The First Recombinant Hydroxynitrile Lyase and its Application in the Synthesis of (S)-Cyanohydrins

Authors

  • Dr. Siegfried Förster,

    1. Institut für Organische Chemie der Universität, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code +(711)6854269
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  • Dipl.-Chem. Jürgen Roos,

    1. Institut für Organische Chemie der Universität, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code +(711)6854269
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  • Prof. Franz Effenberger,

    Corresponding author
    1. Institut für Organische Chemie der Universität, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code +(711)6854269
    • Institut für Organische Chemie der Universität, Pfaffenwaldring 55, D-70569 Stuttgart (Germany), Fax: Int. code +(711)6854269
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  • Dr. Harald Wajant,

    1. Institut für Zellbiologie und Immunologie der Universität Stuttgart (Germany)
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  • Dipl.-Ing.(FH) Achim Sprauer

    1. Institut für Technische Biochemie der Universität Stuttgart (Germany)
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  • Enzyme-Catalyzed Reactions, Part 23. This work was supported by the Bundesministerium für Bildung und Forschung and by the Fonds der Chemischen Industrie. Part 22: F. Effenberger, S. Heid, Tetrahedron Asymmetry1995, 6, 2945–2952.

  • Dedicated to Professor Manfred Regitz on the occasion of his 60th birthday

Abstract

original image

The cassava species Manihot esculenta provided the first recombinant hydroxynitrile lyase (MeHNL) that became accessible by overexpression in E. coli. This MeHNL catalyzes the enantioselective addition of HCN (depicted below) not only to aliphatic, aromatic, and heteroaromatic aldehydes, but also to ketones to give (S)-cyanohydrins in high optical yields. R [DOUBLE BOND] alkyl, aryl, heteroaryl; R1 [DOUBLE BOND] H, CH3.

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