bluuebunny/crossref_metadata_2025 huggingface dataset:
Bhc‐cNMPs as either Water‐Soluble or Membrane‐Permeant Photoreleasable Cyclic Nucleotides for both One‐ and Two‐Photon Excitation
Authors: Furuta Toshiaki , Takeuchi Hiroko , Isozaki Masahiro , Takahashi Yasuhiro , Kanehara Makoto , Sugimoto Masazumi , Watanabe Takayoshi , Noguchi Kousei , Dore Timothy M. , Kurahashi Takashi , Iwamura Michiko , Tsien Roger Y.
Published: August 2004

Cyclic nucleoside monophosphates (cNMPs) play key roles in many cellular regulatory processes, such as growth, differentiation, motility, and gene expression. Caged derivatives that can be activated by irradiation could be powerful tools for studying such diverse functions of intracellular second messengers, since the spatiotemporal dynamics of these molecules can be controlled by irradiation with appropriately focused light. Here we report the synthesis, photochemistry, and biological testing of 6‐bromo‐7‐hydroxycoumarin‐4‐ylmethyl esters of cNMP (Bhc‐cNMP) and their acetyl derivatives (Bhc‐cNMP/Ac) as new caged second messengers. Irradiation of Bhc‐cNMPs quantitatively produced the parent cNMPs with one‐photon uncaging efficiencies (Φε) of up to one order of magnitude better than those of 2‐nitrophenethyl (NPE) cNMPs. In addition, two‐photon induced photochemical release of cNMP from Bhc‐cNMPs (7and8) can be observed with the two‐photon uncaging action cross‐sections (δu) of up to 2.28 GM (1 GM=10−50cm4 s photon−1), which is the largest value among those of the reported Bhc‐caged compounds. The wavelength dependence of the δuvalues of7revealed that the peak wavelength was twice that of the one‐photon absorption maximum. Bhc‐cNMPs showed practically useful water solubility (nearly 500 μM), whereas 7‐acetylated derivatives (Bhc‐cNMPs/Ac) were expected to have a certain membrane permeability. Their advantages were demonstrated in two types of biological systems: the opening of cAMP‐mediated transduction channels in newt olfactory receptor cells and cAMP‐mediated motility responses in epidermal melanophores in scales from medaka fish. Both examples showed that Bhc and Bhc/Ac caged compounds have great potential for use in many cell biological applications.
Dendritic Polyamines: Simple Access to New Materials with Defined Treelike Structures for Application in Nonviral Gene Delivery
Authors: Krämer Michael , Stumbé Jean‐François , Grimm Günther , Kaufmann Brigitte , Krüger Ute , Weber Martin , Haag Rainer
Published: August 2004

Polycationic dendrimers are interesting nonviral vectors for in vitro DNA delivery. We describe a simple approach to the synthesis of dendritic polyamines with different molecular weights and adjustable flexibility (degrees of branching; DB). Both parameters influence the transfection efficiency and the cell toxicity of the polymer. Functionalization of hyperbranched polyethylenimine (PEI) by a two‐step procedure generated fully branched pseudodendrimers (analogues of polypropylenimine (PPI) and polyamidoamine (PAMAM) dendrimers). The DNA transfection efficiencies observed for these polymers depended on the cell line investigated. The highest efficiencies were observed for polymers whose unfunctionalized PEI cores had molecular weights in the range Mw=6000–25 000 g mol−1. The cytotoxicity of the dendrimers generally rises with increasing core size. The data collected for NIH/3T3 and COS‐7 cells indicate a maximum transfection efficiency at around 60 % branching for the PPI analogues, and at a PEI‐core molecular weight of Mw=25 000 g mol−1. PAMAM functionalization of PEI (Mw=5000 and 21 000 g mol−1) leads to polymers with little or no cytotoxity in the cell lines investigated.
Preliminary Characterization of Light Harvesting in E. coli DNA Photolyase
Authors: Henry Allison A. , Jimenez Ralph , Hanway Denise , Romesberg Floyd E.
Published: August 2004

E. coli DNA photolyase is a monomeric light‐harvesting enzyme that utilizes a methenyltetrahydrofolate (MTHF) antenna cofactor to harvest light energy for the repair of thymine dimers in DNA. For this purpose, the enzyme evolved to bind the cofactor and red‐shift its absorption maximum by 25 nm. Using the crystal structure as a guide, we mutated each protein residue that contacts the cofactor in an effort to identify the interactions responsible for this selective stabilization of the cofactor's excited state. Hydrogen bonding, packing, and electrostatic interactions were examined. Remarkably, a single residue, Glu109, appears to play an important, if not exclusive, role in inducing the observed red‐shift. Thus, this protein, the simplest light‐harvesting system known, appears to have evolved a remarkably simple mechanism to tune the photophysical properties of the antenna cofactor appropriately for biological function.
Cell‐free Protein Synthesis through Solubilisate Exchange in Water/Oil Emulsion Compartments
Authors: Pietrini Adriana V. , Luisi Pier Luigi
Published: August 2004

This work is aimed at finding conditions under which synthetic compartments used as cell models can fuse with each other and allow reagents contained in the different compartments to react. This goal seems to be best achieved by the use of water in oil emulsions (w/o) with dimensions in the range of 30–60 μm. In particular, cell‐free EGFP (enhanced green fluorescent protein) synthesis takes place in Tween 80/Span 80 w/o emulsions, and the extent of the reaction can be monitored directly by fluorescence. The medium is mineral oil, containing 0.5 % v/v aqueous solution. Different premixing configurations of the components (plasmid, amino acids, E. Coli extract) are used and compared. The in vitro synthesis of EGFP in emulsion droplets proceeds for 1 h, and the yield is 7.5 ng μL−1 protein. EGFP synthesis in aqueous solution takes place for at least 5 h. The yield is 10.5 ng μL−1 protein after 1 h and 15.8 ng μL−1 protein after 5 h. The results with the w/o emulsions show that solubilisate exchange takes place among the different water droplets, but it is not possible to demonstrate clearly that a true fusion takes place.
A Metal‐Coordinating DNA Hairpin Mimic
Authors: Bianké Gapian , Häner Robert
Published: August 2004

A self‐complementary oligodeoxynucleotide containing a 6,6′′‐substituted terpyridine was found to adopt a highly stable, hairpin‐like structure. In addition to serving as a hairpin‐loop mimic, the terpyridine can act as a coordination site for metals. Thus, the binding of several divalent transition metals (Zn2+, Co2+, Ni2+, Cu2+ and Pd2+) to the terpyridine hairpin mimic was investigated. The terpyridine‐modified hairpin mimic forms a stable secondary structure in the presence of these metals. The stability of the metal‐coordinated hairpin mimic was found to be lower than in the absence of metal. Furthermore, the Tm of the metallohairpin is strongly influenced by the type of the bound metal, with Tm's increasing in the order Co2+∼Ni2+<Zn2+<Cu2+<Pd2+. Model considerations suggest that a conformational change of the terpyridine ligand is required to allow coordination of the metal.
The Identification of an Adenovirus Receptor by Using Affinity Capture and Mass Spectrometry
Authors: Trauger Sunia A. , Wu Eugene , Bark Steve J. , Nemerow Glen R. , Siuzdak Gary
Published: August 2004

A tandem mass spectrometry‐based approach is demonstrated for detecting a receptor for Ad37, one of the causative agents for epidemic keratoconjunctivitis. Partial purification of membrane glycoproteins was performed by using lectin‐affinity chromatography and SDS‐PAGE. Gel bands that were shown to bind Ad37 by using Viral Overlay Protein Blot Assay (VOPBA) were excised, proteolyzed and analyzed by using nanoLC‐MS/MS to identify putative receptors contained in a mixture of proteins. Four candidate receptors were identified among approximately 50 proteins based on a search against a protein database. Inhibition of gene delivery mediated by an Ad37 vector, with antibodies against the glycoproteins identified by tandem mass spectrometry, strongly indicated that Membrane Cofactor Protein (MCP), a member of the complement regulatory family of proteins, is the receptor. This rapid and sensitive MS/MS‐based strategy is perceived to have wide potential applications for the detection of viral receptors.
Conformationally Gated Electrochemical Gene Detection
Authors: Immoos Chad E. , Lee Stephen J. , Grinstaff Mark W.
Published: August 2004

The synthesis and characterization of a 26‐base DNA hairpin containing both a redox‐active reporter (ferrocene) and terminal thiol functionality for electrochemical gene detection is described. This electrochemical DNA sensor exploits electron‐transfer dynamics that alter as a consequence of a large structural rearrangement (hairpin‐to‐duplex) induced by hybridization of the target DNA sequence. Melting temperature and circular dichroism studies confirm that the 26‐mer DNA forms a hairpin structure in the absence of target DNA. The loop region of the DNA hairpin is shown to form a stable duplex in the presence of complementary single‐stranded DNA. Atomic force microscopy and ellipsometry experiments of immobilized self‐assembled DNA monolayers suggest that hybridization with complementary DNA affords a conformational change that alters the electrochemical response.
A High‐Throughput Screen for Porphyrin Metal Chelatases: Application to the Directed Evolution of Ferrochelatases for Metalloporphyrin Biosynthesis
Authors: Kwon Seok Joon , Petri Ralf , deBoer Arjo L. , Schmidt‐Dannert Claudia
Published: August 2004

Porphyrins are of particular interest in a variety of applications ranging from biocatalysis and chemical synthesis to biosensor and electronic technologies as well as cancer treatment. Recently, we have developed a versatile system for the high‐level production of porphyrins in engineered E. coli cells with the aim of diversifying substitution patterns and accessing porphyrin systems not readily available through chemical synthesis. However, this approach failed to produce significant amounts of the metalloporphyrin in vivo from overproduced protoporphyrin due to insufficient metal insertion. Therefore, we systematically assessed the activity of the B. subtilis ferrochelatase in vivo and in vitro. A true high‐throughput‐screening approach based on catalytic in vivo ferrochelatase activity was developed by using fluorescence‐activated cell sorting (FACS). This assay was used to screen a library of 2.4×106 ferrochelatase mutants expressed in protoporphyrin‐overproducing recombinant E. coli cells. Several selected protein variants were purified, and their improved catalytic activity was confirmed in vitro. In addition to ferrochelatase activity, metal transport into E. coli was identified as another limitation for in vivo heme overproduction. Overexpression of the metal transporter zupT as part of the assembled pathway increased the overall metalloporphyrin production twofold. This report represents the most exhaustive in vitro evolution study of a ferrochelatase and demonstrates the effectiveness of our novel high‐throughput‐screening system for directed evolution of ferrochelatases based on their catalytic activity.
Exploring Hoogsteen and Reversed‐Hoogsteen Duplex and Triplex Formation with Tricyclo‐DNA Purine Sequences
Authors: Renneberg Dorte , Leumann Christian J.
Published: August 2004

The duplex‐ and triplex‐formation properties of the tricyclo‐DNA purine decamer 5′p‐gagaaggaaa‐3′ as a single strand or as part of a hairpin duplex with corresponding parallel and antiparallel pyrimidine DNA and RNA complements, as well as with antiparallel purine DNA and RNA complements, were investigated by UV melting curve analysis, circular dichroism spectroscopy, and gel mobility shift experiments. It was found that tricyclo‐DNA forms very stable duplexes with the pyrimidine RNA and DNA complements not only in the Watson–Crick pairing mode, but also in the Hoogsteen one. Below pH 6.0, the tc‐DNA/DNA and tc‐DNA/RNA Hoogsteen duplexes were found to be more stable than the corresponding Watson–Crick DNA duplexes. Triplexes of the hairpin structure with parallel pyrimidine complements revealed even stronger Hoogsteen pairing relative to the duplexes, presumably due to structural preorganization phenomena. Triplex formation with antiparallel pyrimidine and purine third strands (reversed‐Hoogsteen motif) could not be observed and seem to be unstable.
Cover Picture: Dendritic Polyamines: Simple Access to New Materials with Defined Treelike Structures for Application in Nonviral Gene Delivery (ChemBioChem 8/2004)
Authors: Krämer Michael , Stumbé Jean‐François , Grimm Günther , Kaufmann Brigitte , Krüger Ute , Weber Martin , Haag Rainer
Published: August 2004

The cover picture shows the highly branched dendritic polymers obtained from controlled conversion of hyperbranched polyethyleneimine (PEI) by addition of acrylonitrile and subsequent reduction. These PEI–PPI (polypropylenimine) dendritic architectures have been tested for their in vitro DNA‐transfection efficiencies in various cell lines. Surprisingly, not only the molecular‐weight screening but also the precise tailoring of different degrees of branching show clear transfection maxima. The background shows the transfected cells in blue as observed in the galactosidase assay. Detailed information about these highly active nonviral vectors for in vitro DNA delivery is reported by R. Haag et al. on p. 1081 ff.
Factors Affecting Chemical Remediation of Oil Contaminated Water‐Wetted Soil
Authors: Amro M.M.
Published: August 2004

The removal of hydrocarbons from contaminated soil is an essential practice because of environmental concerns, and in order to avoid surface and groundwater contamination. There are different methods applied to remove the hydrocarbons from the soil environment. However, the efficiency of soil remediation depends on several factors, such as the penetration depth of the oil into the soil, the type of oil and polluted soil and the age and degree of contamination. Chemical extraction is one of the approaches employed in handling contaminated sites. Many operations in the petroleum exploration, production and transportation have the potential to affect the environment in different degrees. Leakages from pipelines and stranded oil spills are the major sources of oil‐contamination. If hydrocarbon contamination occurs in the soil, the affected portion of soil must be treated to prevent subsequent pollution of groundwater. In this study, a laboratory investigation of factors affecting the chemical extraction using different solvents was conducted to remove the hydrocarbon from artificially contaminated soil samples in presence of water. Moreover, two different types of crude oil were used to study the effect of oil composition on the removal process. The results have identified large variation in the removal efficiency of the applied solvents, depending mainly on the solvent and the type of oil. The main factors affecting the removal process are presented and investigated. In addition, these results were compared with those of dry soil samples.
Experimental Investigation and Simulation of a Gas‐agitated Sieve Plate Column
Authors: Lü S. , Mi Z. , Wang Y. , Wang L.
Published: August 2004

The extraction of hydrogen peroxide by means of deionized water from anthraquinone working solution via anthraquinone process was carried out in a gas‐agitated sieve plate extraction column. The effects of the superficial velocity of air, dispersed phase and continuous phase on the overall plate extraction efficiency have been investigated. The corrections for the prediction of the overall plate extraction efficiency were presented. The correction proposed to predict the overall plate extraction efficiency in the air, water, anthraquinone working solution three‐phase system agreed satisfactory with experimental data with a maximum absolute deviation of 5.6 %. A new design method for gas‐liquid‐liquid three‐phase extractors is developed based on the multistage countercurrent extraction model. The calculated data by the model agreed well with experimental data and the average relative deviation was less than 10 %. Moreover, the model was used to predict a gas‐agitated sieve plate extraction column for industrial production of hydrogen peroxide. The results show that the plate numbers of gas‐agitated sieve plate extraction column are 30–40 % less than that of liquid‐liquid sieve plate column.
Compatibilization of Polymer Blends from Poly(butadiene‐g‐poly(styrene‐co‐acrylonitrile)) and Polycarbonate through Oxazoline‐ and Benzoxazole‐Modification of ABS
Authors: Becker H.G. , Schmidt‐Naake G.
Published: August 2004

Blends of poly(butadiene‐g‐poly(styrene‐co‐acrylonitrile) (ABS) with polycarbonate (PC) are some of the most successful multiphase materials, with applications in the automotive and electronics industries. The mechanical properties of the complete incompatible blends are mainly determined by the interaction between the poly(styrene‐co‐acrylonitrile) (S/AN) component of the ABS and the PC as well as through the dispersion of the elastomeric component poly(butadiene) in the thermoplastic S/AN‐matrix.

The aim of our work is to optimize the modification process by the use of new substituted amino alcohols and amino phenols, as well as the use of a more efficient catalyst. Both reactive and non reactive compatibilization of polymer blends should be performed with the new ABS‐modifications.
Heat Dispersion Effects on the Functional Characteristics of Industrial‐scale Adiabatic Membrane Reactors
Authors: Vogiatzis E. , Koukou M.K. , Papayannakos N. , Markatos N.C.
Published: August 2004

The influence of heat dispersion on the performance of adiabatic industrial‐scale membrane reactors is studied in this work. The results presented are from the application of the model to a membrane reactor that is introduced in an IGCC plant, to control carbon dioxide emissions. The performance of this reactor equipped with highly selective membranes is studied in detail. The thermal phenomena that take place in the interior of the membrane reactor have a considerable influence on the operation of the reactor thus the assumption of isothermal operation is not valid. The omission of thermal dispersion results on the underestimation of the system operation and the total gaseous fluxes that permeate through the membrane. The temperature distribution in the membrane reactor differs significantly from the calculated distribution predicted from the model that ignores thermal dispersion effects.
Liquid‐Phase Catalytic Hydrogenation of p‐Chlorobenzophenone to p‐Chlorobenzhydrol over a 5 % Pd/C Catalyst
Authors: Bawane S.P. , Sawant S.B.
Published: August 2004

The kinetics of the liquid‐phase catalytic hydrogenation of p‐chlorobenzophenone have been investigated over a 5 % Pd/C catalyst. The effects of hydrogen partial pressure (800–2200 kPa), catalyst loading (0.4–1.6 gm dm–3), p‐chlorobenzophenone concentration (0.37–1.5 mol dm–3), and temperature (303–313 K) were studied. A stirring speed > 20 rps has no effect on the initial rate of reaction. Effects of various catalysts (Pd/C, Pd/BaSO4, Pd/CaCO3, Pt/C, Raney nickel) and solvents (2‐propanol, methanol, dimethylformamide, toluene, xylene, hexane) on the hydrogenation of p‐chlorobenzophenone were also investigated. The reaction was found to be first order with respect to hydrogen partial pressure and catalyst loading, and zero order with respect to p‐chlorobenzophenone concentration. Several Langmuir‐Hinshelwood type models were considered and the experimental data fitted to a model involving reaction between adsorbed p‐chlorobenzophenone and hydrogen in the liquid phase.
A Critical Study of Decentralized Controllers for a Multivariable System
Authors: Viknesh R. , Sivakumaran N. , Chandra J.S. , Radhakrishnan T.K.
Published: August 2004

Industrial processes are naturally multivariable in nature. A comparison of multivariable decentralized controllers has been performed and a multivariable four interconnected water tank system, which exhibits a RHP (Right Half Plane) zero is considered for decentralized control. The characteristics of a four‐tank system are discussed and a decentralized PI (Proportional‐Integral) controller is designed for the system based on various control algorithms. The algorithms are simulated using MATLAB and the performances are compared for reference tracking, disturbance rejection and model uncertainty cases. The comparison of the results show that the controllers based on Gershgorin band and Ideal relay method are suitable for the control of a four‐tank system.
Axial Dispersion and Wall Effects in Narrow Fixed Bed Reactors: A Comparative Study Based on RTD and NMR Measurements
Authors: Tang D. , Jess A. , Ren X. , Bluemich B. , Stapf S.
Published: August 2004

Axial dispersion and wall effects in narrow fixed beds with aspect ratios < 10 were investigated, both by classical methods and by NMR imaging. The residence time distribution (RTD) in the center and at the wall was measured, system water/NaCl‐solution as tracer, and subsequently compared with radial velocity profiles based on NMR imaging. The influence of the aspect ratio and Rep on dispersion and on the degree of non‐uniformity of the velocity profile was studied. The NMR results are consistent with the RTD and also with literature data of numerical simulations. For low aspect ratios, dispersion/wall effects have a strong influence on the reactor behavior, above all, in cases where a low effluent concentration is essential, as proven by breakthrough experiments with the reaction of H2S with ZnO.
Hierarchical Nano‐structuring of Metal Oxide Catalysts – Part 1: Influence of Nano‐structuring on the Activity of the Catalysts
Authors: Stelzer J.B. , Caro J. , Habel D. , Feike E. , Schubert H. , Fait M. , Hidde G.
Published: August 2004

The oxidative dehydrogenation of short‐chain alkanes is a suitable model reaction to show correlations between the catalyst structure and the catalytic performance. For all investigated catalysts propane conversion increases with increasing amounts of the catalyticly active components V2O5, MoO3, or TiO2. It is proposed that the catalytic activity is related to the number and size of the contact zones between support and active component.
Explosion Limits of Hydrogen/Oxygen Mixtures at Initial Pressures up to 200 bar
Authors: Schröder V. , Emonts B. , Janßen H. , Schulze H.‐P.
Published: August 2004

The exact experimental determination of the pressure dependence of the explosion limits of hydrogen/oxygen mixtures at 20 °C and 80 °C was investigated. The anomaly in the pressure dependence of hydrogen explosion limits (decrease of the upper explosion limit with increase in pressure), known for hydrogen/air mixtures, could be confirmed for hydrogen/oxygen mixtures. Furthermore it was shown that the impurities in the product gases of the electrolyzer did not exceed 50 % of the lower explosion level in any case.
Droplet Velocity in Horizontal Two‐phase Air/Water Free Jet Flow in Stagnant Ambient
Authors: Surma R. , Friedel L.
Published: August 2004

For the case of an isothermal free jet flow the velocity and the size of the drops were measured with a Phase‐Doppler‐Anemometer. The axial velocity decay downstream from the nozzle outlet and the radial drop velocity profile are reproducible within reasonable limits, if a so‐called homogeneous flow mixture density in the nozzle outlet is introduced. In case of low mass flow qualities an adjustment of the entrainment coefficient and a virtual jet origin as well as a reduced exponent for the Gaussian function type radial velocity profile is required.
Iridium–Imine and –Amine Complexes Relevant to the (S)‐Metolachlor Process: Structures, Exchange Kinetics, and CH Activation by IrI Causing Racemization
Authors: Dorta Romano , Broggini Diego , Kissner Reinhard , Togni Antonio
Published: August 2004

Iridium complexes of DMA‐imine [2,6‐dimethylphenyl‐1′‐methyl‐2′‐methoxyethylimine, 1 a) and (R)‐DMA‐amine [(1′R)‐2,6‐dimethylphenyl‐1′‐methyl‐2′‐methoxyethylamine, 2 a] that are relevant to the catalytic imine hydrogenation step of the Syngenta (S)‐Metolachlor process were synthesized: metathetical exchange of [Ir2Cl2(cod)2] (cod=1,5‐cyclooctadiene) with [Ag(1 a)2]BF4 and [Ag((R)‐2 a)2]BF4 afforded [Ir(cod)(κ2‐‐1 a)]BF4 (11) and [Ir(cod)(κ2‐(R)‐2 a)]BF4 ((R)‐19)), respectively. These complexes were then used in stopped‐flow experiments to study the displacement of amine 2 a from complex 19 by imine 1 a to form the imine complex 11, thus modeling the product/substrate exchange step in the catalytic cycle. The data suggest a two‐step associative mechanism characterized by k1=(2.6±0.3)×102 M−1 s−1 and k2=(4.3±0.6)×10−2 s−1 with the respective activation energies EA1=(7.5±0.6) kJ mol−1 and EA2=(37±3) kJ mol−1. Furthermore, complex 11 reacted with H2O to afford the hydrolysis product [Ir(cod)(η6‐‐2,6‐dimethylaniline)]BF4 (12), and with I2 to liberate quantitatively the DMA‐iminium salt 14. On the other hand, the chiral amine complex (R)‐19 formed the optically inactive η6‐bound compound [Ir(cod)(η6‐rac‐2 a)]BF4 (rac‐18) upon dissolution in THF at room temperature, presumably via intramolecular CH activation. This racemization was found to be a two‐step event with k′1=9.0×10−4 s−1 and k2=2.89×10−5 s−1, featuring an optically active intermediate prior to sp3 CH activation. Compounds 11, 12, rac‐18, and (R)‐19 were structurally characterized by single‐crystal X‐ray analyses.
Electrophilic Aromatic Substitution by the Fluorofullerene C60F18
Authors: Darwish Adam D. , Avent Anthony G. , Abdul‐Sada Ala'a K. , Gol'dt Ilya V. , Hitchcock Peter B. , Kuvytchko Igor V. , Taylor Roger
Published: August 2004

The FeCl3‐catalysed arylation of C60F18 gives tri‐substituted compounds C60F15Ar3, where Ar=phenyl, 4‐tolyl, 4‐methoxyphenyl, 4‐phenoxyphenyl, 4‐chlorophenyl, 3,4‐dichlorophenyl, 2‐biphylenyl and 2‐fluorenyl, together with some bis‐ and mono‐substituted product. Bis‐substitution was achieved with biphenylene and fluoranthene, and mono‐substitution with biphenylene (2‐position), pyrene (1‐position), and naphthalene (1‐ and 2‐positions); the tris‐phenyl and tris‐biphenylene derivatives are fluorescent. The 2‐naphthyl substituent freely rotates at 328 K, whereas rotation of the 1‐naphthyl substituent is prevented by interaction of the peri‐hydrogen atom with fluorine. The 1‐naphthyl derivative eliminates a molecule of HF during EI mass spectrometry, whilst the 2‐naphthyl derivative eliminates HF and all fluorenes to give a naphthaleno[60]fullerene. The reaction rate is relatively unaffected by electron supply in the aryl rings, but no product was obtained with benzotrifluoride which defines the lower reactivity limit. The low discrimination between aromatics makes it possible to isolate derivatives having different aryl groups attached to the cage. Reactions occur mainly when the reagent solutions (or solutions in 1,2‐dichlorobenzene) are evaporated to dryness. In most FeCl3‐catalysed reactions, unreacted C60F18 was recovered, more if the less effective SnCl4 was used as a catalyst; use of AlCl3 resulted in polyarylation and degradation of the C60F18. The structure of C60F17(1‐biphenylyl) was confirmed by single‐crystal X‐ray analysis. Reaction of C60F18 with perylene/FeCl3/o‐dichlorobenzene gave red fluorescent “tagliatelli”‐like threads (up to 1 cm long) of self‐assembled π‐stacked tetrachloroperylene arising from chlorination by FeCl3.
Structural and Electrochemical Studies of Novel Bis(μ‐methoxo)diiron complexes: Observation of FeIIIFeIV and FeIVFeIV States Resonating with Phenoxyl Radicals
Authors: Houjou Hirohiko , Kanesato Masatoshi , Hiratani Kazuhisa , Mandon Dominique
Published: August 2004

Novel diiron complexes with an Fe2(μ‐OMe)2 core were studied as models of the active site of nonheme iron‐containing enzymes. X‐ray crystal structures of the complexes showed the existence of two types of ligand folding—parallel and twisted—both of which have four virtually equivalent phenolato groups sticking out from the Fe2O2 rhombic plane. Cyclic voltammetry measurements revealed two or more distinct redox waves in a region of relatively high potential, in addition to known FeII/FeIII redox waves in a region of lower potential. These new peaks were assigned to the high‐valence state of iron atoms, that is, FeIIIFeIV and FeIVFeIV, resonating with the phenoxyl radical(s). The split width of the redox waves ranged from 0.14 to 0.20 eV, which may be a measure of the electronic interaction of the phenolate groups through the Fe2(μ‐OMe)2 core.
Synthesis and Determination of the Absolute Configuration of Fugomycin and Desoxyfugomycin: CD Spectroscopy and Fungicidal Activity of Butenolides
Authors: Braun Manfred , Hohmann Andreas , Rahematpura Jaykumar , Bühne Corinna , Grimme Stefan
Published: August 2004

The dibromoalkenes (S)‐3 and (R)‐ and (S)‐4 are intermediates in the syntheses of the naturally occurring fungicidal butenolides fugomycin (1) and desoxyfugomycin (2), respectively. The stereoselective bromine–lithium exchange that leads to the carbenoid 12 and the vinyllithium reagent 17 a on the one hand, and palladium‐catalyzed coupling reactions of the dibromoalkene 3 and the bromolactone 22 on the other are key steps en route to the butenolides 1 and 2. The chiral building blocks (S)‐3, (R)‐4, and (S)‐4 are readily available from (R)‐isopropylideneglyceraldehyde 5, isobutyl (R)‐lactate 6 a, and ethyl (S)‐lactate 6 b, respectively. The synthetic procedure adopted here permits the absolute configuration of the natural products fugomycin (1) and desoxyfugomycin (2) to be assigned by comparison of their chiroptical properties with those of the synthetic products. The CD spectra of the bromolactone 22, calculated by two different density functional methods (TDDFT, DFT/MRCI), are found to be in good agreement with the measured spectra. On the basis of these calculations, the two CD bands observed could be assigned to n–π* and π–π* transitions, respectively. Fugomycin (1) and the synthetic butenolide 20 displayed high fungicidal activity against botrytis in greenhouse experiments, whereas the saturated lactone 21 was practically inactive.
Ligand Lability and Chirality Inversion in Yb Heterobimetallic Catalysts
Authors: Di Bari Lorenzo , Lelli Moreno , Salvadori Piero
Published: August 2004

We have investigated the exchange dynamics between the free and bound ligand in K3[Yb{(R)‐binol}3], the most active heterobimetallic lanthanoid catalyst for cyclic imine hydrophosphonylation; we found that the Yb–binol bond is labile. The rate constant for this exchange was determined through NMR saturation transfer experiments. Upon addition of (S)‐binaphthol, ligand exchange leads to the formation of a small quantity of heterochiral complexes and, in the presence of a molar excess of (S)‐binaphthol, to chirality inversion of the whole complex. This demonstrates that, in contrast to other analogous systems, K3[Yb(binol)3] displays a strong chiral discrimination, with the overwhelming preference for ligands of the same configuration. The lability of Yb–binol bond in THF may suggest a ligand‐to‐substrate exchange as a key step in the catalytic process.
Arachno, Nido, and Closo Aromatic Isomers of the Li6B6H6 Molecule.
Authors: Alexandrova Anastassia N. , Boldyrev Alexander I.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Gas‐Phase Structure, Conformation, and Sulfur 2p Photoelectron Spectroscopy of Pentafluorosulfur Fluorosulfonate, SF5OSO2F
Authors: Leibold Christiane , Oberhammer Heinz , Thomas T. Darrah , Saethre Leif J. , Winter Rolf , Gard Gary L.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Electronic Properties and Chemical Bonding of Single‐Walled MoO3 Nanotubes
Authors: Enyashin Andrei N. , Ivanovskaya Victoria V. , Ivanovskii Alexander L.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Crystal Structure of a Cadmium Iodate Monohydrate: Cd(IO3)2×H2O.
Authors: Bentria Bachir , Benbertal Djamal , Bagieu‐Beucher Muriel , Mosset Alain
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Crystal Structure of Ba3Al2F12.
Authors: Kaiser V. , Babel D.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
The Crystal Structure of K2Cu5Cl8 (OH)4×2H2O.
Authors: Kahlenberg Volker
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Synthesis, Structure, and Characterization of a Cubic Thallium Cluster Phase of the Bergman Type, Na13 (Cd≈0.70Tl≈0.30)27.
Authors: Li Bin , Corbett John D.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Crystal Structure and Spectroscopic Properties of CsVO2SO4.
Authors: Rasmussen S. B. , Boghosian S. , Nielsen K. , Eriksen K. M. , Fehrmann R.
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
Exploiting the Joint Action of Chemical Shielding and Heteronuclear Dipolar Interactions to Probe the Geometries of Strongly Hydrogen‐Bonded Silanols.
Authors: Gardiennet Carole , Marica Florea , Assfeld Xavier , Tekely Piotr
Published: August 2004

For Abstract see ChemInform Abstract in Full Text.
An Oxygen‐Centered Titanium Square Embedded in a Cuboctahedron of Iodine in the Salt K4[{Ti4O}I12].
Authors: Jongen Liesbet , Mudring Anja‐Verena , Moeller Angela , Meyer Gerd
Published: August 2004

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Tantalum Clusters in Oxidic Matrices — Synthesis, Crystal Structure and Magnetic Properties of Eu1.83Ta15O32.
Authors: Alvarez‐Lopez Maria R. , Ritter Arno , Pietzonka Clemens , Harbrecht Bernd
Published: August 2004

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Dawson Type Heteropolyanions. Part 3. Syntheses and 31P, 51V, and 183W NMR Structural Investigation of Octadeca(molybdo‐tungsto‐vanado)diphosphates Related to the [H2P2W12O48]12‐ Anion.
Authors: Contant Roland , Abbessi Mostefa , Thouvenot Rene , Herve Gilbert
Published: August 2004

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Synthesis, Crystal Structure, and Molecular Modeling of a Layered Manganese(II) Phosphate: Mn3(PO4)4×2 (H3NCH2CH2)3N×6 (H2O).
Authors: Thoma Steven G. , Bonhomme Francois , Cygan Randall T.
Published: August 2004

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The First T5‐Supertetrahedron in Oxide Chemistry: Na26Mn39O55.
Authors: Moeller Angela , Amann Peter , Kataev Vladislav , Schittner Norbert
Published: August 2004

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Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by a Camphorsulfonamide Ligand.
Authors: Xu Zhaoqing , Chen Chao , Xu Jiangke , Miao Mingbo , Yan Wenjin , Wang Rui
Published: August 2004

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Asymmetric 1,4‐Reductions of Hindered β‐Substituted Cycloalkenones Using Catalytic SEGPHOS—Ligated CuH.
Authors: Lipshutz Bruce H. , Servesko Jeff M. , Petersen Tue B. , Papa Patrick P. , Lover Andrew A.
Published: August 2004

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Reaction Between Nitrogen—Containing Heterocycles and Dialkyl Acetylenedicarboxylate with Strong CH‐Acid: Synthesis of Stable Highly Functionalized 1,4‐Diionic Nitrogen Betaines.
Authors: Shaabani Ahmad , Bazgir Ayoob , Tavasoli‐Rad Farahnaz , Bijanzadeh Hamid Reza , Razmara Freidoon
Published: August 2004

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Synthesis of α,α′‐Bis(substituted benzylidene)ketones Catalyzed by a SOCl2/EtOH Reagent.
Authors: Hu Zhi Guo , Liu Jun , Zeng Ping Li , Dong Zhi Bing
Published: August 2004

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Synthesis and Structure—Activity Relationships of New Antimicrobial Active Multisubstituted Benzazole Derivatives.
Authors: Yildiz‐Oren Ilkay , Yalcin Ismail , Aki‐Sener Esin , Ucarturk Nejat
Published: August 2004

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A New Approach to 2,2‐Disubstituted Chromenes and Tetrahydroquinolines Through Intramolecular Cyclization of Chiral 3,4‐Epoxy Alcohols.
Authors: Goujon Jean‐Yves , Zammattio Francoise , Chretien Jean‐Mathieu , Beaudet Isabelle
Published: August 2004

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Anomeric Oxygen to Carbon Rearrangements of Alkynyl Tributylstannane Derivatives of Furanyl (γ)‐ and Pyranyl (δ)‐Lactols.
Authors: Buffet Marianne F. , Dixon Darren J. , Ley Steven V. , Reynolds Dominic J. , Storer R. Ian
Published: August 2004

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Nanoflow System for Perfect Regiocontrol in the Baeyer—Villiger Oxidation by Aqueous Hydrogen Peroxide Using Lowest Concentration of a Fluorous Lanthanide Catalyst.
Authors: Mikami Koichi , Islam Md. Nazrul , Yamanaka Masahiro , Itoh Yoshimitsu , Shinoda Masaki , Kudo Kenichi
Published: August 2004

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Phosphine‐Catalyzed Regiospecific Allylic Amination and Dynamic Kinetic Resolution of Morita—Baylis—Hillman Acetates.
Authors: Cho Chang‐Woo , Kong Jong‐Rock , Krische Michael J.
Published: August 2004

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A Convenient Tin‐Free Procedure for Radical Carboazidation and Azidation.
Authors: Panchaud Philippe , Renaud Philippe
Published: August 2004

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Iron‐Catalyzed Grignard Cross‐Coupling with Alkyl Halides Possessing β‐Hydrogens.
Authors: Nagano Takashi , Hayashi Tamio
Published: August 2004

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Reductive Coupling of Benzylic and Allylic Halides with Sodium Dithionite in DMF or HMPA.
Authors: Khurana Jitender M. , Bansal Geeti , Sahoo Prabhat K.
Published: August 2004

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4‐(tert‐Butyldimethylsilyloxy)benzylidene Acetal: A Novel Benzylidene‐Type Protecting Group for 1,2‐Diols.
Authors: Kaburagi Yosuke , Osajima Hiroyuki , Shimada Kousei , Tokuyama Hidetoshi , Fukuyama Tohru
Published: August 2004

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Prenyl Carbamates: Preparation and Deprotection.
Authors: Vatele Jean‐Michel
Published: August 2004

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MoO2(acac)2 Catalyzed Oxidative Deprotection of Oximes.
Authors: De Surya Kanta
Published: August 2004

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Oxidative Deprotection of Trimethylsilyl Ethers Using Bismuth Nitrate Supported onto Montmorillonite k‐10 under Microwave Irradiation in Solventless System.
Authors: Heravi Majid M. , Oskooie Hossein A. , Yazdanpanah Sedigheh , Mojtahedi Majid
Published: August 2004

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Synthesis of Highly Functionalized 1‐Azadienes and Ketenimines.
Authors: Yavari Issa , Djahaniani Hoorieh , Nasiri Farough
Published: August 2004

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Synthesis of Two New Families of Fluorinated Compounds: 1H,1H,2H,2H‐Perfluoro‐3,5‐alkyldiynols and 1H,1H‐Perfluoro‐2,4‐alkyldiynols and Their Acrylates and Methacrylates.
Authors: Robert‐Estelrich Ana , Castella‐Matinez Merce , Lopez‐Calahorra Francisco
Published: August 2004

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Reductive Dimerization of Azides to Secondary Amines under Hydrogenation Conditions.
Authors: An Il‐Hwan , Seong Hye‐Ran , Ahn Kyo Han
Published: August 2004

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Highly Enantioselective Catalytic Asymmetric Claisen Rearrangement of 2‐Alkoxycarbonyl‐Substituted Allyl Vinyl Ethers.
Authors: Abraham Lars , Koerner Marleen , Hiersemann Martin
Published: August 2004

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Palladium‐Catalyzed Reaction of 4‐Cyclopentene‐1,3‐diol Monoacetate with Grignard Reagents Producing Hitherto Unreachable cis‐1,2‐Isomers.
Authors: Hattori Hatsuhiko , Abbas Ashraf A. , Kobayashi Yuichi
Published: August 2004

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A Highly Efficient Oxidation of Cyclohexane over Au/ZSM‐5 Molecular Sieve Catalyst with Oxygen as Oxidant.
Authors: Zhao Rui , Ji Dong , Lv Gaomeng , Qian Guang , Yan Liang , Wang Xiaolai , Suo Jishuan
Published: August 2004

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A Novel Synthesis of Cyclic α‐Amino Aldehydes, Amino Alcohols, and α‐Amino Acid Methyl Esters from Cyclic Ketones Through Sulfinylaziridines.
Authors: Ota Hiroyuki , Chyouma Toshio , Iso Shuyu , Satoh Tsuyoshi
Published: August 2004

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Novel Intramolecular Cyclization of 2‐(Buta‐1,3‐dienyl)‐3‐methylpyrazines and 3‐(Buta‐1,3‐dienyl)‐4‐methyl‐1,2,5‐oxadiazoles into 5H‐Cycloheptapyrazines and 4H‐Cyclohepta‐1,2,5‐oxadiazoles.
Authors: Matsumoto Masakatsu , Hoshiya Naoyuki , Isobe Ryo , Watanabe Yukie , Watanabe Nobuko
Published: August 2004

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Cycloaddition Between Electron‐Deficient Partners: An Efficient Regio‐ and Stereoselective Synthesis of Functionalized Bicyclo[2.2.2]octenones. A Tandem Alkylation, Stereochemical Inversion and Aldol Condensation.
Authors: Singh Vishwakarma , Praveena G. D. , Mobin Shaikh M.
Published: August 2004

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Copper‐Catalyzed Synthesis of 1,3‐Enynes.
Authors: Bates Craig G. , Saejueng Pranorm , Venkataraman D.
Published: August 2004

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Kumada—Corriu Reactions of Alkyl Halides with Alkynyl Nucleophiles.
Authors: Yang Lian‐Ming , Huang Li‐Fu , Luh Tien‐Yau
Published: August 2004

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Phenyl Trifluorovinyl Sulfide: A Radical Acceptor for Preparation of gem‐Difluoromethylene Compounds.
Authors: Okano Takashi , Chokai Masayuki , Hiraishi Makiko , Yoshizawa Michito , Kusukawa Takahiro , Fujita Makoto
Published: August 2004

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Stereoselective Synthesis of Internal Allylic Fluorides.
Authors: Thibaudeau Sebastien , Fuller Robert , Gouverneur Veronique
Published: August 2004

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Chemoenzymatic Preparation of Optically Active β‐Aminocyclohexanols and Their Application in the Enantioselective Addition of Diethylzinc to Benzaldehyde.
Authors: Gonzalez‐Sabin Javier , Gotor Vicente , Rebolledo Francisca
Published: August 2004

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The Acid Accelerated Ruthenium‐Catalyzed Dihydroxylation. Scope and Limitations.
Authors: Plietker Bernd , Niggemann Meike , Pollrich Anja
Published: August 2004

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Mg‐Promoted Mixed Pinacol Coupling.
Authors: Maekawa Hirofumi , Yamamoto Yoshimasa , Shimada Hisashi , Yonemura Kazuaki , Nishiguchi Ikuzo
Published: August 2004

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Efficient and Chemoselective Deprotection of 1,1‐Diacetates Using Fe2(SO4)3×xH2O as a Heterogeneous Catalyst.
Authors: Li Lingjun , Zhang Xinying , Zhang Guisheng , Qu Guirong
Published: August 2004

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A Mild Method for the Preparation of γ‐Hydroxy‐α,β‐acetylenic Esters.
Authors: Shahi Shatrughan P. , Koide Kazunori
Published: August 2004

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Biaryl Amide Glucagon Receptor Antagonists.
Authors: Kurukulasuriya Ravi , et al. et al.
Published: August 2004

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Cleavage of O‐Acylates of Isatin 3‐Oximes in the Presence of Alcohols.
Authors: Stankevicius A. P. , Terentiev P. B. , Janushene L. N. , Vainauskas P. V.
Published: August 2004

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Preparation of New Substituted Bis(benzoyl) Peroxides under Aqueous Conditions in the Presence of Stearyltrimethylammonium Chloride.
Authors: Moorhoff Cornelis M. , Braybrook Carl
Published: August 2004

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Application of Alkoxy‐λ6‐sulfanenitriles as Strong Alkylating Reagents.
Authors: Hao Wei , Fujii Takayoshi , Dong Tiaoling , Wakai Youko , Yoshimura Toshiaki
Published: August 2004

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N‐4‐Methansulfonamidobenzyl‐N′‐2‐substituted‐4‐tert‐butyl‐benzyl Thioureas as Potent Vanilloid Receptor Antagonistic Ligands.
Authors: Park Hyeung‐geun , et al. et al.
Published: August 2004

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Chain‐Branched 1,3‐Dibenzylthioureas as Vanilloid Receptor 1 Antagonists.
Authors: Kim Hee‐Doo , et al. et al.
Published: August 2004

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A Convenient Microwave‐Assisted Arylzinc Generation‐Negishi Coupling Protocol.
Authors: Mutule Ilga , Suna Edgars
Published: August 2004

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Synthesis of Chalcones Catalyzed by SOCl2/EtOH.
Authors: Hu Zhiguo , Liu Jun , Dong Zhibing , Guo Lili , Wang Dong , Zeng Pingli
Published: August 2004

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Microwave‐Accelerated Solventless Sonogashira‐Like Coupling Reaction of 1,1‐Dibromo‐1‐alkenes with Organic Halides on Nickel(0) Powder‐Doped KF/Al2O3.
Authors: Yan Jincan , Wang Zhiyuan , Wang Lei
Published: August 2004

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Design and Synthesis of Macrocyclic Inhibitors of Phosphatase Cdc25B.
Authors: Baeurle Stefan , Blume Thorsten , Guenther Judith , Henschel Daniela , Hillig Roman C. , Husemann Manfred , Mengel Anne , Parchmann Christian , Schmid Elke , Skuballa Werner
Published: August 2004

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Tetracyanoresorcin[4]arene Ion Channel Shows pH Dependent Conductivity Change.
Authors: Chen Wen‐Hua , Nishikawa Masanori , Tan Song‐De , Yamamura Mika , Satake Akiharu , Kobuke Yoshiaki
Published: August 2004

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Synthesis and Reactivity of 1‐Hydroxyspiro[2.5]cyclooct‐4‐en‐3‐ones.
Authors: Bose Gopal , Langer Peter
Published: August 2004

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Synthesis of a Novel Intercalator Based on 2,2′‐Binaphthalene Bearing Dimethylammonium Groups.
Authors: Kondo Shin‐ichi , Kinjo Tomoko , Yano Yumihiko
Published: August 2004

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Easy Access to N‐Alkylation of N‐Unsubstituted [60]Fulleropyrrolidines: Reductive Amination Using Sodium Triacetoxyborohydride.
Authors: Xiao Shengqiang , Li Yongjun , Li Yuliang , Liu Huibiao , Li Hongmei , Zhuang Junpeng , Liu Yang , Lu Fushen , Zhang Deqing , Zhu Daoben
Published: August 2004

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Diastereoselectivity in the Paterno—Buechi Reaction on Furan Derivatives.
Authors: D'Auria Maurizio , Emanuele Lucia , Racioppi Rocco
Published: August 2004

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Synthesis of Polysubstituted Furans by Palladium‐Catalyzed Coupling of Butatrienyl Carbinols with Aryl Halides and Triflates.
Authors: Aurrecoechea Jose M. , Perez Elena
Published: August 2004

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Synthesis and Biological Evaluation of Novel, Selective, Nonsteroidal Glucocorticoid Receptor Antagonists.
Authors: Akritopoulou‐Zanze Irini , Patel Jyoti R. , Hartandi Kresna , Brenneman Jehrod , Winn Martin , Pratt John K. , Grynfarb Marlene , Goos‐Nisson Annika , von Geldern Thomas W. , Kym Philip R.
Published: August 2004

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Synthesis of Donor—Acceptor Substituted Oligothiophenes by Stille Coupling.
Authors: Raposo M. Manuela M. , Fonseca A. Mauricio C. , Kirsch G.
Published: August 2004

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Palladium‐Catalyzed C—H Homocoupling of Thiophenes: Facile Construction of Bithiophene Structure.
Authors: Masui Kentaro , Ikegami Haruka , Mori Atsunori
Published: August 2004

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6‐Aryl‐2,4‐dioxo‐5‐hexenoic Acids, Novel Integrase Inhibitors Active Against HIV‐1 Multiplication in Cell‐Based Assays.
Authors: Artico Marino , et al. et al.
Published: August 2004

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Reactivity of Azafulvenium Methides Derived from Pyrrolo[1,2‐c]thiazole‐2,2‐dioxides: Synthesis of Functionalized Pyrroles.
Authors: Pinho e Melo Teresa M. V. D. , Soares Maria I. L. , Rocha Gonsalves Antonio M. d'A. , McNab Hamish
Published: August 2004

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Cross‐Metathesis Reactions of Vinyl‐Chlorins and ‐porphyrins Catalyzed by a “Second Generation” Grubbs′ Catalyst.
Authors: Liu Xin , Sternberg Ethan , Dolphin David
Published: August 2004

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