125850-28-4Relevant articles and documents
Deracemization of (±)-cis-2,3-epoxyheptane via enantioconvergent biocatalytic hydrolysis using Nocardia EH1-epoxide hydrolase
Kroutil, Wolfgang,Mischitz, Martin,Plachota, Peter,Faber, Kurt
, p. 8379 - 8382 (1996)
Biocatalytic hydrolysis of (±)-cis-2,3-epoxyheptane using lyophilized bacterial cells of Nocardia EH1 gave (2R,3R)-heptane-2,3-dil as the sole product in 79% yield and 91% e.e. at 100% conversion. The pathway of this deracemization was elucidated by 18OH2-labelling experiments using a partially purified epoxide hydrolase preparation and was shown to proceed in an enantioconvergent manner. Thus both substrate enantiomers were hydrolyzed via attack of [OH-] at the respective (S)-configurated C-atom with concomitant inversion of configuration.
Enzyme-catalysed regio- and enantioselective preparative scale synthesis of (S)-2-hydroxy alkanones
Loderer,Ansorge-Schumacher
, p. 38271 - 38276 (2015/05/13)
α-Hydroxy alkanones were synthesised with high enantiomeric purity by stereoselective enzyme-catalysed diketone reduction. Both diketone reduction and cofactor regeneration were accomplished with purified carbonyl reductase from Candida parapsilosis (CPCR2). The reaction products were isolated by column chromatography and analysed by chiral GC measurements, 1H-NMR spectroscopy and determination of optical rotations. Preparative-scale biotransformations yielded 350-600 mg of pure aliphatic α-hydroxy ketones including the difficult to obtain (S)-2-hydroxypentane-3-one. For all the products good enantiomeric excesses in the range of 89-93% were achieved.
Regio- and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer
Edegger, Klaus,Stampfer, Wolfgang,Seisser, Birgit,Faber, Kurt,Mayer, Sandra F.,Oehrlein, Reinhold,Hafner, Andreas,Kroutil, Wolfgang
, p. 1904 - 1909 (2007/10/03)
The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-'A'. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.