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Identification and Structure Analysis of an Unusual Halohydrin Dehalogenase for Highly Chemo-, Regio- and Enantioselective Bio-Nitration of Epoxides.
Wang, Hui-Hui; Wan, Nan-Wei; Miao, Run-Ping; He, Cheng-Li; Chen, Yong-Zheng; Liu, Zhi-Qiang; Zheng, Yu-Guo.
Affiliation
  • Wang HH; Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014, China.
  • Wan NW; Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
  • Miao RP; Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
  • He CL; Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
  • Chen YZ; Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
  • Liu ZQ; Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
  • Zheng YG; Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014, China.
Angew Chem Int Ed Engl ; 61(37): e202205790, 2022 09 12.
Article in En | MEDLINE | ID: mdl-35856897
We report the discovery of an unusual halohydrin dehalogenase, HHDHamb, that can work under relatively low acidic conditions and extremely low temperatures for the bio-nitration of epoxides using nitrite as a nitrating agent. The bio-nitration strategy exhibits high chemo-, regio-, and enantioselectivity, catalyzing the kinetic resolution of various epoxides to enantiopure ß-nitroalcohols with nitro-bearing stereocenters in up to 41 % isolated yield and >99 % enantiomeric excess (ee). Additionally, the bio-nitration method displays a high reaction efficiency and can be performed on a gram scale. We also solved the crystal structure of HHDHamb to understand the possible structural determinants of chemoselectivity control in the bio-nitration reaction.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Epoxy Compounds / Hydrolases Type of study: Diagnostic_studies Language: En Journal: Angew Chem Int Ed Engl Year: 2022 Document type: Article Affiliation country: China Country of publication: Germany
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Epoxy Compounds / Hydrolases Type of study: Diagnostic_studies Language: En Journal: Angew Chem Int Ed Engl Year: 2022 Document type: Article Affiliation country: China Country of publication: Germany