{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T23:58:25Z","timestamp":1790985505544,"version":"4.1.0"},"reference-count":34,"publisher":"American Society for Microbiology","issue":"5","license":[{"start":{"date-parts":[[2007,3,1]],"date-time":"2007-03-01T00:00:00Z","timestamp":1172707200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.asm.org\/non-commercial-tdm-license"}],"content-domain":{"domain":["journals.asm.org"],"crossmark-restriction":true},"short-container-title":["J Bacteriol"],"published-print":{"date-parts":[[2007,3]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n          <jats:p>\n            The\n            <jats:italic>asbABCDEF<\/jats:italic>\n            gene cluster from\n            <jats:italic>Bacillus anthracis<\/jats:italic>\n            is\nresponsible for biosynthesis of petrobactin, a catecholate siderophore\nthat functions in both iron acquisition and virulence in a murine model\nof anthrax. We initiated studies to determine the biosynthetic details\nof petrobactin assembly based on mutational analysis of the\n            <jats:italic>asb<\/jats:italic>\n            operon, identification of accumulated intermediates, and\naddition of exogenous siderophores to\n            <jats:italic>asb<\/jats:italic>\n            mutant strains. As a\nstarting point, in-frame deletions of each of the genes in the\n            <jats:italic>asb<\/jats:italic>\n            locus (\n            <jats:italic>asbABCDEF<\/jats:italic>\n            ) were constructed. The\nindividual mutations resulted in complete abrogation of petrobactin\nbiosynthesis when strains were grown on iron-depleted medium. However,\nin vitro analysis showed that each\n            <jats:italic>asb<\/jats:italic>\n            mutant grew to a very\nlimited extent as vegetative cells in iron-depleted medium. In\ncontrast, none of the\n            <jats:italic>B. anthracis asb<\/jats:italic>\n            mutant strains were\nable to outgrow from spores under the same culture conditions.\nProvision of exogenous petrobactin was able to rescue the growth defect\nin each\n            <jats:italic>asb<\/jats:italic>\n            mutant strain. Taken together, these data provide\ncompelling evidence that AsbA performs the penultimate step in the\nbiosynthesis of petrobactin, involving condensation of\n3,4-dihydroxybenzoyl spermidine with citrate to form\n3,4-dihydroxybenzoyl spermidinyl citrate. As a final step, the\ndata reveal that AsbB catalyzes condensation of a second molecule of\n3,4-dihydroxybenzoyl spermidine with 3,4-dihydroxybenzoyl spermidinyl\ncitrate to form the mature siderophore. This work sets the stage for\ndetailed biochemical studies with this unique acyl carrier\nprotein-dependent, nonribosomal peptide synthetase-independent\nbiosynthetic\nsystem.\n          <\/jats:p>","DOI":"10.1128\/jb.01526-06","type":"journal-article","created":{"date-parts":[[2006,12,23]],"date-time":"2006-12-23T01:34:25Z","timestamp":1166837665000},"page":"1698-1710","update-policy":"https:\/\/doi.org\/10.1128\/asmj-crossmark-policy-page","source":"Crossref","is-referenced-by-count":114,"title":["Biosynthetic Analysis of the Petrobactin Siderophore Pathway from\n            <i>Bacillusanthracis<\/i>"],"prefix":"10.1128","volume":"189","author":[{"given":"Jung Yeop","family":"Lee","sequence":"first","affiliation":[{"name":"Life Sciences Institute and Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brian K.","family":"Janes","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karla D.","family":"Passalacqua","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brian F.","family":"Pfleger","sequence":"additional","affiliation":[{"name":"Life Sciences Institute and Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicholas H.","family":"Bergman","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology"},{"name":"Bioinformatics Program, University of Michigan Medical School, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haichuan","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kristina","family":"Ha\u030akansson","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ravindranadh V.","family":"Somu","sequence":"additional","affiliation":[{"name":"Center for Drug Design, Academic Health Center, University of\rMinnesota, Minneapolis, Minnesota 55455"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Courtney C.","family":"Aldrich","sequence":"additional","affiliation":[{"name":"Center for Drug Design, Academic Health Center, University of\rMinnesota, Minneapolis, Minnesota 55455"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen","family":"Cendrowski","sequence":"additional","affiliation":[{"name":"Medical Technology Program and Department of Microbiology and Molecular\rGenetics, Michigan State University, East Lansing, Michigan\r48824"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philip C.","family":"Hanna","sequence":"additional","affiliation":[{"name":"Department of Microbiology and Immunology"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David H.","family":"Sherman","sequence":"additional","affiliation":[{"name":"Life Sciences Institute and Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"235","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1021\/ja0119088","volume":"124","year":"2002","unstructured":"Barbeau, K., G. Zhang, D. H. Live, and A. Butler. 2002 . Petrobactin, a photoreactive siderophore produced by the oil-degrading marine bacterium Marinobacter hydrocarbonoclasticus. J. Am. Chem. Soc. 124 : 378-379.","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_3_2_3_2","doi-asserted-by":"crossref","first-page":"2007","DOI":"10.1016\/S0040-4020(03)00103-0","volume":"59","year":"2003","unstructured":"Bergeron, R. J., G. Huang, R. E. Smith, N. Bharti, J. S. McManis, and A. Butler. 2003. Total synthesis and structure revision of petrobactin.Tetrahedron 59 : 2007-2014.","journal-title":"Tetrahedron"},{"key":"e_1_3_2_4_2","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1078\/1438-4221-00103","volume":"291","year":"2001","unstructured":"Braun, V. 2001. Iron uptake mechanisms and their regulation in pathogenic bacteria. Int. J. Med. Microbiol. 291 : 67-79.","journal-title":"Int. J. Med. Microbiol."},{"key":"e_1_3_2_5_2","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1099\/jmm.0.46386-0","volume":"55","year":"2006","unstructured":"Bullen, J. J., H. J. Rogers, P. B. Spalding, and C. G. Ward. 2006. Natural resistance, iron and infection: a challenge for clinical medicine. J. Med. Microbiol. 55 : 251-258.","journal-title":"J. Med. Microbiol."},{"key":"e_1_3_2_6_2","doi-asserted-by":"crossref","first-page":"407","DOI":"10.1046\/j.1365-2958.2003.03861.x","volume":"51","year":"2004","unstructured":"Cendrowski, S., W. MacArthur, and P. Hanna. 2004. Bacillus anthracis requires siderophore biosynthesis for growth in macrophages and mouse virulence. Mol. Microbiol. 51 : 407-417.","journal-title":"Mol. Microbiol."},{"key":"e_1_3_2_7_2","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1002\/cbic.200400283","volume":"6","year":"2005","unstructured":"Challis, G. L. 2005. A widely distributed bacterial pathway for siderophore biosynthesis independent of nonribosomal peptide synthetases. ChemBioChem 6 : 601-611.","journal-title":"ChemBioChem"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1128\/MMBR.66.2.223-249.2002"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.165.2.570-578.1986"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.167.1.350-355.1986"},{"key":"e_1_3_2_11_2","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1056\/NEJM199909093411107","volume":"341","year":"1999","unstructured":"Dixon, T. C., M. Meselson, J. Guillemin, and P. C. Hanna. 1999. Anthrax. N. Engl. J. Med. 341 : 815-826.","journal-title":"N. Engl. J. Med."},{"key":"e_1_3_2_12_2","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1016\/S0378-1119(98)00544-7","volume":"226","year":"1999","unstructured":"Dunn, A. K., and J. Handelsman. 1999. A vector for promoter trapping in Bacillus cereus.Gene 226 : 297-305.","journal-title":"Gene"},{"key":"e_1_3_2_13_2","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1038\/nchembio706","volume":"1","year":"2005","unstructured":"Ferreras, J. A., J. S. Ryu, F. Di Lello, D. S. Tan, and L. E. Quadri. 2005. Small-molecule inhibition of siderophore biosynthesis in Mycobacterium tuberculosis and Yersinia pestis. Nat. Chem. Biol. 1 : 29-32.","journal-title":"Nat. Chem. Biol."},{"key":"e_1_3_2_14_2","doi-asserted-by":"crossref","first-page":"8019","DOI":"10.1016\/S0040-4039(00)78412-7","volume":"35","year":"1994","unstructured":"Frigerio, M., and M. Santagostinoand. 1994. A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO.Tetrahedron Lett. 35 : 8019-8022.","journal-title":"Tetrahedron Lett."},{"key":"e_1_3_2_15_2","doi-asserted-by":"crossref","first-page":"4537","DOI":"10.1021\/jo9824596","volume":"64","year":"1999","unstructured":"Frigerio, M., M. Santagostino, and S. Sputore. 1999. A user-friendly entry to 2-iodoxybenzoic acid (IBX). J. Org. Chem. 64 : 4537-4538.","journal-title":"J. Org. Chem."},{"key":"e_1_3_2_16_2","first-page":"3530","volume":"60","year":"2004","unstructured":"Gardner, R. A., R. Kinkade, C. Wang, and O. Phanstiel IV. 2004 . Total synthesis of petrobactin and its homologues as potential growth stimuli for Marinobacter hydrocarbonoclasticus, an oil-degrading bacteria. J. Org. Chem. 60 : 3530-3537.","journal-title":"J. Org. Chem."},{"key":"e_1_3_2_17_2","first-page":"89","volume":"49","year":"2004","unstructured":"Garner, B. L., J. E. L. Arceneaux, and B. R. Byers. 2004. Temperature control of a 3,4-dihydroxybenzoate (protocatechuate)-based siderophore in Bacillus anthracis. Curr. Microbiol. 49 : 89-94.","journal-title":"Curr. Microbiol."},{"key":"e_1_3_2_18_2","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1007\/BF00329663","volume":"209","year":"1987","unstructured":"Haima, P., S. Bron, and G. Venema. 1987. The effect of restriction on shotgun cloning and plasmid stability in Bacillus subtilis Marburg. Mol. Gen. Genet. 209 : 335-342.","journal-title":"Mol. Gen. Genet."},{"key":"e_1_3_2_19_2","doi-asserted-by":"crossref","first-page":"1897","DOI":"10.1021\/np049823i","volume":"67","year":"2004","unstructured":"Hickford, S. J., F. C. K\u00fcpper, G. Zhang, C. J. Carrano, J. W. Blunt, and A. Butler. 2004 . Petrobactin sulfonate, a new siderophore produced by the marine bacterium Marinobacter hydrocarbonoclasticus.J. Nat. Prod. 67 : 1897-1899.","journal-title":"J. Nat. Prod."},{"key":"e_1_3_2_20_2","doi-asserted-by":"crossref","first-page":"2236","DOI":"10.1001\/jama.287.17.2236","volume":"287","year":"2002","unstructured":"Inglesby, T. V., T. O'Toole, D. A. Henderson, J. G. Bartlett, M. S. Ascher, E. Eitzen, A. M. Friedlander, J. Gerberding, J. Hauer, J. Hughes, J. McDade, M. T. Osterholm, G. Parker, T. M. Perl, P. K. Russell, and K. Tonat. 2002. Anthrax as a biological weapon, 2002, updated recommendations for management.JAMA 287 : 2236-2252.","journal-title":"JAMA"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1128\/IAI.70.10.5870-5872.2002"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.1128\/IAI.74.3.1949-1953.2006"},{"key":"e_1_3_2_23_2","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1007\/s00284-005-0400-8","volume":"53","year":"2006","unstructured":"Joshi, F., G. Archana, and A. Desai. 2006. Siderophore cross-utilization amongst rhizospheric bacteria and the role of their differential affinities for Fe(3+) on growth stimulation under iron-limited conditions. Curr. Microbiol. 53 : 141-147.","journal-title":"Curr. Microbiol."},{"key":"e_1_3_2_24_2","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1007\/s10534-005-1782-6","volume":"18","year":"2005","unstructured":"Koppisch, A. T., C. C. Browder, A. L. Moe, J. T. Shelley, B. A. Kinkel, L. E. Hersman, S. Iyer, and C. E. Ruggiero. 2005. Petrobactin is the primary siderophore synthesized by Bacillus anthracis str. Sterne under conditions of iron starvation. Biometals 18 : 577-585.","journal-title":"Biometals"},{"key":"e_1_3_2_25_2","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1016\/S0923-2508(01)01200-1","volume":"152","year":"2001","unstructured":"K\u00f6ster, W. 2001. ABC transporter-mediated uptake of iron, siderophores, heme and vitamin B12. Res. Microbiol. 152 : 291-301.","journal-title":"Res. Microbiol."},{"key":"e_1_3_2_26_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt833"},{"key":"e_1_3_2_27_2","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1111\/j.1742-4658.2005.05077.x","volume":"273","year":"2006","unstructured":"Miethke, M., P. Bisseret, C. L. Beckering, D. Vignard, J. Eustache, and M. A. Marahiel. 2006. Inhibition of aryl acid adenylation domains involved in bacterial siderophore synthesis.FEBS J. 273 : 409-413.","journal-title":"FEBS J."},{"key":"e_1_3_2_28_2","doi-asserted-by":"crossref","first-page":"2453","DOI":"10.1021\/ol050773y","volume":"7","year":"2005","unstructured":"Movassaghi, M., and M. A. Schmidt. 2005. N-heterocyclic carbene-catalyzed amidation of unactivated esters with amino alcohols.Org. Lett. 7 : 2453-2456.","journal-title":"Org. Lett."},{"key":"e_1_3_2_29_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.00239-06"},{"key":"e_1_3_2_30_2","unstructured":"Biochemistry 2007"},{"key":"e_1_3_2_31_2","doi-asserted-by":"crossref","first-page":"881","DOI":"10.1146\/annurev.micro.54.1.881","volume":"54","year":"2000","unstructured":"Ratledge, C., and L. G. Dover. 2000. Iron metabolism in pathogenic bacteria. Annu. Rev. Microbiol. 54 : 881-941.","journal-title":"Annu. Rev. Microbiol."},{"key":"e_1_3_2_32_2","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1021\/jm051060o","volume":"49","year":"2006","unstructured":"Somu, R. V., H. Boshoff, C. Qiao, E. M. Bennett, C. E. Barry III, and C. C. Aldrich. 2006 . Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis. J. Med. Chem. 49 : 31-34.","journal-title":"J. Med. Chem."},{"key":"e_1_3_2_33_2","first-page":"313","volume":"13","year":"1939","unstructured":"Sterne, M. 1939. The immunization of laboratory animals against anthrax. Onderstepoort J. Vet. Sci. Anim. Ind. 13 : 313-317.","journal-title":"Onderstepoort J. Vet. Sci. Anim. Ind."},{"key":"e_1_3_2_34_2","doi-asserted-by":"publisher","DOI":"10.1128\/mr.42.1.45-66.1978"},{"key":"e_1_3_2_35_2","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1016\/j.bbrc.2006.07.055","volume":"348","year":"2006","unstructured":"Wilson, M. K., R. J. Abergel, K. N. Raymond, J. E. L. Arceneaux, and B. R. Byers. 2006 . Siderophores of Bacillus anthracis, Bacillus cereus, and Bacillus thuringiensis.Biochem. Biophys. Res. Commun. 348 : 320-325.","journal-title":"Biochem. Biophys. Res. Commun."}],"container-title":["Journal of Bacteriology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/journals.asm.org\/doi\/pdf\/10.1128\/JB.01526-06","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.asm.org\/doi\/pdf\/10.1128\/JB.01526-06","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,7,29]],"date-time":"2021-07-29T17:38:38Z","timestamp":1627580318000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.asm.org\/doi\/10.1128\/JB.01526-06"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,3]]},"references-count":34,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2007,3]]}},"alternative-id":["10.1128\/JB.01526-06"],"URL":"https:\/\/doi.org\/10.1128\/jb.01526-06","relation":{},"ISSN":["0021-9193","1098-5530"],"issn-type":[{"value":"0021-9193","type":"print"},{"value":"1098-5530","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,3]]},"assertion":[{"value":"2006-09-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2006-12-14","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-12-20","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}