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Papers In Press, published online ahead of print December 8, 2000
Chemistry, Philipps-University Marburg, Marburg 35032
Corresponding Author: marahiel{at}chemie.uni-marburg.de
Bacillus subtilis was reported to produce the catecholic siderophore itoic acid (2,3-dihydroxybenzoate-glycine) in response to iron deprivation. However, by inspecting the DNA sequence 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 monomodular nonribosomal peptide synthetase (NRPS). 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 2,3?dihydroxybenzoate (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 NRPS of 264 kDa, that specifically adenylates threonine and to a lower extent glycine and 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 wild type and the dhbF mutant led to the identification (only in wild type siderophore active extract) of a mass peak of m/z 881 [M-H]1- that corresponds to a cyclic trimeric ester of 2,3-DHB-glycine-threonine.
J. Biol. Chem, 10.1074/jbc.M009140200
Submitted on October 6, 2000
Revised on December 6, 2000
Accepted on December 8, 2000
The dhb Operon of Bacillus subtilis encodes the biosynthetic template for the catecholic siderophore 2,3-dihydroxybenzoate-glycine-threonine trimeric ester bacillibactin
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