Acyl peptidic siderophores: structures, biosyntheses and post-assembly modifications

Kem, Michelle P.; Butler, Alison

doi:10.1007/s10534-015-9827-y

Cited by 24 publications

(25 citation statements)

References 62 publications

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“…Vibrio DS40M5 was shown to produce aerobactin together with ochrobactin (Haygood et al ., ), but also in this case the responsible BGCs are not known. Most of the amphiphilic marine siderophores, like the marinobactins, aquachelins, amphibactins and loihichelins are peptidic siderophores deriving from NRPS, where the CoA fatty acid is transferred to the peptide head via a starter condensation domain (Kem and Butler, ). In the case of aerobactin the acyltransferase IucB is responsible for acetylation of hydroxy lysine.…”

Section: Resultsmentioning

confidence: 99%

Identification and occurrence of the hydroxamate siderophores aerobactin, putrebactin, avaroferrin and ochrobactin C as virulence factors from entomopathogenic bacteria

Hirschmann

Grundmann

Bode

2017

Environmental Microbiology

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Effective iron acquisition and fine-tuned intracellular iron storage systems are the main prerequisites for a successful host invasion by a pathogen. Bacteria have developed several different strategies to sequester this essential element from their environment, one relies on the secretion of low molecular weight compounds with high affinity for ferric iron, the so-called siderophores. Here, we report hydroxamate siderophore structures produced by entomopathogenic bacteria of the species Xenorhabdus and Photorhabdus, which are known for their potential to produce bioactive natural products, required for their role as nematode symbiont and insect pathogen. Four siderophores could be identified, namely aerobactin, putrebactin, avaroferrin and ochrobactin C, which was found previously only in marine bacteria. While the putrebactin and avaroferrin producing biosynthesis gene cluster (BGC) is more widespread and most likely was present in a common ancestor of these bacteria, the aerobactin and ochrobactin producing BGC was probably taken up by a few strains individually. For aerobactin a role in virulence towards Galleria mellonella larvae is shown.

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Section: Resultsmentioning

confidence: 99%

Identification and occurrence of the hydroxamate siderophores aerobactin, putrebactin, avaroferrin and ochrobactin C as virulence factors from entomopathogenic bacteria

Hirschmann

Grundmann

Bode

2017

Environmental Microbiology

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“…Siderophores (greek: sidero = iron; phore = carrier) are secondary metabolites produced by many organisms (plant, bacteria, and fungi) to sequester iron in a physiological context (Kem and Butler 2015;Carroll and Moore 2018;Hofmann et al 2020). Often stress, such as iron limitation or ecological pressure, leads to a response of producing and secreting secondary metabolites.…”

Section: Nmos Involved In Siderophore Biosynthesismentioning

confidence: 99%

Flavin-dependent N-hydroxylating enzymes: distribution and application

Mügge

Heine

Baraibar

et al. 2020

Appl Microbiol Biotechnol

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Amino groups derived from naturally abundant amino acids or (di)amines can be used as "shuttles" in nature for oxygen transfer to provide intermediates or products comprising NO functional groups such as N-hydroxy, oxazine, isoxazolidine, nitro, nitrone, oxime, C-, S-, or N-nitroso, and azoxy units. To this end, molecular oxygen is activated by flavin, heme, or metal cofactorcontaining enzymes and transferred to initially obtain N-hydroxy compounds, which can be further functionalized. In this review, we focus on flavin-dependent N-hydroxylating enzymes, which play a major role in the production of secondary metabolites, such as siderophores or antimicrobial agents. Flavoprotein monooxygenases of higher organisms (among others, in humans) can interact with nitrogen-bearing secondary metabolites or are relevant with respect to detoxification metabolism and are thus of importance to understand potential medical applications. Many enzymes that catalyze N-hydroxylation reactions have specific substrate scopes and others are rather relaxed. The subsequent conversion towards various NO or N-N comprising molecules is also described. Overall, flavin-dependent N-hydroxylating enzymes can accept amines, diamines, amino acids, amino sugars, and amino aromatic compounds and thus provide access to versatile families of compounds containing the NO motif. Natural roles as well as synthetic applications are highlighted. Key points • NO and N-N comprising natural and (semi)synthetic products are highlighted. • Flavin-based NMOs with respect to mechanism, structure, and phylogeny are reviewed. • Applications in natural product formation and synthetic approaches are provided.

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“…There was no ACP domain present in ABO_2092 to tether and transport this activated fatty acid. The biosynthesis then proceeded in a linear fashion, ending with a thioesterase domain which was preceded by a domain with unknown function [458].…”

Section: Biosyntheses Of Marine Peptidesmentioning

confidence: 99%

Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology

Gogineni

Hamann

2018

Biochimica et Biophysica Acta (BBA) - General Subjects

115

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The oceans are a uniquely rich source of bioactive metabolites, of which sponges have been shown to be among the most prolific producers of diverse bioactive secondary metabolites with valuable therapeutic potential. Much attention has been focused on marine bioactive peptides due to their novel chemistry and diverse biological properties. As summarized in this review, marine peptides are known to exhibit various biological activities such as antiviral, anti-proliferative, antioxidant, anti-coagulant, anti-hypertensive, anti-cancer, antidiabetic, antiobesity, and calcium-binding activities. This review focuses on the chemistry and biology of peptides isolated from sponges, bacteria, cyanobacteria, fungi, ascidians, and other marine sources. The role of marine invertebrate microbiomes in natural products biosynthesis is discussed in this review along with the biosynthesis of modified peptides from different marine sources. The status of peptides in various phases of clinical trials is presented, as well as the development of modified peptides including optimization of PK and bioavailability.

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Acyl peptidic siderophores: structures, biosyntheses and post-assembly modifications

Cited by 24 publications

References 62 publications

Identification and occurrence of the hydroxamate siderophores aerobactin, putrebactin, avaroferrin and ochrobactin C as virulence factors from entomopathogenic bacteria

Identification and occurrence of the hydroxamate siderophores aerobactin, putrebactin, avaroferrin and ochrobactin C as virulence factors from entomopathogenic bacteria

Flavin-dependent N-hydroxylating enzymes: distribution and application

Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology

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