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)-HPP-derivatives. 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=43,000. Products were obtained in high yield on a gram scale.
Hildebrand
Falk
F
Institute of Biotechnology, Research Centre Jülich, D-52425 Jülich, Germany.
Kühl
Sven
S
Pohl
Martina
M
Vasic-Racki
Durda
D
Müller
Michael
M
Wandrey
Christian
C
Lütz
Stephan
S
D000096:Acetone / Q000031:analogs & derivatives* / Q000378:metabolism*; D000446:Aldehyde-Lyases / Q000378:metabolism*; D019149:Bioreactors / Q000382:microbiology; D008566:Membranes / Q000378:metabolism* / Q000382:microbiology; D011551:Pseudomonas fluorescens / Q000201:enzymology* / Q000378:metabolism
D000096:Acetone; D000446:Aldehyde-Lyases; C059416:benzaldehyde lyase