An enantioselective artificial metallo-hydratase

Direct addition of water to alkenes to generate important chiral alcohols as key motif in a variety of natural products still remains a challenge in organic chemistry. Here, we report the first enantioselective artificial metallo-hydratase, based on the transcription factor LmrR, which catalyses the...

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Veröffentlicht in:Chemical science (Cambridge) 2013-07, Vol.4 (9), p.3578-3582
Hauptverfasser: Bos, Jeffrey, Garcia-Herraiz, Ana, Roelfes, Gerard
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Sprache:eng
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Zusammenfassung:Direct addition of water to alkenes to generate important chiral alcohols as key motif in a variety of natural products still remains a challenge in organic chemistry. Here, we report the first enantioselective artificial metallo-hydratase, based on the transcription factor LmrR, which catalyses the conjugate addition of water to generate chiral beta -hydroxy ketones with enantioselectivities up to 84% ee. A mutagenesis study revealed that an aspartic acid and a phenylalanine located in the active site play a key role in achieving efficient catalysis and high enantioselectivities.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc51449h