- Synthetic analogues of glycosylphosphatidylinositol-anchored proteins and their behavior in supported lipid bilayers
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Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified proteins in the outer leaflet of the plasma membrane. GPI-anchored proteins play vital ro
- Paulick, Margot G.,Wise, Amber R.,Forstner, Martin B.,Groves, Jay T.,Bertozzi, Carolyn R.
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Read Online
- Chain extender as well as preparation method and application thereof
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The invention relates to a chain extender. The chain extender is 3-(2-(2, 3-dihydroxy propyl) sulfo) ethyoxyl) propyl 3-(3-(tert-butyl)-4-hydroxy-5-methyl phenyl) propionate (GL), and the structural formula of the chain extender is shown in the specification. The prepared chain extender GL has an excellent toughening effect; the elongation at break of a polyurethane elastomer prepared from the GL reaches 1531.1594%, the toughness reaches 12.315% MJ/m , the repairing efficiency reaches 103.62% after the polyurethane elastomer is repaired for 6 h at the normal temperature, and the repairing efficiency reaches 125.53% after the polyurethane elastomer is repaired for 2 h at the temperature of 80 DEG C. The prepared chain extender GL can be compounded with other reinforced chain extenders so as to be used, and the tensile strength and toughness of the polyurethane elastomer are further improved synergistically.
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Paragraph 0038; 0041; 0043; 0046; 0048; 0051
(2022/01/20)
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- Non-natural amino acid and application thereof Recombinant protein and recombinant protein conjugate comprising same
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The invention provides a non-natural amino acid. A compound represented by formula (I) or an enantiomer thereof. The invention also provides application of the non-natural amino acid. Further, the present invention also provides a protein conjugate comprising the recombinant protein and of the non-natural amino acid prepared from the recombinant protein. The non-natural amino acid provided by the invention is simple and convenient to prepare, good in safety, not prone to inactivation when inserted into a protein, high in coupling ratio with a coupling part, good in stability of the obtained conjugate, and capable of being applied to various fields, especially in preparation of recombinant protein or recombinant protein conjugate.
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Paragraph 0094; 0098; 0099-0100
(2021/10/27)
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- Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
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Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
- Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
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p. 13073 - 13091
(2019/10/10)
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- Iterative Design and Optimization of Initially Inactive Proteolysis Targeting Chimeras (PROTACs) Identify VZ185 as a Potent, Fast, and Selective von Hippel-Lindau (VHL) Based Dual Degrader Probe of BRD9 and BRD7
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Developing PROTACs to redirect the ubiquitination activity of E3 ligases and potently degrade a target protein within cells can be a lengthy and unpredictable process, and it remains unclear whether any combination of E3 and target might be productive for degradation. We describe a probe-quality degrader for a ligase-target pair deemed unsuitable: the von Hippel-Lindau (VHL) and BRD9, a bromodomain-containing subunit of the SWI/SNF chromatin remodeling complex BAF. VHL-based degraders could be optimized from suboptimal compounds in two rounds by systematically varying conjugation patterns and linkers and monitoring cellular degradation activities, kinetic profiles, and ubiquitination, as well as ternary complex formation thermodynamics. The emerged structure-activity relationships guided the discovery of VZ185, a potent, fast, and selective degrader of BRD9 and of its close homolog BRD7. Our findings qualify a new chemical tool for BRD7/9 knockdown and provide a roadmap for PROTAC development against seemingly incompatible target-ligase combinations.
- Zoppi, Vittoria,Hughes, Scott J.,Maniaci, Chiara,Testa, Andrea,Gmaschitz, Teresa,Wieshofer, Corinna,Koegl, Manfred,Riching, Kristin M.,Daniels, Danette L.,Spallarossa, Andrea,Ciulli, Alessio
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p. 699 - 726
(2019/01/11)
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- A single-mercapto double-cetyl the ether gathers glycol [...] glycolipid synthesis method (by machine translation)
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The invention discloses a single mercapto double-cetyl [...] glycol [...] glycolipid synthesis method, characterized in that the 2, 3, 4, 6 - O - acetyl - α - D - pyran mannose the heat stability of the polyurethane in the [...][...] benzoic acid with thr
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Paragraph 0062-0065
(2019/11/04)
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- Stereoselective Synthesis of Molecular Square and Granny Knots
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We report on the stereoselective synthesis of both molecular granny and square knots through the use of lanthanide-complexed overhand knots of specific handedness as three-crossing "entanglement synthons". The composite knots are assembled by combining two entanglement synthons (of the same chirality for a granny knot; of opposite handedness for a square knot) in three synthetic steps: first, a CuAAC reaction joins together one end of each overhand knot. Ring-closing olefin metathesis (RCM) then affords the closed-loop knot, locking the topology. This allows the lanthanide ions necessary for stabilizing the entangled conformation of the synthons to subsequently be removed. The composite knots were characterized by 1H and 13C NMR spectroscopy and mass spectrometry and the chirality of the knot stereoisomers compared by circular dichroism. The synthetic strategy of combining building blocks of defined stereochemistry (here overhand knots of λ- or Δ-handed entanglement) is reminiscent of the chiron approach of using minimalist chiral synthons in the stereoselective synthesis of molecules with multiple asymmetric centers.
- Leigh, David A.,Pirvu, Lucian,Schaufelberger, Fredrik
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supporting information
p. 6054 - 6059
(2019/04/26)
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- Salt- and pH-Triggered Helix-Coil Transition of Ionic Polypeptides under Physiology Conditions
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Controlling the helix-coil transition of polypeptides under physiological conditions is an attractive way toward smart functional materials. Here, we report the synthesis of a series of tertiary amine-functionalized ethylene glycol (EGx)-linked polypeptide electrolytes with their secondary structures tunable under physiological conditions. The resultant polymers, denoted as P(EGxDMA-Glu) (x = 1, 2, and 3), show excellent aqueous solubility (>20 mg/mL) regardless of their charge states. Unlike poly-l-lysine that can form a helix only at pH above 10, P(EGxDMA-Glu) undergo a pH-dependent helix-coil switch with their transition points within the physiological range (pH ~5.3-6.5). Meanwhile, P(EGxDMA-Glu) exhibit an unusual salt-induced helical conformation presumably owing to the unique properties of EGx linkers. Together, the current work highlights the importance of fine-tuning the linker chemistry in achieving conformation-switchable polypeptides and represents a facile approach toward stimuli-responsive biopolymers for advanced biological applications.
- Yuan, Jingsong,Zhang, Yi,Sun, Yue,Cai, Zhicheng,Yang, Lijiang,Lu, Hua
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p. 2089 - 2097
(2018/06/15)
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- Stapling of two PEGylated side chains increases the conformational stability of the WW domain via an entropic effect
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Hydrocarbon stapling and PEGylation are distinct strategies for enhancing the conformational stability and/or pharmacokinetic properties of peptide and protein drugs. Here we combine these approaches by incorporating asparagine-linked O-allyl PEG oligomers at two positions within the β-sheet protein WW, followed by stapling of the PEGs via olefin metathesis. The impact of stapling two sites that are close in primary sequence is small relative to the impact of PEGylation alone and depends strongly on PEG length. In contrast, stapling of two PEGs that are far apart in primary sequence but close in tertiary structure provides substantially more stabilization, derived mostly from an entropic effect. Comparison of PEGylation + stapling vs. alkylation + stapling at the same positions in WW reveals that both approaches provide similar overall levels of conformational stability.
- Xiao, Qiang,Bécar, Natalie A.,Brown, Nathaniel P.,Smith, Mason S.,Stern, Kimberlee L.,Draper, Steven R.E.,Thompson, Katherine P.,Price, Joshua L.
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supporting information
p. 8933 - 8939
(2018/12/10)
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- TAU-PROTEIN TARGETING PROTACS AND ASSOCIATED METHODS OF USE
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The present disclosure relates to bifunctional compounds, which find utility as modulators of tau protein. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a VHL or cereblon ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds tau protein, such that tau protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of tau. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of tau protein. Diseases or disorders that result from aggregation or accumulation of tau protein are treated or prevented with compounds and compositions of the present disclosure.
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Paragraph 1461
(2018/05/24)
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- NOVEL TRIAZINE COMPOUND, ALL-SOLID-STATE POLYMER ELECTROLYTE COMPOSITION AND USE THEREOF
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The present invention relates to a novel triazine compound represented by chemical formula 1, an all-solid-state polymer electrolyte composition comprising the same as a cross-linking agent and uses thereof. More specifically, the triazine compound effectively inhibits crystallization of a plasticizer at a low temperature (room temperature) to show significantly improved ion conductivity, and can realize significantly improved electrochemical stability and excellent battery properties, thereby being usefully used as an all-solid-state polymer electrolyte composition such as a lithium-polymer secondary battery, a dye-sensitized solar cell, etc.COPYRIGHT KIPO 2018
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Paragraph 0123; 0139-0142
(2018/04/12)
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- Discovery of a series of efficient, centrally efficacious bace1 inhibitors through structure-based drug design
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The identification of centrally efficacious β-secretase (BACE1) inhibitors for the treatment of Alzheimers disease (AD) has historically been thwarted by an inability to maintain alignment of potency, brain availability, and desired absorption, distribution, metabolism, and excretion (ADME) properties. In this paper, we describe a series of truncated, fused thioamidines that are efficiently selective in garnering BACE1 activity without simultaneously inhibiting the closely related cathepsin D or negatively impacting brain penetration and ADME alignment, as exemplified by 36. Upon oral administration, these inhibitors exhibit robust brain availability and are efficacious in lowering central Amyloid β (Aβ) levels in mouse and dog. In addition, chronic treatment in aged PS1/APP mice effects a decrease in the number and size of Aβ-derived plaques. Most importantly, evaluation of 36 in a 2-week exploratory toxicology study revealed no accumulation of autofluorescent material in retinal pigment epithelium or histology findings in the eye, issues observed with earlier BACE1 inhibitors.
- Butler, Christopher R.,Brodney, Michael A.,Beck, Elizabeth M.,Barreiro, Gabriela,Nolan, Charles E.,Pan, Feng,Vajdos, Felix,Parris, Kevin,Varghese, Alison H.,Helal, Christopher J.,Lira, Ricardo,Doran, Shawn D.,Riddell, David R.,Buzon, Leanne M.,Dutra, Jason K.,Martinez-Alsina, Luis A.,Ogilvie, Kevin,Murray, John C.,Young, Joseph M.,Atchison, Kevin,Robshaw, Ashley,Gonzales, Cathleen,Wang, Jinlong,Zhang, Yong,Oneill, Brian T.
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p. 2678 - 2702
(2015/04/14)
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- Catenation through a Combination of Radical Templation and Ring-Closing Metathesis
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Synthesis of an electrochemically addressable [2]catenane has been achieved following formation by templation of a [2]pseudorotaxane employing radically enhanced molecular recognition between the bisradical dication obtained on reduction of the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), and the radical cation generated on reduction of a viologen disubstituted with p-xylylene units, both carrying tetraethylene glycol chains terminated by allyl groups. This inclusion complex was subjected to olefin ring-closing metathesis, which was observed to proceed under reduced conditions, to mechanically interlock the two components. Upon oxidation, Coulombic repulsion between the positively charged and mechanically interlocked components results in the adoption of a co-conformation where the newly formed alkene resides inside the cavity of the tetracationic cyclophane. 1H NMR spectroscopic analysis of this hexacationic [2]catenane shows a dramatic upfield shift of the resonances associated with the olefinic and allylic protons as a result of them residing inside the tetracationic component. Further analysis shows high diastereoselectivity during catenation, as only a single (Z)-isomer is formed.
- Gibbs-Hall, Ian C.,Vermeulen, Nicolaas A.,Dale, Edward J.,Henkelis, James J.,Blackburn, Anthea K.,Barnes, Jonathan C.,Stoddart, J. Fraser
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supporting information
p. 15640 - 15643
(2016/01/09)
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- Integrating Epigenetic Modulators into NanoScript for Enhanced Chondrogenesis of Stem Cells
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N-(4-Chloro-3-(trifluoromethyl)phenyl)-2-ethoxybenzamide (CTB) is a small molecule that functions by altering the chromatin architecture to modulate gene expression. We report a new CTB derivative with increased solubility and demonstrate CTB's functionality by conjugating it on the recently established NanoScript platform to enhance gene expression and induce stem cell differentiation. NanoScript is a nanoparticle-based artificial transcription factor that emulates the structure and function of transcription factor proteins (TFs) to effectively regulate endogenous gene expression. Modifying NanoScript with CTB will more closely replicate the TF structure and enhance CTB functionality and gene expression. To this end, we first conjugated CTB onto NanoScript and initiated a time-dependent increase in histone acetyltransferase activity. Next, because CTB is known to trigger the pathway involved in regulating Sox9, a master regulator of chondrogenic differentiation, we modifed a Sox9-specific NanoScript with CTB to enhance chondrogenic gene activity and differentiation. Because NanoScript is a tunable and robust platform, it has potential for various gene-regulating applications, such as stem cell differentiation.
- Patel, Sahishnu,Pongkulapa, Thanapat,Yin, Perry T.,Pandian, Ganesh N.,Rathnam, Christopher,Bando, Toshikazu,Vaijayanthi, Thangavel,Sugiyama, Hiroshi,Lee, Ki-Bum
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supporting information
p. 4598 - 4601
(2015/04/27)
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- The silane compound surface modification material phosphorylcholine-
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PROBLEM TO BE SOLVED: To provide a novel compound serving as a surface modifying material for a high sensitivity biosensing element, which enables forming of a monomolecular film capable of inhibiting nonspecific adsorption of protein. SOLUTION: The compound is a phosphorylcholine-silane compound represented by chemical formula 1, wherein X1to X3each independently represent halogen, 1-3C alkoxy or 1-3C alkyl, provided that at least one of X1to X3is halogen or 1-3C alkoxy; R1represents -(CH2)m- or -(CH2CH2O)n-(CH2)2-; R2represents -(CH2)s- or -(CH2)3-(OCH2CH2)p-; m is an integer of 2-20, n is an integer of 1-5, s is an integer of 3-20, and p is an integer of 1-5. COPYRIGHT: (C)2013,JPOandINPIT
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Paragraph 0022
(2018/06/29)
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- Structurally Simple Benzyl-Type Photolabile Protecting Groups for Direct Release of Alcohols and Carboxylic Acids
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Structurally simple benzyl-type photolabile protecting groups (PPGs) have been developed to release alcohols and carboxylic acids. Release of two substrates from one PPG chromophore has also been accomplished. (Chemical Equation Presented).
- Wang, Pengfei,Lu, Wenya,Devalankar, Dattatray A.,Ding, Zhenying
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supporting information
p. 2114 - 2117
(2015/05/13)
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- Self-assembly formation of mechanically interlocked [2]- and [3]catenanes using lanthanide ion [Eu(iii)] templation and ring closing metathesis reactions
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The formation of interlocked lanthanide-based catenanes using Eu(iii)-directed synthesis is described (catenation being achieved via a ring-closing metathesis reaction); the self-assembly formation of the supramolecular structures was analysed by HRMS, NM
- Lincheneau, Christophe,Jean-Denis, Bernard,Gunnlaugsson, Thorfinnur
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supporting information
p. 2857 - 2860
(2014/03/21)
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- Gold nanoparticles decorated with mannose-6-phosphate analogues
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Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.
- Combemale, Stephanie,Assam-Evoung, Jean-Norbert,Houaidji, Sabrina,Bibi, Rashda,Barragan-Montero, Veronique
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p. 1120 - 1149
(2014/02/14)
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- Synthesis and characterization of monoallyl-end-capped diethylene oxide-based polyurethane surfactant
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Diethylene glycol monoallyl ether (DGME) was synthesized by reaction of diethylene glycol with allyl chloride. Then, a novel non-ionic functional polyurethane surfactant (PUS) was synthesized by the polycondensation of hexamethylene diisocyanate (HMDI) with polypropylene glycol (PPG-1000) and DGME. Next, a series of polyvinyl acetate (PVAc), polybutyl acrylate (PBA), and polystyrene (PSt) latexes have been successfully synthesized, each one throughout by the emulsion copolymerization in the presence of a PUS. This polymeric surfactant exhibited excellent surface activity, and the surface tension decreased with an increase in the concentration of the polyurethane surfactant.
- Naghash, Hamid Javaherian,Iravani, Mohammad,Akhtarian, Rouhollah
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p. 927 - 934
(2014/04/03)
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- Controlled-length efficient synthesis of heterobifunctionalized oligo ethylene glycols
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A set of heterobifunctional oligo ethylene glycols have been synthesized in a straightforward and stepwise manner starting from inexpensive, commercially available, tetraethylene glycol. Introduction of terminal allyl moieties followed by reductive ozonolysis allowed controlled elongation. Mono-allyl derivatives were used for the elongation with a functionalized moiety and for successive introduction of different functional groups on the chain terminal. Georg Thieme Verlag Stuttgart - New York.
- Zona, Cristiano,D'Orazio, Giuseppe,La Ferla, Barbara
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p. 709 - 712
(2013/05/09)
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- A generalized strategy for immobilizing uniformly oriented membrane proteins at solid interfaces
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We have developed a method based on self-assembly of thiols on Au substrates to immobilize membrane proteins at interfaces. Using water soluble nitrilotriacetic acid (NTA)-terminated oligo(ethylene glycol) thiols, a histidine-tagged G protein-coupled membrane receptor (GPCR) was captured in a defined orientation with little nonspecific binding. The Royal Society of Chemistry 2013.
- Vaish, Amit,Silin, Vitalii,Walker, Marlon L.,Steffens, Kristen L.,Krueger, Susan,Yeliseev, Alexei A.,Gawrisch, Klaus,Vanderah, David J.
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supporting information
p. 2685 - 2687
(2013/04/10)
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- THIOL-ENE CLICK CHEMISTRY FOR DRUG CONJUGATES
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The present invention relates to linker molecules that readily conjugate cellular recognition ligand at one end and drug payload at the other, and are useful in treating or preventing cancer, an autoimmune disease, an inflammatory condition, a central nervous system disorder or an infection. The linker inker molecules of the invention are represented by Formula I, II and III; Linker-Drug compounds represented by Formula IV, V and VI; and Ligand-Linker-Drug conjugates represented by Formula VII, VIII and IX:
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Paragraph 0293; 0292
(2014/01/07)
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- Fluoroalkenyl sulfate surfactants
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Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where Rf is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.
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Page/Page column
(2013/09/12)
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- OLEFIN METATHESIS REACTIONS OF AMINO ACIDS, PEPTIDES AND PROTEINS CONTAINING ALLYL SULFIDE GROUPS
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A method for the modification of an amino acid, protein or peptide is disclosed. The method comprises reacting a carbon-carbon double bond-containing compound with an amino acid, a protein or a peptide containing an allyl sulfide group in the presence of a catalyst which promotes olefin metathesis, to form a modified amino acid, protein or peptide. Preferred carbon-carbon double bond-containing compounds include carbohydrates.
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- Pd-catalyzed reaction of allyl carbonate with polyols: The role of CO 2 in transesterification versus etherification of glycerol
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An intermolecular Pd/PPh3-catalyzed transesterification of diallyl carbonate with glycerol to generate glycerol carbonate has been developed. Analysis of the reaction kinetics in THF indicates a first-order dependence on Pd and diallyl carbonate, that the Pd bears two phosphines during the turnover limiting event, and that increasing the glycerol concentration inhibits reaction, possibly via change in the polarity of the medium. 13C isotopic labeling studies demonstrate that the Pd-catalyzed transesterification requires at least one allyl carbonate moiety and that there is rapid equilibrium of the allyl carbonate with CO2 in solution, even when present only at low concentrations. A mechanism that is consistent with these results involves oxidative addition of the allyl carbonate to Pd followed by reversible decarboxylation, with the intermediate I·1- and I·3-allyl Pd alkoxides mediating direct and indirect transesterification reactions with the glycerol. Using this model, successful simulations of the kinetics of reactions conducted under atmospheres of N2 or CO2 could be achieved, including switching in selectivity between etherification and transesterification in the early stages of reaction. Reactions with the higher polyols threitol and erythritol are also efficient, generating the terminal (1,2) monocarbonates with high selectivity. It's a gas: A Pd-catalyzed transesterification of diallyl carbonate with polyols has been developed. The CO2 concentration is shown to control the relative rates of etherification and transesterification. Kinetic and isotopic labeling studies suggest that intermediate I·1-allyl Pd alkoxides mediate indirect intermolecular transesterification. The higher polyols erythritol and threitol selectively generate monocarbonates. Copyright
- Gordillo, Alvaro,Lloyd-Jones, Guy C.
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supporting information; experimental part
p. 2660 - 2665
(2012/04/11)
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- Design of functionalized cellulosic honeycomb films: Site-specific biomolecule modification via "click chemistry"
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Value-added materials from naturally abundant polymers such as cellulose are of significant importance. In particular, cellulosic open-framework structures with controlled chemical functionality of the internal surface have great potential in many biosens
- Xu, William Z.,Zhang, Xinyue,Kadla, John F.
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experimental part
p. 350 - 357
(2012/06/15)
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- Preparation of bifunctional mesoporous silica nanoparticles by orthogonal click reactions and their application in cooperative catalysis
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The synthesis of bifunctional mesoporous silica nanoparticles is described. Two chemically orthogonal functionalities are incorporated into mesoporous silica by co-condensation of tetraethoxysilane with two orthogonally functionalized triethoxyalkylsilanes. Post-functionalization is achieved by orthogonal surface chemistry. A thiol-ene reaction, Cu-catalyzed 1,3-dipolar alkyne/azide cycloaddition, and a radical nitroxide exchange reaction are used as orthogonal processes to install two functionalities at the surface that differ in reactivity. Preparation of mesoporous silica nanoparticles bearing acidic and basic sites by this approach is discussed. Particles are analyzed by solid state NMR spectroscopy, elemental analysis, infrared-spectroscopy, and scanning electron microscopy. As a first application, these particles are successfully used as cooperative catalysts in the Henry reaction. Cooperative clicking: Bifunctional mesoporous silica particles were synthesized by orthogonal surface chemistry. A thiol-ene reaction, a copper-catalyzed 1,3-dipolar cycloaddition and a radical nitroxide exchange reaction were used as orthogonal processes for the introduction of the acid and base functionalities (see scheme). Catalytic activities of these bifunctionalized inorganic/organic hybrid materials were studied on the Henry reaction. Copyright
- Dickschat, Arne T.,Behrends, Frederik,Bühner, Martin,Ren, Jinjun,Wei?, Mark,Eckert, Hellmut,Studer, Armido
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supporting information
p. 16689 - 16697
(2013/03/14)
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- Synthesis of atorvastatin lactone linker constructs for target fishing
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With the aim of connecting atorvastatin lactone 9 to a linker for affinity-based target fishing, a concise route to the pyrrolecarboxylic acid 8 was developed. Key features of the synthesis of the diol-containing side-chain were a catalytic enantioselecti
- Sawant, Pramod,Maier, Martin E.
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p. 6576 - 6585
(2013/01/15)
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- AVOIDANCE OF NON-SPECIFIC BINDING ON AN ACOUSTIC WAVE BIOSENSOR USING LINKER AND DILUENT MOLECULES FOR DEVICE SURFACE MODIFICATION
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An acoustic wave biosensor comprising a surface of a mixed self-assembling monolayer for receiving a probe-biomolecule is described herein. The biosensor surface may comprise a piezoelectric quartz crystal,—for detection purposes with the electromagnetic piezoelectric acoustic sensor (EMPAS)—upon which a mixed self-assembling monolayer is formed, which includes at least one linker, such as 2,2,2-trifluoroethyl-13-trichlorosilyl-tridecanoate (TTTA); its oligoethylene glycol (OEG) analog OEGylated TTTA (OEG-TTTA); S-(2-(2-(2-(3-trichlorosilyl-propyloxy)-ethoxy)-ethoxy)-ethyl)-benzenethiosulfonate (OEG-TU BTS). Linker/diluent systems for attaching a functionalizing entity to the surface of a biosensor are described, as well as methods for preparing a biosensor surface with an oligoethylene glycol linker.
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- Synthesis and characterization of glycoside-based trisiloxane surfactant
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The synthesis of glycoside-based trisiloxane surfactants of the general formula Me3SiOSiMeR1OSiMe3 (R1 = (CH2)3(OCH2CH2)2OR 2, R2 = gl
- Han, Fu,Chen, Yan-Hong,Zhou, Ya-Wen,Xu, Bao-Cai
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experimental part
p. 515 - 520
(2012/07/28)
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- Olefin cross-metathesis on proteins: Investigation of allylic chalcogen effects and guiding principles in metathesis partner selection
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Olefin metathesis has recently emerged as a viable reaction for chemical protein modification. The scope and limitations of olefin metathesis in bioconjugation, however, remain unclear. Herein we report an assessment of various factors that contribute to productive cross-metathesis on protein substrates. Sterics, substrate scope, and linker selection are all considered. It was discovered during this investigation that allyl chalcogenides generally enhance the rate of alkene metathesis reactions. Allyl selenides were found to be exceptionally reactive olefin metathesis substrates, enabling a broad range of protein modifications not previously possible. The principles considered in this report are important not only for expanding the repertoire of bioconjugation but also for the application of olefin metathesis in general synthetic endeavors.
- Lin, Yuya A.,Chalker, Justin M.,Davis, Benjamin G.
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supporting information; experimental part
p. 16805 - 16811
(2011/02/17)
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- A catenated anion receptor based on indolocarbazole
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A catenated anion receptor 7 comprising two indolocarbazole units was prepared by olefin ring-closing metathesis using Grubbs' catalyst. Receptor 7 possesses a cage-like cavity where anions are encapsulated by forming four hydrogen bonds in the order of C
- Chae, Min Kyung,Suk, Jae-Min,Jeong, Kyu-Sung
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scheme or table
p. 4240 - 4242
(2010/09/07)
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- Cytotoxic agents comprising new tomaymycin derivatives and their therapeutic use
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The present invention is related to new tomaymycin derivatives having a linking chain between two units of pyrrolo[2,1c][1,4]benzodiazepines, substituted by a non-cleavable linker and their conjugated to cell binding agents, their process of preparation a
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Page/Page column 28
(2009/02/10)
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- Phototriggering of cell adhesion by caged cyclic RGD peptides
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Restrained potential: A caged cyclic peptide attached to a surface is able to trigger cell attachment to the surface with spatiotemporal definition upon exposure to light (λ = 351 nm). The peptide shows no integrin-binding activity in its caged form, but mediates cell adhesion effectively after irradiation (see optical microscopy image of cells on a surface irradiated through a mask in bands 100 μm in width). (Figure Presented).
- Petersen, Svea,Alonso, Jose Maria,Specht, Alexandre,Duodu, Portia,Goeldner, Maurice,Del Campo, Aranzazu
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p. 3192 - 3195
(2008/12/23)
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- Conjugates of antithrombin binding oligosaccharide derivatives and therapeutic proteins
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The present invention is concerned with protein or glycoprotein derivatives, their intermediates, uses thereof and processes for their production. In particular, the present invention relates to improving the pharmacokinetic profile of drugs that contain proteins.
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Page/Page column 20
(2010/11/30)
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- Allyl sulfides are privileged substrates in aqueous cross-metathesis: Application to site-selective protein modification
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Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported. Copyright
- Lin, Yuya A.,Chalker, Justin M.,Floyd, Nicola,Bernardes, Goncalo J. L.,Davis, Benjamin G.
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supporting information; experimental part
p. 9642 - 9643
(2009/02/04)
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- Structural control of the monolayer stability of water-soluble gold nanoparticles
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The thermodynamic and kinetic stability of three structurally related monolayer-protected gold clusters have been systematically investigated, revealing that the nanoparticles display significantly different stability against thermo- and cyanide-induced decomposition and external thiol agents. The Royal Society of Chemistry.
- Agasti, Sarit S.,You, Chang-Cheng,Arumugam, Palaniappan,Rotello, Vincent M.
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- Coupling across a DNA helical turn yields a hybrid DNA/organic catenane doubly tailed with functional termini
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We describe the synthesis of a hybrid DNA/organic macrocycle that is prepared by formation of an amide linkage across one full turn of DNA. Formation of a catenane proved that the linkage crossed a turn rather than running along the phosphodiester backbone contour. The product, a doubly tailed catenane, contains 5′- and 3′-termini that can be functionalized further or used to incorporate the catenane structure into other DNA assemblies. Copyright
- Liu, Yu,Kuzuya, Akinori,Sha, Ruojie,Guillaume, Johan,Wang, Risheng,Canary, James W.,Seeman, Nadrian C.
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supporting information; experimental part
p. 10882 - 10883
(2009/02/05)
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- Novel linker compound, substrate coated with the compound, method of producing microarray using the compound and microarray produced by the method
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A compound represented by formula (4), a substrate coated with the compound, a method of producing a microarray using the compound, and a microarray produced by the method are provided.
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- CYCLIC SILOXANE-BASED COMPOUNDS AND SOLID POLYMER ELECTROLYTE COMPOSITION CONTAINING THE SAME AS A CROSSLINKING AGENT
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The present invention relates to a cyclic siloxane-based compound and a solid polymer electrolyte composition containing the same as a crosslinking agent, more particularly to a cyclic siloxane-based compound having a novel structure in which polyalkylene oxide acrylate groups are introduced into a cyclic siloxane compound and a solid polymer electrolyte composition containing the cyclic siloxane-based compound as a crosslinking agent along with other electrolyte components such as a plasticizer, lithium salt and a curing initiator. Since the solid polymer electrolyte composition of the present invention improves ion conductivity and electrochemical stability at room temperature, it can be useful as polymer electrolyte for electrolyte films, small-sized to high-capacity lithium-polymer secondary batteries, etc. Also, physical properties of the polymer electrolyte can be controlled easily by controlling the length of the polyalkylene oxide group in the cyclic siloxane-based crosslinking agent.
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Page/Page column 16
(2008/06/13)
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- Polyether macrocycles from intramolecular cyclopropanation and ylide formation. Effect of catalyst and coordination
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The use of catalytic metal carbene methodology with diazoacetates for the construction in high yield of polyether macrocycles having ring sizes greater than 25 has been achieved by preventing access to γ-C-H positions for intramolecular insertion. Cyclopr
- Weathers Jr., Thomas M.,Wang, Yuanhua,Doyle, Michael P.
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p. 8183 - 8189
(2007/10/03)
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- A water-compatible, highly active and reusable PEG-coated mesoporous silica-supported palladium complex and its application in Suzuki coupling reactions
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A highly active heterogeneous palladium catalyst was prepared from coated mesoporous materials which contain a layer of readily available PEG with a labile coordinating ability for palladium. The aqueous suspension of the catalyst may be reused several times by simple extraction of the aqueous reaction mixture with ether to remove the product. The Royal Society of Chemistry 2006.
- Yang, Qing,Ma, Shengming,Li, Jixue,Xiao, Fengshou,Xiong, Hai
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p. 2495 - 2497
(2008/09/16)
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- General approach for template-directed synthesis of macroheterocycles by ring-closing metathesis (RCM)
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A general method to prepare macroheterocycles is reported in which a rigid symmetric platinated tris-pincer tricationic complex (3) is used as a template. The system uses bisolefin functionalized pyridine ligands (1, 2) which selectively bind to the three platinum centers of the template resulting in pre-organization of the olefinic tails. By subjecting these pre-organized complexes (4) to olefin metathesis reaction conditions, the olefinic tails were interconnected affording several macroheterocycles of different compositions and sizes. Various pyridines with different substitution patterns (2,6- and 3,5-disubstituted) and different olefinic tails (aliphatic, polyether, and styryl) were synthesized and used in the cyclization reactions, showing the diversity of this method. It was found that only the use of 2,6-disubstituted pyridines resulted in the formation of the desired macrocycles while 3,5-difunctionalized pyridines gave only pyridinophane formation. Furthermore, the length of the olefinic tails needs to be at least eleven atoms (C or O) in order to suppress oligomerization in favor of macrocycle formation. Yields of up to 70% of the macrocycles were obtained using the first-generation [Cl 2(Cy3P)2Ru=CHPh] or second-generation [Cl 2(Cy3P)(IMeS)Ru=CHPh] Grubbs' catalysts. Reactions of the platinated pincer pyridines with Schrock Mo-based metathesis catalysts results in exclusive olefin isomerization and no productive metathesis. The generated macrocycles (hosts) could effectively be separated from the template by addition of aqueous sodium chloride and reattached to the (recycled) template (guest). The X-ray structure determination of host-guest complex 10 is the definite proof for this reattachment and the perfect cyclic structure of the macrocycle.
- Chuchuryukin, Alexey V.,Chase, Preston A.,Dijkstra, Harm P.,Suijkerbuijk, Bart M. J. M.,Mills, Allison M.,Spek, Anthony L.,Van Klink, Gerard P. M.,Van Koten, Gerard
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p. 447 - 462
(2007/10/03)
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- Design, synthesis, and evaluation of original carriers for targeting vascular endothelial growth factor receptor interactions
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Purpose. Angiogenesis is a key event in tumor growth and metastasis, chronic inflammatory disease, and cardiovascular disease. It is controlled by positive and negative regulators, which include vascular endothelial growth factor (VEGF) as the most active
- Goncalves, Mario,Estieu-Gionnet, Karine,Berthelot, Thomas,Lain, Georges,Bayle, Mireille,Canron, Xavier,Betz, Natacha,Bikfalvi, Andreas,Deleris, Gerard
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p. 1411 - 1421
(2007/10/03)
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- Diphilic carbosilane dendrimers with different densities of the hydrophilic layer
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A universal method for the synthesis of hydrophilic dendrimers was considered. The method is based on a combination of carbosilane dendrimers with different molecular organizations and hydrophilizing agents, viz., substituted hydride silanes containing one and three protected hydroxyl groups. The combination of a limited set of the mentioned reagents makes it possible to control the ratio of hydrophilic and hydrophobic moieties of the molecular structure in wide limits. A simple and convenient method for the removal of trimethylsilyl protection of hydroxyl groups in the surface layer of dendrimers was developed.
- Getmanova,Tereshchenko,Ignat'eva,Tatarinova,Myakushev,Muzafarov
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p. 137 - 143
(2007/10/03)
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- An expedient synthesis of monodispersed oligo(ethylene glycols)
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A convenient approach to the synthesis of oligo(ethylene glycols) under phase transfer conditions is described. Oligo(ethylene glycols) (x = 7-12) are obtained in excellent yields and high purity via modular, bi-directional elongation of readily available ethylene glycol bis-tosylates.
- Burkett, Brendan A.,Chan, Tak Hang
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p. 1007 - 1010
(2007/10/03)
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- Synthesis and characterization of network type single ion conductors
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New single ion conductors were synthesized by grafting the allyl group-containing lithium salt, lithium bis(allylmalonato)borate (LiBAMB), onto allyl group-containing comb-branch polyacrylate or polymethacrylate ethers by means of hydrosilylation. The highest ambient temperature conductivity of 3.5 × 10-7 S cm-1 was obtained for a polyacrylate ether-based single ion conductor containing eight EO units in the side chain and five EO units in the cross-linking side chain, to which the anion was fixed with a salt concentration of EO/Li = 20. For polyacrylate ether-based single ion conductors, an increase of chain length in both side chains and cross-linking anion chains favors an increase of ionic conductivity. The addition of 50 wt % EC/DMC (1/1, wt/wt) increased the ionic conductivity by more than 2 orders of magnitude due to both the increase in ionic mobility from the liquid phase and the increase in the concentration of free ions from the high dielectric constant of the solvent. The preliminary Li/Li cycling profiles of dry polyacrylate- and polymethacrylate ether-based single ion conductors are encouraging as almost no concentration polarization or relaxation was observed. The observed increase in cell potential with cycling is apparently due to an increase in the interfacial impedance associated with the SEI layer, and the cell failure is accompanied by the decomposition of the ester bond of the polyacrylate backbone.
- Sun, Xiao-Guang,Reeder, Craig L.,Kerr, John B.
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p. 2219 - 2227
(2007/10/03)
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- MULTIVALENT INHIBITORS OF SERUM AMYLOID P COMPONENT
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Novel glycerol cyclic pyruvate derivates were prepared and demonstrated to inhibit the binding of an immobilized D-proline derivative to serum amyloid P component (SAP) have been prepared. As such, the compounds of the invention are useful for treating am
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- Stereoselective synthesis of a topologically chiral molecule: The trefoil knot
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Tying nice neat knots is demonstrated on a molecular level with the stereoselective synthesis of a trefoil knot. The key reaction was the completely stereoselective formation of a double-stranded helical precursor from two pinene-bipyridine threads around two CuI centers (the pinene moieties contain stereogenic centers). The helix was then transformed through several steps into 1; demetallation of the complex 1 yielded the configurationally predetermined free trefoil knot.
- Perret-Aebi, Laure-Emmanuelle,Von Zelewsky, Alexander,Dietrich-Buchecker, Christiane,Sauvage, Jean-Pierre
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p. 4482 - 4485
(2007/10/03)
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