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The production of ( R )‐2‐hydroxy‐1‐phenyl‐propan‐1‐one derivatives by benzaldehyde lyase from Pseudomonas fluorescens in a continuously operated membrane reactor
Author(s) -
Hildebrand Falk,
Kühl Sven,
Pohl Martina,
VasicRacki Durda,
Müller Michael,
Wandrey Christian,
Lütz Stephan
Publication year - 2006
Publication title -
biotechnology and bioengineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.136
H-Index - 189
eISSN - 1097-0290
pISSN - 0006-3592
DOI - 10.1002/bit.21189
Subject(s) - pseudomonas fluorescens , benzaldehyde , membrane reactor , chemistry , yield (engineering) , batch reactor , selectivity , organic chemistry , catalysis , bacteria , materials science , genetics , metallurgy , biology
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. © 2006 Wiley Periodicals, Inc.