Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst

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	Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst
	Chen, Xi 1,2; Mei, Ting 1,2,3; Cui, Yunfeng 1,2; Chen, Qijia 1,2,4; Liu, Xiangtao 1,2; Feng, Jinhui 1,2; Wu, Qiaqing 1,2; Zhu, Dunming 1,2,4
刊名	CHEMISTRYOPEN
	2015-08-01
卷号	4 期号:4 页码:483-488
关键词	asymmetric synthesis biocatalysis bioreductions carbonyl reductases stereochemistry vicinal diols
英文摘要	Terminal vicinal diols are important chiral building blocks and intermediates in organic synthesis. Reduction of alpha-hydroxy ketones provides a straightforward approach to access these important compounds. In this study, it has been found that asymmetric reduction of a series of alpha-hydroxy aromatic ketones and 1-hydroxy-2-pentanone, catalyzed by Candida magnolia carbonyl reductase (CMCR) with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration, afforded 1-aryl-1,2- ethanediols and pentane-1,2-diol, respectively, in up to 99% ee. In order to evaluate the efficiency of the bioreduction, lyophilized recombinant Escherichia coli whole cells coexpress-ing CMCR and GDH genes were used as the biocatalyst and alpha-hydroxy acetophenone as the model substrate, and the reaction conditions, such as pH, cosolvent, the amount of biocatalyst and the presences of a cofactor (i.e., NADP(+)), were optimized. Under the optimized conditions (pH 6, 16 h), the bioreduction proceeded smoothly at 1.0(M) substrate concentration without the external addition of cofactor, and the product (S)-1-phenyl-1,2-ethanediol was isolated with 90% yield and 99% ee. This offers a practical biocatalytic method for the preparation of these important vicinal diols.
WOS标题词	Science & Technology ; Physical Sciences
类目[WOS]	Chemistry, Multidisciplinary
研究领域[WOS]	Chemistry
关键词[WOS]	METHYL O-CHLOROBENZOYLFORMATE ; CARBONYL REDUCTASE ; CANDIDA-PARAPSILOSIS ; ENANTIOSELECTIVE OXIDATION ; ASYMMETRIC HYDROGENATION ; SACCHAROMYCES-CEREVISIAE ; ALCOHOL-DEHYDROGENASE ; ENZYMATIC RESOLUTION ; BACTERIAL REDUCTASE ; ESCHERICHIA-COLI
收录类别	SCI
语种	英语
WOS记录号	WOS:000362191700011
内容类型	期刊论文
源URL	[http://124.16.173.210/handle/834782/1567]
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 300308, Peoples R China 2.Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin Engn Ctr Biocatalyt Technol, Tianjin 300308, Peoples R China 3.Tianjin Univ Sci & Technol, Coll Bioengn, Tianjin 300457, Peoples R China 4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Chen, Xi,Mei, Ting,Cui, Yunfeng,et al. Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst[J]. CHEMISTRYOPEN,2015,4(4):483-488.
APA	Chen, Xi.,Mei, Ting.,Cui, Yunfeng.,Chen, Qijia.,Liu, Xiangtao.,...&Zhu, Dunming.(2015).Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst.CHEMISTRYOPEN,4(4),483-488.
MLA	Chen, Xi,et al."Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst".CHEMISTRYOPEN 4.4(2015):483-488.