Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases - a review.
The first enantioselective synthesis was the selective addition of cyanide to benzaldehyde catalysed by a hydroxynitrile lyase (HNL). Since then these enzymes have been developed into a reliable tool in organic synthesis. HNLs to prepare either the (R)- or the (S)-enantiomer of the desired cyanohydrin are available and a wide variety of reaction conditions can be applied. As a result of this, numerous applications of these enzymes in organic synthesis have been described. Here the examples of the last decade are summarised, the enzyme catalysed step is discussed and the follow-up chemistry is shown. This proves HNLs to be part of main stream organic synthesis. Additionally the newest approaches via immobilisation and reaction engineering are introduced.
Gebouw voor Scheikunde, Biokatalyse, Afdeling Biotechnologie, Technische Universiteit Delft, Julianalaan 136, 2628BL Delft, The Netherlands. u.hanefeld@tudelft.nl.
Paula
P
Bracco
Gebouw voor Scheikunde, Biokatalyse, Afdeling Biotechnologie, Technische Universiteit Delft, Julianalaan 136, 2628BL Delft, The Netherlands. u.hanefeld@tudelft.nl.
Hanna
H
Busch
Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Jan
J
von Langermann
Gebouw voor Scheikunde, Biokatalyse, Afdeling Biotechnologie, Technische Universiteit Delft, Julianalaan 136, 2628BL Delft, The Netherlands. u.hanefeld@tudelft.nl.
Ulf
U
Hanefeld
D000446:Aldehyde-Lyases / Q000737:chemistry / Q000378:metabolism*; D060326:Chemistry Techniques, Synthetic; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004800:Enzymes, Immobilized; D009570:Nitriles; C430593:cyanohydrin; D000446:Aldehyde-Lyases; C021541:mandelonitrile lyase