ArticleACS catalysis2019
Enantioselective Synthesis of Pharmaceutically Active γ-Aminobutyric Acids Using a Tailor-Made Artificial Michaelase in One-Pot Cascade Reactions.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Secondary Amine Catalysis in Enzyme Design: Broadening Protein Template Diversity through Genetic Code Expansion.Angewandte Chemie (International ed. in English) · 2024Article
- Tailored photoenzymatic systems for selective reduction of aliphatic and aromatic nitro compounds fueled by light.Nature communications · 2023Article
- Stereoselective Three-Step One-Pot Cascade Combining Amino- and Biocatalysis to Access Chiral γ-Nitro Alcohols.Angewandte Chemie (International ed. in English) · 2022Article
- Enantiocomplementary Michael Additions of Acetaldehyde to Aliphatic Nitroalkenes Catalyzed by Proline-Based Carboligases.Chembiochem : a European journal of chemical biology · 2022Article
- Gene Fusion and Directed Evolution to Break Structural Symmetry and Boost Catalysis by an Oligomeric C-C Bond-Forming Enzyme.Angewandte Chemie (International ed. in English) · 2022Article
- The role of streptavidin and its variants in catalysis by biotinylated secondary amines.Organic & biomolecular chemistry · 2021Article
- Unlocking Asymmetric Michael Additions in an Archetypical Class I Aldolase by Directed Evolution.ACS catalysis · 2021Article
- Biocatalytic Asymmetric Cyclopropanations via Enzyme-Bound Iminium Ion Intermediates.Angewandte Chemie (International ed. in English) · 2021Article
- Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut.Organic letters · 2020Article
- Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase.Angewandte Chemie (International ed. in English) · 2020Article
- Tuning Enzyme Activity for Nonaqueous Solvents: Engineering an Enantioselective "Michaelase" for Catalysis in High Concentrations of Ethanol.Chembiochem : a European journal of chemical biology · 2020Article
- In Situ Acetaldehyde Synthesis for Carboligation Reactions.Chembiochem : a European journal of chemical biology · 2020Article
- Enabling protein-hosted organocatalytic transformations.RSC advances · 2020Review
- Selective Colorimetric "Turn-On" Probe for Efficient Engineering of Iminium Biocatalysis.ACS omega · 2020Article
- Biocatalytic Asymmetric Michael Additions of Nitromethane to α,β-Unsaturated Aldehydes via Enzyme-bound Iminium Ion Intermediates.ACS catalysis · 2019Article
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral γ-aminobutyric acid (GABA) analogues represent abundantly prescribed drugs, which are broadly applied as anticonvulsants, as antidepressants, and for the treatment of neuropathic pain. Here we report a one-pot two-step biocatalytic cascade route for synthesis of the pharmaceutically relevant enantiomers of γ-nitrobutyric acids, starting from simple precursors (acetaldehyde and nitroalkenes), using a tailor-made highly enantioselective artificial "Michaelase" (4-oxalocrotonate tautomerase mutant L8Y/M45Y/F50A), an aldehyde dehydrogenase with a broad non-natural substrate scope, and a cofactor recycling system. We also report a three-step chemoenzymatic cascade route for the efficient chemical reduction of enzymatically prepared γ-nitrobutyric acids into GABA analogues in one pot, achieving high enantiopurity (e.r. up to 99:1) and high overall yields (up to 70%). This chemoenzymatic methodology offers a step-economic alternative route to important pharmaceutically active GABA analogues, and highlights the exciting opportunities available for combining chemocatalysts, natural enzymes, and designed artificial biocatalysts in multistep syntheses.
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Registered trials
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