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Transaminase-mediated synthesis of enantiopure drug-like 1-(3',4'-disubstituted phenyl)propan-2-amines.

ABSTRACT: Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88-89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee.

SUBMITTER: Lako A

PROVIDER: S-EPMC9057730 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Transaminase-mediated synthesis of enantiopure drug-like 1-(3',4'-disubstituted phenyl)propan-2-amines.

Lakó Ágnes Á Molnár Zsófia Z Mendonça Ricardo R Poppe László L Poppe László L

RSC advances 20201110 67

Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88- ...[more]

PMID: 35519186

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