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DOI | 10.1126/science.aaw1143 |
Photoexcitation of flavoenzymes enables a stereoselective radical cyclization | |
Biegasiewicz, Kyle F.1; Cooper, Simon J.1; Gao, Xin1; Oblinsky, Daniel G.1; Kim, Ji Bye1; Garfinkle, Samuel E.1; Joyce, Leo A.2; Sandoval, Braddock A.1; Scholes, Gregory D.1; Hyster, Todd K.1 | |
2019-06-21 | |
发表期刊 | SCIENCE
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ISSN | 0036-8075 |
EISSN | 1095-9203 |
出版年 | 2019 |
卷号 | 364期号:6446页码:1166-+ |
文章类型 | Article |
语种 | 英语 |
国家 | USA |
英文摘要 | Photoexcitation is a common strategy for initiating radical reactions in chemical synthesis. We found that photoexcitation of flavin-dependent "ene"-reductases changes their catalytic function, enabling these enzymes to promote an asymmetric radical cyclization. This reactivity enables the construction of five-, six-, seven-, and eight-membered lactams with stereochemical preference conferred by the enzyme active site. After formation of a prochiral radical, the enzyme guides the delivery of a hydrogen atom from flavin-a challenging feat for small-molecule chemical reagents. The initial electron transfer occurs through direct excitation of an electron donor-acceptor complex that forms between the substrate and the reduced flavin cofactor within the enzyme active site. Photoexcitation of promiscuous flavoenzymes has thus furnished a previously unknown biocatalytic reaction. |
领域 | 地球科学 ; 气候变化 ; 资源环境 |
收录类别 | SCI-E |
WOS记录号 | WOS:000472175100038 |
WOS关键词 | MOLECULAR-ORBITAL METHODS ; SET MODEL CHEMISTRY ; ENANTIOSELECTIVE SYNTHESIS ; CATALYTIC PROMISCUITY ; TOTAL ENERGIES ; ENZYMES ; BIOCATALYSIS ; DISCOVERY ; ESTERS ; ATOMS |
WOS类目 | Multidisciplinary Sciences |
WOS研究方向 | Science & Technology - Other Topics |
引用统计 | |
文献类型 | 期刊论文 |
条目标识符 | http://119.78.100.173/C666/handle/2XK7JSWQ/201705 |
专题 | 地球科学 资源环境科学 气候变化 |
作者单位 | 1.Princeton Univ, Dept Chem, Princeton, NJ 08544 USA; 2.Merck, Dept Proc Res & Dev, Rahway, NJ 07065 USA |
推荐引用方式 GB/T 7714 | Biegasiewicz, Kyle F.,Cooper, Simon J.,Gao, Xin,et al. Photoexcitation of flavoenzymes enables a stereoselective radical cyclization[J]. SCIENCE,2019,364(6446):1166-+. |
APA | Biegasiewicz, Kyle F..,Cooper, Simon J..,Gao, Xin.,Oblinsky, Daniel G..,Kim, Ji Bye.,...&Hyster, Todd K..(2019).Photoexcitation of flavoenzymes enables a stereoselective radical cyclization.SCIENCE,364(6446),1166-+. |
MLA | Biegasiewicz, Kyle F.,et al."Photoexcitation of flavoenzymes enables a stereoselective radical cyclization".SCIENCE 364.6446(2019):1166-+. |
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