Chemoenzymatic Synthesis of Selegiline: An Imine Reductase-Catalyzed Approach.

Autor: Hu Y; College of Bioscience and Bioengineering, Jiangxi Agricultural University, Nanchang 330045, China.; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China., Bao J; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China., Tang D; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China., Gao S; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China.; National Technology Innovation Center of Synthetic Biology, Tianjin 300308, China., Wang F; College of Bioscience and Bioengineering, Jiangxi Agricultural University, Nanchang 330045, China., Ding Z; College of Bioscience and Bioengineering, Jiangxi Agricultural University, Nanchang 330045, China.; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China., Cui C; Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin 300308, China.; National Technology Innovation Center of Synthetic Biology, Tianjin 300308, China.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2024 Mar 16; Vol. 29 (6). Date of Electronic Publication: 2024 Mar 16.
DOI: 10.3390/molecules29061328
Abstrakt: ( R )-Homobenzylic amines are key structural motifs present in ( R )-selegiline, a drug indicated for the treatment of early-stage Parkinson's disease. Herein, we report a new short chemoenzymatic approach (in 2 steps) towards the synthesis of ( R )-selegiline via stereoselective biocatalytic reductive amination as the key step. The imine reductase IR36-M5 mutant showed high conversion (97%) and stereoselectivity (97%) toward the phenylacetone and propargyl amine substrates, offering valuable biocatalysts for synthesizing alkylated homobenzylic amines.
Databáze: MEDLINE
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