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Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to β-Nitrostyrenes Catalyzed by a Promiscuous Proline-Based Tautomerase

Authors

  • Ellen Zandvoort,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Dr. Edzard M. Geertsema,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Bert-Jan Baas,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Prof. Dr. Wim J. Quax,

    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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  • Dr. Gerrit J. Poelarends

    Corresponding author
    1. Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
    • Department of Pharmaceutical Biology, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands)
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Errata

This article is corrected by:

  1. Errata: Berichtigung: Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to β-Nitrostyrenes Catalyzed by a Promiscuous Proline-Based Tautomerase Volume 124, Issue 25, 6140, Article first published online: 13 June 2012

  • The research leading to these results has received funding from the Netherlands Organisation for Scientific Research (VIDI grant 700.56.421) and the European Research Council under the European Community’s Seventh Framework Programme (FP7/2007-2013)/ERC Grant agreement no. 242293. We thank Monique Smith (University of Groningen) for her expert assistance in acquiring the HPLC chromatograms using a chiral stationary phase.

Abstract

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Nichtnatürliche Schönheit: Das Enzym 4-Oxalocrotonat-Tautomerase (4-OT) zeigt eine nichtnatürliche Aktivität, indem es eine Michael-Addition von Acetaldehyd an Nitrostyrol katalysiert. Die Reaktion verläuft wahrscheinlich über die Bildung eines Enamins zwischen dem N-terminalen Prolin von 4-OT und Acetaldehyd in Anlehnung an organokatalysierte Reaktionen. Eine hohe Stereoselektivität, geringe Katalysatormengen und Durchführbarkeit in Wasser zeichnen die Methode aus.

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