On the origin of amphi-enterobactin fragments produced by Vibrio campbellii species

Jelowicki, Aneta M.; Butler, Alison

doi:10.1007/s00775-022-01949-0

Cited by 4 publications

(3 citation statements)

References 15 publications

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“…The Ser-DHB on the TE domain then engages with newly synthesized Ser-DHB on the CPC domain to form a dimer on the TE domain of EntF . Interestingly, at this point, there is no self-cleavage to form the cyclic dimer natural product, however this dimer can be detected by tandem mass spectroscopy analysis . This process repeats itself to finally furnish a trimer on the TE domain which is then terminated via an intramolecular cyclization to produce Ent.…”

Section: Catecholate and Phenolate Siderophores: Enterobactinmentioning

confidence: 96%

“…14 Interestingly, at this point, there is no self-cleavage to form the cyclic dimer natural product, however this dimer can be detected by tandem mass spectroscopy analysis. 81 This process repeats itself to finally furnish a trimer on the TE domain which is then terminated via an intramolecular cyclization to produce Ent. The genes encoding for the biosynthesis ((entC, entB, entA, entE, entD, and entF), cellular intake (FepA, FepB, FepC, FepD, FepG) and degradation (fes) are all clustered together (Figure 14c).…”

Section: Siderophores: Enterobactinmentioning

confidence: 99%

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Siderophores: A Case Study in Translational Chemical Biology

LeBlanc,

Wuest

2024

Biochemistry

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Siderophores are metal-binding secondary metabolites that assist in iron homeostasis and have been of interest to the scientific community for the last half century. Foundational siderophore research has enabled several translational applications including siderophore-antibiotic and siderophorepeptide conjugates, identification of new antimicrobial targets, advances in disease imaging, and novel therapeutics. This review aims to connect the basic science research (biosynthesis, cellular uptake, gene regulation, and effects on homeostasis) of well-known siderophores with the successive translational application that results. Intertwined throughout are connections to the career of Christopher T. Walsh, his impact on the field of chemical biology, and the legacy of his trainees who continue to innovate.

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Section: Catecholate and Phenolate Siderophores: Enterobactinmentioning

confidence: 96%

Section: Siderophores: Enterobactinmentioning

confidence: 99%

Siderophores: A Case Study in Translational Chemical Biology

LeBlanc,

Wuest

2024

Biochemistry

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“…1) [12]. AebF (V. campbellii BAA1116) is 36% identical to EntF (E. coli UTI89) and was originally annotated as EntF; however, it does not produce enterobactin [12,13]. Instead biosynthesis of amphi-enterobactin is initiated by the fatty acyl CoA ligase, AebG ligating a fatty acid to the first loaded L Ser; then subsequently, AebF adds three DHB-L Ser groups in an iterative fashion to yield a unique tetra L Ser macrolactone siderophore appended by one FA and three DHB catechols.…”

mentioning

confidence: 99%

Mining elements of siderophore chirality encoded in microbial genomes

et al. 2022

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The vast majority of bacteria require iron to grow. A significant iron acquisition strategy is the production of siderophores, which are secondary microbial metabolites synthesized to sequester iron(III). Siderophore structures encompass a variety of forms, of which highly modified peptidic siderophores are of interest herein. State‐of‐the‐art genome mining tools, such as antiSMASH (antibiotics & Secondary Metabolite Analysis SHell), hold the potential to predict and discover new peptidic siderophores, including a combinatoric suite of triscatechol siderophores framed on a triserine‐ester backbone of the general class, (DHB‐l/dCAA‐lSer)3 (CAA, cationic amino acid). Siderophores with l/dArg, l/dLys and lOrn, but not dOrn, were predicted in bacterial genomes. Fortuitously the dOrn siderophore was identified, yet its lack of prediction highlights the limitation of current genome mining tools. The full combinatoric suite of these siderophores, which form chiral iron(III) complexes, reveals stereospecific coordination chemistry encoded in microbial genomes. The chirality embedded in this suite of Fe(III)‐siderophores raises the question of whether the relevant siderophore‐mediated iron acquisition pathways are stereospecific and selective for ferric siderophore complexes of a defined configuration.

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Characterization and Statistical Optimization of Enterobatin Synthesized by Escherichia coli OQ866153

Khazaal,

Faraag,

Hamada

et al. 2024

Biochem Genet

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Microorganisms produce siderophores, which are secondary metabolites with a high affinity for iron. Siderophores have received significant attention due to their diverse applications in ecological and clinical research. In this study, siderophores production by Escherichia coli OQ866153 was optimized using two-stage statistical approach involving Plackett–Burman design (PBD) and response surface methodology (RSM) using central composite design (CCD). Out of 23 variables, succinate, tryptophan, Na2HPO4, CaCl2, agitation, and KH2PO4 were found to have the most significant effect on siderophores production in the first optimization stage with the highest SU% of 43.67%. In the second stage, RSM using CCD was utilized, and the optimal conditions were determined to be 0.3 g/l succinate, 0 g/l tryptophan, 6 g/l Na2HPO4, 0.1 g/l CaCl2, 150 RPM agitation, and 0.6 g/l KH2PO4, resulting in a maximum siderophore units (SU%) of 89.13%. The model was significant, as indicated by the model f-value of 314.14 (p-value = 0.0004) and coefficient of determination R2 of 0.9950. During validation experiments, the obtained maximum SU% was increased up to 87.1472%, which was two times as the value obtained under ordinary conditions (46.62%). The produced siderophores were purified and characterized using 1H, 13C NMR, IR spectroscopy. The obtained results indicated that the compound was enterobactin and entABCDEF genes were further detected in Escherichia coli OQ866153 extracted DNA. To our knowledge, this is the first report of statistical optimization for enterobactin synthesis by an E. coli strain isolated from a clinical source in Egypt.

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On the origin of amphi-enterobactin fragments produced by Vibrio campbellii species

Cited by 4 publications

References 15 publications

Siderophores: A Case Study in Translational Chemical Biology

Siderophores: A Case Study in Translational Chemical Biology

Mining elements of siderophore chirality encoded in microbial genomes

Characterization and Statistical Optimization of Enterobatin Synthesized by Escherichia coli OQ866153

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