116297-02-0Relevant articles and documents
Assessing the stereoselectivity of: Serratia marcescens CECT 977 2,3-butanediol dehydrogenase
Médici, Rosario,Stammes, Hanna,Kwakernaak, Stender,Otten, Linda G.,Hanefeld, Ulf
, p. 1831 - 1837 (2017/07/15)
α-Hydroxy ketones and vicinal diols constitute well-known building blocks in organic synthesis. Here we describe one enzyme that enables the enantioselective synthesis of both building blocks starting from diketones. The enzyme 2,3-butanediol dehydrogenase (BudC) from S. marcescens CECT 977 belongs to the NADH-dependent metal-independent short-chain dehydrogenases/reductases family (SDR) and catalyses the selective asymmetric reductions of prochiral α-diketones to the corresponding α-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions.
Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
Vetere, Virginia,Faraoni, María B.,Podestá, Julio C.,Casella, Mónica L.
, p. 209 - 214 (2013/02/23)
In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (-)-menthyl group: (-)-Pt-MenSnBu 3 and (-)-Men3Sn-Sn-(-)-Men3. The organotin chiral modifiers were carefully synthesized and characterized in order to obtain optically pure compounds. The catalysts were prepared through a controlled surface reaction between the supported transition metal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25-27% for 4-hydroxy-3-hexanone.
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.
