Inhibition of aryl acid adenylation domains involved in bacterial siderophore synthesis

FEBS Journal

Volumn 273, Issue 2, 2006, Pages 409-419

  Miethke, Marcus ^a   Bisseret, Philippe ^b   Beckering, Carsten L ^a   Vignard, David ^b   Eustache, Jacques ^b   Marahiel, Mohamed A ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

Aryl acid adenylation domain; Enzyme inhibition; Iron limitation; Pathogenicity; Siderophore

Indexed keywords

2,3 DIHYDROXYBENZOIC ACID; 5' O [N (2 FLUOROBENZOYL)HYDROXAMOYL]ADENOSINE; 5' O [N (2 FLUOROBENZOYL)SULFAMOYL]ADENOSINE; 5' O [N (2,3 DIHYDROXYBENZOYL)SULFAMOYL]ADENOSINE; 5' O [N (BENZOYL)HYDROXAMOYL]ADENOSINE; 5' O [N (BENZOYL)SULFAMOYL]ADENOSINE; 5' O [N (SALICYL)SULFAMOYL]ADENOSINE; ADENOSINE DERIVATIVE; ANTIINFECTIVE AGENT; BACILLIBACTIN; BACTERIAL PROTEIN; IRON; SIDEROPHORE; SULFONAMIDE; UNCLASSIFIED DRUG; YERSINIABACTIN;

ADENYLATION; ARTICLE; CHEMICAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; PATHOGENICITY; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN SYNTHESIS;

ADENOSINE MONOPHOSPHATE; AMINO ACID SEQUENCE; BACTERIAL PROTEINS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; SIDEROPHORES; YERSINIA PESTIS;

ANIMALIA; BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS; YERSINIA PESTIS;

EID: 33645032211     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2005.05077.x     Document Type: Article

References (26)

1. Neilands JB 1981 Microbial iron compounds Annu Rev Biochem 50 715 731
2. Wandersman C Delepelaire P 2004 Bacterial iron sources: from siderophores to hemophores Annu Rev Microbiol 58 611 647
3. Ratledge C Dover LG 2000 Iron metabolism in pathogenic bacteria Annu Rev Microbiol 54 881 941
4. Challis GL 2005 A widely distributed bacterial pathway for siderophore biosynthesis independent of nonribosomal peptide synthetases Chembiochem 6 601 611
5. Quadri LEN 2000 Assembly of aryl-capped siderophores by modular peptide synthetases and polyketide synthases Mol Microbiol 37 1 12
6. Crosa JH Walsh CT 2002 Genetics and assembly line enzymology of siderophore biosynthesis in bacteria Microbiol Mol Biol Rev 66 223 249
7. May JJ Kessler N Marahiel MA Stubbs MT 2002 Crystal structure of DhbE, an archetype for aryl acid activating domains of modular nonribosomal peptide synthetases Proc Natl Acad Sci USA 99 12120 12125
8. Ferreras JA Ryu JS Di Lello F Tan DS Quadri LEN 2005 Small-molecule inhibition of siderophore biosynthesis in Mycobacterium tuberculosis and Yersinia pestis Nature Chem Biol 1 29 32
9. May JJ Wendrich TM Marahiel MA 2001 The dhb operon of Bacillus subtilis encodes the biosynthetic template for the catecholic siderophore 2,3-dihydroxybenzoate-glycine-threonine trimeric ester bacillibactin J Biol Chem 276 7209 7217
10. Hantke K Nicholson G Rabsch W Winkelmann G 2003 Salmochelins, siderophores of Salmonella enterica and uropathogenic Escherichia coli strains, are recognized by the outer membrane receptor IroN Proc Natl Acad Sci USA 100 3677 3682
11. Rabsch W Methner U Voigt W Tschape H Reissbrodt R Williams PH 2003 Role of receptor proteins for enterobactin and 2,3-dihydroxybenzoylserine in virulence of Salmonella enterica Infect Immun 71 6953 6961
12. Henderson DP Payne SM 1994 Vibrio cholerae iron transport systems: roles of heme and siderophore iron transport in virulence and identification of a gene associated with multiple iron transport systems Infect Immun 62 5120 5125
13. Gehring AM Mori I Perry RD Walsh CT 1998 The nonribosomal peptide synthetase HMWP2 forms a thiazoline ring during biogenesis of yersiniabactin, an iron-chelating virulence factor of Yersinia pestis Biochemistry 37 11637 11650
14. Stachelhaus T Mootz HD Marahiel MA 1999 The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases Chem Biol 6 493 505
15. Kim S Lee SW Choi EC Choi SY 2003 Aminoacyl-tRNA synthetases and their inhibitors as a novel family of antibiotics Appl Microbiol Biotechnol 61 278 288
16. Forrest AK Jarvest RL Mensah LM O'Hanlon PJ Pope AJ Sheppard RJ 2000 Aminoalkyl adenylate and aminoacyl sulfamate intermediate analogues differing greatly in affinity for their cognate Staphylococcus aureus aminoacyl tRNA synthetases Bioorg Med Chem Lett 10 1871 1874
17. Finking R Neumüller A Solsbacher J Konz D Kretzschmar G Schweitzer M Krumm T Marahiel MA 2003 Aminoacyl adenylate substrate analogues for the inhibition of adenylation domains of nonribosomal peptide synthetases Chembiochem 4 903 906
18. May JJ Finking R Wiegeshoff F Weber TT Bandur N Koert U Marahiel MA 2005 Inhibition of the d -alanine: d -alanyl carrier protein ligase from Bacillus subtilis increases the bacterium's susceptibility to antibiotics that target the cell wall FEBS J 272 2993 3003
19. Heacock D Forsyth CJ Shiba K Musier-Forsyth K 1996 Synthesis and aminoacyl-tRNA synthetase inhibitory activity of prolyl adenylate analogs Bioorg Chem 24 273 289
20. Castro-Pichel J Garcia-Lopez MT De Las Heras FG 1987 A facile synthesis of ascamycin and related analogues Tetrahedron 43 383 389
21. Lee J Kim SE Lee JY Kim SY Kang SU Seo SH Chun MW Kang T Choi SY Kim HO 2003 N-Alkoxysulfamide, N-hydroxysulfamide, and sulfamate analogues of methionyl and isoleucyl adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases Bioorg Med Chem Lett 13 1087 1092
22. Ward JL Beale MH 1995 Caged plant hormones Phytochemistry 38 811 816
23. Sengle G Jenne A Arora PS Seelig B Nowick JS Jaschke A Famulok M 2000 Synthesis, incorporation efficiency, and stability of disulfide bridged functional groups at RNA 5′-ends Bioorg Med Chem 8 1317 1329
24. McMurry TJ Rodgers SJ Raymond KN 1987 Template and stepwise syntheses of a macrobicyclic catechoylamide ferric ion sequestering agent J Am Chem Soc 109 3451 3453
25. Amos RA Emblidge RW Havens N 1983 Esterification using a polymer-supported phosphine reagent J Org Chem 48 3598 3600
26. Linne U Marahiel MA 2004 Reactions catalyzed by mature and recombinant nonribosomal peptide synthetases Methods Enzymol 388 293 315