TY  - JOUR
AU  - Kulig, J.
AU  - Simon, R.C.
AU  - Rose, C.A.
AU  - Husain, S.M.
AU  - Häckh, M.
AU  - Lüdeke, S.
AU  - Zeitler, K.
AU  - Kroutil, W.
AU  - Pohl, M.
AU  - Rother, D.
TI  - Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases
JO  - Catalysis Science & Technology
VL  - 2
SN  - 2044-4753
M1  - PreJuSER-20493
SP  - 1580 - 1589
PY  - 2012
N1  - 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.
AB  - 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.
KW  - J (WoSType)
LB  - PUB:(DE-HGF)16
UR  - <Go to ISI:>//WOS:000306229800011
DO  - DOI:10.1039/c2cy20120h
UR  - https://juser.fz-juelich.de/record/20493
ER  -