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

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.

SUBMITTER: Hu Y

PROVIDER: S-EPMC10974447 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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

Hu Yuliang Y Bao Jinping J Tang Dongyu D Gao Shushan S Wang Fei F Ding Zhongtao Z Cui Chengsen C

Molecules (Basel, Switzerland) 20240316 6

(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, offer ...[more]

PMID: 38542964

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