engleski

The production of (R)-2-hydroxy-1-phenyl-propan-1-one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor

Benzaldehyde lyase (BAL ; E.C. 4.1.2.38) from Pseudomonas fluorescens Biovar I catalyzes the reversible formation of benzoins from aromatic aldehydes, and, moreover, the coupling of aromatic with aliphatic aldehydes yielding derivatives of (R)-2-hydroxy-1-phenyl-propan-1-one ((R)-HPPs), which are important chiral building blocks. In this paper we report on the development of a reactor system that allows the selective production of substituted (R)-HPPderivatives. The reaction systems yielding (R)-1-(3-chloro-phenyl)-2-hydroxy-propan-1-one, (R)-2-hydroxy-3- methoxy-1-(4-methoxy-phenyl)-propan-1-one and (R)-2-hydroxy-3, 3-dimethoxy-1-phenyl-propan-1-one were investigated. A kinetic model optimized by batch experiments was developed, for the description of both batch and continuously operated reactors. This model was used to describe the HPP production in a continuously operated enzyme membrane reactor. The reactor type used combines the advantages of high conversion and excellent selectivity with high space-time yields and total turnover numbers of up to ttn = 43000. Products were obtained in high yield on a gram scale.

carboligation; enzyme membrane reactor; enantioselective; C-C-coupling; enzyme kinetics

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