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Search for "siderophore" in Full Text gives 14 result(s) in Beilstein Journal of Organic Chemistry.

Chemical and biosynthetic potential of Penicillium shentong XL-F41

  • Ran Zou,
  • Xin Li,
  • Xiaochen Chen,
  • Yue-Wei Guo and
  • Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

Graphical Abstract
  • version of antiSMASH 7.0 [25] software for the analysis of the Penicillium shentong XL-F41 genome, we identified 46 BGCs. These include 13 NRPS-like fragments, 6 NRPS, 13 type I PKS, 2 PKS/NRPS hybrids, 1 NI-siderophore, 2 NRP-metallophore/NRPS hybrids, 1 fungal RiPP with POP or UstH peptidase types, 1
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Published 15 Mar 2024

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

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  • biosynthetic intermediates or shunt products of massiliachelin. Their bioactivity was tested against one Gram-positive and three Gram-negative bacteria. Keywords: Massilia; massiliachelin; siderophore; structure elucidation; Introduction Iron is crucial for many important biological processes, such as
  • chelate environmental Fe3+. Ligand groups, such as hydroxamate, phenolate, catecholate, carboxylate, or oxazoline/thiazoline residues, confer siderophores their high affinity for the binding of Fe3+ [3][4][5]. Following the coordination of the metal, the Fe3+-loaded siderophore complex is transported back
  • for microbial communication processes [8]. Another unusual siderophore, gramibactin, is released by the rhizosphere bacterium Paraburkholderia graminis [9]. Gramibactin features an extremely rare diazeniumdiolate ligand with potent complexing properties [9][10]. Noteworthy is also bolagladin from
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Published 23 Jun 2023

Amamistatins isolated from Nocardia altamirensis

  • Till Steinmetz,
  • Wolf Hiller and
  • Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

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  • iron-chelating properties of the retrieved metabolites were evaluated in a chrome azurol S assay. Keywords: actinomycete; amamistatin; Nocardia; siderophore; structure elucidation; Introduction Iron is known to easily interconvert between a reduced ferrous (Fe2+) and an oxidized ferric state (Fe3
  • featuring ligand groups with nitrogen or sulfur as donor atoms [4]. The siderophore–iron complexes are recognized by highly selective microbial transporters. Following their translocation into the cell, the bound iron is released via a reductive or hydrolytic mechanism [2] Members of the genus Nocardia are
  • Nocardia as a whole is considered to be a rich source of bioactive secondary metabolites, including many structurally diverse siderophores [6]. Up to now, however, chemical studies in this taxonomic group mainly focused on pathogenic strains. In the present study we explored siderophore production in the
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Published 30 Mar 2022

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

  • Emmanuel T. Oluwabusola,
  • Olusoji O. Adebisi,
  • Fernando Reyes,
  • Kojo S. Acquah,
  • Mercedes De La Cruz,
  • Larry L. Mweetwa,
  • Joy E. Rajakulendran,
  • Digby F. Warner,
  • Deng Hai,
  • Rainer Ebel and
  • Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

Graphical Abstract
  • pseudomonine [28] are produced under iron deficiency by various Pseudomonas species to acquire iron which is essential for cell metabolism and growth [29][30]. Studies show that siderophore–antibiotic complexes may be used as a Trojan horse strategy in which the antibiotics utilize the iron-siderophore
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Published 13 Sep 2021

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

  • Shun Saito,
  • Kota Atsumi,
  • Tao Zhou,
  • Keisuke Fukaya,
  • Daisuke Urabe,
  • Naoya Oku,
  • Md. Rokon Ul Karim,
  • Hisayuki Komaki and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

Graphical Abstract
  • appendage in compound 2 is unprecedented in natural products, only to see its (Z)-isomer in a siderophore of Mycobacterium avium [32]; the side chain on the spiroacetal rings in compounds 2–4 lack hydroxylation at C-31, which is the common modification shared with all oligomycin class antibiotics
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Published 25 May 2020

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Naoya Oku,
  • Nobuyasu Matsuura,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

Graphical Abstract
  • ongoing screening program to discover new natural products from coral-associated bacteria, we have recently reported a catecholate siderophore, labrenzbactin, from an alphaproteobacterium Labrenzia [17] and an unsaturated fatty acid with unique methylation pattern from a gammaproteobacterium Microbulbifer
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Published 02 Mar 2020

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

  • David C. B. Siebert,
  • Roman Sommer,
  • Domen Pogorevc,
  • Michael Hoffmann,
  • Silke C. Wenzel,
  • Rolf Müller and
  • Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

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  • has been observed in many cases that exogenous substrates can be incorporated by bacteria into biosynthesis cascades of natural products. The use of substrates which lead to nonnatural derivatives of the natural product coined the field of mutasynthesis, e.g., siderophore analogue biosynthesis by P
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Published 05 Dec 2019

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Tao Zhou,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

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  • second report on the small molecule from this underexplored taxon. According to the genome sequence database, biosynthetic genes for NRPS and siderophore are present in Microbulbifer species which will be pursued in our future investigation. Experimental General experimental procedures The UV spectrum
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Published 30 Sep 2019

Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1

  • Jan Diettrich,
  • Hirokazu Kage and
  • Markus Nett

Beilstein J. Org. Chem. 2019, 15, 1298–1303, doi:10.3762/bjoc.15.128

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  • Jan Diettrich Hirokazu Kage Markus Nett Department of Biochemical and Chemical Engineering, Laboratory of Technical Biology, TU Dortmund University, Emil-Figge-Strasse 66, 44227 Dortmund, Germany 10.3762/bjoc.15.128 Abstract A putative siderophore locus was detected in the genome of the violacein
  • -producing bacterium Massilia sp. NR 4-1 and predicted to direct the biosynthesis of a molecule that is structurally related to the thiazoline-containing siderophore micacocidin. In order to track this compound, we analyzed the metabolic profiles of Massilia cultures grown under different iron concentrations
  • product, which was named massiliachelin, corresponds to the assembly line encoded by the identified siderophore locus. Keywords: agrochelin; genome mining; Massilia; massiliachelin; siderophore; stereochemistry; Introduction In recent years, chemical investigations as well as genomics led to the
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Published 13 Jun 2019

The design and synthesis of an antibacterial phenothiazine–siderophore conjugate

  • Abed Tarapdar,
  • James K. S. Norris,
  • Oliver Sampson,
  • Galina Mukamolova and
  • James T. Hodgkinson

Beilstein J. Org. Chem. 2018, 14, 2646–2650, doi:10.3762/bjoc.14.242

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  • , Department of Infection, Immunity and Inflammation, University of Leicester, Maurice Shock Medical Sciences Building, University Road, Leicester, LE1 9HN, UK 10.3762/bjoc.14.242 Abstract Siderophore–antibiotic conjugates consist of an antibiotic covalently linked by a tether to a siderophore. Such
  • latent TB. Herein we report the design and synthesis of the first phenothiazine–siderophore conjugate. A convergent synthetic route was developed whereby the functionalised phenothiazine component was prepared in four steps and the siderophore component also prepared in four steps. In M. smegmatis the
  • chelating groups of the siderophore. The synthesis is readily amenable to the preparation of analogues whereby the siderophore component of the conjugate can be modified. The route will be used to prepare a library of siderophore–phenothiazine conjugates for full biological evaluation of much needed new
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Published 16 Oct 2018

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

  • Christian Schütz and
  • Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

Graphical Abstract
  • synthesis, a Resistance-Nodulation-Cell division (RND) efflux pump encoded by mexGHI-opmD operon, components of Type 3 and Type 6 secretion as well as the exotoxin ExoS, and siderophore synthases [33]. In addition to virulence regulation, some remarkable secondary effects have been attributed to the PQS
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Review
Published 15 Oct 2018

Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

  • Felix Scheidt,
  • Christian Thiehoff,
  • Gülay Yilmaz,
  • Stephanie Meyer,
  • Constantin G. Daniliuc,
  • Gerald Kehr and
  • Ryan Gilmour

Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

Graphical Abstract
  • siderophore antibiotic D-fluviabactin, the cytotoxic agent westiellamide, the antifungal macrodiolide leupyrrin A1 and the antitumour compound BE-70016 (Figure 1). In addition, synthetic polymers based on the 2-oxazoline building block constitute versatile platforms for a range of biomedical applications
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Published 09 May 2018

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

  • Antonio Dávila-Céspedes,
  • Peter Hufendiek,
  • Max Crüsemann,
  • Till F. Schäberle and
  • Gabriele M. König

Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96

Graphical Abstract
  • , with a predominance of hybrid PKS-NRPS systems [37]. M. xanthus strain DK1622 is responsible for the synthesis of metabolites like DKxanthene-534 (8, Figure 4), a pigment required for fruiting body formation and sporulation processes [37] and the siderophore myxochelin A (9), which belongs to a class
  • molecules. Additionally, the siderophore nannochelin A (23) also from other myxobacteria was isolated [50]. All three compounds were tested against a broad range of microorganisms and mammalian cell lines. The most relevant antimicrobial activity was shown by 21 towards Mycobacterium diernhoferi (DSM 43542
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Review
Published 13 May 2016

An enantiomerically pure siderophore type ligand for the diastereoselective 1 : 1 complexation of lanthanide(III) ions

  • Markus Albrecht,
  • Olga Osetska,
  • Thomas Abel,
  • Gebhard Haberhauer and
  • Eva Ziegler

Beilstein J. Org. Chem. 2009, 5, No. 78, doi:10.3762/bjoc.5.78

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  • absorbtion data set. For a simple 1 : 1 binding model the calculations were carried out with the SigmaPlot program. Best results and lowest error could be observed at 279 nm in the case of lanthanum(III) and at 281 nm in the case of europium(III). Structural formula of the siderophore enterobactine. 1H NMR
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Published 11 Dec 2009
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