Synthesis of alpha,beta-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction
文献类型：期刊论文
| 作者 | Duan, Yitao; Yao, Peiyuan; Du, Yuncheng; Feng, Jinhui; Wu, Qiaqing1; Zhu, Dunming |
| 刊名 | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2015-11-19 |
| 卷号 | 11页码:2245-2251 |
| 关键词 | alpha,beta-unsaturated esters carboxylic acid reductase chemoenzymatic synthesis reduction Wittig reaction |
| 英文摘要 | alpha,beta-Unsaturated esters are versatile building blocks for organic synthesis and of significant importance for industrial applications. A great variety of synthetic methods have been developed, and quite a number of them use aldehydes as precursors. Herein we report a chemo-enzymatic chain elongation approach to access alpha,beta-unsaturated esters by combining an enzymatic carboxylic acid reduction and Wittig reaction. Recently, we have found that Mycobacterium sp. was able to reduce phenylacetic acid (1a) to 2-phenyl-1-ethanol (1c) and two sequences in the Mycobacterium sp. genome had high identity with the carboxylic acid reductase (CAR) gene from Nocardia iowensis. These two putative CAR genes were cloned, overexpressed in E. coli and one of two proteins could reduce 1a. The recombinant CAR was purified and characterized. The enzyme exhibited high activity toward a variety of aromatic and aliphatic carboxylic acids, including ibuprofen. The Mycobacterium CAR catalyzed carboxylic acid reduction to give aldehydes, followed by a Wittig reaction to afford the products alpha,beta-unsaturated esters with extension of two carbon atoms, demonstrating a new chemo-enzymatic method for the synthesis of these important compounds. |
| WOS标题词 | Science & Technology ; Physical Sciences |
| 类目[WOS] | Chemistry, Organic |
| 研究领域[WOS] | Chemistry |
| 关键词[WOS] | ARYL-ALDEHYDE OXIDOREDUCTASE ; (E)-ALPHA,BETA-UNSATURATED ESTERS ; MECHANISM ; CATALYSTS ; EFFICIENT ; ENZYME |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000365079900001 |
| 源URL | [http://124.16.173.210/handle/834782/1558]  |
| 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, Natl Engn Lab Ind Enzymes, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R China 2.Chinese Acad Sci, Tianjin Engn Ctr Biocatalyt Technol, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R China |
| 推荐引用方式 GB/T 7714 | Duan, Yitao,Yao, Peiyuan,Du, Yuncheng,et al. Synthesis of alpha,beta-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,2015,11:2245-2251. |
| APA | Duan, Yitao,Yao, Peiyuan,Du, Yuncheng,Feng, Jinhui,Wu, Qiaqing,&Zhu, Dunming.(2015).Synthesis of alpha,beta-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction.BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,11,2245-2251. |
| MLA | Duan, Yitao,et al."Synthesis of alpha,beta-unsaturated esters via a chemo-enzymatic chain elongation approach by combining carboxylic acid reduction and Wittig reaction".BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 11(2015):2245-2251. |
入库方式： OAI收割
来源：天津工业生物技术研究所
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