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Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins |
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| Authors: | Manuela Avi Martin H Fechter Karl Gruber Ferdinand Belaj Herfried Griengl |
| Institution: | a Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria b Research Centre Applied Biocatalysis, Graz, Austria c Institute of Chemistry, Karl-Franzens-Universität, Heinrichstraße 28, A-8010 Graz, Austria d DSM Fine Chemicals Austria, St. Peter-Straße 25, A-4021 Linz, Austria |
| Abstract: | Heterocyclic saturated five- and six-membered ring ketones sometimes bearing a methyl substituent were reacted with HCN under enzyme catalysis using recombinant hydroxynitrile lyase from Hevea brasiliensis, as a rule (S)-selective, and Prunus amygdalus, (R)-selective. The resulting cyanohydrins were stereochemically characterised. The steric outcome of these transformations was interpreted by molecular modelling. |
| Keywords: | Hydroxynitrile lyase Cyanohydrins Heterocyclic ketones Enzyme-catalysed |
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