In vitro characterization of an enzymatic redox cascade composed of an alcohol dehydrogenase, an enoate reductases and a Baeyer-Villiger monooxygenase

Journal of Biotechnology

Volumn 192, Issue , 2014, Pages 393-399

  Oberleitner, Nikolin ^a   Peters, Christin ^b   Rudroff, Florian ^a   Bornscheuer, Uwe T ^b   Mihovilovic, Marko D ^a  

^a VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^b UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Alcohol dehydrogenase; Baeyer Villiger monooxygenase; Biorenewable polyesters; Enoate reductase; Multi step biocatalysis

Indexed keywords

BIOCATALYSTS; CATALYSIS; ENZYMES; POLYESTERS;

ALCOHOL DEHYDROGENASE; BAEYER-VILLIGER MONOOXYGENASES; BIOCATALYSIS; BIORENEWABLE; ENOATE REDUCTASE;

ENZYME ACTIVITY;

ALCOHOL DEHYDROGENASE; OXIDOREDUCTASE; POLYESTER; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; CYCLOHEXANOL DERIVATIVE; MIXED FUNCTION OXIDASE; RECOMBINANT PROTEIN;

ARTICLE; BAEYER VILLIGER REACTION; BIOCATALYSIS; BIOCATALYST; CHIRALITY; ENZYME MECHANISM; ENZYME SUBSTRATE COMPLEX; IN VITRO STUDY; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS; CHEMISTRY; ESCHERICHIA COLI; GENETICS; METABOLISM;

ALCOHOL DEHYDROGENASE; CYCLOHEXANOLS; ESCHERICHIA COLI; MIXED FUNCTION OXYGENASES; OXIDOREDUCTASES; RECOMBINANT PROTEINS;

EID: 84925368917     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2014.04.008     Document Type: Article

References (20)

1. Bertani G. Studies on lysogenesis. I. The mode of phage liberation by lysogenic Escherichia coli. J. Bacteriol. 1951, 62:293-300.
2. Chen G., Kayser M.M., Mihovilovic M.D., Mrstik M.E., Martinez C.A., Stewart J.D. Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase. New J. Chem. 1999, 23:827-832. 10.1039/a902283j.
3. Chung C.T., Niemela S.L., Miller R.H. One-step preparation of competent Escherichia coli: transformation and storage of bacterial cells in the same solution. Proc. Natl. Acad. Sci 1989, 86:2172-2175.
4. Donoghue N.A., Norris D.B., Trudgill P.W. The purification and properties of cyclohexanone oxygenase from nocardia globerula CL1 and acinetobacter NCIB 9871. Eur. J. Biochem. 1976, 63:175-192. 10.1111/j.1432-1033.1976.tb10220.x.
5. Jankowski M.D., Henry C.S., Broadbelt L.J., Hatzimanikatis V. Group contribution method for thermodynamic analysis of complex metabolic networks. Biophys. J. 2008, 95:1487-1499. 10.1529/biophysj.107.124784.
6. Lopez-Gallego F., Schmidt-Dannert C. Multi-enzymatic synthesis. Curr. Opin. Chem. Biol. 2010, 14:174-183. 10.1016/j.cbpa.2009.11.023.
7. Lowe J.R., Martello M.T., Tolman W.B., Hillmyer M.A. Functional biorenewable polyesters from carvone-derived lactones. Polym. Chem. 2011, 2:702-708. 10.1039/C0py00283f.
8. Mavrovouniotis M.L. Group contributions for estimating standard gibbs energies of formation of biochemical-compounds in aqueous-solution. Biotechnol. Bioeng. 1990, 36:1070-1082. 10.1002/bit.260361013.
9. Mavrovouniotis M.L. Estimation of standard gibbs energy changes of biotransformations. J. Biol. Chem. 1991, 266:14440-14445.
10. Meyer A., Pellaux R., Panke S. Bioengineering novel in vitro metabolic pathways using synthetic biology. Curr. Opin.Microbiol. 2007, 10:246-253. 10.1016/j.mib.2007.05.009.
11. Mueller N.J., Stueckler C., Hauer B., Baudendistel N., Housden H., Bruce N.C., Faber K. The substrate spectra of pentaerythritol tetranitrate reductase, morphinone reductase, N-ethylmaleimide reductase and estrogen-binding protein in the asymmetric bioreduction of activated alkenes. Adv.Synth. Catal. 2010, 352:387-394. 10.1002/adsc.200900832.
12. Oberleitner N., Peters C., Muschiol J., Kadow M., Saß S., Bayer T., Schaaf P., Iqbal N., Rudroff F., Mihovilovic M.D., Bornscheuer U.T. An enzymatic toolbox for cascade reactions: a showcase for an in vivo redox sequence in asymmetric synthesis. ChemCatChem 2013, 3524-3528. 10.1002/cctc.201300604.
13. Padhi S.K., Bougioukou D.J., Stewart J.D. Site-saturation mutagenesis of tryptophan 116 of saccharomyces pastorianus old yellow enzyme uncovers stereocomplementary variants. J. Am. Chem. Soc. 2009, 131:3271-3280. 10.1021/ja8081389.
14. Ricca E., Brucher B., Schrittwieser J.H. Multi-enzymatic cascade reactions: overview and perspectives. Adv. Synth. Catal. 2011, 353:2239-2262. 10.1002/adsc.201100256.
15. Stampfer W., Kosjek B., Kroutil W., Faber K. Purification and Characterization of a Secondary Alcohol Dehydrogenase ADH-A With High Solvent and Temperature Stability from Rhodococcus ruber 2003, 56 pp. CIBA Specialty Chemicals Holding Inc. (Ed.).
16. Terrific Broth Cold Spring Harbor Protocols 2006, pdb.rec8620. 10.1101/pdb.rec8620.
17. Turner N.J., O'Reilly E. Biocatalytic retrosynthesis. Nat. Chem. Biol. 2013, 9:285-288. 10.1038/nchembio.1235.
18. Warren S., Wyatt P. Organic Synthesis. The Disconnection Approach 2008, Wiley-VCH, Weinheim.
19. Weckbecker A., Hummel W. Cloning, expression, and characterization of an (R)-specific alcohol dehydrogenase from Lactobacillus kefir. Biocatal. Biotransform. 2006, 24:380-389.
20. Wohlgemuth R. Asymmetric biocatalysis with microbial enzymes and cells. Curr. Opin. Microbiol. 2010, 13:283-292. 10.1016/j.mib.2010.04.001.