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

• the A-band polysaccharide of Pseudomonas aeruginosa. One of the key steps involved 6-O-deoxygenation of either partially or fully acylated 4,6-O-benzylidene-1-thiomannopyranoside by radical-mediated redox rearrangement in high yields and regioselectivity. The D-rhamno-thioglycosides so obtained

• -rhamno-trisaccharide; deoxygenation on thioglycoside; multivalent glycosystems; one-pot sequential glycosylation; Pseudomonas aeruginosa; Introduction With the firm establishment of the critical roles played by oligosaccharides in diverse biological processes [1][2][3][4], the field of oligosaccharide

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

• Jens Schmidt,
• Zeinab Khalil,
• Robert J. Capon and
• Christian B. W. Stark

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

• activity against the Gram-positive bacteria Staphylococcus aureus ATCC 25923 (IC50 1.8 μM), Staphylococcus epidermidis ATCC 12228 (IC50 0.9 μM) and Bacillus subtilis ATCC 6633 (IC50 1.8 μM), but was inactive (IC50 > 30 μM) against the Gram-negative bacteria Pseudomonas aeruginosa ATCC 10145 and Escherichia

Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles

• Antonio Arcadi,
• Emanuela Pietropaolo,
• Antonello Alvino and
• Véronique Michelet

Beilstein J. Org. Chem. 2014, 10, 449–458, doi:10.3762/bjoc.10.42

• biosynthesis mechanism as well as synthetic target for the development of novel medicinal agents [12]. Recently, 7-fluoroindole has been proposed as a potential candidate for the use in an antivirulence approach against persistent Pseudomonas aeruginosa infections [13]. Fluorine introduction in the benzene

Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

• Yong-Chul Jeong and
• Mark G. Moloney

Beilstein J. Org. Chem. 2013, 9, 1899–1906, doi:10.3762/bjoc.9.224

• susceptible Enterococcus faecalis (VSE, E1), vancomycin resistant E. faecium (VanA VRE, E2)), and 2 strains of Streptococcus pneumoniae, including multi-drug resistant strain (MDRSP, P9), as well as 3 species of Gram-negative bacteria, consisting of Pseudomonas aeruginosa and 2 strains of Haemophilus

De novo synthesis of D- and L-fucosamine containing disaccharides

• Daniele Leonori and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 332–341, doi:10.3762/bjoc.9.38

• -Garner aldehydes. These differentially protected monosaccharide building blocks were utilized to prepare disaccharides present on the surface of Pseudomonas aeruginosa bacteria. Keywords: de novo synthesis; fucosamine; glycan; pseudomonas aeruginosa; vaccine; Introduction Protein functions are directly

• bacteria Pseudomonas aeruginosa. P. aeruginosa is a nosocomial pathogen that is involved in ventilator-associated pneumonia and has become resistant to many antimicrobials. The somatic pili of P. aeruginosa are a major virulence factor playing a pivotal role in the adherence and invasiveness of the

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• phenylene units. Preliminary applications of these rods in divalent systems are shown. Inhibition studies with Pseudomonas Aeruginosa lectin LecA showed that the rigid spacer proved greatly beneficial for the inhibitory potency. Keywords: multivalent carbohydrates; LecA inhibition; phenylene ethynylene

• of aromatic rings. One of the spacers was incorporated into the structure of a divalent galactoside ligand and was used to inhibit the virulence-linked lectin LecA of Pseudomonas aeruginosa [27][28]. Results and Discussion Synthetic strategies Depending on the number of units in the spacer, two

• obtained after deprotection of the alkyne moieties with K2CO3. Preliminary application As part of our program on bacterial adhesion inhibition by multivalent carbohydrates, the bacterial lectin LecA, a virulence factor of the problematic pathogen Pseudomonas aeruginosa is a target of interest [30][31

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• pathogens. Even if differences can be seen in the Gram-negative values, none of the RW-peptides was very active. Unfortunately, none of the peptides showed significant activity against Pseudomonas aeruginosa, a prominent pathogen that causes infections in e.g., cystic fibrosis patients. However, activities

• in Table 2) The minimal inhibitory concentrations (MIC) were tested against Escherichia coli DSM 30083, Acinetobacter baumannii DSM 30007, Pseudomonas aeruginosa DSM 50071, Bacillus subtilis DSM 402, Staphylococcus aureus DSM 20231 (type strain), and Staphylococcus aureus ATCC 43300 (MRSA) in a

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

• Marta De Zotti,
• Barbara Biondi,
• Cristina Peggion,
• Matteo De Poli,
• Haleh Fathi,
• Simona Oancea,
• Claudio Toniolo and
• Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

• , Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Klebsiella pneumoniae ATCC 13883, Salmonella entereditis 13076, and Proteus mirabilis ATCC 10975. The well-known antibiotics bacitracin and tetracyclin (10 μg/disk) were used as controls. List of primary structures and abbreviations for the

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• enhance the avidity of interactions between glycans and lectins [15]. Some glycocalixarenes have shown remarkable inhibition properties towards galectins [21][22] or Pseudomonas Aeruginosa lectin [23], the inhibition ability being dependent on the macrocyclic conformation and presentation of the glycoside

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

• distance (Figure 2) [140][141][142]. In another study, a combinatorial library of fucosyl-peptide dendrimers was synthesized and screened for binding to the fucose-specific lectin (LecB) from Pseudomonas aeruginosa, a pathogen causing severe infections in patients leading to chronic inflammation in the

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• the center of the endophenazine cluster In between the mevalonate pathway genes and the dihydro-PCA biosynthesis genes, four further genes are situated, i.e., ppzTUVM (Figure 1). The gene ppzM (1023 bp) shows similarities to PhzM from Pseudomonas aeruginosa PAO1, a putative phenazine-specific

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

• Lucie Brulikova and
• Jan Hlavac

Beilstein J. Org. Chem. 2011, 7, 678–698, doi:10.3762/bjoc.7.80

• tested for their antimicrobial activity against standard reference gram-positive and gram-negative bacterial strains such as Enterococcus faecalis CCM 4224, Staphylococcus aureus CCM 3953, Escherichia coli CCM 3954 and Pseudomonas aeruginosa CCM 3955 and against gram-positive and gram-negative bacteria

• obtained from clinical material of patients treated at the University Hospital in Olomouc (methicillin resistant Staphylococcus aureus - MRSA, Staphylococcus haemolyticus, Escherichia coli and Pseudomonas aeruginosa) with resistance to currently used fluoroquinolones. Only the octyl and nonyl derivatives