|
Originally published In Press as doi:10.1074/jbc.M009140200 on December 8, 2000
J. Biol. Chem., Vol. 276, Issue 10, 7209-7217, March 9, 2001
The dhb Operon of Bacillus subtilis
Encodes the Biosynthetic Template for the Catecholic Siderophore
2,3-Dihydroxybenzoate-Glycine-Threonine Trimeric Ester
Bacillibactin*
Jürgen J.
May,
Thomas M.
Wendrich, and
Mohamed A.
Marahiel
From the Department of Chemistry, Philipps-Universität
Marburg, D-35032 Marburg, Germany
Bacillus subtilis was reported
to produce the catecholic siderophore itoic acid (2,3-dihydroxybenzoate
(DHB)-glycine) in response to iron deprivation. However, by inspecting
the DNA sequences of the genes dhbE, dhbB, and
dhbF as annotated by the B. subtilis genome
project to encode the synthetase complex for the siderophore assembly, various sequence errors within the dhbF gene were
predicted and confirmed by re-sequencing. According to the corrected
sequence, dhbF encodes a dimodular instead of a monomodular
nonribosomal peptide synthetase. We have heterologously expressed,
purified, and assayed the substrate selectivity of the recombinant
proteins DhbB, DhbE, and DhbF. DhbE, a stand-alone adenylation domain
of 59.9 kDa, activates, in an ATP-dependent reaction, DHB,
which is subsequently transferred to the free thiol group of the
cofactor phosphopantetheine of the bifunctional isochorismate
lyase/aryl carrier protein DhbB. The third synthetase, DhbF, is a
dimodular nonribosomal peptide synthetase of 264 kDa that specifically
adenylates threonine and, to a lesser extent, glycine and that
covalently loads both amino acids onto their corresponding peptidyl
carrier domains. To functionally link the dhb gene cluster
to siderophore synthesis, we have disrupted the dhbF gene.
Comparative mass spectrometric analysis of culture extracts from both
the wild type and the dhbF mutant led to the identification
of a mass peak at m/z 881 ([M-H]1 ) that
corresponds to a cyclic trimeric ester of
DHB-glycine-threonine.
*
This work was supported by the Deutsche
Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the
Graduiertenkolleg "Proteinfunktion auf atomarer Ebene."The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AF184977.
To whom correspondence should be addressed. Tel.:
49-6421-282-5722; Fax: 49-6421-282-2191; E-mail:
marahiel@chemie.uni-marburg.de.
Copyright © 2001 by The American Society for Biochemistry and Molecular Biology, Inc.

CiteULike Complore Connotea Del.icio.us Digg Reddit Technorati What's this?
This article has been cited by other articles:

|
 |

|
 |
 
Z. Xiong, Y. Jiang, D. Qi, H. Lu, F. Yang, J. Yang, L. Chen, L. Sun, X. Xu, Y. Xue, et al.
Complete Genome Sequence of the Extremophilic Bacillus cereus Strain Q1 with Industrial Applications
J. Bacteriol.,
February 1, 2009;
191(3):
1120 - 1121.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
E. J. Dimise, P. F. Widboom, and S. D. Bruner
Structure elucidation and biosynthesis of fuscachelins, peptide siderophores from the moderate thermophile Thermobifida fusca
PNAS,
October 7, 2008;
105(40):
15311 - 15316.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Miethke, S. Schmidt, and M. A. Marahiel
The Major Facilitator Superfamily-Type Transporter YmfE and the Multidrug-Efflux Activator Mta Mediate Bacillibactin Secretion in Bacillus subtilis
J. Bacteriol.,
August 1, 2008;
190(15):
5143 - 5152.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. A. Fischbach, C. T. Walsh, and J. Clardy
Chemical Ecology Special Feature: The evolution of gene collectives: How natural selection drives chemical innovation
PNAS,
March 25, 2008;
105(12):
4601 - 4608.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. Miranda-CasoLuengo, J. F. Prescott, J. A. Vazquez-Boland, and W. G. Meijer
The Intracellular Pathogen Rhodococcus equi Produces a Catecholate Siderophore Required for Saprophytic Growth
J. Bacteriol.,
March 1, 2008;
190(5):
1631 - 1637.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. J. Siezen, M. J. C. Starrenburg, J. Boekhorst, B. Renckens, D. Molenaar, and J. E. T. van Hylckama Vlieg
Genome-Scale Genotype-Phenotype Matching of Two Lactococcus lactis Isolates from Plants Identifies Mechanisms of Adaptation to the Plant Niche
Appl. Envir. Microbiol.,
January 15, 2008;
74(2):
424 - 436.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Miethke and M. A. Marahiel
Siderophore-Based Iron Acquisition and Pathogen Control
Microbiol. Mol. Biol. Rev.,
September 1, 2007;
71(3):
413 - 451.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
A. D. Berti, N. J. Greve, Q. H. Christensen, and M. G. Thomas
Identification of a Biosynthetic Gene Cluster and the Six Associated Lipopeptides Involved in Swarming Motility of Pseudomonas syringae pv. tomato DC3000
J. Bacteriol.,
September 1, 2007;
189(17):
6312 - 6323.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
G.-L. Tang, Y.-Q. Cheng, and B. Shen
Chain Initiation in the Leinamycin-producing Hybrid Nonribosomal Peptide/Polyketide Synthetase from Streptomyces atroolivaceus S-140: DISCRETE, MONOFUNCTIONAL ADENYLATION ENZYME AND PEPTIDYL CARRIER PROTEIN THAT DIRECTLY LOAD D-ALANINE
J. Biol. Chem.,
July 13, 2007;
282(28):
20273 - 20282.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
K. D. Passalacqua, N. H. Bergman, J. Y. Lee, D. H. Sherman, and P. C. Hanna
The Global Transcriptional Responses of Bacillus anthracis Sterne (34F2) and a {Delta}sodA1 Mutant to Paraquat Reveal Metal Ion Homeostasis Imbalances during Endogenous Superoxide Stress
J. Bacteriol.,
June 1, 2007;
189(11):
3996 - 4013.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Miethke, H. Westers, E.-J. Blom, O. P. Kuipers, and M. A. Marahiel
Iron Starvation Triggers the Stringent Response and Induces Amino Acid Biosynthesis for Bacillibactin Production in Bacillus subtilis
J. Bacteriol.,
December 15, 2006;
188(24):
8655 - 8657.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. J. Abergel, M. K. Wilson, J. E. L. Arceneaux, T. M. Hoette, R. K. Strong, B. R. Byers, and K. N. Raymond
Anthrax pathogen evades the mammalian immune system through stealth siderophore production
PNAS,
December 5, 2006;
103(49):
18499 - 18503.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
J. Ollinger, K.-B. Song, H. Antelmann, M. Hecker, and J. D. Helmann
Role of the Fur Regulon in Iron Transport in Bacillus subtilis.
J. Bacteriol.,
May 1, 2006;
188(10):
3664 - 3673.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
J. Grunewald and M. A. Marahiel
Chemoenzymatic and Template-Directed Synthesis of Bioactive Macrocyclic Peptides
Microbiol. Mol. Biol. Rev.,
March 1, 2006;
70(1):
121 - 146.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Zhu, M. Valdebenito, G. Winkelmann, and K. Hantke
Functions of the siderophore esterases IroD and IroE in iron-salmochelin utilization
Microbiology,
July 1, 2005;
151(7):
2363 - 2372.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Ehling-Schulz, N. Vukov, A. Schulz, R. Shaheen, M. Andersson, E. Martlbauer, and S. Scherer
Identification and Partial Characterization of the Nonribosomal Peptide Synthetase Gene Responsible for Cereulide Production in Emetic Bacillus cereus
Appl. Envir. Microbiol.,
January 1, 2005;
71(1):
105 - 113.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. Annamalai, B. Jin, Z. Cao, S. M. C. Newton, and P. E. Klebba
Recognition of Ferric Catecholates by FepA
J. Bacteriol.,
June 1, 2004;
186(11):
3578 - 3589.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
S. A. Sieber and M. A. Marahiel
Learning from Nature's Drug Factories: Nonribosomal Synthesis of Macrocyclic Peptides
J. Bacteriol.,
December 15, 2003;
185(24):
7036 - 7043.
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
L. Steil, T. Hoffmann, I. Budde, U. Volker, and E. Bremer
Genome-Wide Transcriptional Profiling Analysis of Adaptation of Bacillus subtilis to High Salinity
J. Bacteriol.,
November 1, 2003;
185(21):
6358 - 6370.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. M. Berka, X. Cui, and C. Yanofsky
Genomewide transcriptional changes associated with genetic alterations and nutritional supplementation affecting tryptophan metabolism in Bacillus subtilis
PNAS,
May 13, 2003;
100(10):
5682 - 5687.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
K. N. Raymond, E. A. Dertz, and S. S. Kim
Bioinorganic Chemistry Special Feature: Enterobactin: An archetype for microbial iron transport
PNAS,
April 1, 2003;
100(7):
3584 - 3588.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
R. Finking, J. Solsbacher, D. Konz, M. Schobert, A. Schafer, D. Jahn, and M. A. Marahiel
Characterization of a New Type of Phosphopantetheinyl Transferase for Fatty Acid and Siderophore Synthesis in Pseudomonas aeruginosa
J. Biol. Chem.,
December 20, 2002;
277(52):
50293 - 50302.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
J. J. May, N. Kessler, M. A. Marahiel, and M. T. Stubbs
Crystal structure of DhbE, an archetype for aryl acid activating domains of modular nonribosomal peptide synthetases
PNAS,
September 17, 2002;
99(19):
12120 - 12125.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
J. H. Crosa and C. T. Walsh
Genetics and Assembly Line Enzymology of Siderophore Biosynthesis in Bacteria
Microbiol. Mol. Biol. Rev.,
June 1, 2002;
66(2):
223 - 249.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
T. Hoffmann, A. Schutz, M. Brosius, A. Volker, U. Volker, and E. Bremer
High-Salinity-Induced Iron Limitation in Bacillus subtilis
J. Bacteriol.,
February 1, 2002;
184(3):
718 - 727.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
M. Ogura, H. Yamaguchi, K.-i. Yoshida, Y. Fujita, and T. Tanaka
DNA microarray analysis of Bacillus subtilis DegU, ComA and PhoP regulons: an approach to comprehensive analysis of B.subtilis two-component regulatory systems
Nucleic Acids Res.,
September 15, 2001;
29(18):
3804 - 3813.
[Abstract]
[Full Text]
[PDF]
|
 |
|

|
 |

|
 |
 
H. D. Mootz, R. Finking, and M. A. Marahiel
4'-Phosphopantetheine Transfer in Primary and Secondary Metabolism of Bacillus subtilis
J. Biol. Chem.,
September 28, 2001;
276(40):
37289 - 37298.
[Abstract]
[Full Text]
[PDF]
|
 |
|
Copyright © 2001 by the American Society for Biochemistry and Molecular Biology.
|
Advertisement
Advertisement
|