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Biocatalytic Applications of Hydroxynitrile Lyases

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Part of the book series: Advances in Biochemical Engineering/Biotechnology ((4143,volume 63))

Abstract

Hydroxynitrile lyases (Hnls) are enzymes that catalyse the stereoselective addition of hydrocyanic acid to aldehydes and ketones and the reverse reaction, the decomposition of cyanohydrins. This biotransformation (in the synthesis direction) can generate a product with a new chiral centre which possesses geminal difunctionality, i.e. a hydroxyl and nitrile moiety at a single carbon atom, and which also represents a versatile synthetic intermediate in organic chemistry. Currently, this area of research is sufficiently well established that enzymes for the synthesis of either (R)- or (S)-cyanohydrins are available. The Hnl from almonds, Prunus amygdalus (PaHnl), provides an easy access to (R)-cyanohydrins. Further, recent advances in cloning and overexpression techniques have provided two of these (S)-Hnl enzymes, those from Hevea brasiliensis (HbHnl) and Manihot esculenta (MeHnl), in sufficient quantities for potential application to industrial syntheses. Further, the crystallisation of the Hnl from HbHnl has revealed new information about their 3D structure and a tentative reaction mechanism for cyanohydrin cleavage has been postulated.

This review surveys the practical sources of Hnls and the development of their use in aqueous, organic and biphasic systems to yield enantiomerically enriched cyanohydrins.

The potential of cyanohydrins as synthetic intermediates in organic chemistry will also be presented.

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  1. Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, A-8010, Graz, Austria

    Dean V. Johnson & Herfried Griengl

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  1. Dean V. Johnson
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  2. Herfried Griengl
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  1. Institute of Organic Chemistry, University of Graz, Heinrichstraße 28, A-8010, Graz, Austria

    Kurt Faber

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Johnson, D.V., Griengl, H. (1999). Biocatalytic Applications of Hydroxynitrile Lyases. In: Faber, K. (eds) Biotransformations. Advances in Biochemical Engineering/Biotechnology, vol 63. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69791-8_2

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