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

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Abstract
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. Biotechnol. Bioeng. 2007;96:835–843.