Enantioselective Cascade Biocatalysis for Deracemization of Racemic β‐Amino Alcohols to Enantiopure ( S )‐β‐Amino Alcohols by Employing Cyclohexylamine Oxidase and ω‐Transaminase
| Autor: | Honghong Chang, Jing Li, Chaofeng Zhang, Li-Li Gao, Ya-Wen Chang, Rui Dong, Xiao-Xiao Yang, Shuangping Huang, Xing-Mei Guo, Jian-Dong Zhang |
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| Rok vydání: | 2020 |
| Předmět: |
Stereochemistry
Cyclohexylamine oxidase Deamination Alcohol 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Arthrobacter Enantiomeric excess Molecular Biology Transaminases Amination Oxidoreductases Acting on CH-NH Group Donors Molecular Structure 010405 organic chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Amino Alcohols 0104 chemical sciences Enantiopure drug chemistry Biocatalysis Molecular Medicine |
| Zdroj: | ChemBioChem. 22:124-128 |
| ISSN: | 1439-7633 1439-4227 |
| DOI: | 10.1002/cbic.202000491 |
| Popis: | Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg-1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78-94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L-1 ) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee. |
| Databáze: | OpenAIRE |
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