Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• strategies to explore access to triazole–pyrazole hybrids. Triazole–pyrazole hybrids, particularly non-fused heterocycles of this class, have not been investigated systematically. Selected known derivatives (Figure 1, 1–4) inhibit the serine-threonine kinase ERK3 [12] or the cholera-causing bacterium Vibrio

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• –3 were tested against seven human- and marine-derived aquatic pathogenetic bacteria (Edwardsiella tarda, Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, Vibrio anguillarum, Vibrio harveyi, and Vibrio vulnificus), and six plant pathogenic fungi (Alternaria brassicae, Colletotrichum

• pathogenic bacteria (Escherichia coli QDIO-1 and Pseudomonas aeruginosa QDIO-4) and aquatic pathogens (Edwardsiella tarda QDIO-2, Micrococcus luteus QDIO-3, V. anguillarum QDIO-6, Vibrio harveyi QDIO-7, and V. vulnificus QDIO-10), as well as plant pathogenic fungi (Colletotrichum gloeosporioides QDAU-2

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

• Fumihiro Ishikawa,
• Sho Konno,
• Hideaki Kakeya and
• Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

• inhibitors of NRPSs, A-domain inhibitors have been widely developed as potential therapeutic agents for treating infectious diseases. Aryl acid A-domains are involved in the synthesis of several bacterial siderophores such as vibriobactin from Vibrio cholera, yersiniabactin from Yersinia pestis, and

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• parameters KM and vmax of selected enzymes (Table S6, Supporting Information File 1) [5][10][11][15][19][20][21]. A sequence-based classification of PPKs is in most cases straightforward and unambiguous. Nevertheless, there seem to be exceptions: regarding the amino acid sequence, the PPK1 from Vibrio

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• that VOCs of cheese rind-associated fungi have both growth-stimulating and -inhibiting properties on members of the rind microbiome [60]. The authors could reveal that the VOC-mediated shift of the bacterial community was caused due to growth promotion of Vibrio spp. These studies and the results from

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• Dandan Li Enjuro Harunari Tao Zhou Naoya Oku Yasuhiro Igarashi Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan 10.3762/bjoc.16.154 Abstract Liquid cultures of Vibrio sp. SI9, isolated from the outer tissue

• . Keywords: 3-hydroxybutyric acid; polyhydroxyalkanoate; sea anemone; Tenacibaculum maritimum; Vibrio; Introduction The genus Vibrio, within the class Gammaproteobacteria, are a group of Gram-negative, halophilic, facultatively anaerobic, rod-shaped bacteria, which are motile with sheathed polar flagella [1

• bacteria, Vibrio sp. SI9, isolated from the sea anemone Radianthus crispus, was found to produce a known ester 4 and its new congeners 1–3 (Figure 1). Compound 4 is the shortest among the five oligomers of O-isocrotonyl-oligo(3-hydroxybutyrate) (5) previously discovered from Vibrio [9]. In this study, we

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

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

• Matthew J. Styles and
• Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

• tumefaciens [45][51][52][53][54]; AbaR from Acinetobacter baumannii [47][55]; LasR [45][51][52][53][54][56], QscR [57], and RhlR [48][56] from Pseudomonas aeruginosa; ExpR1 and ExpR2 from Pectobacterium carotovora [46][58]; and LuxR from Vibrio fischeri [45][51][52][53][54]. The full set of 151 compounds

Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

• Bimal Koirala,
• Robert A. Hillman,
• Erin K. Tiwold,
• Michael A. Bertucci and
• Yftah Tal-Gan

Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

• modulators against a multitude of Gram-negative bacterial species, including Pseudomonas aeruginosa, Vibrio fischeri, Vibrio harveyi, Vibrio cholerae, and Acinetobacter baumannii has been conducted [6][7][8][9][10]. Contrary, with the exception of the accessory gene regulator (agr) QS circuitry in

Carbohydrate inhibitors of cholera toxin

• Vajinder Kumar and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34

• released by Vibrio cholera in the host’s intestine. The toxin enters intestinal epithelial cells after binding to specific carbohydrates on the cell surface. Over recent years, considerable effort has been invested in developing inhibitors of toxin adhesion that mimic the carbohydrate ligand, with

• ; Introduction Cholera, meaning a flow of bile, is caused by an acute enteric infection of the Gram-negative facultative anaerobe Vibrio cholerae. Not only does this disease have a disastrous effect on health, it also impacts on the socioeconomic status of societies where it is endemic. The V. cholerae bacterium

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• , on the base of different expression level of the bacterial lectin FimH with a colorimetric assay. A simple and fast bioassay has been developed by Lee et al. [83] to recognize cholera toxin (CT), a protein secreted by the Vibrio cholerae bacterium which is responsible for cholera disease. A thiol

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• using two different techniques: The Vibrio harveyi luminescence assay and the Ames test. The obtained results support previous findings contesting QAS safety and indicate that QAS, specifically pyridinium derivatives, might be mutagenic. Keywords: 6-bromohexyl D-glucopyranoside; microbiological

• assays were applied. In the first approach, a recently developed Vibrio harveyi bioluminescence assay was used. This assay has been reported as being highly sensitive and therefore capable for antimutagenicity screening [33][34]. Moreover, all QASs synthesized in this work were tested for their mutagenic

• , 5a, 5b, 6b, and 7b exhibited a substantial mutagenic activity in the Vibrio bioluminescence assay (Figure 1). The extent of their mutagenic activity was comparable to that of a model acridine mutagen, ICR191, used as a positive control. Compounds 4a, 6a, and 7a did not display mutagenic activity in

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• biosensor (Table 1). Escherichia coli JB523 is a highly sensitive reporter strain that contains plasmid pJBA130 derived from the LuxR-PluxI quorum sensing operon of Vibrio fischeri expressing the production of stable green fluorescent protein (GFP) in response to exogenous AHLs [31]. In addition, the

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• the synthesis of the interesting compound vibrindole A (Scheme 2), an isolated metabolite of the marine bacteria Vibrio parahaemolyticus, which is active against Bacillus subtilis, Staphylococcus aureus and Staphylococcus albus as has been previously demonstrated [43]. In order to prevent the loss of

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

• Patrick Rabe,
• Tim A. Klapschinski,
• Nelson L. Brock,
• Christian A. Citron,
• Paul D’Alvise,
• Lone Gram and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure–activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than

• , the Gram-positive Staphylococcus aureus 8325 and the Gram-negative Vibrio anguillarum 90-11-287 (Table 1). These organisms were selected for our bioactivity tests, because S. aureus is a clinically important human pathogen and strains with resistances against multiple antibiotic drugs cause severe

• problems with nosocomial infections. The bioactivity against V. anguillarum is interesting from an ecological point of view, because P. inhibens was originally isolated from scallop rearings [18][19][20], suggesting that the natural function of P. inhibens may be to prevent molluscs from Vibrio infections

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• microbe and lectin binding studies, glycopeptide based glycoclusters/dendrimers were applied, employing linear peptide backbones, cyclic peptide scaffolds or multi-lysine scaffolds [106][107][108][109][110][111][112][113][114][115][116][117][118]. The pentavalent cholera toxin protein secreted by Vibrio

Chemical synthesis using enzymatically generated building units for construction of the human milk pentasaccharides sialyllacto-N-tetraose and sialyllacto-N-neotetraose epimer

• Dirk Schmidt and
• Joachim Thiem

Beilstein J. Org. Chem. 2010, 6, No. 18, doi:10.3762/bjoc.6.18

• the β,1-3-linked isolactosamine derivative. Further sialylation at position 3′-OH with pNp-αNeu5Ac and either sialidase from Vibrio cholerae or Clostridium perfringens afforded the α,2-6-sialylated trisaccharide 9 exclusively [7]. Later studies showed that 9 could be obtained in an enhanced yield of