Enabling Selective and Sustainable P450 Oxygenation Technology. Production of 4-Hydroxy-α-isophorone on Kilogram Scale

Organic Process Research and Development

Volumn 20, Issue 4, 2016, Pages 814-819

  Kaluzna, Iwona ^a   Schmitges, Thomas ^a   Straatman, Harrie ^a   Van Tegelen, Dennis ^a,b   Müller, Monika ^a   Schürmann, Martin ^a   Mink, Daniel ^a  

^a DSM RESOLVE   (Netherlands)

^b Pathonostics   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

COST EFFECTIVE; CYTOCHROME P450; CYTOCHROME P450 ENZYMES; ECONOMICAL EVALUATION; PLATFORM TECHNOLOGY; PRODUCT CONCENTRATION; SPACE TIME YIELD; SUSTAINABLE PRODUCTION;

COST EFFECTIVENESS;

EID: 84966298420     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/acs.oprd.5b00282     Document Type: Article

References (27)

1. Dordick, J. S.; Khmelnitsky, Y. L.; Sergeeva, M. V. Curr. Opin. Microbiol. 1998, 1, 311-318 10.1016/S1369-5274(98)80035-0
2. Maimone, T. J.; Baran, P. S. Nat. Chem. Biol. 2007, 3, 396-407 10.1038/nchembio.2007.1
3. Schrader, J. In Flavours and fragrances: Chemistry, Bioprocessing and Sustainability; Berger, R. G., Ed.; Springer: Berlin, 2007, pp 507-574.
4. Pichler, H.; Wriessnegger, T.; Augustin, P.; Engleder, M.; Leitner, E.; Müller, M.; Kaluzna, I.; Schürmann, M.; Mink, D.; Zellnig, G.; Schwab, H. Metab. Eng. 2014, 24, 18-29 10.1016/j.ymben.2014.04.001
5. Bordeaux, M.; Galarneau, A.; Drone, J. Angew. Chem., Int. Ed. 2012, 51, 10712-10723 10.1002/anie.201203280
6. Hollmann, F.; Arends, I.; Buehler, K.; Schallmey, A.; Buhler, B. Green Chem. 2011, 13, 226-265 10.1039/C0GC00595A
7. Monti, D.; Ottolina, G.; Carrea, G.; Riva, S. Chem. Rev. 2011, 111, 4111-4140 10.1021/cr100334x
8. Davies, H. G.; Green, R. H.; Kelly, D. R.; Roberts, S. M., Eds. Biotransformations in preparative organic chemistry: The use of isolated enzymes and whole-cell systems in synthesis; Academic Press: London, 1989.
9. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2363 10.1021/cr050523v
10. Urlacher, V. B.; Lutz-Wahl, S.; Schmid, R. D. Appl. Microbiol. Biotechnol. 2004, 64, 317-325 10.1007/s00253-003-1514-1
11. Roduner, E.; Kaim, W.; Sarkar, B.; Urlacher, V. B.; Pleiss, J.; Glaser, R.; Einicke, W. D.; Sprenger, G. A.; Beifuss, U.; Klemm, E.; Liebner, C.; Hieronymus, H.; Hsu, S. F.; Plietker, B.; Laschat, S. ChemCatChem 2013, 5, 82-112 10.1002/cctc.201200266
12. Lewis, J. C.; Coelho, P. S.; Arnold, F. H. Chem. Soc. Rev. 2011, 40, 2003-2021 10.1039/C0CS00067A
13. Van Beilen, J. B.; Duetz, W. A.; Schmid, A.; Witholt, B. Trends Biotechnol. 2003, 21, 170-177 10.1016/S0167-7799(03)00032-5
14. Lundemo, M. T.; Woodley, J. M. Appl. Microbiol. Biotechnol. 2015, 99, 2465-2483 10.1007/s00253-015-6403-x
15. Kaluzna, I.; de Vries, A.; Mink, D. Chimica Oggi 2015, 33, 54-57
16. Bellut, H. U. S. Patent US4898984A, 1990.
17. Lu, Y.; Mei, L. H. J. Zhejiang Univ., Sci., B 2007, 8, 27-32 10.1631/jzus.2007.B0027
18. Pflug, S.; Richter, S. M.; Urlacher, V. B. J. Biotechnol. 2007, 129, 481-488 10.1016/j.jbiotec.2007.01.013
19. Schrewe, M.; Julsing, M. K.; Bühler, B.; Schmid, A. Chem. Soc. Rev. 2013, 42, 6346-6377 10.1039/c3cs60011d
20. Julsing, M. K.; Cornelissen, S.; Bühler, B.; Schmid, A. Appl. Microbiol. Biotechnol. 2015, 99, 2465-248
21. Brummund, J.; Müller, M.; Sonke, T. Org. Process Res. Dev. 2015, 19, 1590-1595 10.1021/op500307e
22. Schewe, H.; Kaup, B. A.; Schrader, J. Appl. Microbiol. Biotechnol. 2008, 78, 55-65 10.1007/s00253-007-1277-1
23. Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-3980 10.1021/cr020443g
24. Hass, V. C.; Pörtner, R. Praxis der Bioprozesstechnik; Spektrum: Heidelberg, 2011; p 180.
25. Shakunthala, N. Expert Opin. Drug Metab. Toxicol. 2010, 6, 1-15 10.1517/17425250903329095
26. Wolberg, M.; Filho, M. V.; Bode, S.; Geilenkirchen, P.; Feldmann, R.; Liese, A.; Hummel, W.; Muller, M. Bioprocess Biosyst. Eng. 2008, 31, 183-191 10.1007/s00449-008-0205-9
27. Hennig, M.; Püntener, K.; Scalone, M. Tetrahedron: Asymmetry 2000, 11, 1849-1858 10.1016/S0957-4166(00)00141-5