Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins
2004; Elsevier BV; Volume: 60; Issue: 46 Linguagem: Inglês
10.1016/j.tet.2004.07.099
ISSN1464-5416
AutoresManuela Avi, Martin Fechter, Karl Gruber, Ferdinand Belaj, Peter Pöchlauer, Herfried Griengl,
Tópico(s)Plant biochemistry and biosynthesis
ResumoHeterocyclic 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.
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