NMR confirmation that tryptophan dehydrogenation occurs with syn stereochemistry during the biosynthesis of CDA in Streptomyces coelicolor

Journal of Organic Chemistry

Volumn 72, Issue 23, 2007, Pages 8950-8953

  Amir Heidari, Bagher ^a,b   Micklefield, Jason ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b KERMAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROTRYPTOPHAN; LIPOPEPTIDE ANTIBIOTIC; METHYLENE GROUP;

ANTIBIOTICS; BIOSYNTHESIS; DEUTERIUM; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

DEHYDROGENATION;

2',3' DEHYDROTRYPTOPHAN; CALCIUM DEPENDENT ANTIBIOTIC; DEUTERIUM; POLYPEPTIDE ANTIBIOTIC AGENT; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DEHYDROGENATION; MASS SPECTROMETRY; NONHUMAN; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; STREPTOMYCES COELICOLOR;

HYDROGENATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PEPTIDES; REFERENCE STANDARDS; STEREOISOMERISM; STREPTOMYCES COELICOLOR; TRYPTOPHAN;

EID: 35948996504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701660v     Document Type: Article

References (31)

1. (a) Hojati, Z.; Milne, C.; Harvey, B.; Gordon, L.; Borg, M.; Flett, F.; Wilkinson, B.; Sidebottom, P. J.; Rudd, B. A. M.; Hayes, M. A.; Smith, C. P.; Micklefield, J. Chem. Biol. 2002, 9, 1175-1187.
2. (b) Kempter, C.; Kaiser, D.; Haag, S.; Nicholson, G.; Gnau, V.; Walk, T.; Gierling, K. H.; Decker, H.; Zaehner, H.; Jung, G.; Metzger, J. W. Angew. Chem., Int. Ed. 1997, 36, 498-501.
3. (a) Baltz R. H.; Miao, V.; Wrigley, S. K. Nat. Prod. Rep. 2005, 22, 717-741.
4. (b) Miao, V.; Coëffet-LeGal, M.-F.; Brian, P.; Brost, R.; Penn, J.; Whiting, A.; Martin, S.; Ford, R.; Parr, I.; Bouchard, M.; Silva, C. J.; Wrigley S. K.; Baltz R. H. Microbiol. 2005, 151, 1507-1523.
5. (c) Debono, M.; Abbott, B. J.; Molloy, R. M.; Fukuda, D. S.; Hunt, A. H.; Daupert, V. M.; Counter, F. T.; Ott. J. L.; Carrell, C. B.; Howard, L. C.; Boeck, L. D.; Hamill, R. L. J. Antibiot. 1988, 41, 1093-1105.
6. (a) Milne, C.; Powell, A.; Jim, J.; Al, Nakeeb, M.; Smith, C. P.; Micklefield, J. J. Am. Chem. Soc. 2006, 128, 11250-11259.
7. (b) Powell, A.; Al Nakeeb, M.;, Wilkinson B.; Micklefield J. Chem. Commun. 2007, 2683-2685.
8. Neary, J.; Powell, A.; Gordon, L.; Milne, C.; Flett, F.; Wilkinson, B.; Smith, C. P.; Micklefield, J. Microbiol. 2007, 153, 768-776.
9. Amir-Heidari, B.; Thirlway, J.; Micklefield, J. Org. Lett. 2007, 9, 1513-1516.
10. (a) Strieker, M.; Kopp, F.; Mahlert, C.; Essen, L.-O.; Marahiel, M. A. ACS Chem. Biol. 2007, 2, 187-196.
11. (b) Chen, H.; Thomas, M.G.; O'Connor, S.E.; Hubbard, B.K.; Burkart, M.D.; Walsh C.T. Biochemistry 2001, 40, 11651-11659.
12. (a) Kumar, N. G.; Urry.; D. W. Biochemistry 1973, 12, 3811-3817.
13. (c) Itagaki, F.; Shigemori, H.; Ishibashi, M.; Nakamura, T.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 5540-5542.
14. (d) Quershi, A.; Colin, P. L.; Faulkner, D. J. Tetrahedron 2000, 56, 3679-3685.
15. Barona-Gomez, F.; Hodgson, D. A. EMBO Rep. 2003, 4, 296-300.
16. Reinecke, M. G.; Sebastian, J. F.; Johnson, H. W., Jr.; Pyun, C. J. Org. Chem. 1972, 37, 3066-3068.
17. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1977, 42, 1213-1216.
18. Hengartner, U.; Jr., D. V.; Johnson, K. K.; Larscheid, M. E.; Pigott, F.; Scheidl, F.; Scott, J. W.; Sun, R. C.; Towsend, J. M.; Willias, T. H. J. Org. Chem. 1979, 44, 3741-3747.
19. (a) Hammadi, A.; Meunier, G.; Menez, A.; Genet, R. Tetrahedron Lett. 1998, 39, 29552958.
20. (b) Hammadi, A.; Menez, A.; Genet, R. Tetrahedron 1997, 53, 16115-16122.
21. Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364.
22. Klepp, J.; Oberfrank, M.; Retey, J.; Tritsch, D.; Biellmann, J. F.; Hull, W. E. J. Am. Chem. Soc. 1989, 111, 4440-4447.
23. Gustafson, M. E.; Miller, D.; Davis, P. J.; Rosazza, J. P.; Chang, C. J.; Floss, H. G. J. Chem. Soc., Chem. Commun. 1977, 842-843.
24. Genet, R.; Bénetti, P.-H.; Hammadi, A.; Ménez, A. J. Biol. Chem. 1995, 270, 23540-23545.
25. Ghisla, S.; Thorpe. C. Eur. J. Biochem. 2004, 271, 494-508.
26. Thomas, M. G. Burkart, M. D. Walsh C. T. Chem. Biol. 2002, 9, 171-184.
27. Tsuji, Y.; Kotachi, S.; Huh, K.-T.; Watanabe, Y. J. Org. Chem. 1990, 55, 580-584.
28. Moriya, T.; Yoneda, N.; Miyoshi, M.; Matsumoto, K. J. Org. Chem. 1982, 47, 94-98.
29. Huang, H. T.; Niemann, C. J. Am. Chem. Soc. 1951, 73, 1541-1548.
30. Lobell, M.; Schneider, M. P. J. Chem. Soc., Perkin Trans. 1998, 319-326.
31. Gowda, D. C.; Abiraj, K.; Augustine, P. Lett. Pept. Sci. 2002, 9, 43-47.