Commercial Transaminases for the Asymmetric Synthesis of Bulky Amines

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Abstract: Transaminase‐catalysed asymmetric amination is a valuable transformation for the synthesis of chiral amines. However, its use in synthetic chemistry has been curtailed by a narrow substrate scope and limited information on commercially available catalysts. In this work we have explored the substrate scope of selected commercially available transaminases, focusing on prochiral ketones bearing two bulky substituents and their application in both enzyme‐catalysed and enzyme‐triggered reactions. (R)‐ and/or (S)‐selective enzymes converted methyl‐, isopropyl‐, n‐butyl‐, and cyclohexyl‐phenone substrates to the corresponding amines in the range of 6–>99 % ee. In some cases, a stereochemical switch was detected, in which (R)‐enantioselectivity was observed with enzymes typically assigned as (S)‐selective. Upscaling of selected biotransformations provided chiral amines, in >99 % ee and up to 40 % isolated yield. Furthermore, transaminase‐triggered reactions, which were previously limited to methyl‐ and ethyl‐derivatives, were expanded to phenyl‐derivatives for the formation of a cis‐2,6‐disubstituted piperidine and 2,4‐diphenyl pyrroline, and isolated in up to 67 % yield.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Commercial Transaminases for the Asymmetric Synthesis of Bulky Amines ; day:22 ; month:05 ; year:2024 ; extent:7
European journal of organic chemistry ; (22.05.2024) (gesamt 7)

Creator: Haarr, Marianne B.
Sriwong, Kotchakorn T.
O'Reilly, Elaine

DOI: 10.1002/ejoc.202400257

URN: urn:nbn:de:101:1-2405231408534.583539466375

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:47 AM CEST

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Haarr, Marianne B.
Sriwong, Kotchakorn T.
O'Reilly, Elaine

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Commercial Transaminases for the Asymmetric Synthesis of Bulky Amines

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Other Objects (12)

Asymmetric organocatalytic synthesis of chiral homoallylic amines

Spontaneous absolute asymmetric synthesis promoted by achiral amines in conjunction with asymmetric autocatalysis

Actinomycetes-derived imine reductases with a preference towards bulky amine substrates

Engineering the Active Site of an (S)‐Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines

Asymmetric synthesis of allylic amines via hydroamination of allenes with benzophenone imine

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Asymmetric organocatalytic synthesis of chiral homoallylic amines

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Actinomycetes-derived imine reductases with a preference towards bulky amine substrates

Engineering the Active Site of an (S)‐Selective Amine Transaminase for Acceptance of Doubly Bulky Primary Amines

Asymmetric synthesis of γ-branched amines via rhodium-catalyzed reductive amination

Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines

Asymmetric synthesis of allylic amines via hydroamination of allenes with benzophenone imine

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Enantioselective Synthesis of Pharmaceutically Relevant Bulky Arylbutylamines Using Engineered Transaminases

Enantioselective Synthesis of Pharmaceutically Relevant Bulky Arylbutylamines Using Engineered Transaminases

Asymmetric hydrogenation of γ ‐branched allylamines for the efficient synthesis of γ ‐chirogenic amines

Aliphatic Amines Formed by Asymmetric Copper-Catalyzed Hydroamination

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Spontaneous absolute asymmetric synthesis promoted by achiral amines in conjunction with asymmetric autocatalysis

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Aliphatic Amines Formed by Asymmetric Copper-Catalyzed Hydroamination

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