A whole cell biocatalyst for double oxidation of cyclooctane
Müller CA, Weingartner AM, Dennig A, Ruff AJ, Gröger H, Schwaneberg U (2016)
Journal of Industrial Microbiology & Biotechnology 43(12): 1641-1646.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Müller, C. A.;
Weingartner, A. M.;
Dennig, A.;
Ruff, A. J.;
Gröger, HaraldUniBi;
Schwaneberg, Ulrich
Abstract / Bemerkung
A novel whole cell cascade for double oxidation of cyclooctane to cyclooctanone was developed. The one-pot oxidation cascade requires only a minimum of reaction components: resting E. coli cells in aqueous buffered medium (=catalyst), the target substrate and oxygen as environmental friendly oxidant. Conversion of cyclooctane was catalysed with high efficiency (50% yield) and excellent selectivity (>94%) to cyclooctanone. The reported oxidation cascade represents a novel whole cell system for double oxidation of non-activated alkanes including an integrated cofactor regeneration. Notably, two alcohol dehydrogenases from Lactobacillus brevis and from Rhodococcus erythropolis with opposite cofactor selectivities and one monooxygenase P450 BM3 were produced in a coexpression system in one single host. The system represents the most efficient route with a TTN of up to 24363 being a promising process in terms of sustainability as well.
Stichworte
Alkanes;
Directed evolution;
Oxidation;
Oxidoreductases;
Cascade reaction;
Monooxygenase
Erscheinungsjahr
2016
Zeitschriftentitel
Journal of Industrial Microbiology & Biotechnology
Band
43
Ausgabe
12
Seite(n)
1641-1646
ISSN
1367-5435, 1476-5535
Page URI
https://pub.uni-bielefeld.de/record/2907316
Zitieren
Müller CA, Weingartner AM, Dennig A, Ruff AJ, Gröger H, Schwaneberg U. A whole cell biocatalyst for double oxidation of cyclooctane. Journal of Industrial Microbiology & Biotechnology. 2016;43(12):1641-1646.
Müller, C. A., Weingartner, A. M., Dennig, A., Ruff, A. J., Gröger, H., & Schwaneberg, U. (2016). A whole cell biocatalyst for double oxidation of cyclooctane. Journal of Industrial Microbiology & Biotechnology, 43(12), 1641-1646. doi:10.1007/s10295-016-1844-5
Müller, C. A., Weingartner, A. M., Dennig, A., Ruff, A. J., Gröger, Harald, and Schwaneberg, Ulrich. 2016. “A whole cell biocatalyst for double oxidation of cyclooctane”. Journal of Industrial Microbiology & Biotechnology 43 (12): 1641-1646.
Müller, C. A., Weingartner, A. M., Dennig, A., Ruff, A. J., Gröger, H., and Schwaneberg, U. (2016). A whole cell biocatalyst for double oxidation of cyclooctane. Journal of Industrial Microbiology & Biotechnology 43, 1641-1646.
Müller, C.A., et al., 2016. A whole cell biocatalyst for double oxidation of cyclooctane. Journal of Industrial Microbiology & Biotechnology, 43(12), p 1641-1646.
C.A. Müller, et al., “A whole cell biocatalyst for double oxidation of cyclooctane”, Journal of Industrial Microbiology & Biotechnology, vol. 43, 2016, pp. 1641-1646.
Müller, C.A., Weingartner, A.M., Dennig, A., Ruff, A.J., Gröger, H., Schwaneberg, U.: A whole cell biocatalyst for double oxidation of cyclooctane. Journal of Industrial Microbiology & Biotechnology. 43, 1641-1646 (2016).
Müller, C. A., Weingartner, A. M., Dennig, A., Ruff, A. J., Gröger, Harald, and Schwaneberg, Ulrich. “A whole cell biocatalyst for double oxidation of cyclooctane”. Journal of Industrial Microbiology & Biotechnology 43.12 (2016): 1641-1646.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
3 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization.
Kinzel J, Sauer DF, Bocola M, Arlt M, Mirzaei Garakani T, Thiel A, Beckerle K, Polen T, Okuda J, Schwaneberg U., Beilstein J Org Chem 13(), 2017
PMID: 28845193
Kinzel J, Sauer DF, Bocola M, Arlt M, Mirzaei Garakani T, Thiel A, Beckerle K, Polen T, Okuda J, Schwaneberg U., Beilstein J Org Chem 13(), 2017
PMID: 28845193
Inversion of cpADH5 Enantiopreference and Altered Chain Length Specificity for Methyl 3-Hydroxyalkanoates.
Ensari Y, Dhoke GV, Davari MD, Bocola M, Ruff AJ, Schwaneberg U., Chemistry 23(51), 2017
PMID: 28727189
Ensari Y, Dhoke GV, Davari MD, Bocola M, Ruff AJ, Schwaneberg U., Chemistry 23(51), 2017
PMID: 28727189
Engineering of versatile redox partner fusions that support monooxygenase activity of functionally diverse cytochrome P450s.
Bakkes PJ, Riehm JL, Sagadin T, Rühlmann A, Schubert P, Biemann S, Girhard M, Hutter MC, Bernhardt R, Urlacher VB., Sci Rep 7(1), 2017
PMID: 28852040
Bakkes PJ, Riehm JL, Sagadin T, Rühlmann A, Schubert P, Biemann S, Girhard M, Hutter MC, Bernhardt R, Urlacher VB., Sci Rep 7(1), 2017
PMID: 28852040
35 References
Daten bereitgestellt von Europe PubMed Central.
Designer cells for stereocomplementary de novo enzymatic cascade reactions based on laboratory evolution.
Agudo R, Reetz MT., Chem. Commun. (Camb.) 49(93), 2013
PMID: 24135920
Agudo R, Reetz MT., Chem. Commun. (Camb.) 49(93), 2013
PMID: 24135920
Redox biocatalysis and metabolism: molecular mechanisms and metabolic network analysis.
Blank LM, Ebert BE, Buehler K, Buhler B., Antioxid. Redox Signal. 13(3), 2010
PMID: 20059399
Blank LM, Ebert BE, Buehler K, Buhler B., Antioxid. Redox Signal. 13(3), 2010
PMID: 20059399
Industrial methods for the production of optically active intermediates.
Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T., Angew. Chem. Int. Ed. Engl. 43(7), 2004
PMID: 14767950
Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T., Angew. Chem. Int. Ed. Engl. 43(7), 2004
PMID: 14767950
Large-scale oxidations in the pharmaceutical industry.
Caron S, Dugger RW, Ruggeri SG, Ragan JA, Ripin DH., Chem. Rev. 106(7), 2006
PMID: 16836305
Caron S, Dugger RW, Ruggeri SG, Ragan JA, Ripin DH., Chem. Rev. 106(7), 2006
PMID: 16836305
RH, J Chem Soc Dalton Trans 17(), 2001
Atmospheric-pressure, liquid-phase, selective aerobic oxidation of alkanes catalysed by metal-organic frameworks.
Dhakshinamoorthy A, Alvaro M, Garcia H., Chemistry 17(22), 2011
PMID: 21495095
Dhakshinamoorthy A, Alvaro M, Garcia H., Chemistry 17(22), 2011
PMID: 21495095
Hydrocarbon oxidation catalyzed by self-folded metal-coordinated cavitands.
Djernes KE, Padilla M, Mettry M, Young MC, Hooley RJ., Chem. Commun. (Camb.) 48(94), 2012
PMID: 23093093
Djernes KE, Padilla M, Mettry M, Young MC, Hooley RJ., Chem. Commun. (Camb.) 48(94), 2012
PMID: 23093093
Engineered alkane-hydroxylating cytochrome P450(BM3) exhibiting nativelike catalytic properties.
Fasan R, Chen MM, Crook NC, Arnold FH., Angew. Chem. Int. Ed. Engl. 46(44), 2007
PMID: 17886313
Fasan R, Chen MM, Crook NC, Arnold FH., Angew. Chem. Int. Ed. Engl. 46(44), 2007
PMID: 17886313
F, Green Chem 13(), 2011
K, Adv Synth Catal 349(), 2007
Metal-free activation of dioxygen by graphene/g-C3N4 nanocomposites: functional dyads for selective oxidation of saturated hydrocarbons.
Li XH, Chen JS, Wang X, Sun J, Antonietti M., J. Am. Chem. Soc. 133(21), 2011
PMID: 21561075
Li XH, Chen JS, Wang X, Sun J, Antonietti M., J. Am. Chem. Soc. 133(21), 2011
PMID: 21561075
J, ACS Catal 3(), 2013
D, Tetrahedron Lett 49(), 2008
CA, Adv Synth Catal 355(), 2013
Whole-cell double oxidation of n-heptane.
Muller CA, Dennig A, Welters T, Winkler T, Ruff AJ, Hummel W, Groger H, Schwaneberg U., J. Biotechnol. 191(), 2014
PMID: 24925696
Muller CA, Dennig A, Welters T, Winkler T, Ruff AJ, Hummel W, Groger H, Schwaneberg U., J. Biotechnol. 191(), 2014
PMID: 24925696
R, Chem Commun 23(), 1996
THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. II. SOLUBILIZATION, PURIFICATION, AND PROPERTIES.
OMURA T, SATO R., J. Biol. Chem. 239(), 1964
PMID: 14209972
OMURA T, SATO R., J. Biol. Chem. 239(), 1964
PMID: 14209972
S, J Mol Catal B Enzym 103(), 2014
High-cell-density cultivation of microorganisms.
Riesenberg D, Guthke R., Appl. Microbiol. Biotechnol. 51(4), 1999
PMID: 10341426
Riesenberg D, Guthke R., Appl. Microbiol. Biotechnol. 51(4), 1999
PMID: 10341426
P450(BM-3)-catalyzed whole-cell biotransformation of alpha-pinene with recombinant Escherichia coli in an aqueous-organic two-phase system.
Schewe H, Holtmann D, Schrader J., Appl. Microbiol. Biotechnol. 83(5), 2009
PMID: 19266193
Schewe H, Holtmann D, Schrader J., Appl. Microbiol. Biotechnol. 83(5), 2009
PMID: 19266193
Whole-cell biocatalysis for selective and productive C-O functional group introduction and modification.
Schrewe M, Julsing MK, Buhler B, Schmid A., Chem Soc Rev 42(15), 2013
PMID: 23475180
Schrewe M, Julsing MK, Buhler B, Schmid A., Chem Soc Rev 42(15), 2013
PMID: 23475180
M, Adv Synth Catal 355(), 2013
RA, 2008
Activation of Cminus signH Bonds by Metal Complexes.
Shilov AE, Shul'pin GB., Chem. Rev. 97(8), 1997
PMID: 11851481
Shilov AE, Shul'pin GB., Chem. Rev. 97(8), 1997
PMID: 11851481
C-H functionalization: thoroughly tuning ligands at a metal ion, a chemist can greatly enhance catalyst's activity and selectivity.
Shul'pin GB., Dalton Trans 42(36), 2013
PMID: 23873447
Shul'pin GB., Dalton Trans 42(36), 2013
PMID: 23873447
GB, Tetrahedron Lett 42(), 2001
AR, Catal Today 203(), 2013
Development of a whole-cell biocatalyst co-expressing P450 monooxygenase and glucose dehydrogenase for synthesis of epoxyhexane.
Siriphongphaew A, Pisnupong P, Wongkongkatep J, Inprakhon P, Vangnai AS, Honda K, Ohtake H, Kato J, Ogawa J, Shimizu S, Urlacher VB, Schmid RD, Pongtharangkul T., Appl. Microbiol. Biotechnol. 95(2), 2012
PMID: 22555910
Siriphongphaew A, Pisnupong P, Wongkongkatep J, Inprakhon P, Vangnai AS, Honda K, Ohtake H, Kato J, Ogawa J, Shimizu S, Urlacher VB, Schmid RD, Pongtharangkul T., Appl. Microbiol. Biotechnol. 95(2), 2012
PMID: 22555910
Direct oxidation of cycloalkanes to cycloalkanones with oxygen in water.
Staudt S, Burda E, Giese C, Muller CA, Marienhagen J, Schwaneberg U, Hummel W, Drauz K, Groger H., Angew. Chem. Int. Ed. Engl. 52(8), 2013
PMID: 23339093
Staudt S, Burda E, Giese C, Muller CA, Marienhagen J, Schwaneberg U, Hummel W, Drauz K, Groger H., Angew. Chem. Int. Ed. Engl. 52(8), 2013
PMID: 23339093
AJJ, 2006
T, J Chem Soc Chem Commun 6(), 1990
A, J Chem Soc Chem Commun 9(), 1994
Cytochrome P450 monooxygenases: perspectives for synthetic application.
Urlacher VB, Eiben S., Trends Biotechnol. 24(7), 2006
PMID: 16759725
Urlacher VB, Eiben S., Trends Biotechnol. 24(7), 2006
PMID: 16759725
K, 2003
D, J Mol Catal B Enzym 84(), 2012
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 27771781
PubMed | Europe PMC
Suchen in