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

Biotechnology and Bioengineering

Volumn 93, Issue 6, 2006, Pages 1138-1144

  Hilker, Iris ^a,c   Baldwin, Chris ^b   Alphand, Véronique ^c   Furstoss, Roland ^c   Woodley, John ^b   Wohlgemuth, Roland ^a  

^a Fluka Group   (Switzerland)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c CNRS   (France)

Author keywords

Baeyer Villiger oxidation; Cyclohexanone monooxygenase; In situ SFPR; Oxygen transfer; Oxygenation; Whole cell biotransformation

Indexed keywords

CATALYSIS; CELLS; MATHEMATICAL MODELS; OPTIMIZATION; OXIDATION; SUBSTRATES;

BAEYER-VILLIGER OXIDATION; CYCLOHEXANONE MONOOXYGENASE; IN SITU SFPR; OXYGEN TRANSFER; OXYGENATION; WHOLE CELL BIOTRANSFORMATION;

OXYGEN;

ARTICLE; BAEYER VILLIGER REACTION; BIOCATALYST; BIOTRANSFORMATION; CELL DENSITY; CELL FUNCTION; CELL TRANSFORMATION; OXYGEN CONCENTRATION; OXYGEN CONSUMPTION;

BICYCLO COMPOUNDS, HETEROCYCLIC; BIOREACTORS; BIOTRANSFORMATION; CELL DIVISION; ESCHERICHIA COLI; FERMENTATION; KETONES; KINETICS; LACTONES; OXIDATION-REDUCTION; OXYGEN; OXYGENASES; PARTIAL PRESSURE;

EID: 33646022877     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.20829     Document Type: Article

References (30)

1. Alphand V, Furstoss R. 1992. Microbiological transformations 22. Microbiologically mediated Baeyer-Villiger reactions: A unique route to several bicyclic gamma-lactones in high enantiomeric purity. J Org Chem 57:1306-1309.
2. Alphand V, Archelas A, Furstoss R. 1989. Microbial transformations 16. One-step synthesis of a pivotal prostaglandin chiral synthon via a highly enantioselective microbiological Baeyer-Villiger type reaction. Tetrahedron Lett 30:3663-3664.
3. Alphand V, Carrea G, Wohlgemuth R, Furstoss R, Woodley JM. 2003. Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases. Trends Biotechnol 21(7):318-323.
4. Atkinson B, Mavituna F. 1991. Gas-liquid mass transfer and mixing. Biochemical engineering and biotechnology handbook, 2nd edition, New York: Stockton Press. pp 697-751.
5. Baeyer A, Villiger V. 1899. Einwirkung des caro'schen reagens auf ketone. Berichte der Deutschen Chemischen Gesellschaft 32:3625-3633.
6. Cheesman MJ, Kneller MB, Kelly EJ, Thompson SJ, Yeung CK, Eaton DL, Rettie AE. 2001. Purification and characterization of hexahistidine-tagged cyclohexanone monooxygenase expressed in Saccharomyces cerevisiae and Escherichia coli. Protein Expr Purif 21:81-86.
7. Chen YC, Peoples OP, Walsh CT. 1988. Acinetobacter cyclohexanone monooxygenase gene cloning and sequence determination. J Bacteriol 170:781-789.
8. Doig SD, O'Sullivan LM, Patel S, Ward JM, Woodley JM. 2001. Large scale production of cyclohexanone monooxygenase from Escherichia coli TOP10 pQR239. Enzyme Microb Technol 28:265-274.
9. Doig SD, Avenell PJ, Bird PA, Gallati P, Lander KS, Lye GL, Wohlgemuth R, Woodley JM. 2002. Reactor operation and scale-up of whole cell Baeyer-Villiger catalyzed lactone synthesis. Biotechnol Prog 18:1039-1046.
10. Hensirisak P, Prasukulsatid P, Agblevor FA, Cundiff JS, Velander W. 2002. Scale-up of a microbubble dispersion generator for aerobic fermentation. Appl Biochem Biotechnol 101:211-227.
11. Hilker I, Alphand V, Wohlgemuth R, Furstoss R. 2004. Microbial transformations 56. Preparative scale asymmetric Baeyer-Villiger oxidation using a highly productive two-in-one resin-based in situ SFPR concept. Adv Synth Catal 346:203-214.
12. Hilker I, Wohlgemuth R, Alphand V, Furstoss R. 2005. Microbial transformations 59. First kilogram scale asymmetric microbial Baeyer-Villiger oxidation with optimised productivity using a resin based in situ SFPR strategy. Biotechnol Bioeng 92:702-710.
13. Iwaki H, Hasegawa Y, Teraoka M, Tokuyama T, Bergeron H, Lau PCK. 1999. 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. Appl Environ Microbiol 65:5158-5162.
14. Kamerbeek NM, Janssen DB, van Berkel WJH, Fraaje MW. 2003. Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts. Adv Synth Catal 345:667-678.
15. Mihovilovic MD, Müller B, Stanetty P. 2002. Monooxygenase-mediated Baeyer-Villiger oxidations. Eur J Org Chem 22:3711-3730.
16. Murahashi SI, Ono S, Imada Y. 2002. Asymmetric Baeyer-Villiger reaction with hydrogen peroxide catalyzed by a novel planar chiral bisflavin. Angew Chem Int Ed 41(13):2366-2368.
17. Reuss M. 1993. Oxygen transfer and mixing: Scale-up implications. In: Rehm HJ, Reed G in cooperation with Pühler A, Stadler P, editors. Biotechnology, 2nd completely revised edition, Vol. 3. Stephanopoulos G, editor, Weinheim: Wiley-VCH. pp 185-217.
18. Roberts SM, Wan PWH. 1998. Enzyme-catalysed Baeyer-Villiger oxidations. J Mol Cat B 4(3):111-136.
19. Simpson HD, Alphand V, Furstoss R. 2001. Microbiological transformations 49. Asymmetric biocatalysed Baeyer-Villiger oxidation: Improvement using a recombinant Escherichia coli whole cell biocatalyst in the presence of an adsorbent resin. J Mol Cat B 16(2): 101-108.
20. Stark D, von Stockar U. 2003. In situ product removal (ISPR) in whole cell biotechnology during the last twenty years. Adv Biochem Eng Biotechnol. Series Editor: T Scheper 80:150-169.
21. Stewart JD. 1998. Cyclohexanone monooxygenase: A useful reagent for asymmetric Baeyer-Villiger reactions. Curr Org Chem 2:195-216.
22. Stewart JD, Reed KW, Kayser MM. 1996. 'Designer yeast': A new reagent for enantioselective Baeyer-Villiger oxidations. J Chem Soc Perkin Trans 1:755-757.
23. Stewart JD, Reed KW, Martinez CA, Zhu J, Chen G, Kayser MM. 1998. Recombinant baker's yeast as a whole-cell catalyst for asymmetric Baeyer-Villiger oxidations. J Am Chem Soc 120:3541-3548.
24. ten Brink G-J, Arends IWCE, Sheldon RA. 2004. The Baeyer-Villiger reaction: New Developments towards greener procedures. Chem Rev 104:4105-4123.
25. van Beilen JB, Duetz WA, Schmid A, Witholt B. 2003. Practical issues in the application of oxygenases. Trends Biotechnol 21(4):170-177.
26. Walton AZ, Stewart JD. 2002. An efficient enzymatic Baeyer-Villiger oxidation by engineered Escherichia coli cells under non-growing conditions. Biotechnol Progress 18:262-268.
27. Walton AZ, Stewart JD. 2004. Understanding and improving NADPH-dependent reactions by nongrowing Escherichia coli cells. Biotechnol Progress 20:403-411.
28. Watanabe A, Uchida T, Irie R, Katsuki T. 2004. Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: Stereospecific synthesis of abnormal and normal lactones. PNAS 101(16):5737-5742.
29. Willetts A. 1997. Structural studies and synthetic applications of Baeyer-Villiger monooxygenases. Trends Biotechnol 15:55-62.
30. Wise DL, Wang DIC, Matelles RI. 1969. Increased oxygen mass transfer rates from single bubbles in microbial systems at low Reynolds numbers. Biotechnol Bioeng 11:647-681.