Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

• Tapasi Manna,
• Arin Gucchait and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 106–110, doi:10.3762/bjoc.16.12

• enteropathogenic Escherichia coli [5] are commonly known for causing diarrheal infections. Besides the mainstream enteropathogenic bacterium, Escherichia albertii (E. albertii) is an emerging human pathogen causing gastroenteric infections in different countries [6]. Although, this species was identified earlier

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• compounds 1–6, various assays were carried out. The antimicrobial activity of the isolated compounds against Bacillus subtilis DSM10, Escherichia coli DSM498, Candida tenuis MUCL29892, and Mucor plumbeus MUCL49355 was determined as described by Kuephadungphan and co-workers [8]. The nematicidal activity

Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

• Xinlu Chen,
• Tobias G. Köllner,
• Wangdan Xiong,
• Guo Wei and
• Feng Chen

Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281

• 28–73% of sequence identities. Full-length cDNAs for the four TPS genes were cloned and expressed in Escherichia coli to produce recombinant proteins, which were tested for sesquiterpene synthase and monoterpene synthase activities. While neither PpolyTPS2 nor PpolyTPS3 was active, PpolyTPS1 and

• To determine whether PpolyTPS genes encode functional terpene synthases, full-length cDNAs were amplified by RT-PCR and cloned into the protein expression vector pEXP-5-CT/TOPO. Recombinant PpolyTPSs were heterologously expressed in Escherichia coli and then tested for terpene synthase activities

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• determined in serial dilution assays using several microorganisms, as described previously [8][9]. Herein, Gram-positive bacteria used were B. subtilis DSM10, MRSA DSM11822, S. aureus DSM346, M. luteus DSM20030, and Mycobacterium smegmatis (M. smegmatis) ATCC700084, Gram-negative bacteria were Escherichia

• coli (E. coli) DSM498, Chromobacterium violaceum (C. violaceum) DSM30191, and Pseudomonas aeruginosa (P. aeruginosa) PA14. Moreover, the filamentous fungus Mucor plumbeus (M. plumbeus) MUCL49355 and the yeasts Candida tenuis (C. tenuis) MUCL29892, Pichia anomala (P. anomala) DSM6766, and Candida

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• three human cell lines. None of the compounds tested showed any activity up to 100 μg mL−1 against the Gram-negative bacterium Escherichia coli (ATCC 25922), the fungus Candida albicans (ATCC 10231) or the plant Eragrostis tef (teff). Proposed biosynthesis and gene cluster The biosynthesis of drimane

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

• Debasish Pal and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

• expensive to get reasonable quantities of material with adequate purity. Therefore, the chemical syntheses of these complex structures become the only option to afford the material for detailed biological studies leading to the exploration of the vaccine potential. Escherichia coli is a Gram-negative

• pentasaccharide repeating unit of the O-specific polysaccharide of Escherichia coli O132 was accomplished through a convergent [3 + 2] strategy. The target pentasaccharide was obtained as its 2-aminoethyl glycoside that offers further possibilities for conjugation with suitable aglycons without hampering the

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

• luteus ATCC9341, Bacillus subtilis ATCC6633, Escherichia coli NIHJ JC-2, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, and Candida albicans NBRC0197 (MIC > 100 μg/mL) but weakly active against Saccharomyces cerevisiae S100 (MIC 100 μg/mL). Conclusion In summary, chemical investigation

• microtiter plates against six bacteria, Bacillus subtilis ATCC6633, Micrococcus luteus ATCC9341, Staphylococcus aureus FDA209P JC-1, Ralstonia solanacearum SUPP1541, Rhizobium radiobacter NBRC14554, Escherichia coli NIHJ JC-2, and two yeasts Candida albicans NBRC0197 and Saccharomyces cerevisiae S100 as

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• antimicrobial activities against Gram-negative and Gram-positive bacteria, an ascomycete, a basidiomycete and a zygomycete, i.e., Escherichia coli, Bacillus megaterium, Eurotium rubrum, Microbotryum violaceum and Mycotypha microspora. Ethyl acetate extracts of C. rosea, I. europaea grown on BM medium and of the

• Escherichia coli were used as representatives for Gram-positive and Gram-negative bacteria. Microbotryum violaceum (Basidiomycete), Eurotium rubrum (Ascomycete), and Mycotypha microspora (Zygomycete) were used as fungal test organisms. Raw extracts were dissolved in MeOH to give a concentration of 1 mg/mL per

Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products

• Xiang Sun,
• You-Sheng Cai,
• Yujie Yuan,
• Guangkai Bian,
• Ziling Ye,
• Zixin Deng and
• Tiangang Liu

Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202

• products, heterologous expression of various sources of terpene synthases in Escherichia coli and Saccharomyces cerevisiae is a feasible approach [25][26]. In this study, a combination of genome mining and metabolic engineering was used for sesquiterpenoid discovery, utilizing farnesyl diphosphate

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• (strain 1211), Staphylococcus aureus (strain 2231) (gram-positive) and Escherichia coli (strain 1257), Pseudomonas aeruginosa (strain 1111) (gram-negative). Generally, the compounds were found to be less active than nitroxoline being the reference substance. The results obtained indicate that some

Back to the future: Why we need enzymology to build a synthetic metabolism of the future

• Tobias J. Erb

Beilstein J. Org. Chem. 2019, 15, 551–557, doi:10.3762/bjoc.15.49

• allows life to organize itself in three and four dimensions [6]. The incredible metabolic potential of biology is impressively demonstrated by the more than 2,000 different chemical transformations that can simultaneously take place inside of an Escherichia coli cell [7][8], as well as by the more than

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• bacterial lectins are the mannose-specific FimH of type 1 fimbriae and the galabiose-specific PapG of P fimbriae, expressed by Enterobactericea, such as Escherichia coli (E. coli). While type 1-fimbrial expression of E. coli is associated with urinary tract infections, the presence of P fimbriae is

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• among several other Pt(II)-based compounds to kill P. aeruginosa. It was previously reported that cisplatin had antimicrobial effects on nosocomial pathogens, such as Escherichia coli, Klebsiella pneumonia and Staphylococcus aureus [10] and persister cells [11]. Transcriptomic analysis was employed to

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• filamentous fungus Mucor hiemalis. In addition, 11 displayed moderate active on Mycobacterium smegmatis and the efflux-deficient Escherichia coli TolC strain. The 2-aminobutyric acid derivative 7 was active against M. hiemalis, M. luteus and S. aureus, while the unsaturated analogue 8 was mainly active

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

• Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

• forge the bacterial interactome [35]. However, despite the potential of these bacterial PPI maps, they have only been studied in detail in a few microorganisms including Escherichia coli (one of the best-studied model organisms in this field) [36][37][38][39], Mycobacterium tuberculosis [40

• and Gram-negative pathogens, namely Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Acinetobacter baylyi with MICs ranging from 39 to 78 μM [62]. A year later, further SAR investigations from the same research group led to the identification of another tetrahydrocarbazole derivative 12

• the bacterial interactome without impacting the eukaryotic cell processes. Keck and co-workers identified four small molecules that disrupt the Escherichia coli SSB interaction with one of its well-studied binding partners, exonuclease I (ExoI) [75]. The screening by means of a high-throughput

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• slightly out of the protein cavity led to improved conversion (Scheme 3) [46]. The combination of the GH-type catalyst and (strept)avidin was further developed in a system that performs RCM reactions within a whole cell [47][48]. The scaffold protein Sav was produced into the periplasm of Escherichia coli

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

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

• Stephen M. Geddis,
• Teodora Coroama,
• Suzanne Forrest,
• James T. Hodgkinson,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

• potent antibacterial activity against Helicobacter pylori and induce growth defects in Escherichia coli and Staphylococcus aureus. Taking inspiration from a methodology used in our total synthesis of natural products, we applied this methodology to access analogues possessing bulky N-substituents

• Escherichia coli reporter system [9]), an intriguing effect upon the growth of E. coli and Staphylococcus aureus was noted, which showed an extended lag phase in response to the compounds (except 4, which was inactive towards E. coli. It should be noted that in this previous publication, the graphical data

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

• ][19] and has high sequence identity with SdiA from other genera: for example, S. Typhimurium (GeneBank AAC08299.1) SdiA is 72% identical to Escherichia coli (GeneBank AWF10864.1) SdiA, 67% identical to Klebsiella pneumoniae (GeneBank CDO1572.1) SdiA, 71% identical to Enterobacter clocae (GeneBank

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

• inhibition of this adhesion process using glycomimetics as pathoblockers has developed as an area of active research in the last two decades [11][12]. Uropathogenic Escherichia coli (UPEC) is a major cause for chronic and recurrent urinary tract infections. These bacteria employ lectins in order to attach to

• ]. Therefore, it is likely that combinations of drugs will be applied for drug-resistant bacterial infections, as is currently the state of the art for many viral infections. Mannosides as inhibitors of the lectin FimH from uropathogenic Escherichia coli. Galactosides targeting uropathogenic Escherichia coli

Synthesis of a leopolic acid-inspired tetramic acid with antimicrobial activity against multidrug-resistant bacteria

• Luce Mattio,
• Loana Musso,
• Leonardo Scaglioni,
• Andrea Pinto,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2018, 14, 2482–2487, doi:10.3762/bjoc.14.224

• the plant Juniperus excelsa [3][4]. Leopolic acid A is endowed with antibacterial activity against Staphylococcus aureus and Staphylococcus pseudintermedius with a MIC of 16 μg/mL, and against Escherichia coli with a MIC of 128 µg/mL [3][4]. In terms of structural features, this compound contains a 4

• antibacterial activity of compound 1 was tested on Staphylococcus pseudintermedius and Escherichia coli strains chosen as representative of Gram-positive and Gram-negative bacteria. In particular, we demonstrated the ability of compound 1 to inhibit Staphylococcus pseudintermedius strains expressing a multidrug

• activity against 80 strains of Staphylococcus pseudintermedius and 25 strains of Escherichia coli. Bacterial isolates of S. pseudintermedius and E. coli, previously identified using selective and differential cultural media (e.g., Mannitol Salt Agar; MacConkey Agar, Oxoid, Italy), were isolated on blood

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• could facilitate DNA cleavage. Moreover, these complexes showed improved biocidal activity than the free ligands against various bacterial strains such as Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Staphylococcus epidermidis, and Klebsiella pneumonia. Nair et al. synthesized and

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• detection of 16S RNA from a single cell of Escherichia coli [79]. In addition to the detection of DNA and RNA targets, hybrid PNA-peptide beacons were designed for the detection of non-DNA targets, such as proteins (Figure 10A). According to this design, which was simultaneously proposed in 2007 by Seitz

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

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

• studied lipid A of Escherichia coli and Neisseria meningitidis contains six acyl chains (C14–C12) differently distributed across the diglucosamine backbone and two phosphate groups – one at the anomeric position of the proximal GlcN residue and the second at position 4’ of the distal GlcN moiety (Figure 2

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• tests in order to assess their interaction with a model plasmid DNA (pUC19) and to evaluate whether they may influence the internalization of exogenous DNA in bacterial systems, in particular the Gram-negative model microorganism Escherichia coli. Results and Discussion Polarimetric behavior of AmCDs A