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Publisher DOI: 10.1039/C4CY00171K
Title: Reversibility of asymmetric catalyzed C-C bond formation by benzoylformate decarboxylase
Language: English
Authors: Berheide, Marco 
Kara, Selin 
Liese, Andreas  
Issue Date: 3-Feb-2015
Publisher: Royal Society of Chemistry (RSC)
Source: Catalysis Science & Technology (5): 2418-2426 (2015)
Journal or Series Name: Catalysis science & technology 
Abstract (english): Benzoylformate decarboxylase (BFD) from Pseudomonas putida catalyzed the formation of 2-hydroxy-1-phenylpropanone (2-HPP), a 2-hydroxy ketone, from the kinetic resolution of rac-benzoin in the presence of acetaldehyde. The formation rate of 2-HPP via kinetic resolution of benzoin was 700-fold lower compared to the formation via direct carboligation of benzaldehyde and acetaldehyde. Further investigations revealed that BFD not only accepts (R)-benzoin but also 2-HPP as the substrate. A typical Michaelis–Menten type kinetics was observed starting from enantiopure (S)- or (R)-2-HPP. The formation of racemic 2-HPP while using benzoin as the donor in the presence of acetaldehyde and the racemization of (R/S)-2-HPP were detected. The equilibrium constant determined, showed favoured conditions towards the product side i.e. (R)-benzoin and 2-HPP. In the end, an extended reaction mechanism was proposed by supplementing the already known mechanism with the C-C bond cleavage activity of BFD towards 2-hydroxy ketones.
DOI: 10.15480/882.2238
ISSN: 2044-4761
Institute: Technische Biokatalyse V-6 
Type: (wissenschaftlicher) Artikel
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