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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Chemoenzymatic Synthesis of Selegiline: An Imine Reductase-Catalyzed Approach
Yuliang Hu1,2, Jinping Bao2, Dongyu Tang2
1College of Bioscience and Bioengineering, Jiangxi Agricultural University, Nanchang 330045, China.
Abstract:
(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.
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