Regio- and chemoselective enzymatic N-oxygenation in vivo, in vitro, and in flow

Angewandte Chemie - International Edition

Volumn 45, Issue 47, 2006, Pages 8016-8018

  Winkler, Robert ^a   Richter, Martin E A ^a   Knüpfer, Uwe ^a   Merten, Dirk ^b   Hertweck, Christian ^a,b  

^a HKI   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Amines; Biotransformations; Enzymes; Oxygenation; Regioselectivity

Indexed keywords

AMINES; AROMATIC COMPOUNDS; ENZYME IMMOBILIZATION; HYDROGEN; PROTEINS;

AROMATIC AMINES; BIOTRANSFORMATIONS; OXYGENATION; REGIOSELECTIVITY;

ENZYME KINETICS;

4 AMINOBENZOIC ACID; AMINE; OXYGEN; OXYGENASE;

ARTICLE; BINDING SITE; BIOTRANSFORMATION; CHEMICAL MODEL; CHEMISTRY; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; METABOLISM; SPECTROPHOTOMETRY;

4-AMINOBENZOIC ACID; AMINES; BINDING SITES; BIOTRANSFORMATION; CATALYTIC DOMAIN; ENZYME ACTIVATION; MODELS, CHEMICAL; OXYGEN; OXYGENASES; SPECTROPHOTOMETRY; SUBSTRATE SPECIFICITY;

EID: 33845496066     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603060     Document Type: Article

References (24)

1. K. Faber, Biotransformations in Organic Chemistry: A Textbook, Springer, Heidelberg, 2004.
2. Z. Li, J. B. van Beilen, W. A. Duetz, A. Schmid, A. de Raadt, H. Griengl, B. Withold, Curr. Opin. Chem. Biol. 2002, 6, 136.
3. R. D. Schmid, V. Urlacher, Curr. Opin. Biotechnol. 2002, 13, 557.
4. A. Straathof, S. Panke, A. Schmid, Curr. Opin. Biotechnol. 2002, 13, 548.
5. S. Fetzner, Appl. Microbiol. Biotechnol. 2002, 60, 243.
6. S. Kirner, P. E. Hammer, D. S. Hill, A. Altmann, I. Fischer, L. J. Weislo, M. Lanahan, K.-H. van Pee, J. M. Ligon, J. Bacteriol. 1998, 180, 1939.
7. J. He, C. Hertweck, Chem. Biol. 2003, 10, 1225.
8. M. Ziehl, J. He, H.-M. Dahse, C. Hertweck, Angew. Chem. 2005, 117, 1226;
9. Angew. Chem. Int. Ed. 2005, 44, 1202.
10. R. Winkler, C. Hertweck, Angew. Chem. 2005, 117, 4152;
11. Angew. Chem. Int. Ed. 2005, 44, 4083.
12. This finding has been confirmed for PrnD; D. J. Lee, H. Zhao, Angew. Chem. 2006, 118, 638;
13. Angew. Chem. Int. Ed. 2006, 45, 622.
14. Previously reported results obtained with a S. thioluteus strain (S. Kawai, K. Kobayashi, T. Oshima, F. Egami, Arch. Biochem. Biophys. 1965, 112, 537) could not be reproduced.
15. U. Horn, W. Strittmatter, A. Krebber, U. Knüpfer, M. Kujau, R. Wenderoth, K. Müller, S. Matzku, A. Plückthun, D. Riesenberg, Appl. Microbiol. Biotechnol. 1996, 46, 524.
16. M. Ferrer, T. Chernikova, M. Yakimov, P. Golyshin, K. Timmis, Nat. Biotechnol. 2003, 21, 1266.
17. J. Lee, M. Simurdiak, H. Zhao, J. Biol. Chem. 2005, 280, 36 719.
18. M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841.
19. N. Itoh, N. Morinaga, T. Kouzai, Biochem. Mol. Biol. Int. 1993, 29, 785.
20. M. D. Corbett, B. R. Chipko, A. O. Batchelor, Biochem. J. 1980, 187, 893.
21. S. Kirner, K.-H. van Pee, Angew. Chem. 1994, 106, 346;
22. Angew. Chem. Int. Ed. Engl. 1994, 33, 352.
23. G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708.
24. A. Bruggink, A. Straathof, L. van der Wielen, Adv. Biochem. Eng. Biotechnol. 2003, 80, 69.