Journal Article PreJuSER-20493

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Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases

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2012

Catalysis Science & Technology 2, 1580 - 1589 () [10.1039/c2cy20120h]

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Abstract: Although biotransformations implementing alcohol dehydrogenases (ADHs) are widespread, enzymes which catalyse the reduction and oxidation of sterically demanding substrates, especially 2-hydroxy ketones, are still rare. To fill this gap eight ADHs were investigated concerning their potential to reduce bulky 2-hydroxy ketones. All of these enzymes showed good activities along with excellent enantio( ee > 99%) and diastereoselectivities (de > 99%). Due to their differences in substrate preferences and stereoselectivity a broad range of diastereomerically pure 1,2-diols is now accessible via biotransformation. Best results were obtained using the alcohol dehydrogenase from Ralstonia sp. (Cupriavidus sp.) (RADH), which showed a broad substrate range, especially for sterically demanding compounds. Araliphatic 2-hydroxy ketones, like (R)-2-hydroxy-1-phenylpropan-1-one ((R)-2-HPP), were reduced much faster than aliphatic or aromatic aldehydes (e. g. benzaldehyde) under the applied conditions. Additionally (R)-as well as (S)-2-hydroxy ketones were converted with high diastereoselectivities (de > 99%). RADH, which was up to now only studied as a whole cell biocatalyst overexpressed in E. coli, was purified and thoroughly characterised concerning its catalytic properties.

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Note: This work was financed by the Marie Curie Initial Training Network "BIOTRAINS-a European biotechnology training network for the support of chemical manufacturing'', grant agreement no. 238531, and partially financed by the DFG (German Research Foundation) in frame of the Research Group FOR 1296.

Contributing Institute(s):
  1. Biotechnologie 2 (IBT-2)
Research Program(s):
  1. Biotechnologie (PBT)
  2. BIOTRAINS - A EUROPEAN BIOTECHNOLOGY TRAINING NETWORK FOR THE SUPPORT OF CHEMICAL MANUFACTURING (238531) (238531)

Appears in the scientific report 2012
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Current Contents - Social and Behavioral Sciences ; JCR ; Science Citation Index Expanded ; Thomson Reuters Master Journal List ; Web of Science Core Collection
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 Record created 2012-11-13, last modified 2019-06-25



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