High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols
Objectives To screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols. Results A new strain named Arthrobacter sp. TYUT010-15 with the ( R )-selective deamination activity of cyclic β-amino alcohol has been isolated from nature via a high throughput solid-phase screening method. The reaction conditions of TYUT010-15 were optimized. Using the resting cell of TYUT010-15 as the catalyst, kinetic resolution of trans -2-aminocyclopentanol, trans -2-aminocyclohexanol and cis -1-amino-2-indanol was carried out to afford (1 S , 2 S )- trans -2-aminocyclopentanol, (1 S , 2 S )- trans -2-aminocyclohexanol and (1 R , 2 S )- cis -1-amino-2-indanol in > 99% ee and 49.6–50% conversion. Four aromatic β-amino alcohols and two amines were also resolved, ( S )-β-amino alcohols and ( R )-amines were obtained in > 99% ee. Preparation experiment was conducted with 200 mM (23.2 g L −1 ) racemic trans -2-aminocyclohexanol, yielding the desired (1 S , 2 S )- trans -2-aminocyclohexanol in 40% isolated yield, > 99% ee and 5.8 g L −1 d −1 space time yields. Conclusions This study provides a high throughput solid-phase method for screening of bacteria with cyclic amino alcohol deamination activity and a first example for practical preparation of chiral cyclic β-amino alcohol by Arthrobacter sp. TYUT010-15.
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