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An Artificial Enzyme for Asymmetric Nitrocyclopropanation of α,ß-Unsaturated Aldehydes-Design and Evolution.
Yu, Ming-Zhu; Yuan, Ye; Li, Zhen-Jie; Kunthic, Thittaya; Wang, He-Xiang; Xu, Chen; Xiang, Zheng.
Afiliação
  • Yu MZ; State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, University Town of Shenzhen, Nanshan District, 518055, Shenzhen,
  • Yuan Y; State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, University Town of Shenzhen, Nanshan District, 518055, Shenzhen,
  • Li ZJ; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology Nanshan District, 518055, Shenzhen, P. R. China.
  • Kunthic T; State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, University Town of Shenzhen, Nanshan District, 518055, Shenzhen,
  • Wang HX; State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, University Town of Shenzhen, Nanshan District, 518055, Shenzhen,
  • Xu C; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology Nanshan District, 518055, Shenzhen, P. R. China.
  • Xiang Z; State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, AI for Science (AI4S) Preferred Program, School of Chemical Biology and Biotechnology Peking University Shenzhen Graduate School, University Town of Shenzhen, Nanshan District, 518055, Shenzhen,
Angew Chem Int Ed Engl ; 63(25): e202401635, 2024 06 17.
Article em En | MEDLINE | ID: mdl-38597773
ABSTRACT
The introduction of an abiological catalytic group into the binding pocket of a protein host allows for the expansion of enzyme chemistries. Here, we report the generation of an artificial enzyme by genetic encoding of a non-canonical amino acid that contains a secondary amine side chain. The non-canonical amino acid and the binding pocket function synergistically to catalyze the asymmetric nitrocyclopropanation of α,ß-unsaturated aldehydes by the iminium activation mechanism. The designer enzyme was evolved to an optimal variant that catalyzes the reaction at high conversions with high diastereo- and enantioselectivity. This work demonstrates the application of genetic code expansion in enzyme design and expands the scope of enzyme-catalyzed abiological reactions.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ciclopropanos / Aldeídos Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Ciclopropanos / Aldeídos Idioma: En Ano de publicação: 2024 Tipo de documento: Article