Azido‐Desferrioxamine Siderophores as Functional Click‐Chemistry Probes Generated in Culture upon Adding a Diazo‐Transfer Reagent

Gotsbacher, Michael P.; Codd, Rachel

doi:10.1002/cbic.201900661

Cited by 9 publications

(5 citation statements)

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“…46 Interestingly, researchers have also found that under putrescine-depleted conditions, Shewanella putrefaciens shifts to producing desferrioxamine B when cadaverine precursors are available. 47 In desferrioxamine biosynthesis, incorporation of the putrescine precursor in desferrioxamine A1 has been shown before in multiple species 30,44,48 and now in this study with the discovery of legonoxamine G.…”

Section: Molecular Networking and Ms/ms Based Structure Elucidationsupporting

confidence: 65%

“…Legonoxamine F contains one 1,6-diaminohexane instead of cxthe typical 1,5-diaminopentane. This is a well-established phenomenon in siderophore biosynthesis 31,44 linking it to the promiscuity of the S29 des biosynthetic gene cluster. Legonoxamine G contains a N-hydroxyputrescine moiety due to the initial loss of 104 Da instead of the typical 118 Da associated to N-hydroxycadaverine.…”

Section: Molecular Networking and Ms/ms Based Structure Elucidationmentioning

confidence: 98%

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Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerant Streptomyces sp. S29 desferrioxamine production

et al. 2021

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Section: Molecular Networking and Ms/ms Based Structure Elucidationsupporting

confidence: 65%

Section: Molecular Networking and Ms/ms Based Structure Elucidationmentioning

confidence: 98%

Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerant Streptomyces sp. S29 desferrioxamine production

et al. 2021

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“…Legonoxamine F contains one 1,6-diaminohexane instead of the typical 1,5diaminopentane. This is a well-established phenomenon in siderophore biosynthesis 31,44 linking it to the promiscuity of the S29 des biosynthetic gene cluster. Legonoxamine G contains a N-hydroxyputrescine moiety due to the initial loss of 104 Da instead of the typical 118 Da associated to N-hydroxycadaverine.…”

Section: Streptomyces Sp S29 Cocultivation and Lc-ms Of Desferrioxammentioning

confidence: 98%

Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerantStreptomycessp. S29 desferrioxamine production

Jarmusch

Lagos-Susaeta

Diab

et al. 2020

Preprint

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ABSTRACTSiderophores are iron-chelating compounds that aid iron uptake, one of the key strategies for microorganisms to carve out ecological niches in microbially diverse environments. Desferrioxamines are the principal siderophores produced by Streptomyces spp. Their biosynthesis has been well studied and as a consequence, the chemical potential of the pathway continues to expand. With all of this in mind, our study aimed to explore extremotolerant and Lupine rhizosphere-derived Streptomyces sp. S29 for its potential antifungal capabilities. Cocultivation of isolate S29 was carried out with Aspergillus niger and Botrytis cinerea, both costly fungal phytopathogens in the wine industry. The results indicate that not only is Streptomyces sp. S29 extraordinary at producing hydroxamate siderophores but uses siderophore production as a means to ‘starve’ the fungi of iron. High resolution LC-MS/MS followed by GNPS molecular networking was used to observe the datasets for desferrioxamines and guided structure elucidation of new desferrioxamine analogues. Comparing the new chemistry, using tools like molecular networking and MS2LDA, with the known biosynthesis, we show that the chemical potential of the desferrioxamine pathway has further room for expansion.

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“…Such conjugates can be further used as drugs to treat infections with pathogenic bacteria. More recently, the team attempted to incorporate azido amine substates but failed to produce azido DFOB analogs [ 70 ], suggesting that although the biosynthetic enzymes are somewhat permissive, not any substrate can be tolerated.…”

Section: Precursor-directed Biosynthesismentioning

confidence: 99%

Engineering Siderophore Biosynthesis and Regulation Pathways to Increase Diversity and Availability

2023

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Siderophores are small metal chelators synthesized by numerous organisms to access iron. These secondary metabolites are ubiquitously present on Earth, and because their production represents the main strategy to assimilate iron, they play an important role in both positive and negative interactions between organisms. In addition, siderophores are used in biotechnology for diverse applications in medicine, agriculture and the environment. The generation of non-natural siderophore analogs provides a new opportunity to create new-to-nature chelating biomolecules that can offer new properties to expand applications. This review summarizes the main strategies of combinatorial biosynthesis that have been used to generate siderophore analogs. We first provide a brief overview of siderophore biosynthesis, followed by a description of the strategies, namely, precursor-directed biosynthesis, the design of synthetic or heterologous pathways and enzyme engineering, used in siderophore biosynthetic pathways to create diversity. In addition, this review highlights the engineering strategies that have been used to improve the production of siderophores by cells to facilitate their downstream utilization.

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Azido‐Desferrioxamine Siderophores as Functional Click‐Chemistry Probes Generated in Culture upon Adding a Diazo‐Transfer Reagent

Cited by 9 publications

References 53 publications

Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerant Streptomyces sp. S29 desferrioxamine production

Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerant Streptomyces sp. S29 desferrioxamine production

Iron-meditated fungal starvation by lupine rhizosphere-associated and extremotolerantStreptomycessp. S29 desferrioxamine production

Engineering Siderophore Biosynthesis and Regulation Pathways to Increase Diversity and Availability

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