The analysis and application of a recombinant monooxygenase library as a biocatalyst for the Baeyer-Villiger reaction

Journal of Microbiology and Biotechnology

Volumn 17, Issue 7, 2007, Pages 1083-1089

  Park, Jiyeoun ^a,b   Kim, Donghyun ^a   Kim, Sujin ^a   Kim, Jinhee ^a   Bae, Kihwan ^b   Lee, Choonghwan ^a,c  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Chungnam National University   (South Korea)

^c Konkuk University   (South Korea)

Author keywords

Baeyer Villiger oxidation; Biocatalysis; GC MS; Monooxygenase; Sulfide oxidation

Indexed keywords

2 OXABICYCLO[3.3.0]OCT 6 EN 2 ONE; 3 OXABICYCLO[3.3.0]OCT 6 EN 2 ONE; BICYCLO[3.2.0]HEPT 2 EN 6 ONE; OXIDOREDUCTASE; RECOMBINANT ENZYME; SULFOXIDE; THIOANISOLE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

AMINO ACID SEQUENCE; ARTICLE; BAEYER VILLIGER REACTION; BIOCATALYST; BIOTECHNOLOGICAL PRODUCTION; CHEMICAL REACTION; ENZYME ASSAY; ENZYME MECHANISM; ESCHERICHIA COLI; GAS CHROMATOGRAPHY; GENETIC DATABASE; MASS SPECTROMETRY; MICROBIAL GENETICS; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTEIN MOTIF; PSEUDOMONAS AERUGINOSA; STREPTOMYCES COELICOLOR; SULFOXIDATION;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CLONING, MOLECULAR; DATABASES, GENETIC; ESCHERICHIA COLI; GENE LIBRARY; GENOME, BACTERIAL; KINETICS; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; PSEUDOMONAS AERUGINOSA; RECOMBINANT PROTEINS; REPRODUCIBILITY OF RESULTS; SEQUENCE HOMOLOGY, AMINO ACID; STREPTOMYCES COELICOLOR; SUBSTRATE SPECIFICITY; SULFIDES; TEMPERATURE;

ESCHERICHIA COLI; PSEUDOMONAS AERUGINOSA; STREPTOMYCES COELICOLOR;

EID: 34547972034     PISSN: 10177825     EISSN: 17388872     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Baeyer, A. and V. Villiger. 1899. Eniwirkung des caro'schen Reagens auf Ketone. Ber. Dtsch. Chem. Ges. 32: 3625-3633.
2. Beecher, J., P. Richardson, and A. Willetts. 1994. Baeyer-Villiger monooxygenase dependent biotransformations: Stereospecific heteroatom oxidations by camphor-grown Pseudomonas putida to produce chiral sulfoxides. Biotechnol. Lett. 16: 909-912.
3. Baldwin, C. V. and J. M. Woodley. 2006. On oxygen limitation in a whole cell biocatalytic Baeyer-Villiger oxidation process. Biotechnol. Bioeng. 95: 362-369.
4. Carrea, G., B. Redigolo, S. Riva, N. Colonna, E. Gaggero, D. Battistel, and D. Bianchi. 1992. Effects of substrate structure on the enantioselectivity and stereochemical course of sulfoxidation catalyzed by cyclohexanone monooxygenase. Tetrahedron: Asymmetry 3: 1063-1068.
5. Carrea, G. and S. Riva. 2000. Properties and synthetic applications of enzymes in organic solvents. Angew. Chem. Int. Ed. Engl. 39: 2226-2254.
6. Chen, Y. C., O. P. Peoples, and C. T. Walsh. 1988. Acinetobacter cyclohexanone monooxyganase: Gene cloning and sequence determination. J. Bacteriol. 170: 781-789.
7. Choi, J. H., T. K. Kim, Y. M. Kim, W. C. Kim, K. B. Park, and I. K. Rhee. 2006. Cloning and characterization of a gene cluster for cyclohexanone oxidation in Rhodococcus sp. TK6. J. Microbiol. Biotechnol. 16: 511-518.
8. Donoghue, N. et al. 1976. The purification and properties of cyclohexanone oxygenase from Nocardia globurela CL1 and Acinetobacter NCIB 9871. Eur. J. Biochem. 63: 175-192.
9. Fraaije, M. W. and N. M. Kamerbeek. 2002. Identification of a Baeyer-Villiger monooxygenase sequence motif. FEBS Lett. 518: 43-47.
10. Fraaije, M. W., J. Wu, D. P. H. M. Heuts, E. W. van Hellemond, J. H. L. Spelberg, and D. B. Janssen. 2005. Discovery of a thermostable Baeyer-Villiger monooxygenase by genome mining. Appl. Microbiol. Biotechnol. 66: 393-400.
11. Han, N. S., Y. S. Jung, H. J. Eom, Y. H. Koh, J. F. Robyt, and J. H. Seo. 2002. Simultaneous biocatalytic synthesis of panose during lactate fermentation in Kimchi. J. Microbiol. Biotechnol. 12: 46-52.
12. Iwaki, N., Y. Hasegawa, S. Wang, M. M. Kayser, and P. C. K. Lau. 2002. Cloning and characterization of a gene cluster involved in cyclopentanol metabolism in Comamonas sp. strain NCIMB 9872 and biotransformations effected by Escherichia coli expressed cyclopentanone 1,2-monooxygenase. Appl. Environ. Microbiol. 68: 5671-5684.
13. Kamerbeek, N. M., D. E. Janssen, W. J. H. van Berkel, and M. W. Fraije. 2003. Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts. Adv. Synth. Catal. 345: 667-678.
14. Kamerbeek, N. M., M. J. Moonen, J. G. Van Der Ven, W. J. H. Van Berkel, M. W. Fraaije, and D. B. Janssen. 2001. 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB. A novel flavoprotein catalyzing Baeyer-villiger oxidation of aromatic compounds. Eur. J. Biochem. 268: 2547-2557.
15. Kayser, M. M. and C. M. Clouthier. 2006. New bioorganic reagents: Evolved cyclohexanone monooxygenase - why is it more selective? J. Org. Chem. 71: 8424-8430.
16. Kelly, D. R., C. J. Knowles, J. G. Mahdi, I. N. Taylor, and M. A. Wright. 1996. Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S, 5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane. Tetrahedron Asymmetry 6: 365-368.
17. Kostichka, K., S. M. Thomas, K. J. Gibson, V. Nagarajan, and Q. Cheng. 2001. Cloning and characterization of a gene cluster for cyclododecanone oxidation in Rhodococcus rubber CS1. J. Bacteriol. 183: 6478-6486.
18. Lee, C. Y., K. H. Kim, S. Y. Hur, J. H. Heo, M. H. Choi, S. K. Rhee, and C. H. Kim. 2006. Enzymatic synthesis of ascorbic acid fructoside by transfructosylation using levan fructotransferase. J. Microbiol. Biotechnol. 16: 64-67.
19. Mihovilovic, M. D., F. Rudroff, B. Muller, and P. Stanetty. 2003. First enantiodivergent Baeyer-Villiger oxidation by recombinant whole-cells expressing two monooxygenases from Brevibacterium. Bioorg. Med. Chem. Lett. 13: 1479-1482.
20. Mihovilovic, M. D., B. Muller, and P. Stanetty. 2002. Monooxygenase-mediated Baeyer-Villiger oxidations. Eur. J. Org. Chem. 2002: 3711-3730.
21. Morii, S., S. Sawamoto, Y. Yamauchi, M. Miyamoto, M. Iwami, and E. Itagaki. 1999. Steroid monooxygenase of Rhodococcus rhodochrous: Sequencing of the genomic DNA, and hyperexpression, purification, and characterization of the recombinant enzyme. J. Biochem. 126: 624-631.
22. Panke, S., V. deLorenzo, A. Kaiser, B. Witholt, and M. G. Wubbolts. 1999. Engineering a stable whole cell biocatalyst capable of (S)-styrene oxide formation for continuous two-liquid phase applications. Appl. Environ. Microbiol. 65: 5619-5623.
23. Roberts, S. M. and P. W. H. Wan. 1998. Enzyme-catalysed Baeyer-Villiger oxidations. J. Mol. Cat. B Enzym. 4: 111-136.
24. Schmid, A. et al. 2001. Industrial biocatalysis today and tomorrow. Nature 409: 258-268.
25. Shin, S. Y. and J. H. Park. 1997. Activities of oxidative enzymes related with oxygen tolerance in Bifidobacterium sp. 7: 356-359.
26. Stewart, J. D. 1998. Cyclohexanone monooxygenase: A useful reagent for asymmetric Baeyer-Villiger reactions. Curr. Org. Chem. 2: 195-216.
27. Van der Werf M. J. and A. M. Boot. 2000. Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14. Microbiology 146: 1129-1141.
28. Wilkinson, B. and B. O. Bachmann. 2006. Biocatalysis in pharmaceutical preparation and alteration. Curr. Opin. Chem. Biol. 10: 169-176.
29. Willetts, A. 1997. Structural studies and synthetic applications of Baeyer-Villiger monooxygenases. TIBTECH 15: 55-62.
30. Wubbolts, M. G., O. Favre-Bulle, and B. Witholt. 1996. Biosynthesis of synthons in two liquid phase media. Biotechnol. Bioeng. 52: 301-308.
31. Yabe, K., N. Chihaya, S. Hamamatsu, E. Sakuno, T. Hamasaki, H. Nakajima, and J. W. Bennett. 2003. Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis. Appl. Environ. Microbiol. 69: 66-73.
32. Yoon, B. D., H. S. Kim, T. J. Kwon, J. W. Yang, G. S. Kwon, H. S. Lee, J. S. Ahn, and T. I. Mheen. 1992. Biocatalytic production of aldehyde by a methanol utilizing yeast, Hansemula nonfermentans KYP-1 grown in methanol-limited continuous culture. J. Microbiol. Biotechnol. 2: 278-283.
33. Zambianchi, F., P. Pasta, G. Carrea, S. Colonna, N. Gaggero, and J. M. Woodley. 2002. Use of isolated cyclohexanone monooxygenase from recombinant Escherichia coli as a biocatalyst for Baeyer-Villiger and sulfide oxidations. Biotechnol. Bioeng. 78: 489-496.