1 could improve its anti-Prelog stereoselectivity or switch its stereopreference to Prelog. Moreover, the knowledge obtained from LfSDR1 could be further transferred to other five SDRs (four mined SDRs and one reported SDR) that have 21-48% sequence identities with LfSDR1. The stereopreferences of these SDRs were able to be switched either from anti-Prelog to Prelog or from Prelog to anti-Prelog by mutagenesis at related positions. In addition, further optimization of LfSDR1 can access stereo-complementary reduction of several halogen-substituted acetophenones with high stereoselectivity (up to >99%), resulting in some valuable chiral alcs. for synthesis of pharmaceutical agents. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Reference of 171032-87-4).
(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 171032-87-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts