Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 36, Pages 11415-11422Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800609
Keywords
cyanohydrins; enzyme catalysis; enzyme engineering; hydroxynitrile lyase; substrate engineering
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Funding
- FWF Austrian Science Fund [120-B03, 121-B03]
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Even if biocatalysis is finding increasing application. it still has to gain widespread use in synthetic chemistry. Reasons for this are limitations that enzymes have with regard to substrate range. reaction scope, and insufficient selectivity with unnatural compounds. These shortcomings can be challenged by enzyme and/or substrate engineering, which are employed to alter substrate specificity and enhance the enzyme selectivity toward unnatural Substrates. Herein. these two approaches are coupled to improve the hydroxynitrile lyase catalyzed synthesis of 2-hydroxy-(4'-oxocyclohexyl)aceto-nitrile (4). The ketone functionality is masked as an enol ether, and the oxy-nitrilase of Hevea brasiliensis is engineered towards this masked substrate to give the product with a high optical purity and to drastically lower the amount of enzyme needed.
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