Total synthesis and structure revision of petrobactin

Bergeron, Raymond J.; Huang, Guangfei; Smith, Richard E.; Bharti, Neelam; McManis, James S.; Butler, Alison

doi:10.1016/s0040-4020(03)00103-0

Cited by 73 publications

(68 citation statements)

References 26 publications

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“…Excess iron, which cannot be bound by ferritin, is able to participate in the Haber-Weiss reaction and in turn induces oxidative stress. This production of free radicals can result in severe damage to tissue and organs and can be fatal if left untreated (Bergeron et al, 2003a). Iron chelation therapy represents an avenue of treatment for these conditions, preventing oxidative effects by removing catalytically active iron (for review, see Chaston and Richardson, 2003a).…”

Section: Iron Overload Diseasementioning

confidence: 99%

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

2005

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Section: Iron Overload Diseasementioning

confidence: 99%

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

2005

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“…This result implies that production of PB is necessary for the full pathogenicity of B. anthracis. PB, first isolated from the marine bacterium Marinobacter hydrocarbonoclasticus (12), is an unusual hexadentate citrate-and 3,4-dihydroxybenzoate-containing natural siderophore (13). To our knowledge, a complete hexadentate 3,4-catecholate siderophore has never been observed in a pathogenic bacterium other than B. anthracis and the related Bacillus cereus.…”

mentioning

confidence: 98%

Anthrax pathogen evades the mammalian immune system through stealth siderophore production

Abergel

Wilson

Arceneaux

et al. 2006

Proc. Natl. Acad. Sci. U.S.A.

182

213

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Systemic anthrax, caused by inhalation or ingestion of Bacillus anthracis spores, is characterized by rapid microbial growth stages that require iron. Tightly bound and highly regulated in a mammalian host, iron is scarce during an infection. To scavenge iron from its environment, B. anthracis synthesizes by independent pathways two small molecules, the siderophores bacillibactin (BB) and petrobactin (PB). Despite the great efficiency of BB at chelating iron, PB may be the only siderophore necessary to ensure full virulence of the pathogen. In the present work, we show that BB is specifically bound by siderocalin, a recently discovered innate immune protein that is part of an antibacterial iron-depletion defense. In contrast, neither PB nor its ferric complex is bound by siderocalin. Although BB incorporates the common 2,3-dihydroxybenzoyl iron-chelating subunit, PB is novel in that it incorporates the very unusual 3,4-dihydroxybenzoyl chelating subunit. This structural variation results in a large change in the shape of both the iron complex and the free siderophore that precludes siderocalin binding, a stealthy evasion of the immune system. Our results indicate that the blockade of bacterial siderophore-mediated iron acquisition by siderocalin is not restricted to enteric pathogenic organisms and may be a general defense mechanism against several different bacterial species. Significantly, to evade this innate immune response, B. anthracis produces PB, which plays a key role in virulence of the organism. This analysis argues for antianthrax strategies targeting siderophore synthesis and uptake.bacillibactin ͉ Bacillus anthracis ͉ petrobactin ͉ siderocalin

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“…16,17 As a result of the -hydroxy carboxylate group, the Fe(III)-complex of petrobactin is photoreactive in natural sunlight. 16,17 Recently, a Vibrio species isolated from the 4 These Gulf of Mexico after the BP oil spill was found to produce the suite of amphiphilic ochrobactins-OH siderophores, which are also photoreactive when complexed to Fe(III). 18 We report the structural characterization and iron(III) binding properties of lystabactin A, B 19 Bacterial growth was determined by measuring the optical density of the culture at 600 nm.…”

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confidence: 99%

Isolation, Structure Elucidation, and Iron-Binding Properties of Lystabactins, Siderophores Isolated from a Marine Pseudoalteromonas sp.

Zane

Butler

2013

J. Nat. Prod.

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The marine bacterium Pseudoalteromonas sp. S2B, isolated from the Gulf of Mexico after the Deepwater Horizon oil spill, was found to produce lystabactins A, B, and C (1−3), three new siderophores. The structures were elucidated through mass spectrometry, amino acid analysis, and NMR. The lystabactins are composed of serine (Ser), asparagine (Asn), two formylated/hydroxylated ornithines (FOHOrn), dihydroxy benzoic acid (Dhb), and a very unusual nonproteinogenic amino acid, 4,8-diamino-3-hydroxyoctanoic acid (LySta). The iron-binding properties of the compounds were investigated through a spectrophotometric competition.

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Total synthesis and structure revision of petrobactin

Cited by 73 publications

References 26 publications

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

Anthrax pathogen evades the mammalian immune system through stealth siderophore production

Isolation, Structure Elucidation, and Iron-Binding Properties of Lystabactins, Siderophores Isolated from a Marine Pseudoalteromonas sp.

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