Enzymatic formation and esterification of (S)-mandelonitrile |
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Authors: | Ulf Hanefeld Adrie J J Straathof and Joseph J Heijnen |
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Institution: | Kluyver Laboratory for Biotechnology, Delft University of Technology, Julianalaan 67, 2628 BC Delft, Netherlands |
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Abstract: | The (S)-selective hydroxynitrile lyase from Hevea brasiliensis (HbHNL) catalyzes the trans-cyanohydrin reaction (transcyanation). The equilibrium of this two-step reaction sequence is not favorable unless a large excess of acetone cyanohydrin (1) is used. Therefore, the coupling of this reaction with a follow-up reaction was investigated. It was established that the trans-cyanohydrin reaction could be performed in organic media, making it possible to couple it with a lipase-catalyzed acylation. Candida antarctica lipase B (CAL-B) shows a high selectivity (E=100) for (S)-mandelonitrile (4) and is, therefore, the ideal candidate for this type of multi-step one-pot reaction. |
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Keywords: | Hydroxynitrile lyase Oxynitrilase Hevea brasiliensis Candida antarctica lipase B Trans-cyanohydrin reaction Transcyanation (S)-Cyanohydrin |
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