Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• (34) [74], resistoflavin (35) [75], and tetracenomycin D (36) [76] were also identified as HSMs from Streptomyces sp. HN66. Carlson et al. reported the production of resistomycin by co-cultivating Streptomyces sp. B033 and Burkholderia vietnamiensis ATCC BAA-248 [77]. These results suggest that high

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• variochelins [20]. Biological activity The antimicrobial activities of 1–5 were evaluated against several Gram-negative and Gram-positive bacteria (Table 1). As a result, 1–5 inhibited the growth of the Gram-negative bacteria Escherichia coli and Burkholderia multivorans, but lacked activity against Bacillus

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

• , Burkholderia thailandensis produces malleobactins (Figure 1), which possess nitro, nitroso, and azoxy groups [6]. Although the malleobactins are weaker iron chelators than related siderophores featuring hydroxamate groups [7], recent evidence suggests that their structural peculiarities might be of relevance

• Burkholderia gladioli, which possesses an unprecedented citrate-derived fatty acid moiety [11]. Furthermore, lipopeptide siderophores with photocleavable moieties, like taiwachelin, were reported from bacteria of the genera Cupriavidus and Variovorax [12][13][14]. The β-proteobacterial genus Massilia was

Syntheses of spliceostatins and thailanstatins: a review

• William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

• (Figure 1) are a family of linear peptide/polyketide natural products isolated from the bacteria Burkholderia sp. FERM BP-3421 [1][2][3] (originally identified as Pseudomonas sp. No 2663) and Burkholderia sp. MSMB 43 [4][5]. These compounds are of interest due to their ability to bind to a subunit of the

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

• Dandan Li,
• Naoya Oku,
• Yukiko Shinozaki,
• Yoichi Kurokawa and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

• providing sufficient evidence to support the structure, was isolated from a fermentation extract of Burkholderia sp. 3Y-MMP isolated from a soil by a Zn2+ enrichment culture. Detailed spectroscopic analyses by MS and NMR, combined with 13C chemical shift comparison with literature values of the related

• in liquid production cultures, quenched hydroxy radical-induced chemiluminescence emitted by luminol by 86%. Because some Burkholderia species are pathogenic to plants and animals, the above result suggests that 1 is a potential antioxidant to counteract reactive oxygen species-based immune response

• in the host organisms. Keywords: antioxidant; Burkholderia sp; quinolone; soil bacterium; Zn2+ enrichment culture; Findings 4-Hydroxy-2(1H)-quinolone (3) is a unique structural motif mostly found in alkaloids from rutaceous plants (family Rutaceae) [1][2]. This motif has several tautomeric forms

Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• nature. For instance, when toluene was tested as cosolvent, conversions varied from 40% (in KPi) to 9% in (Tris·HCl), and for DMSO conversions range from 90% (in KPi) to 20% (Tris·HCl, Table 1, entry 4). Candida rugosa lipase (CRL, entry 5) and immobilised Burkholderia cepacia lipase (PSL-IM, Table 1

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

• Sven Thierbach,
• Max Wienhold,
• Susanne Fetzner and
• Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

• )-quinolones (AQs) have been identified as natural products produced by higher plants of the Rutaceae family as well as by some microorganisms including Alteromonas, Burkholderia and Pseudomonas species [1][2][3][4][5][6][7][8][9]. Plant-derived AQs occur with alkyl chains of different lengths, branches and

Synthesis of α-D-GalpN₃-(1-3)-D-GalpN₃: α- and 3-O-selectivity using 3,4-diol acceptors

• Emil Glibstrup and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2018, 14, 2805–2811, doi:10.3762/bjoc.14.258

• development [9] and further biological evaluations [10]. The disaccharide motif is also commonly found in viruses and bacteria. In bacteria, as an example, it has been found in pathogenic bacteria such as in Salmonella [11], Shigella [12], several Burkholderia [13], Escherichia coli [14], Vibrio chlorae [15

• Shigella dysenteriae [23], as derivatives of the mucin O-glycan core structures for glycosidase studies [24], for the synthesis of T-antigen analogues [25], for the synthesis of E. coli O-antigens [26][27][28][29], for the development of Burkholderia vaccines [30][31][32], for the synthesis of PS A1

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• (PQS) and its biosynthetic precursors in P. aeruginosa some of which are also found in Burkholderia [71], two species that often co-infect patients for example in cystic fibrosis airways infections. By blocking QS processes, the release of virulence factors such as host degrading enzymes or chemicals

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• -1 Yanagido, Gifu 501-1193, Japan 10.3762/bjoc.14.122 Abstract Exploration of rhizobacteria of the genus Burkholderia as an under-tapped resource of bioactive molecules resulted in the isolation of two new antimicrobial 2-alkyl-4-quinolones. (E)-2-(Hept-2-en-1-yl)quinolin-4(1H)-one (1) and (E)-2

• inhibited the growth of the marine bacterium Tenacibaculum maritimum, an etiological agent of skin ulcers in marine fish, offering new opportunities to develop antibacterial drugs for fish farming. Keywords: antimicrobial; Burkholderia; quinolone; skin ulcer; Tenacibaculum maritimum; Findings Bacteria of

• the genus Burkholderia within the family Burkholderiaceae [1], along with their neighboring genera, Paraburkholderia, Caballeronia [2], and Robbsia [3] constitute a distinct group of bacteria within the class Betaproteobacteria. These bacteria are obligatory aerobic, mostly motile, non-spore-forming

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• diglucosamine backbone of lipid A which allows for a stepwise introduction of multiple functional groups into the molecule are discussed. Thorough consideration is also given to the synthesis of 1,1′-glycosyl phosphodiesters comprising partial structures of 4-amino-4-deoxy-β-L-arabinose modified Burkholderia

• and Salmonella [2][26], ethanolamine in Helicobacter pylori, 4-amino-4-deoxy-β-L-arabinose (β-L-Ara4N) [27][28] in E. coli [29], Burkholderia [27] and Yersinia pestis [30] or galactosamine in Francisella [2][26], and glucosamine in Bordetella species [31] (Figure 2). Covalent attachment of aminosugar

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• lectin LecB [29][30] and Burkholderia cenocepacia with its characteristic B. cenocepacia lectin A (BC2L-A) [31][32], both playing an important role in the social life of bacterial cells. A further example is the bacterial adhesin FimH, which plays a crucial role in urinary tract infections (UTIs). FimH

• additional hydroxy group would not contribute the maximum penalty associated with an isolated one. The cost of desolvating calcium ions (Figure 5). Opportunistic bacteria such as Pseudomonas aeruginosa or Burkholderia cenocepacia have incorporated a second calcium ion into their binding site, coordinating

Selective enzymatic esterification of lignin model compounds in the ball mill

• Ulla Weißbach,
• Saumya Dabral,
• Laure Konnert,
• Carsten Bolm and
• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1788–1795, doi:10.3762/bjoc.13.173

• (Scheme 1a) [8]. Similarly, immobilized lipases (triglycerol acylhydrolases EC 3.1.1.3) such as Amano lipase PS-IM from Burkholderia cepacia immobilized on diatomaceous earth and lipase B from Candida antarctica (expressed in Aspergillus niger) adsorbed on polymethacrylate beads (ca. 400 μm–600 μm in

• Immobead), immobilized lipase from Burkholderia cepacia (PS-IM) and lipase A from Aspergillus niger were tested. Firstly, hoping to find differences between the two hydrolases derived from Candida antarctica, an experiment using CALA was conducted. Despite CALB and CALA being produced by the same yeast

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• data acquisition systems [81]. An illustration of how BioSAXS experiments can help to complete data obtained by protein crystallography is given by the characterization of the full structural assembly of the lectin of Burkholderia cenocepacia, an opportunistic bacterial pathogen. Throughout biochemical

O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside

• Roman Sommer,
• Dirk Hauck,
• Annabelle Varrot,
• Anne Imberty,
• Markus Künzler and
• Alexander Titz

Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282

• determination [21][22]. This method has now successfully been applied to solve the structure of the bacterial lectins RSL from Ralstonia solanacearum [23], BC2L-C from Burkholderia cenocepacia [24], and the fungal lectin AFL from Aspergillus fumigatus [25] using methyl α-L-selenofucoside (1, Figure 1) as heavy

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

• Mariano Goldberg,
• Denis Sartakov,
• Jan W. Bats,
• Michael Bolte and
• Michael W. Göbel

Beilstein J. Org. Chem. 2016, 12, 1870–1876, doi:10.3762/bjoc.12.176

• ][21]. A kinetic resolution of the enantiomers was achieved by enzymatic hydrolysis with Amano lipase PS from Burkholderia cepacia [22][23], a method already optimized for technical use [24]. The best results were obtained with methyl tert-butyl ether as a cosolvent [24]. By simple precipitation

• . Conditions: (a) 1 equiv HOOC-CH2-COOH, 2 equiv NH4OAc, EtOH, 78 °C, 5 h, 38%; (b) 10 equiv n-PrOH, 1.5 equiv H2SO4, 97 °C, 4 h, 82%; (c) Amano-Lipase PS (from Burkholderia cepacia), aqueous Na2HPO4 buffer, pH 7.00, 50 °C, 1 h, methyl tert-butyl ether, 50 °C, 24 h, 90% (45% based on rac-12), >99% ee; (d) 2.5

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• residue – indicating a mechanism distinct from the ketoacyl–ketoacyl-connecting KSs – and were identified in different bacterial genera, i.e., Burkholderia, Legionella, Nocardia, Microcystis and Streptomyces, therewith also in clinically relevant pathogens [63]. Future work will reveal which natural

Recent highlights in biosynthesis research using stable isotopes

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

• [20]. It was investigated in the biosynthesis of the phytotoxin rhizoxin (4, Scheme 1), a potent antimitotic agent binding to β-tubulin from the bacterium Burkholderia rhizoxinica, which lives in symbiosis with the fungus Rhizopus microsporus [23]. The mechanism includes a Michael addition of a

A novel and widespread class of ketosynthase is responsible for the head-to-head condensation of two acyl moieties in bacterial pyrone biosynthesis

• Darko Kresovic,
• Florence Schempp,
• Zakaria Cheikh-Ali and
• Helge B. Bode

Beilstein J. Org. Chem. 2015, 11, 1412–1417, doi:10.3762/bjoc.11.152

• . The biosynthetic importance of the second group including PpyS homologues from Burkholderia, Legionella, Nocardia, Microcystis and Streptomyces needs to be determined in future work. In contrary, MxnB and CorB are located within the FabH clade, showing that not only the reaction mechanism of these two

Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa

• Aritra Chaudhury,
• Sajal K. Maity and
• Rina Ghosh

Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153

• synthesis has seen a rapid development over the last two decades [5][6][7]. The D-rhamnoside motif is of particular interest with its presence established in the LPS/EPS systems of various bacterial strains which are pathogenic towards both plants and animals. These species include the Burkholderia cepacia