Hydroxynitrile Lyase-Catalyzed Enzymatic Nitroaldol (Henry) Reaction

The hydroxynitrile lyase from Hevea brasiliensis not only catalyzes – according to the natural activity of this enzyme – the formation and cleavage of cyanohydrins but also the reaction of nitroalkanes with aldehydes (Henry reaction). This is the first example of an enzymatic nitroaldol reaction. Wi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2007-06, Vol.349 (8-9), p.1445-1450
Main Authors: Gruber-Khadjawi, Mandana, Purkarthofer, Thomas, Skranc, Wolfgang, Griengl, Herfried
Format: Article
Language:English
Subjects:
biotransformations
CC bond formation
Henry reaction
hydroxynitrile lyase
stereoselectivity
β-nitro alcohols
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Summary:The hydroxynitrile lyase from Hevea brasiliensis not only catalyzes – according to the natural activity of this enzyme – the formation and cleavage of cyanohydrins but also the reaction of nitroalkanes with aldehydes (Henry reaction). This is the first example of an enzymatic nitroaldol reaction. With nitromethane and nitroethane a broad range of aldehydes can be transformed into the corresponding nitro alcohols in yields up to 77 % and enantiomeric excess (ee) up to 99 %.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200700064