Biocatalytic Asymmetric Reduction of γ-Keto Esters to Access Optically Active γ-Aryl-γ-butyrolactones

Paweł Borowiecki , Natalia Telatycka , Mateusz Tataruch , Anna Żądło-Dobrowolska , Tamara Reiter , Karola Schühle , Johann Heider , Maciej Szaleniec , Wolfgang Kroutil

Abstract

An efficient stereoselective syntheses of a series of functionalized optically active γ-aryl-γ-butyrolactones is achieved by enzymatic asymmetric reduction of the corresponding sterically demanding γ-keto esters employing wild-type and recombinant alcohol dehydrogenases. The best stereoselectivities for the reduction via hydrogen transfer was obtained with two short chain dehydrogenases (SDRs) of complementary stereospecificity from Aromatoleum aromaticum, namely the Prelog-specific NADH-dependent (S)-1-phenylethanol dehydrogenase [(S)-PED] and the anti-Prelog-specific (R)-1-(4-hydroxyphenyl)-ethanol dehydrogenase [(R)-HPED], respectively.Biotransformations catalyzed by both enzymes, followed by TFA-catalyzed cyclization of the resulting γ-hydroxy esters, furnished the respective (S)- and (R)-configured products with exquisite optical purity (up to >99% ee). The synthetic value was demonstrated on preparative scale for the asymmetric bioreduction of the model compound, methyl 4-oxo-4-phenylbutanoate, affording optically pure (S)-γ-phenyl-γ-butyrolactone (>99% ee) in 67–74% isolated yield at 89–95% conversion depending on the applied scale. (Figure presented.).

Author Paweł Borowiecki (FC / CDSB)
Paweł Borowiecki,,
- Chair of Drug and Cosmetics Biotechnology
, Natalia Telatycka (WUT)
Natalia Telatycka,,
- Warsaw University of Technology
, Mateusz Tataruch - [Institute of Catalysis and Surface Chemistry of the Polish Academy of Sciences]
Mateusz Tataruch,,
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, Anna Żądło-Dobrowolska - [Institute of Organic Chemistry of the Polish Academy of Sciences]
Anna Żądło-Dobrowolska,,
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, Tamara Reiter - [Karl-Franzens-Universitat Graz]
Tamara Reiter,,
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, Karola Schühle - [Philipps-Universität Marburg]
Karola Schühle,,
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, Johann Heider - [Philipps-Universität Marburg]
Johann Heider,,
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, Maciej Szaleniec - [Institute of Catalysis and Surface Chemistry of the Polish Academy of Sciences]
Maciej Szaleniec,,
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, Wolfgang Kroutil - [Karl-Franzens-Universitat Graz]
Wolfgang Kroutil,,
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Journal seriesAdvanced Synthesis & Catalysis, [Advanced Synthesis and Catalysis], ISSN 1615-4150, e-ISSN 1615-4169
Issue year2020
Vol362
Pages2012-2029
Publication size in sheets0.85
Keywords in EnglishBiocatalysis; Biotransformations; Stereo-selective Bioreductions; Alcohol Dehydrogenases; Optically Active Aromatic γ-Butyrolactones
ASJC Classification1503 Catalysis; 1605 Organic Chemistry
DOIDOI:10.1002/adsc.201901483
URL https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.201901483
Languageen angielski
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wdpb_publikacje_pliki_plik_publikacja_3956_org.pdf 2.88 MB
Score (nominal)140
Score sourcejournalList
ScoreMinisterial score = 140.0, 22-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 0; WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.935; WoS Impact Factor: 2018 = 5.451 (2) - 2018=5.176 (5)
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