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J. Biol. Chem., Vol. 276, Issue 10, 7209-7217, March 9, 2001
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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 The nucleotide sequence(s) reported in this paper has been submitted to the GenBankTM/EMBL Data Bank with accession number(s) AF184977.
The dhb Operon of Bacillus subtilis
Encodes the Biosynthetic Template for the Catecholic Siderophore
2,3-Dihydroxybenzoate-Glycine-Threonine Trimeric Ester
Bacillibactin*
) 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.
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.
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