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Angewandte Chemie. international edition 84건

  1. [해외논문]   Rational Tuning of Fluorobenzene Probes for Cysteine‐Selective Protein Modification   SCI SCIE

    Embaby, Ahmed M. (Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark) , Schoffelen, Sanne (Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark) , Kofoed, Christian (Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark) , Meldal, Morten (Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark) , Diness, Frederik (Center for Evolutionary Chemical Biology, Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8022 - 8026 , 2018 , 1433-7851 ,

    초록

    Abstract Fluorobenzene probes for protein profiling through selective cysteine labeling have been developed by rational reactivity tuning. Tuning was achieved by selecting an electron‐withdrawing para substituent in combination with variation of the number of fluorine substituents. Optimized probes chemoselectively arylated cysteine residues in proteins under aqueous conditions. Probes linked to azide, biotin, or a fluorophore were applicable to labeling of eGFP and albumin. Selective inhibition of cysteine proteases was also demonstrated with the probes. Additionally, probes were tuned for site‐selective labeling of cysteine residues and for activity‐based protein profiling in cell lysates.

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  2. [해외논문]   Blue‐Emissive Cobalt(III) Complexes and Their Use in the Photocatalytic Trifluoromethylation of Polycyclic Aromatic Hydrocarbons   SCI SCIE

    Pal, Amlan K. (Département de Chimie, Université) , Li, Chenfei (de Montréal, Montréal, Québec, H3T 1J4, Canada) , Hanan, Garry S. (Organic Semiconductor Center, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK) , Zysman‐ (Département de Chimie, Université) , Colman, Eli (de Montréal, Montréal, Québec, H3T 1J4, Canada)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8027 - 8031 , 2018 , 1433-7851 ,

    초록

    Abstract Room‐temperature luminescent Co III complexes ( 1 and 2 ) are presented that exhibit intense ligand‐to‐metal and ligand‐to‐ligand charge transfer absorption in the low‐energy UV region ( λ abs ≈360–400 nm) and low‐negative quasi‐reversible reduction events ( E 1/2 (red) =&min −0.58 V and −0.39 V vs. SCE for 1 and 2 , respectively). The blue emission of 1 and 2 at RT is due to the large bite angles and strong σ‐donation of the ligands, the combined effect of which helps to separate the emissive 3 LMCT (triplet ligand‐to‐metal charge transfer) and the non‐emissive 3 MC (triplet metal‐centered) states. 1 and 2 were found to be powerful photo‐oxidants ( E Co III */Co II =2 2.26 V and 2.75 V vs. SCE of 1 and 2 , respectively) and were used as inexpensive photoredox catalysts for the regioselective mono(trifluoromethylation) of polycyclic aromatic hydrocarbons (PAHs) in good yields (ca. 40–58 %).

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  3. [해외논문]   Molecular Dynamics, Phase Transition and Frequency‐Tuned Dielectric Switch of an Ionic Co‐Crystal   SCI SCIE

    Liu, Jing‐ (College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, China) , Yan (College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, China) , Zhang, Shi‐ (MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, China) , Yong (College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, China) , Zeng, Ying (College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, 341000, China) , Shu, Xia (MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, China) , Du, Zi‐ (MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou,) , Yi , He, Chun‐ , Ting , Zhang, Wei‐ , Xiong , Chen, Xiao‐ , Ming
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8032 - 8036 , 2018 , 1433-7851 ,

    초록

    Abstract Dielectric switches that can be converted between high and low dielectric states by thermal stimuli have attracted much interest owing to their many potential applications. Currently one main drawback for practical application lies in the non‐tunability of their switch temperatures ( T S ). We report here an ionic co‐crystal (Me 3 NH) 4 [Ni(NCS) 6 ] that contains a multiply rotatable Me 3 NH + ion and a solely rotatable one due to a more spacious supramolecular cage for the former one. This compound undergoes an isostructural order–disorder phase transition and it can function as a frequency‐tuned dielectric switch with highly adjustable T S , which is further revealed by the variable‐temperature structure analyses and molecular dynamics simulations. In addition, the distinct arrangements and molecular dynamics of two coexisting Me 3 NH + ions confined in different lattice spaces as well as the notable offset effect on the promoting/hindering of dipolar reorientation after dielectric transition provide a rarely observed but fairly good model for understanding and modulating the dipole motion in crystalline environment.

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  4. [해외논문]   One‐step Synthesis and Enhanced Thermoelectric Properties of Polymer–Quantum Dot Composite Films   SCI SCIE

    Shi, Wei (State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Chinese Academy of Sciences, 1295 Dingxi Road, Shanghai, 200050, China) , Qu, Sanyin (State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Chinese Academy of Sciences, 1295 Dingxi Road, Shanghai, 200050, China) , Chen, Hongyi (State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Chinese Academy of Sciences, 1295 Dingxi Road, Shanghai, 200050, China) , Chen, Yanling (State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of Ceramics, Chinese Academy of Sciences, 1295 Dingxi Road, Shanghai, 200050, China) , Yao, Qin (State Key Laboratory of High Performance Ceramics and Superfine Microstructures, Shanghai Institute of C) , Chen, Lidong
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8037 - 8042 , 2018 , 1433-7851 ,

    초록

    Abstract Conventional syntheses of polymer–inorganic composite thermoelectric materials suffer major problems such as inhomogeneity, large particle size, and oxidation that result in ineffective loading. Now a one‐step synthesis can be used to fabricate high‐quality small‐sized anions codoped poly(3,4‐ethylenedioxythiophene):dodecylbenzenesulfonate/Cl‐tellurium (PEDOT:DBSA/Cl‐Te) composite films using a series of novel Te IV ‐based oxidants. The synchronized production of PEDOT and Te results in thick and homogeneous films containing evenly distributed and well‐protected Te quantum dots. Owing to the heavily doped crystalline polymer matrix as well as the −1 K −2 , which is 50 % higher compared to a pure PEDOT:DBSA film.

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  5. [해외논문]   Emulsion‐Assisted Polymerization‐Induced Hierarchical Self‐Assembly of Giant Sea Urchin‐like Aggregates on a Large Scale   SCI SCIE

    Xu, Qingsong (School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China) , Huang, Tong (School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China) , Li, Shanlong (School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China) , Li, Ke (School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China) , Li, Chuanlong (School of Chemistry and Chemical Engineering, State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 2002) , Liu, Yannan , Wang, Yuling , Yu, Chunyang , Zhou, Yongfeng
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8043 - 8047 , 2018 , 1433-7851 ,

    초록

    Abstract Hierarchical solution self‐assembly has become an important biomimetic method to prepare highly complex and multifunctional supramolecular structures. However, despite great progress, it is still highly challenging to prepare hierarchical self‐assemblies on a large scale because the self‐assembly processes are generally performed at high dilution. Now, an emulsion‐assisted polymerization‐induced self‐assembly (EAPISA) method with the advantages of in situ self‐assembly, scalable preparation, and facile functionalization was used to prepare hierarchical multiscale sea urchin‐like aggregates (SUAs). The obtained SUAs from amphiphilic alternating copolymers have a micrometer‐sized rattan ball‐like capsule (RBC) acting as the hollow core body and radiating nanotubes tens of micrometers in length as the hollow spines. They can capture model proteins effectively at an ultra‐low concentration (ca. 10 n m ) after functionalization with amino groups through click copolymerization.

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  6. [해외논문]   In Vitro Reconstitution of OxyC Activity Enables Total Chemoenzymatic Syntheses of Vancomycin Aglycone Variants   SCI SCIE

    Forneris, Clarissa C. (Department of Chemistry, Princeton University, Princeton, NJ, 08544, USA) , Seyedsayamdost, Mohammad R. (Department of Chemistry, Princeton University, Princeton, NJ, 08544, USA)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8048 - 8052 , 2018 , 1433-7851 ,

    초록

    Abstract The bioactivity of vancomycin is enabled by three aromatic crosslinks, the biosynthesis of which has been an active area of investigation for two decades. Two cytochrome P450 enzymes, OxyB and OxyA, have been shown to introduce bisaryl ether linkages with the help of a so‐called X‐domain. The final crosslink, however, a biaryl bond thought to be installed by OxyC, has remained elusive. We report the in vitro reconstitution of the OxyC reaction and formation of the first carbon–carbon crosslink in any glycopeptide antibiotic. Using a cascade sequence, in which the peptide substrate was incubated with the Oxy enzymes in turn, we completed the chemoenzymatic synthesis of a vancomycin aglycone variant. This approach was also used to generate a new analogue carrying a thioamide linkage at residue 4, a precursor to the amidine derivative, which is effective against vancomycin‐resistant pathogens. Our results set the stage for creating therapeutic vancomycin derivatives by using the native metalloenzymes.

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  7. [해외논문]   In Situ Generation of Silylzinc by Si−B Bond Activation Enabling Silylzincation and Silaboration of Terminal Alkynes   SCI SCIE

    Nagashima, Yuki (Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan) , Yukimori, Daiki (Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan) , Wang, Chao (Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan) , Uchiyama, Masanobu (Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8053 - 8057 , 2018 , 1433-7851 ,

    초록

    Abstract A new protocol has been designed for the in situ generation of unstable Si−Zn species through the reaction of dialkylzinc, phosphine, and silylborane (Si−B). Successive reactions with various terminal alkynes using this protocol enabled highly controllable regio‐/stereo‐/chemoselective silylzincation and silaboration on demand without the need for a transition‐metal catalyst.

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  8. [해외논문]   Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst   SCI SCIE

    Tamura, Masazumi (Graduate School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8579, Japan) , Yuasa, Naoto (Graduate School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8579, Japan) , Cao, Ji (Graduate School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8579, Japan) , Nakagawa, Yoshinao (Graduate School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8579, Japan) , Tomishige, Keiichi (Graduate School of Engineering, Tohoku University, Aoba 6-6-07, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8579, Japan)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8058 - 8062 , 2018 , 1433-7851 ,

    초록

    Abstract Transformation of sugars, while maintaining the intrinsic stereochemical structure, is desirable. However, such a transformation requires multistep synthesis with protection and deprotection of the OH groups. Herein, a new method for selective transformation of sugar derivatives into chiral building blocks and a diol synthon, with retention of the intrinsic configuration (stereo‐ and regioselectively), is demonstrated. The method is based on the selective recognition of cis ‐vicinal OH groups in sugars and leads to the one‐pot removal of the cis ‐vicinal OH groups, without protection of OH groups (except the OH group of the hemiacetal group), over a heterogeneous CeO 2 ‐supported ReO x and Pd (ReO x ‐Pd/CeO 2 ) catalyst by using H 2 as a reducing agent.

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  9. [해외논문]   Solvent Effects on the Actinic Step of Donor–Acceptor Stenhouse Adduct Photoswitching   SCI SCIE

    Lerch, Michael M. (Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands) , Di Donato, Mariangela (European Laboratory for Non Linear Spectroscopy (LENS), via N. Carrara 1, 50019 Sesto, Fiorentino, Italy) , Laurent, Adè (CEISAM, UMR CNRS 6230, BP 92208, 2 Rue de la Houssinière, 44322, Nantes, Cedex 3, France) , le D. (Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký) , Medved', Miroslav (University in Olomouc, 17. listopadu 1192/12, CZ-771 46, Olomouc, Czech Republic) , Iagatti, Alessandro (European Laboratory for Non Linear Spectroscopy (LENS), via N. Carrara 1, 50019 Sesto, Fiorentino, Italy) , Bussotti, Laura (European Laboratory for Non Linear Spectroscopy (LENS), via N. Carrara 1, 50019 Sesto, Fiorentino, Italy) , Lapini, Andrea (Eur) , Buma, Wybren Jan , Foggi, Paolo , Szymań , ski, Wiktor , Feringa, Ben L.
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8063 - 8068 , 2018 , 1433-7851 ,

    초록

    Abstract Donor–acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD‐DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time‐resolved visible pump‐probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent‐dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.

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  10. [해외논문]   Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity   SCI SCIE

    Zhou, Cheng (School of Chemical and Biomedical Engineering, Singapore) , Chia, Geraldine W. N. (Interdisciplinary Graduate School, Singapore) , Ho, James C. S. (Centre for Biomimetic Sensor Science, School of Materials Science & Engineering, Nanyang Technological University (NTU), Singapore, 639798, Singapore) , Seviour, Thomas (Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Singapore) , Sailov, Talgat (Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Singapore) , Liedberg, Bo (Interdisciplinary Graduate School, Singapore) , Kjelleberg, Staffan (Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Singapore) , Hinks, Jamie (Singapore Centre on Environmental Life Sciences Engineering (SCELSE), Singapore) , Bazan, Guillermo C. (School of Chemical and Biomedical Engineering, Singapore<countr)
    Angewandte Chemie. international edition v.57 no.27 ,pp. 8069 - 8072 , 2018 , 1433-7851 ,

    초록

    Abstract Membrane‐intercalating conjugated oligoelectrolytes (COEs) are emerging as potential alternatives to conventional, yet increasingly ineffective, antibiotics. Three readily accessible COEs, belonging to an unreported series containing a stilbene core, namely D4 , D6 , and D8 , were designed and synthesized so that the hydrophobicity increases with increasing side‐chain length. Decreased aqueous solubility correlates with increased uptake by E. coli . The minimum inhibitory concentration (MIC) of D8 is 4 μg mL −1 against both E. coli and E. faecalis , with an effective uptake of 72 %. In contrast, the MIC value of the shortest COE, D4 , is 128 μg mL −1 owing to the low cellular uptake of 3 %. These findings demonstrate the application of rational design to generate efficacious antimicrobial COEs that have potential as low‐cost antimicrobial agents.

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