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Stereoselective De Novo Construction of Cyclopropane by a Multifunctional Class I Aldolase

文献类型：期刊论文

作者Li, Yulian1,2; Li, Qiaoqiao2; Zhang, Rui2; Liao, Cangsong1,2
刊名JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
出版日期2025-11-19
卷号147期号:46页码:42532-42538
ISSN号0002-7863
DOI10.1021/jacs.5c13402
通讯作者Zhang, Rui(zhangrui4@simm.ac.cn) ; Liao, Cangsong(csliao@simm.ac.cn)
英文摘要Cyclopropane is a widely distributed structural unit in natural products and pharmaceuticals. Current strategies in both organic and enzymatic synthesis of cyclopropane scaffolds mainly rely on alkene-based transformations, and de novo construction of all three carbon-carbon bonds of cyclopropane using a single catalyst has not been documented to date. Here, we report that class I pyruvate aldolase NahE can be engineered to catalyze this challenging transformation. NahE facilitates a cascade involving sequential aldol reaction, dehydration, Michael addition, and intramolecular S(N)2-like substitution, forging all three C-C bonds and establishing three stereocenters in a single catalytic cycle. Three engineered NahE variants synthesize 30 diverse aromatic and aliphatic cyclopropanes in up to 84% isolated yield with excellent stereoselectivity (>20:1 dr, >99% ee).
WOS关键词CARBENE-TRANSFER ; PROTEINS ; DESIGN
资助项目Chinese Academy of Sciences[XDB1060000] ; Shanghai Institute of Materia Medica, Chinese Academy of Sciences[NA] ; National Natural Science Foundation of China[22161132029]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001613651800001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/321717]  
专题中国科学院上海药物研究所
通讯作者Zhang, Rui; Liao, Cangsong
作者单位1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Li, Yulian,Li, Qiaoqiao,Zhang, Rui,et al. Stereoselective De Novo Construction of Cyclopropane by a Multifunctional Class I Aldolase[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2025,147(46):42532-42538.
APA Li, Yulian,Li, Qiaoqiao,Zhang, Rui,&Liao, Cangsong.(2025).Stereoselective De Novo Construction of Cyclopropane by a Multifunctional Class I Aldolase.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,147(46),42532-42538.
MLA Li, Yulian,et al."Stereoselective De Novo Construction of Cyclopropane by a Multifunctional Class I Aldolase".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 147.46(2025):42532-42538.

入库方式： OAI收割

来源：上海药物研究所

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