An artificial pathway to 3,4-dihydroxybenzoic acid allows generation of new aminocoumarin antibiotic recognized by catechol transporters of E. coli

Chemistry and Biology

Volumn 18, Issue 3, 2011, Pages 304-313

  Alt, Silke ^a   Burkard, Nadja ^a   Kulik, Andreas ^a   Grond, Stephanie ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOATE 3 MONOOXYGENASE; ANTIINFECTIVE AGENT; CELL SURFACE RECEPTOR; CHORISMATE PYRUVATE LYASE; CLOROBIOCIN; DNA TOPOISOMERASE (ATP HYDROLYSING); DRUG DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE; LYASE; NOVOBIOCIN; NOVOBIOCIN 401; OUTER MEMBRANE PROTEIN; PROTOCATECHUIC ACID; SIDEROPHORE RECEPTORS;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; CORYNEBACTERIUM; DISK DIFFUSION; DRUG ANTAGONISM; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; METABOLISM; MULTIGENE FAMILY; STREPTOMYCES COELICOLOR;

4-HYDROXYBENZOATE-3-MONOOXYGENASE; ANTI-BACTERIAL AGENTS; BACTERIAL OUTER MEMBRANE PROTEINS; CORYNEBACTERIUM; DISK DIFFUSION ANTIMICROBIAL TESTS; DNA GYRASE; ESCHERICHIA COLI; HYDROXYBENZOIC ACIDS; MULTIGENE FAMILY; NOVOBIOCIN; OXO-ACID-LYASES; RECEPTORS, CELL SURFACE; STREPTOMYCES COELICOLOR;

CORYNEBACTERIUM CYCLOHEXANICUM; ESCHERICHIA COLI; STAPHYLOCOCCUS AUREUS; STREPTOMYCES COELICOLOR;

EID: 79953034977     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2010.12.016     Document Type: Article

References (50)

1. J.R. Alves, A.C. Pereira, M.C. Souza, S.B. Costa, A.S. Pinto, A.L. Mattos-Guaraldi, R. Hirata-Junior, A.C. Rosa, and L.M. Asad Iron-limited condition modulates biofilm formation and interaction with human epithelial cells of enteroaggregative Escherichia coli (EAEC) J. Appl. Microbiol. 108 2010 246 255
2. C. Anderle, S. Hennig, B. Kammerer, S.M. Li, L. Wessjohann, B. Gust, and L. Heide Improved mutasynthetic approaches for the production of modified aminocoumarin antibiotics Chem. Biol. 14 2007 955 967 (Pubitemid 47268784)
3. C. Anderle, M. Stieger, M. Burrell, S. Reinelt, A. Maxwell, M. Page, and L. Heide Biological activities of novel gyrase inhibitors of the aminocoumarin class Antimicrob. Agents Chemother. 52 2008 1982 1990 (Pubitemid 351758533)
4. T. Baba, T. Ara, M. Hasegawa, Y. Takai, Y. Okumura, M. Baba, K.A. Datsenko, M. Tomita, B.L. Wanner, and H. Mori Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection Mol. Syst. Biol. 2 2006 2006 2008
5. J.M. Blair, and L.J. Piddock Structure, function and inhibition of RND efflux pumps in Gram-negative bacteria: an update Curr. Opin. Microbiol. 12 2009 512 519
6. V. Braun, and K. Hantke Mechanisms of bacterial iron transport G. Winkelmann, Microbial Transport Systems 2001 Wiley-VCH Verlag GmbH Weinheim, Germany 289 311
7. B.C. Chu, A. Garcia-Herrero, T.H. Johanson, K.D. Krewulak, C.K. Lau, R.S. Peacock, Z. Slavinskaya, and H.J. Vogel Siderophore uptake in bacteria and the battle for iron with the host; a bird's eye view Biometals 23 2010 601 611
8. J.H. Crosa, and C.T. Walsh Genetics and assembly line enzymology of siderophore biosynthesis in bacteria Microbiol. Mol. Biol. Rev. 66 2002 223 249 (Pubitemid 34625709)
9. M. Doumith, P. Weingarten, U.F. Wehmeier, K. Salah-Bey, B. Benhamou, C. Capdevila, J.M. Michel, W. Piepersberg, and M.C. Raynal Analysis of genes involved in 6-deoxyhexose biosynthesis and transfer in Saccharopolyspora erythraea Mol. Gen. Genet. 264 2000 477 485
10. A.S. Eustáquio, B. Gust, T. Luft, S.M. Li, K.F. Chater, and L. Heide Clorobiocin biosynthesis in Streptomyces. Identification of the halogenase and generation of structural analogs Chem. Biol. 10 2003 279 288 (Pubitemid 36380285)
11. A.S. Eustáquio, B. Gust, U. Galm, S.M. Li, K.F. Chater, and L. Heide Heterologous expression of novobiocin and clorobiocin biosynthetic gene clusters Appl. Environ. Microbiol. 71 2005 2452 2459 (Pubitemid 40646988)
12. 1, clorobiocin and caprazamycins in genetically modified Streptomyces coelicolor strains Biopolymers 93 2010 823 832
13. B. Floriano, and M. Bibb AfsR is a pleiotropic but conditionally required regulatory gene for antibiotic production in Streptomyces coelicolor A3(2) Mol. Microbiol. 21 1996 385 396 (Pubitemid 26291543)
14. T. Fujii, and T. Kaneda Purification and properties of NADH/NADPH-dependent p-hydroxybenzoate hydroxylase from Corynebacterium cyclohexanicum Eur. J. Biochem. 147 1985 97 104
15. U. Galm, M.A. Dessoy, J. Schmidt, L.A. Wessjohann, and L. Heide In vitro and in vivo production of new aminocoumarins by a combined biochemical, genetic, and synthetic approach Chem. Biol. 11 2004 173 183 (Pubitemid 38300288)
16. U. Galm, S. Heller, S. Shapiro, M. Page, S.M. Li, and L. Heide Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis Antimicrob. Agents Chemother. 48 2004 1307 1312 (Pubitemid 38405486)
17. J.P. Gomez-Escribano, and M. Bibb Engineering Streptomyces coelicolor for heterologous expression of secondary metabolite gene clusters Microb. Biotechnol. 2010 in press. Published online October 26, 2010. doi:10.1111/j.1751-7915.2010.00219.x
18. B. Gust Cloning and analysis of natural product pathways Methods Enzymol. 458 2009 159 180
19. B. Gust, G.L. Challis, K. Fowler, T. Kieser, and K.F. Chater PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin Proc. Natl. Acad. Sci. USA 100 2003 1541 1546 (Pubitemid 36254483)
20. L. Heide The aminocoumarins: biosynthesis and biology Nat. Prod. Rep. 26 2009 1241 1250
21. L. Heide Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins Biotechnol. Adv. 27 2009 1006 1014
22. L. Heinisch, S. Wittmann, T. Stoiber, I. Scherlitz-Hofmann, D. Ankel-Fuchs, and U. Mollmann Synthesis and biological activity of tris-and tetrakiscatecholate siderophores based on poly-aza alkanoic acids or alkylbenzoic acids and their conjugates with beta-lactam antibiotics Arzneimittelforschung 53 2003 188 195 (Pubitemid 36363615)
23. D.A. Hopwood Complex Enzymes in Microbial Natural Product Biosynthesis; Part A: Overview Articles and Peptides. Methods in Enzymology 2009 Elsevier/ Academic Press San Diego, CA
24. D.A. Hopwood Complex Enzymes in Microbial Natural Product Biosynthsis. Part B: Polyketides, Aminocoumarins and Carbohydrates. Methods in Enzymology 2009 Elsevier/ Academic Press San Diego, CA
25. D.A. Hopwood, F. Malpartida, H.M. Kieser, H. Ikeda, J. Duncan, I. Fujii, B.A. Rudd, H.G. Floss, and S. Omura Production of "hybrid" antibiotics by genetic engineering Nature 314 1985 642 644 (Pubitemid 15080845)
26. Y. Huang, K.X. Zhao, X.H. Shen, C.Y. Jiang, and S.J. Liu Genetic and biochemical characterization of a 4-hydroxybenzoate hydroxylase from Corynebacterium glutamicum Appl. Microbiol. Biotechnol. 78 2008 75 83
27. B. Kammerer, R. Kahlich, S. Laufer, S.M. Li, L. Heide, and C.H. Gleiter Mass spectrometric pathway monitoring of secondary metabolites: systematic analysis of culture extracts of Streptomyces species Anal. Biochem. 335 2004 17 29 (Pubitemid 39446226)
28. T. Kieser, M.J. Bibb, M.J. Buttner, K.F. Chater, and D.A. Hopwood Practical Streptomyces Genetics 2000 John Innes Foundation Norwich, UK
29. L.A. Kominek Biosynthesis of novobiocin by Streptomyces niveus Antimicrob. Agents Chemother. 1 1972 123 134
30. L.A. Kominek, and H.F. Meyer Novobiocic acid synthetase Methods Enzymol. 43 1975 502 508
31. P. Laurin, D. Ferroud, M. Klich, C. Dupuis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, and B. Musicki Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B Bioorg. Med. Chem. Lett. 9 1999 2079 2084 (Pubitemid 29336405)
32. T. Luft, S.M. Li, H. Scheible, B. Kammerer, and L. Heide Overexpression, purification and characterization of SimL, an amide synthetase involved in simocyclinone biosynthesis Arch. Microbiol. 183 2005 277 285 (Pubitemid 40768017)
33. Mancy, D., Ninet, L., and Preudi Homme, J. (1974). U.S. Patent 3793147.
34. A. Maxwell, and D.M. Lawson The ATP-binding site of type II topoisomerases as a target for antibacterial drugs Curr. Top. Med. Chem. 3 2003 283 303
35. R. Meganathan Ubiquinone biosynthesis in microorganisms FEMS Microbiol. Lett. 203 2001 131 139 (Pubitemid 32913605)
36. H. Merkens, G. Beckers, A. Wirtz, and A. Burkovski Vanillate metabolism in Corynebacterium glutamicum Curr. Microbiol. 51 2005 59 65 (Pubitemid 41160040)
37. M. Miethke, and M.A. Marahiel Siderophore-based iron acquisition and pathogen control Microbiol. Mol. Biol. Rev. 71 2007 413 451 (Pubitemid 47429279)
38. U. Möllmann, L. Heinisch, A. Bauernfeind, T. Kohler, and D. Ankel-Fuchs Siderophores as drug delivery agents: application of the "Trojan Horse" strategy Biometals 22 2009 615 624
39. J.B. Neilands Siderophores: structure and function of microbial iron transport compounds J. Biol. Chem. 270 1995 26723 26726
40. F. Pojer, E. Wemakor, B. Kammerer, H. Chen, C.T. Walsh, S.M. Li, and L. Heide CloQ, a prenyltransferase involved in clorobiocin biosynthesis Proc. Natl. Acad. Sci. USA 100 2003 2316 2321 (Pubitemid 36297497)
41. J. Sambrook, and D.W. Russell Molecular Cloning. A Laboratory Manual 2001 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
42. 1 biosynthetic gene cluster from Streptomyces rishiriensis DSM 40489 Eur. J. Biochem. 270 2003 4413 4419 (Pubitemid 37452517)
43. J. Shima, A. Penyige, and K. Ochi Changes in patterns of ADP-ribosylated proteins during differentiation of Streptomyces coelicolor A3(2) and its development mutants J. Bacteriol. 178 1996 3785 3790 (Pubitemid 26227193)
44. M. Siebert, A. Bechthold, M. Melzer, U. May, U. Berger, G. Schröder, J. Schröder, K. Severin, and L. Heide Ubiquinone biosynthesis. Cloning of the genes coding for chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyl transferase from Escherichia coli FEBS Lett. 307 1992 347 350
45. M. Steffensky, S.M. Li, and L. Heide Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891 J. Biol. Chem. 275 2000 21754 21760 (Pubitemid 30481885)
46. M. Steffensky, A. Mühlenweg, Z.X. Wang, S.M. Li, and L. Heide Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891 Antimicrob. Agents Chemother. 44 2000 1214 1222 (Pubitemid 30228297)
47. M. Takei, H. Fukuda, R. Kishii, and M. Hosaka Target preference of 15 quinolones against Staphylococcus aureus, based on antibacterial activities and target inhibition Antimicrob. Agents Chemother. 45 2001 3544 3547 (Pubitemid 33107875)
48. B.E. Tropp, L. Ragolia, W. Xia, W. Dowhan, R. Milkman, K.E. Rudd, R. Ivanišević, and D.J. Savić Identity of the Escherichia coli cls and nov genes J. Bacteriol. 177 1995 5155 5157
49. P.V. Viitanen, A.L. Devine, M.S. Khan, D.L. Deuel, D.E. Van Dyk, and H. Daniell Metabolic engineering of the chloroplast genome using the Echerichia coli ubiC gene reveals that chorismate is a readily abundant plant precursor for p-hydroxybenzoic acid biosynthesis Plant Physiol. 136 2004 4048 4060 (Pubitemid 41096282)
50. I. Wiegand, K. Hilpert, and R.E. Hancock Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances Nat. Protoc. 3 2008 163 175 (Pubitemid 351266501)