New myxothiazols from the predatory bacterium myxococcus fulvus

Journal of Antibiotics

Volumn 67, Issue 7, 2014, Pages 519-525

  Schieferdecker, Sebastian ^a   Exner, Thomas E ^b   Gross, Harald ^b,c   Roth, Martin ^a   Nett, Markus ^a  

^a HANS KNÖLL INSTITUTE   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c German Center for Research in Infectious Disease (DZIF)   (Germany)

Author keywords

antibiotic; Myxococcus fulvus; myxothiazol; predatory bacteria

Indexed keywords

ANTI-BACTERIAL AGENTS; METHACRYLATES; MYXOCOCCUS; THIAZOLES;

EID: 84904961152     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2014.31     Document Type: Article

References (53)

1. Fischbach, M. A. & Walsh, C. T. Antibiotics for emerging pathogens. Science 325, 1089-1093 (2009).
2. Cain, C. C. et al. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob. Agents Chemother. 47, 2113-2117 (2003). (Pubitemid 36753559)
3. Volz, C., Kegler, C. & Mü ller, R. Enhancer binding proteins act as hetero-oligomers and link secondary metabolite production to myxococcal development, motility, and predation. Chem. Biol. 19, 1447-1459 (2012).
4. Xiao, Y., Wei, X., Ebright, R. & Wall, D. Antibiotic production by myxobacteria plays a role in predation. J. Bacteriol. 193, 4626-4633 (2011).
5. Wenzel, S. C. & Mü ller, R. The impact of genomics on the exploitation of the myxobacterial secondary metabolome. Nat. Prod. Rep. 26, 1385-1407 (2009).
6. Nett, M. & König, G. M. The chemistry of gliding bacteria. Nat. Prod. Rep. 24, 1245-1261 (2007). (Pubitemid 350151354)
7. Weissman, K. J. & Müller, R. Myxobacterial secondary metabolites: Bioactivities and modes-of-action. Nat. Prod. Rep. 27, 1276-1295 (2010).
8. Shimkets, L. J., Dworkin, M. & Reichenbach, H. The myxobacteria. in The Prokaryotes (eds Dworkin, M., Falkow, S., Rosenberg, E., Schleifer, K.-H. & Stackebrandt, E.) 31-115 (Springer, New York, 2006).
9. Pretsch, E. Structure Determination of Organic Compounds: Tables of Spectral Data (Springer, Berlin, Heidelberg, 2009).
10. Trowitzsch, W., Reifenstahl, G., Wray, V. & Gerth, K. Myxothiazol, an antibiotic from Myxococcus fulvus (myxobacterales). II. Structure elucidation. J. Antibiot. 33, 1480-1490 (1980). (Pubitemid 11186867)
11. Ojika, M. et al. Cystothiazoles A and B, new bithiazole-type antibiotics from the myxobacterium Cystobacter fuscus. J. Antibiot. 51, 275-281 (1998). (Pubitemid 28174941)
12. Böhlendorf, B. et al. Melithiazols A-N: New antifungal b-methoxyacrylates from myxobacteria. Eur. J. Org. Chem. 2601-2608 (1999).
13. Ahn, J. W. et al. Bithiazole metabolites from the myxobacterium Myxococcus fulvus. Chem. Pharm. Bull. 55, 477-479 (2007).
14. Hoye, T. R., Jeffrey, C. S. & Shao, F. Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons. Nat. Protoc. 2, 2451-2458 (2007).
15. Smith, W. B. & Barfield, M. Predictions of 3J(HH) near 1801-reparametrization of the sp3-sp3 equation. Magn. Res. Chem. 31, 696-697 (1993).
16. Chow, H.-F. & Seebach, D. Diastereoselective aldol addition using boron trichloride or alkoxydichloroborane. Helv. Chim. Acta 69, 604-614 (1986).
17. Evans, D. A., Nelson, J. V., Vogel, E. & Taber, T. R. Stereoselective aldol condensations via boron enolates. J. Am. Chem. Soc. 103, 3099-3111 (1981).
18. Yoshida, W. Y., Bryan, P. J., Baker, B. J. & McClintock, J. B. Pteroenone: A defensive metabolite of the abducted antarctic pteropod Clione antarctica. J. Org. Chem. 60, 780-782 (1995).
19. Gebauer, J., Arseniyadis, S. & Cossy, J. A concise total synthesis of melithiazole C. Org. Lett. 9, 3425-3427 (2007).
20. Horstmann, N. & Menche, D. Configurational assignment of rhizopodin, an actinbinding macrolide from the myxobacterium Myxococcus stipitatus. Chem. Commun. 2008, 5173-5175 (2008).
21. Carmeli, S., Moore, R. E. & Patterson, G. M. L. Tolytoxin and new scytophycins from three species of Scytonema. J. Nat. Prod. 53, 1533-1542 (1990).
22. Trowitzsch, W., Höfle, G. & Sheldrick, W. S. The stereochemistry of myxothiazol. Tetrahedron Lett. 22, 3829-3832 (1981). (Pubitemid 12232874)
23. Silakowski, B. et al. New lessons for combinatorial biosynthesis from myxobacteria. The myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3-1. J. Biol. Chem. 274, 37391-37399 (1999).
24. Borgen, G. et al. Proton magnetic resonance spectra of thiazoles. Chemical shifts and substituent effects. Acta Chem. Scand. 20, 2593-2600 (1966).
25. Ahn, J. W., Woo, S. H., Lee, C. O., Cho, K. Y. & Kim, B. S. KR025, a new cytotoxic compound from Myxococcus fulvus. J. Nat. Prod. 62, 495-496 (1999).
26. Steinmetz, H., Forche, E., Reichenbach, H. & Höfle, G. Biosynthesis of myxothiazol Z, the ester-analog of myxothiazol A in Myxococcus fulvus. Tetrahedron 56, 1681-1684 (2000). (Pubitemid 30190435)
27. Thierbach, G. & Reichenbach, H. Myxothiazol, a new antibiotic interfering with respiration. Antimicrob. Agents Chemother. 19, 504-507 (1981). (Pubitemid 11079450)
28. Von Jagow, G., Ljungdahl, P. O., Graf, P., Ohnishi, T. & Trumpower, B. L. An inhibitor of mitochondrial respiration which binds to cytochrome b and displaces quinone from the iron-sulfur protein of the cytochrome bc1 complex. J. Biol. Chem 259, 6318-6326 (1984). (Pubitemid 14108174)
29. Gómez-Vidal, J. A., Forrester, M. T. & Silverman, R. B. Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters. Org. Lett. 3, 2477-2479 (2001). (Pubitemid 33627156)
30. Molecular Operating Environment (MOE). (2012.10). 2012. 1010 Sherbooke St West, Suite #910, Montreal, QC, Canada, H3A 2R7, Chemical Computing Group Inc.
31. Halgren, T. A. The Merck Force Field. J. Comp. Chem. 17, 490-641 (1996).
32. Frisch, M. J. et al. Gaussian 09, Revision B.01 (Gaussian, Inc., Wallingford CT, 2009).
33. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652 (1993).
34. Hariharan, P. C. & Pople, J. A. Accuracy of AH, equilibrium geometries by single determinant molecular orbital theory. Mol. Phys. 27, 209-214 (1974).
35. Hariharan, P. C. & Pople, J. A. The influence of polarization functions on molecular orbital hydrogenation energies. Theor. Chim. Acta 28, 213-222 (1973).
36. Francl, M. M. et al. Self-consistent molecular orbital methods. XXIII. A polarizationtype basis set for second-row elements. J. Chem. Phys. 77, 3654-3665 (1982).
37. Blaudeau, J.-P., McGrath, M. P., Curtiss, L. A. & Radom, L. Extension of Gaussian-2 (G2) theory to molecules containing third-row atoms K and Ca. J. Chem. Phys. 107, 5016-5021 (1997). (Pubitemid 127560673)
38. Binning, R. C. Jr. & Curtiss, L. A. Compact contracted basis sets for third-row atoms: Ga-Kr. J. Comput. Chem. 11, 1206-1216 (1990).
39. Rassolov, V. A., Ratner, M. A., Pople, J. A., Redfern, P. C. & Curtiss, L. A. 6-31G* basis set for third-row atoms. J. Comput. Chem. 22, 976-984 (2001). (Pubitemid 32455735)
40. Rassolov, V. A., Pople, J. A., Ratner, M. A. & Windus, T. L. 6-31G* basis set for atoms K through Zn. J. Chem. Phys. 109, 1223-1229 (1998). (Pubitemid 128678537)
41. Gordon, M. S. The isomers of silacyclopropane. Chem. Phys. Lett. 76, 163-168 (1980).
42. Cances, E., Mennucci, B. & Tomasi, J. A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 107, 3032-3041 (1997). (Pubitemid 127568923)
43. Mennucci, B. & Tomasi, J. Continuum solvation models: A new approach to the problem of solutés charge distribution and cavity boundaries. J. Chem. Phys. 106, 5151-5158 (1997). (Pubitemid 126596815)
44. Cossi, M., Barone, V., Mennucci, B. & Tomasi, J. Ab-initio study of ionic solutions by a polarizable continuum dielectric model. Chem. Phys. Lett. 286, 253-260 (1998). (Pubitemid 128181148)
45. Clark, T., Chandrasekhar, J., Spitznagel, G. W. & Schleyer, P. V. R. Efficient diffuse function-augmented basis-sets for anion calculations. 3. The 3-21\+G basis set for 1st-row elements, Li-F. J. Comp. Chem. 4, 294-301 (1983).
46. McLean, A. D. & Chandler, G. S. Contracted Gaussian-basis sets for molecular calculations. 1. 2nd row atoms, Z11-18. J. Chem. Phys. 72, 5639-5648 (1980).
47. Raghavachari, K, Binkley, J. S., Seeger, R. & Pople, J. A. Self-consistent molecular orbital methods. 20. Basis set for correlated wave-functions. J. Chem. Phys. 72, 650-654 (1980).
48. Frisch, M. J., Pople, J. A. & Binkley, J. S. Self-consistent molecular orbital methods. 25.Supplementary functions for Gaussian basis sets. J. Chem. Phys. 80, 3265-3269 (1984).
49. McWeeny, R. Perturbation theory for Fock-Dirac density matrix. Phys. Rev. 126, 1028-1034 (1962).
50. Ditchfield, R. Self-consistent perturbation theory of diamagnetism. 1. Gauge-invariant LCAO method for NMR chemical shifts. Mol. Phys. 27, 789-807 (1974).
51. Wolinski, K., Hilton, J. F. & Pulay, P. Efficient implementation of the Gaugeindependent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 112, 8251-8260 (1990).
52. Deng, W., Cheeseman, J. R. & Frisch, M. J. Calculation of nuclear spin-spin coupling constants of molecules with first and second row atoms in study of basis set dependence. J. Chem. Theory Comput. 2, 1028-1037 (2006).
53. Navarro-Vazquez, A., Cobas, J. C., Sardina, F. J., Casanueva, J. & Diez, E. A graphical tool for the prediction of vicinal proton-proton 3JHH coupling constants. J. Chem. Inf. Comput. Sci. 44, 1680-1685 (2004).