Total synthesis and biological evaluation of transvalencin Z

Journal of Natural Products

Volumn 75, Issue 6, 2012, Pages 1037-1043

  Nelson, Kathryn M ^a,b   Salomon, Christine E ^a   Aldrich, Courtney C ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; TRANSVALENCIN Z; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; OXAZOLE DERIVATIVE; SALICYLIC ACID DERIVATIVE;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG ISOLATION; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NOCARDIA; NOCARDIA TRANSVALENSIS; NONHUMAN; OPTICAL ROTATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS; ACINETOBACTER BAUMANNII; ANIMAL; BACILLUS SUBTILIS; CANDIDA ALBICANS; CERCOPITHECUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; MICROBIOLOGICAL EXAMINATION; MYCOBACTERIUM; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; SYNTHESIS;

CORYNEBACTERINEAE; MYCOBACTERIUM SMEGMATIS; NOCARDIA TRANSVALENSIS;

ACINETOBACTER BAUMANNII; ANIMALS; ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; CANDIDA ALBICANS; CERCOPITHECUS AETHIOPS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; KLEBSIELLA PNEUMONIAE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM; NOCARDIA; OXAZOLES; PSEUDOMONAS AERUGINOSA; SALICYLIC ACIDS; STAPHYLOCOCCUS AUREUS;

EID: 84866464360     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200972s     Document Type: Article

References (32)

1. Lönnroth, K.; Castro, K. G.; Chakaya, J. M.; Chauhan, L. S.; Floyd, K.; Glaziou, P.; Raviglione, M. C. The Lancet 2010, 375, 1814-1829.
2. World Health Organization. Global Tuberculosis Control 2009: Epidemiology, Strategy, Financing; WHO: Geneva, Switzerland, 2009.
3. Gutierrez-Lugo, M.-T.; Bewley, C. A. J. Med. Chem. 2008, 51, 2606-2612.
4. Velayati, A. A.; Masjedi, M. R.; Farnia, P.; Tabarsi, P.; Ghanavi, J.; Ziazarifi, A. H.; Hoffner, S. E. Chest 2009, 136, 420-425.
5. Udwadia, Z. F.; Amale, R. A.; Ajbani, K. K. Clin. Infect. Dis. 2012, 54, 579-581.
6. Mukai, A.; Fukai, T.; Matsumoto, Y.; Ishikawa, J.; Hoshino, Y.; Yazawa, K.; Harada, K.-i.; Mikami, Y. J. Antibiot. 2006, 59, 366-369.
7. Snow, G. A. Biochem. J. 1965, 97, 166-175.
8. Miethke, M.; Marahiel, M. A. Microbiol. Mol. Biol. Rev. 2007, 71, 413-451.
9. Ratledge, C.; Dover, L. G. Annu. Rev. Microbiol. 2000, 54, 881-941.
10. Snow, G. A. Bacteriol. Rev. 1970, 34, 99-125.
11. Vergne, A. F.; Walz, A. J.; Miller, M. J. Nat. Prod. Rep. 2000, 17, 99-116.
12. Hu, J.; Miller, M. J. J. Am. Chem. Soc. 1997, 119, 3462-3468.
13. Xu, Y.; Miller, M. J. J. Org. Chem. 1998, 63, 4314-4322.
14. Walz, A. J.; Mollmann, U.; Miller, M. J. Org. Biomol. Chem. 2007, 5, 1621-1628.
15. Tse, B.; Kishi, Y. J. Org. Chem. 1994, 59, 7807-7814.
16. Sakakura, A.; Kondo, R.; Umemura, S.; Ishihara, K. Tetrahedron 2009, 65, 2102-2109.
17. Sattely, E. S.; Walsh, C. T. J. Am. Chem. Soc. 2008, 130, 12282-12284.
18. Wuest, W. M.; Sattely, E. S.; Walsh, C. T. J. Am. Chem. Soc. 2009, 131, 5056-5057.
19. Yamamoto, S.; Okujo, N.; Sakakibara, Y. Arch. Microbiol. 1994, 162, 249-254.
20. Hughes, R. M.; Waters, M. L. J. Am. Chem. Soc. 2006, 128, 13586-13591.
21. The reported conditions require overnight heating and a large excess (14 equivalents) of formic acid; however transformation was achieved in 3 h at room temperature using only 7 equivalents of formic acid.
22. Wuts, P. G. M.; Greene, T. W. Greene's Protecting Groups in Organic Synthesis, 4th ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007.
23. Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91-93.
24. Field, L. D.; Sternhell, S.; Kalman, J. R. Organic Structures from Spectra, 4th ed. ed.; John Wiley & Sons Ltd: West Sussex, England, 2008.
25. Schneider, K.; Rose, I.; Vikineswary, S.; Jones, A. L.; Goodfellow, M.; Nicholson, G.; Beil, W.; Süssmuch, R. D.; Fiedler, H.-P. J. Nat. Prod. 2007, 70, 932-935.
26. Young, D. C.; Kasmar, A.; Moraski, G.; Cheng, T. Y.; Walz, A. J.; Hu, J.; Xu, Y.; Endres, G. W.; Uzieblo, A.; Zajonc, D.; Costello, C. E.; Miller, M. J.; Moody, D. B. J. Biol. Chem. 2009, 284, 25087-25096.
27. Mitchell, J. M.; Shaw, J. T. Org. Lett. 2007, 9, 1679-1681.
28. Fennell, K. A.; Mollmann, U.; Miller, M. J. J. Org. Chem. 2008, 73, 1018-1024.
29. Hoshino, Y.; Mukai, A.; Yazawa, K.; Uno, J.; Ando, A.; Mikami, Y.; Fukai, T.; Ishikawa, J.; Yamaguchi, K. J. Antibiot. 2004, 57, 803-807.
30. Williams, K. J.; Boshoff, H. I.; Krishnan, N.; Gonzales, J.; Schnappinger, D.; Robertson, B. D. Tuberculosis 2011, 91, 549-555.
31. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.
32. Denizot, F.; Lang, R. J. Immunol. Methods 1986, 89, 271-277.