On the influence of oxygen and cell concentration in an SFPR whole cell biocatalytic Baeyer–Villiger oxidation process

Efficient whole cell biotransformations, in particular microbial whole cell Baeyer–Villiger oxidation with molecular oxygen, demand comprehension and optimization of the process details involved. Optimal provision of oxygen and control of bioprocess parameters are pivotal for their success. The interrelation of cell density and oxygen supply in an in situ substrate feeding and product removal (SFPR) whole cell Baeyer–Villiger oxidation process was investigated in detail. Both parameters were optimized with respect to practical considerations. The outcome of this study supports a schematic process model, allows estimation of optimum process conditions and exploration of its limits. © 2006 Wiley Periodicals, Inc.

[1]  M. Mihovilovic,et al.  Monooxygenase‐Mediated Baeyer−Villiger Oxidations , 2002 .

[2]  A. Rettie,et al.  Purification and characterization of hexahistidine-tagged cyclohexanone monooxygenase expressed in Saccharomyces cerevisiae and Escherichia coli. , 2001, Protein expression and purification.

[3]  C. Walsh,et al.  Acinetobacter cyclohexanone monooxygenase: gene cloning and sequence determination , 1988, Journal of bacteriology.

[4]  A. Willetts Structural studies and synthetic applications of Baeyer-Villiger monooxygenases. , 1997, Trends in biotechnology.

[5]  J. Stewart,et al.  An Efficient Enzymatic Baeyer–Villiger Oxidation by Engineered Escherichiacoli Cells under Non‐Growing Conditions , 2002, Biotechnology progress.

[6]  V. Alphand,et al.  Microbial transformations 59: first kilogram scale asymmetric microbial Baeyer-Villiger oxidation with optimized productivity using a resin-based in situ SFPR strategy. , 2005, Biotechnology and bioengineering.

[7]  A. Baeyer,et al.  Einwirkung des Caro'schen Reagens auf Ketone , 1899 .

[8]  T. Tokuyama,et al.  Identification of a Transcriptional Activator (ChnR) and a 6-Oxohexanoate Dehydrogenase (ChnE) in the Cyclohexanol Catabolic Pathway in Acinetobacter sp. Strain NCIMB 9871 and Localization of the Genes That Encode Them , 1999, Applied and Environmental Microbiology.

[9]  J. Woodley,et al.  Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases. , 2003, Trends in biotechnology.

[10]  Jon D. Stewart,et al.  Cyclohexanone Monooxygenase: A Useful Reagent for Asymmetric Baeyer-Villiger Reactions , 1998, Current Organic Chemistry.

[11]  R. Sheldon,et al.  The Baeyer-Villiger reaction: new developments toward greener procedures. , 2004, Chemical reviews.

[12]  H. D. Simpson,et al.  Microbiological transformations: 49. Asymmetric biocatalysed Baeyer–Villiger oxidation: improvement using a recombinant Escherichia coli whole cell biocatalyst in the presence of an adsorbent resin , 2001 .

[13]  F. Agblevor,et al.  Scale-up of microbubble dispersion generator for aerobic fermentation , 2002, Applied biochemistry and biotechnology.

[14]  D. Wise,et al.  Increased oxygen mass transfer rates from single bubbles in microbial systems at low reynolds numbers , 1969, Biotechnology and bioengineering.

[15]  J. Stewart,et al.  Recombinant Baker's Yeast as a Whole-Cell Catalyst for Asymmetric Baeyer−Villiger Oxidations , 1998 .

[16]  V. Alphand,et al.  Microbial Transformations 16. One-step synthesis of a pivotal prostaglandin chiral synthon via a highly enantioselective microbiological Baeyer-Villiger type reaction , 1989 .

[17]  Peter W. H. Wan,et al.  Enzyme-catalysed Baeyer–Villiger oxidations , 1998 .

[18]  V. Alphand,et al.  Microbiological transformations. 22. Microbiologically mediated Baeyer-Villiger reactions: a unique route to several bicyclic .gamma.-lactones in high enantiomeric purity , 1992 .

[19]  Andreas Schmid,et al.  Practical issues in the application of oxygenases. , 2003, Trends in biotechnology.

[20]  John M Woodley,et al.  Reactor Operation and Scale‐Up of Whole Cell Baeyer‐Villiger Catalyzed Lactone Synthesis , 2002, Biotechnology progress.

[21]  Urs von Stockar,et al.  In situ product removal (ISPR) in whole cell biotechnology during the last twenty years. , 2003, Advances in biochemical engineering/biotechnology.

[22]  V. Alphand,et al.  Microbial Transformations, 56. Preparative Scale Asymmetric Baeyer–Villiger Oxidation using a Highly Productive “Two‐in‐One” Resin‐Based in situ SFPR Concept , 2004 .

[23]  J. Stewart,et al.  ‘Designer yeast’: a new reagent for enantioselective Baeyer–Villiger oxidations , 1996 .

[24]  J. Woodley,et al.  Large scale production of cyclohexanone monooxygenase from Escherichia coli TOP10 pQR239. , 2001, Enzyme and microbial technology.

[25]  Marco W. Fraaije,et al.  Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts , 2003 .

[26]  Y. Imada,et al.  Asymmetric baeyer-villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin. , 2002, Angewandte Chemie.

[27]  J. Stewart,et al.  Understanding and Improving NADPH‐Dependent Reactions by Nongrowing Escherichia coli Cells , 2008, Biotechnology progress.

[28]  T. Uchida,et al.  Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: stereospecific synthesis of abnormal and normal lactones. , 2004, Proceedings of the National Academy of Sciences of the United States of America.