Reference of (S)-2-Amino-2-(4-fluorophenyl)ethanol《Cascade biocatalysis for regio- and stereoselective aminohydroxylation of styrenyl olefins to enantiopure arylglycinols》 was published in 2020. The authors were Zhang, Jiandong;Yang, Xiaoxiao;Dong, Rui;Gao, Lili;Li, Jing;Li, Xing;Huang, Shuangping;Zhang, Chaofeng;Chang, Honghong, and the article was included in《ACS Sustainable Chemistry & Engineering》. The author mentioned the following in the article:
Chiral β-amino alcs. are privileged scaffolds frequently found in pharmaceutically active mols. and natural products. Aminohydroxylation of olefins is one of the most powerful strategies to access chiral vicinal amino alcs. However, the direct regio- and stereoselective aminohydroxylation of olefins to unprotected enantioenriched β-amino alcs. remains a long-standing challenge. Herein, we report that a novel one-pot four-enzyme [styrene monooxygenase (SMO)/epoxide hydrolase (EH)/alc. dehydrogenase (ADH)/ω-transaminase (TA)] biocatalytic cascade efficiently catalyzes the direct transformation of readily available styrenyl olefins into unprotected 2-amino-2-Ph ethanols in good yields and excellent enantioselectivity. In vitro cascade biocatalysis aminohydroxylation of styrenyl olefins was first investigated by the combined four enzymes (SMO/EH/ADH/TA) with a trace amount of NADH (0.02 mM) and pyridoxal-5′-phosphate (0.1 mM), affording both enantiomers of β-amino alcs. 5a-j in 13.9-98.7% conversions and 86-99% ee. Whole-cell-based cascade biocatalysis was achieved by using the constructed recombinant Escherichia coli pairwise combinations and single tailor-made whole-cell biocatalyst without an addnl. NADH cofactor; (R)- and (S)-β-amino alcs. 5a-j could be obtained in 14.6-99.7% conversions and 86-99% ee. Moreover, the preparative experiments of this new cascade biocatalysis were demonstrated by the single tailor-made whole-cell biocatalyst [E. coli (CGS-DEM) and E. coli (CGS-DEB)] with the substrates 1a-b and 1h in an aqueous-organic two-phase system, affording chiral β-amino alcs. [(R)- or (S)-5a-b, h] in good yields (50.9-64.3%) and excellent ee (>99%). A new type of cascade biocatalysis was developed for regio- and enantioselective aminohydroxylation of styrenyl olefins to useful and valuable chiral arylglycinols in good yields and excellent ee. To complete the study, the researchers used (S)-2-Amino-2-(4-fluorophenyl)ethanol (cas: 224434-01-9) .
(S) – 2-amino-2 – (4-fluorophenyl) ethanol (cas: 224434-01-9) has the characteristics of alcohol. In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one another and to most other compounds. Reference of (S)-2-Amino-2-(4-fluorophenyl)ethanol
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