Concerted action of P450 plus helper protein to form the amino-hydroxy-piperidone moiety of the potent protease inhibitor crocapeptin

Journal of the American Chemical Society

Volumn 135, Issue 45, 2013, Pages 16885-16894

  Viehrig, Konrad ^a   Surup, Frank ^b   Harmrolfs, Kirsten ^a   Jansen, Rolf ^b   Kunze, Brigitte ^b   Müller, Rolf ^a  

^a SAARLAND UNIVERSITY   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS GENE CLUSTER; CYCLIC DEPSIPEPTIDES; CYTOCHROME P450 ENZYMES; MUTAGENESIS EXPERIMENT; PRECURSOR MOLECULES; PROTEASE INHIBITOR; SERINE PROTEASE INHIBITOR; STRUCTURE ELUCIDATION;

AMINO ACIDS; BIOCHEMISTRY; GENES; PROTEINS;

ENZYME INHIBITION;

CHYMOTRYPSIN; CROCAPEPTIN; CROCAPEPTIN A1; CROCAPEPTIN A2; CROCAPEPTIN A3; CROCAPEPTIN B; CYCLODEPSIPEPTIDE; CYTOCHROME P450; STRATUM CORNEUM CHYMOTRYPTIC ENZYME; UNCLASSIFIED DRUG;

ADENYLATION; AMINO ACID SEQUENCE; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; GENE CLUSTER; GENE INACTIVATION; HYDROXYLATION; IC 50; IN VITRO STUDY; LACTONIZATION; LIQUID CULTURE; MUTAGENESIS; NONHUMAN; OXIDATION; OXIDATION REDUCTION REACTION; PROMOTER REGION; PROTEIN ANALYSIS; PROTEIN STRUCTURE; PROTEINASE INHIBITION;

CYTOCHROME P-450 ENZYME SYSTEM; DEPSIPEPTIDES; HYDROXYLATION; MULTIGENE FAMILY; MUTATION; MYXOCOCCALES; PIPERIDONES; SERINE PROTEINASE INHIBITORS;

EID: 84887758301     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4047153     Document Type: Article

References (30)

1. Wenzel, S. C.; Müller, R. Mol. BioSyst. 2009, 5, 567
2. Weissman, K. J.; Müller, R. Nat. Prod. Rep. 2010, 27, 1276
3. Wenzel, S. C.; Müller, R. Nat. Prod. Rep. 2007, 24, 1211
4. Kunze, B.; Jansen, R.; Höfle, G.; Reichenbach, H. J. Antibiot. 2004, 57, 151
5. Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1995, 48, 1262
6. Kunze, B.; Jansen, R.; Höfle, G.; Reichenbach, H. J. Antibiot. 1994, 47, 881
7. Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2003, 2684
8. Steinmetz, H.; Irschik, H.; Kunze, B.; Reichenbach, H.; Höfle, G.; Jansen, R. Chemistry 2007, 13, 5822
9. Cortina, N. S.; Krug, D.; Plaza, A.; Revermann, O.; Müller, R. Angew. Chem., Int. Ed. 2012, 51, 811
10. Welker, M.; von Döhren, H. FEMS Microbiol. Rev. 2006, 30, 530
11. Yamaki, H.; Sitachitta, N.; Sano, T.; Kaya, K. J. Nat. Prod. 2005, 68, 14
12. Matern, U.; Schleberger, C.; Jelakovic, S.; Weckesser, J.; Schulz, G. E. Chem. Biol. 2003, 10, 997
13. Stolze, S. C.; Meltzer, M.; Ehrmann, M.; Kaiser, M. Chem. Commun. (Cambridge, U.K.) 2010, 46, 8857
14. Martin, C.; Oberer, L.; Ino, T.; Konig, W. A.; Busch, M.; Weckesser, J. J. Antibiot. 1993, 46, 1550
15. Zainuddin, E. N.; Mentel, R.; Wray, V.; Jansen, R.; Nimtz, M.; Lalk, M.; Mundt, S. J. Nat. Prod. 2007, 70, 1084
16. Rounge, T. B.; Rohrlack, T.; Kristensen, T.; Jakobsen, K. S. BMC Microbiol. 2008, 8, 141
17. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591
18. Itou, Y.; Ishida, K.; Shin, S. J.; Murakami, M. Tetrahedron 1999, 55, 6871
19. Bachmann, B. O.; Ravel, J. Methods Enzymol. 2009, 458, 181
20. Rachid, S.; Krug, D.; Kunze, B.; Kochems, I.; Scharfe, M.; Zabriskie, T. M.; Blocker, H.; Müller, R. Chem. Biol. 2006, 13, 667
21. Koulov, A. V.; LaPointe, P.; Lu, B.; Razvi, A.; Coppinger, J.; Dong, M. Q.; Matteson, J.; Laister, R.; Arrowsmith, C.; Yates, J. R., III; Balch, W. E. Mol. Biol. Cell 2010, 21, 871
22. Stachelhaus, T.; Mootz, H. D.; Marahiel, M. A. Chem. Biol. 1999, 6, 493
23. Buntin, K.; Irschik, H.; Weissman, K. J.; Luxenburger, E.; Blocker, H.; Müller, R. Chem. Biol. 2010, 17, 342
24. Khatri, Y.; Hannemann, F.; Ewen, K. M.; Pistorius, D.; Perlova, O.; Kagawa, N.; Brachmann, A. O.; Müller, R.; Bernhardt, R. Chem. Biol. 2010, 17, 1295
25. Khatri, Y.; Girhard, M.; Romankiewicz, A.; Ringle, M.; Hannemann, F.; Urlacher, V. B.; Hutter, M. C.; Bernhardt, R. Appl. Microbiol. Biotechnol. 2010, 88, 485
26. Ewen, K. M.; Hannemann, F.; Khatri, Y.; Perlova, O.; Kappl, R.; Krug, D.; Huttermann, J.; Müller, R.; Bernhardt, R. J. Biol. Chem. 2009, 284, 28590
27. Foulston, L. C.; Bibb, M. J. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 13461
28. Hussain, H. A.; Ward, J. M. Appl. Environ. Microbiol. 2003, 69, 373
29. Krastel, P.; Liechty, B.-M.; Meingassner, J. G.; Schmitt, E.; Schreiner, E. P. Cyclic Depsipeptides. WO Patent WO 2009/024527 A1, February 26, 2009.
30. Krastel, P.; Liechty, B.-M.; Meingassner, J. G.; Moore, C.; Schmitt, E. Nucleic Acid of a Biosynthetic Cluster Encoding Non Ribosomal Peptide Synthases and Uses Therof. WO Patent WO 2010/092109 A2, August 19, 2010.