Biocatalytic conversion of cycloalkanes to lactones using an in-vivo cascade in Pseudomonas taiwanensis VLB120

Biotechnology and Bioengineering

Volumn 115, Issue 2, 2018, Pages 312-320

  Karande, Rohan ^a   Salamanca, Diego ^a   Schmid, Andreas ^a   Buehler, Katja ^a  

^a HELMHOLTZ CENTRE FOR ENVIRONMENTAL RESEARCH UFZ   (Germany)

Author keywords

cycloalkanes; in vivo cascade; lactones; Pseudomonas; whole cell biocatalysis

Indexed keywords

BACTERIA; BIOCATALYSTS; CYCLOHEXANE; ENVIRONMENTAL MANAGEMENT; SYNTHESIS (CHEMICAL);

CYCLO-ALKANES; IN-VIVO; LACTONES; PSEUDOMONAS; WHOLE-CELL BIOCATALYSIS;

ESTERS;

CYCLOALKANE DERIVATIVE; CYCLODECANE; CYCLOHEXANE; CYCLOHEXANOL; CYCLOHEXANONE; CYCLOOCTANE; CYTOCHROME P450; GENOMIC DNA; LACTONE DERIVATIVE; OXIDOREDUCTASE; POLYCAPROLACTONE; UNSPECIFIC MONOOXYGENASE; CAPROLACTONE; HEXANOIC ACID DERIVATIVE; LACTONE; OXYGENASE;

ACIDOVORAX; ARTICLE; BIOCATALYSIS; BIOTRANSFORMATION; CELL DENSITY; CONTROLLED STUDY; ENZYME KINETICS; HOST; HYDROLYSIS; HYDROXYLATION; IN VIVO STUDY; MICHAELIS MENTEN KINETICS; NONHUMAN; OPERON; OXIDATION; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERASE CHAIN REACTION; PSEUDOMONAS; PSEUDOMONAS TAIWANENSIS VLB120; TURNOVER NUMBER; BIOREACTOR; METABOLISM; MICROBIOLOGY;

BIOCATALYSIS; BIOREACTORS; CAPROATES; CYCLOPARAFFINS; LACTONES; METABOLIC NETWORKS AND PATHWAYS; OXYGENASES; PSEUDOMONAS;

EID: 85041912765     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.26469     Document Type: Article

References (30)

1. Bayer, T., Milker, S., Wiesinger, T., Rudroff, F., & Mihovilovic, M. D. (2015). Designer microorganisms for optimized redox cascade reactions—Challenges and future perspectives. Advanced Synthesis & Catalysis, 357, 1587–1618.
2. Berezin, I. V., Denisov, E. T., & Emanuel, N. M. (1966). The oxidation of cyclohexane (p. 294). Oxford: Pergamon Press.
3. Bornadel, A., Hatti-Kaul, R., Hollmann, F., & Kara, S. (2016). Enhancing the productivity of the bi-enzymatic convergent cascade forϵ-caprolactone synthesis through design of experiments and a biphasic system. Tetrahedron, 72, 7222–7228.
4. Cornelissen, S., Liu, S., Deshmukh, A. T., Schmid, A., & Bühler, B. (2011). Cell physiology rather than enzyme kinetics can determine the efficiency of cytochrome P450-catalyzed C-H-oxyfunctionalization. Journal of Industrial Microbiology and Biotechnology, 38, 1359–1370.
5. de Carvalho, C. C. C. R. (2016). Whole cell biocatalysts: Essential workers from nature to the industry. Microbial Biotechnology, 10, 250–263.
6. Emmerling, M., Dauner, M., Ponti, A., Fiaux, J., Hochuli, M., Szyperski, T., & Sauer, U. (2002). Metabolic flux responses to pyruvate kinase knockout in Escherichia coli. Journal of Bacteriology, 184, 152–164.
7. Guengerich, F. P., Martin, M. V., Sohl, C. D., & Cheng, Q. (2009). Measurement of cytochrome P450 and NADPH-cytochrome P450 reductase. Nature Protocols, 4, 1245–1251.
8. 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-basedin situ SFPR concept. Advanced Synthesis & Catalysis, 346, 203–214.
9. Hilker, I., Wohlgemuth, R., Alphand, V., & Furstoss, R. (2005). Microbial transformations 59: First kilogram scale asymmetric microbial Baeyer-Villiger oxidation with optimized productivity using a resin-based in situ SFPR strategy. Biotechnology and Bioengineering, 92, 702–710.
10. Karande, R., Debor, L., Salamanca, D., Bogdahn, F., Engesser, K. H., Buehler, K., & Schmid, A. (2016). Continuous cyclohexane oxidation to cyclohexanol using a novel cytochrome P450 monooxygenase from Acidovorax sp. CHX100 in recombinant P. taiwanensis VLB120 biofilms. Biotechnology and Bioengineering, 113, 52–61.
11. Laemmli, U. K. (1970). Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680–685.
12. Mallin, H., Wulf, H., & Bornscheuer, U. T. (2013). A self-sufficient Baeyer-Villiger biocatalysis system for the synthesis of ϵ−caprolactone from cyclohexanol. Enzyme and Microbial Technology, 53, 283–287.
13. Muschiol, J., Peters, C., Oberleitner, N., & Mihovilovic, M. D. (2015). ChemComm Cascade catalysis—Strategies and challenges en route to preparative synthetic biology. Chemical Communications, 51, 5798–5811.
14. Oberleitner, N., Ressmann, A. K., Bica, K., Gärtner, P., Fraaije, M. W., Bornscheuer, U. T., … Mihovilovic, M. D. (2017). From waste to value—Direct utilization of limonene from orange peel in a biocatalytic cascade reaction towards chiral carvolactone. Green Chemistry, 19, 367–371.
15. Oberleitner, N., Peters, C., Muschiol, J., Kadow, M., Saß, S., Bayer, T., … Bornscheuer, U. T. (2013). An enzymatic toolbox for cascade reactions: A showcase for an in vivo redox sequence in asymmetric synthesis. ChemCatChem, 5, 3524–3528.
16. Oberleitner, N., Peters, C., Rudroff, F., Bornscheuer, U. T., & Mihovilovic, M. D. (2014). In vitro characterization of an enzymatic redox cascade composed of an alcohol dehydrogenase, an enoate reductases and a Baeyer-Villiger monooxygenase. Journal of Biotechnology, 192, 393–399.
17. Pennec, A., Hollmann, F., Smit, M. S., & Opperman, D. J. (2015). One-pot conversion of cycloalkanes to lactones. ChemCatChem, 7, 236–239.
18. Salamanca, D., & Engesser, K. H. (2014). Isolation and characterization of two novel strains capable of using cyclohexane as carbon source. Environmental Science and Pollution Research, 21, 12757–12766.
19. Sambrook, J., & Russell, D. W. (2001). Molecular cloning—A laboratory manual. New York, USA: Cold Spring Harbor Laboratory Press.
20. Sattler, J. H., Fuchs, M., Mutti, F. G., Grischek, B., Engel, P., Pfeffer, J., & Kroutil, W. (2014). Introducing an in situ capping strategy in systems biocatalysis to access 6-aminohexanoic acid. Angewandte Chemie International Edition, 53, 14153–14157.
21. Scherkus, C., Schmidt, S., Bornscheuer, U. T., Gröger, H., Kara, S., & Liese, A. (2017). Kinetic insights into e-caprolactone synthesis: Improvement of an enzymatic cascade reaction. Biotechnology and Bioengineering, 114, 1215–1221.
22. Scherkus, C., Schmidt, S., Bornscheuer, U. T., Gröger, H., Kara, S., & Liese, A. (2016). A fed-batch synthetic strategy for a three-step enzymatic synthesis of poly-ε-caprolactone. ChemCatChem, 8, 3446–3452.
23. Schmidt, S., Scherkus, C., Muschiol, J., Menyes, U., Winkler, T., Hummel, W., & Bornscheuer, U. T. (2015). An enzyme cascade synthesis of ϵ-caprolactone and its oligomers. Angewandte Chemie International Edition, 54, 2784–2787.
24. Schrewe, M., Julsing, M. K., Bühler, B., & Schmid, A. (2013). Whole-cell biocatalysis for selective and productive C-O functional group introduction and modification. Chemical Society Reviews, 42, 6346–6377.
25. Schrittwieser, J. H., Velikogne, S., & Kroutil, W. (2017). Artificial biocatalytic linear cascades for preparation of organic molecules. Chemical Reviews Article ASAP, http://doi.org/10.1021/acs.chemrev.7b00033
26. Schuchardt, U., Carvalho, W., & Spinace, E. (1992). Why is it interesting to study cyclohexane oxidation. SYNLETT, 10, 713–718.
27. Schuchardt, U., Cardoso, D., Sercheli, R., Pereira, R., Da Cruz, R. S., Guerreiro, M. C., & Pires, E. L. (2001). Cyclohexane oxidation continues to be a challenge. Applied Catalysis A: General, 211, 1–17.
28. Staudt, S., Bornscheuer, U. T., Menyes, U., Hummel, W., & Gröger, H. (2013). Direct biocatalytic one-pot-transformation of cyclohexanol with molecular oxygen into ϵ-caprolactone. Enzyme and Microbial Technology, 53, 288–292.
29. Volmer, J., Neumann, C., Bühler, B., & Schmid, A. (2014). Engineering of Pseudomonas taiwanensis VLB120 for constitutive solvent tolerance and increased specific styrene epoxidation activity. Applied and Environmental Microbiology, 80, 6539–6548.
30. Weissermel, K., & Arpe, H.-J. (2003). Components for polyamides. Indian Organic Chemistry (pp. 239–266). Weinheim: Wiley-VCH Verlag GmbH.