Deracemization of 2-Methyl-1,2,3,4-Tetrahydroquinoline Using Mutant Cyclohexylamine Oxidase Obtained by Iterative Saturation Mutagenesis
文献类型：期刊论文
| 作者 | Li, Guangyue1,2; Ren, Jie1,2; Yao, Peiyuan1,2; Duan, Yitao1,2; Zhang, Hailing1,2; Wu, Qiaqing1,2; Feng, Jinhui1,2; Lau, Peter C. K.3,4,5,6; Zhu, Dunming1,2 |
| 刊名 | ACS CATALYSIS
 |
| 出版日期 | 2014-03-01 |
| 卷号 | 4期号:3页码:903-908 |
| 关键词 | biocatalysis amine oxidase iterative saturation mutagenesis chiral amines deracemization |
| 英文摘要 | The current toolkit of biocatalysts for the production of enantiomerically pure chiral amines is largely restricted to amine transaminases, ammonia lyases, or the genetic variants of monoamine oxidase N(MAO-N) from Aspergillus niger. Flavin-dependent amine oxidases have the apparent advantage of using molecular oxygen as a stoichiometric oxidant and their reactions are irreversible. To expand the toolkit and increase the substrate spectrum of a bacterial and flavin-dependent cyclohexylamine oxidase (CHAO) to enable deracemization of secondary amines, saturation mutagenesis of 11 amino acid residues located around the cyclohexanone substrate within a distance of 5 angstrom, followed by iterative saturation mutagenesis of four beneficial mutants, were performed. Screening with 2-methyl-1,2,3,4-tetrahydroquinoline as the substrate generated two improved CHAO variants, T198FL199S and T198FL199SM226F, that exhibited up to 406 times higher catalytic efficiency than the wild-type CHAO. Besides, high stereoselectivity for 2-methyl-1,2,3,4-tetrahydroquinoline and other 2-substituted-1,2,3,4-tetrahydroquinolines was demonstrated. In particular, deracemization of 2-methyl-1,2,3,4-tetrahydroquinoline by Escherichia coli whole cells expressing CHAO mutant T198FL199SM226F led to the production of (R)-2-methyl-1,2,3,4-tetrahydroquinoline with high yield (76%) and enantiomeric excess (ee, 9896). Tetrahydroquinolines are important building blocks of natural and synthetic products useful in the pharmaceutical and agrochemical industries. |
| WOS标题词 | Science & Technology ; Physical Sciences |
| 类目[WOS] | Chemistry, Physical |
| 研究领域[WOS] | Chemistry |
| 关键词[WOS] | HIGHLY ENANTIOSELECTIVE HYDROGENATION ; BREVIBACTERIUM-OXYDANS IH-35A ; PROTEIN FARNESYLTRANSFERASE ; ASYMMETRIC HYDROGENATION ; QUINOLINE ; BIOCATALYSIS ; DERIVATIVES ; PURIFICATION ; MODULATORS ; INHIBITORS |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000332756700021 |
| 源URL | [http://124.16.173.210/handle/834782/1411]  |
| 专题 | 天津工业生物技术研究所_生物催化与绿色化工 朱敦明_期刊论文 |
| 作者单位 | 1.Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Natl Engn Lab Ind Enzymes, Tianjin Airport Econ Area, Tianjin 300308, Peoples R China 2.Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin Engn Ctr Biocatalyt Technol, Tianjin Airport Econ Area, Tianjin 300308, Peoples R China 3.Natl Res Council Canada, Montreal, PQ H4P 2R2, Canada 4.McGill Univ, Dept Chem, Montreal, PQ H3A 2B4, Canada 5.McGill Univ, Dept Microbiol & Immunol, Montreal, PQ H3A 2B4, Canada 6.FQRNT Ctr Green Chem & Catalysis, Montreal, PQ, Canada |
| 推荐引用方式 GB/T 7714 | Li, Guangyue,Ren, Jie,Yao, Peiyuan,et al. Deracemization of 2-Methyl-1,2,3,4-Tetrahydroquinoline Using Mutant Cyclohexylamine Oxidase Obtained by Iterative Saturation Mutagenesis[J]. ACS CATALYSIS,2014,4(3):903-908. |
| APA | Li, Guangyue.,Ren, Jie.,Yao, Peiyuan.,Duan, Yitao.,Zhang, Hailing.,...&Zhu, Dunming.(2014).Deracemization of 2-Methyl-1,2,3,4-Tetrahydroquinoline Using Mutant Cyclohexylamine Oxidase Obtained by Iterative Saturation Mutagenesis.ACS CATALYSIS,4(3),903-908. |
| MLA | Li, Guangyue,et al."Deracemization of 2-Methyl-1,2,3,4-Tetrahydroquinoline Using Mutant Cyclohexylamine Oxidase Obtained by Iterative Saturation Mutagenesis".ACS CATALYSIS 4.3(2014):903-908. |
入库方式： OAI收割
来源：天津工业生物技术研究所
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