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Concept: Ammonium


Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-α,ω-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides), a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and (1)H and (13)C NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.

Concepts: Spectroscopy, Surfactant, Quaternary ammonium cation, Ammonium, Ascomycota, Salt, Cocamidopropyl betaine, Fabric softener


Subsequent to binding pocket modifications designed to provide dual d-Ala-d-Ala/d-Ala-d-Lac binding that directly overcome the molecular basis of vancomycin resistance, peripheral structural changes have been explored to improve antimicrobial potency and provide additional synergistic mechanisms of action. A C-terminal peripheral modification, introducing a quaternary ammonium salt, is reported and was found to provide a binding pocket-modified vancomycin analog with a second mechanism of action that is independent of d-Ala-d-Ala/d-Ala-d-Lac binding. This modification, which induces cell wall permeability and is complementary to the glycopeptide inhibition of cell wall synthesis, was found to provide improvements in antimicrobial potency (200-fold) against vancomycin-resistant Enterococci (VRE). Furthermore, it is shown that this type of C-terminal modification may be combined with a second peripheral (4-chlorobiphenyl)methyl (CBP) addition to the vancomycin disaccharide to provide even more potent antimicrobial agents [VRE minimum inhibitory concentration (MIC) = 0.01-0.005 μg/mL] with activity that can be attributed to three independent and synergistic mechanisms of action, only one of which requires d-Ala-d-Ala/d-Ala-d-Lac binding. Finally, it is shown that such peripherally and binding pocket-modified vancomycin analogs display little propensity for acquired resistance by VRE and that their durability against such challenges as well as their antimicrobial potency follow now predictable trends (three > two > one mechanisms of action). Such antibiotics are expected to display durable antimicrobial activity not prone to rapidly acquired clinical resistance.

Concepts: Antibiotic resistance, Cell wall, Vancomycin, Quaternary ammonium cation, Ammonium, Enterococcus, Vancomycin-resistant enterococcus, Antimicrobial


We report an ion exchange chromatographic purification method powerful for preparation of virus particles with ultrapure quality. The technology is based on large pore size monolithic anion exchangers, quaternary amine (QA) and diethyl aminoethyl (DEAE). These were applied to membrane-containing icosahedral bacteriophage PRD1, which bound specifically to both matrices. Virus particles eluted from the columns retained their infectivity, and were homogenous with high specific infectivity. The yields of infectious particles were up to 80%. Purified particles were recovered at high concentrations, approximately 5mg/ml, sufficient for virological, biochemical and structural analyses. We also tested the applicability of the monolithic anion exchange purification on a filamentous bacteriophage phi05_2302. Monolithic ion exchange chromatography is easily scalable and can be combined with other preparative virus purification methods.

Concepts: Protein, Chemistry, Chromatography, High performance liquid chromatography, Analytical chemistry, Gas chromatography, Ammonium, Ion exchange


A previous study identified an association between high MICs of quaternary ammonium compounds (QACs) and antibiotic resistance. The current aim was to investigate the genetic background of this association.

Concepts: Bacteria, Antibiotic resistance, Escherichia coli, Quaternary ammonium cation, Ammonium, Salt, Quaternary ammonium compounds


This study uses molecular dynamics (MD) modeling to examine the interlayer microstructures of montmorillonite intercalated with single chain QACs. Three types of QACs-tetramethylammonium (TMA), decyltrimethylammonium (DTMA), and hexadecyltrimethylammonium (HDTMA)-were selected to synthesize the organoclay complex, and the surfactant arrangement was analyzed quantitatively in systems in the absence of water. A series of arrangement patterns of interlayer QAC surfactant were observed, including lateral monolayers, lateral bilayers, pseudotrilayers, and paraffin monolayers, in agreement with previous experimental results. The effects of increasing one carbon chain length and amount of loading of QAC on the resultant QAC arrangement are summarized, yielding a model that provides insight into the prediction of synthesized QAC-clay microstructure and engineering behavior in practice.

Concepts: Scientific method, Atom, Surfactant, Quaternary ammonium cation, Ammonium, Salt, Cocamidopropyl betaine, Fabric softener


Imidazolium and quaternary ammonium-functionalized poly(fluorenyl ether ketone sulfone)s were synthesized successfully with the same degree of cationic functionalization and identical polymer backbones for a comparative study of anion exchange membranes (AEMs) for solid-state alkaline membrane fuel cells (AMFCs). Both anion exchange membranes were synthesized using a new methyl-containing monomer that avoided the use of toxic chloromethylation reagents. The polymer chemical structures were confirmed by (1)H NMR and FTIR. The derived AEMs were fully characterized by water uptake, anion conductivity, stability under aqueous basic conditions, and thermal stability. Interestingly, both the cationic groups and the polymer backbone were found to be degraded in 1 M NaOH solution at 60 °C over 48 h as measured by changes of ion exchange capacity and intrinsic viscosity. Imidazolium-functionalized poly(fluorenyl ether ketone sulfone)s had similar aqueous alkaline stability to quaternary ammonium-functionalized materials at 60 °C but much lower stability at 80 °C. This work demonstrates that quaternary ammonium and imidazolium cationic groups are not stable on poly(arylene ether sulfone) backbones under relatively mild conditions. Additionally, the poly(arylene ether sulfone) backbone, which is one of the most common polymers used in ion exchange membrane applications, is not stable in the types of molecular configurations analyzed.

Concepts: Electron, Chemistry, Polymer, Ion, Monomer, Ammonium, Cation exchange capacity, Alkali anion exchange membrane


A very simple and efficient stereoselective approach to cis-2,3-disubstituted piperdines via the reduction of N-acyl iminium ion intermediates is described. Application of this methodology is exemplified by the enantioselective total synthesis of (+)-(2S, 3S)-CP-99,994.

Concepts: Total synthesis, Paclitaxel total synthesis, Chemical synthesis, Ammonium, Iminium


G-quadruplex nucleic acids can bind ammonium ions in solution, and these complexes can be detected by electrospray mass spectrometry (ESI-MS). However, because ammonium ions are volatile, the extent to which ESI-MS quantitatively could provide an accurate reflection of such solution-phase equilibria is unclear. Here we studied five G-quadruplexes having known solution-phase structure and ammonium ion binding constants: the bimolecular G-quadruplexes (dG(4)T(4)G(4))(2), (dG(4)T(3)G(4))(2), and (dG(3)T(4)G(4))(2), and the intramolecular G-quadruplexes dG(4)(T(4)G(4))(3) and dG(2)T(2)G(2)TGTG(2)T(2)G(2) (thrombin binding aptamer). We found that not all mass spectrometers are equally suited to reflect the solution phase species. Ion activation can occur in the electrospray source, or in a high-pressure traveling wave ion mobility cell. When the softest instrumental conditions are used, ammonium ions bound between G-quartets, but also additional ammonium ions bound at specific sites outside the external G-quartets, can be observed. However, even specifically bound ammonium ions are in some instances too labile to be fully retained in the gas phase structures, and although the ammonium ion distribution observed by ESI-MS shows biases at specific stoichiometries, the relative abundances in solution are not always faithfully reflected. Ion mobility spectrometry results show that all inter-quartet ammonium ions are necessary to preserve the G-quadruplex fold in the gas phase. Ion mobility experiments, therefore, help assign the number of inner ammonium ions in the solution phase structure.  

Concepts: Ammonia, Mass spectrometry, Ion, Electrospray ionization, Taylor cone, Ion source, Ammonium, Ion mobility spectrometry


Different solid state fermentation (SSF) sources were tested such as cantaloupe and watermelon rinds, orange and banana peels, for the production of polygalacturonase (PG) and xylanase (Xyl) by Trichoderma harzianum and Trichoderma virens. The maximum production of both PG and Xyl were obtained by T. harzianum and T. virnes grown on cantaloupe and watermelon rinds, respectively. Time course, moisture content, temperature, pH, supplementation with carbon and nitrogen sources were optimized to achieve the maximum production of both PG and Xyl of T. harzianum and T. virens using cantaloupe and watermelon rinds, respectively. The maximum production of PG and Xyl of T. harzianum and T. virens was recorded at 4-5 days of incubation, 50-66% moisture, temperature 28-35°C and pH 6-7. The influence of supplementary carbon and nitrogen sources was studied. For T. harzianum, lactose enhanced PG activity from 87 to 120 units/g solid, where starch and maltose enhanced Xyl activity from 40 to 55-60 units/g solid for T. virnes. Among the nitrogen sources, ammonium sulphate, ammonium nitrate, yeast extract and urea increased PG activity from 90 to 110-113 units/g solid for T. harzianum. Similarly, ammonium chloride, ammonium sulphate and yeast extract increased Xyl activity from 45 to 55-70 units/g solid for T. virens.

Concepts: Carbon dioxide, Ammonia, Enzyme, Nitrogen, Starch, Ammonium, Ammonium nitrate, Trichoderma


A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.

Concepts: Ammonia, Hydrogen, Nucleophilic substitution, Organic reaction, Functional groups, Organic chemistry, Ammonium, Substitution reactions