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Issue 15, 2019
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Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions

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Abstract

The biocatalytic stereocontrolled synthesis of various acyclic anti- or syn-α-alkyl-β-amino amides through a dynamic kinetic resolution strategy is demonstrated. A series of commercially available and in-house transaminases (TAs) were employed to perform the transamination of a series of chemically synthesized racemic α-alkyl-β-keto amides. Among them, commercial (R)-selective TAs showed the best activities and selectivities, giving access preferentially to the anti-diastereoisomers with low to high diastereomeric ratios (up to 96%) and excellent enantiomeric excess (>99%). The stereoselective biotransamination experiments were successfully demonstrated at a semi-preparative scale (25 mM, 100 mg substrate), leading to the corresponding optically active α-alkyl-β-amino amides in 45–90% isolated yields after a simple liquid–liquid extraction protocol.

Graphical abstract: Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions

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Publication details

The article was received on 22 May 2019, accepted on 01 Jul 2019 and first published on 02 Jul 2019


Article type: Paper
DOI: 10.1039/C9CY01004A
Catal. Sci. Technol., 2019,9, 4083-4090

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    Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions

    Á. Mourelle-Insua, D. Méndez-Sánchez, J. L. Galman, I. Slabu, N. J. Turner, V. Gotor-Fernández and I. Lavandera, Catal. Sci. Technol., 2019, 9, 4083
    DOI: 10.1039/C9CY01004A

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