Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 31

July 28, 2014

Volume 53, Issue 31

Pages 7959–8250

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. You have free access to this content
      Cover Picture: Protein Interactions with Polymer Coatings and Biomaterials (Angew. Chem. Int. Ed. 31/2014) (page 7959)

      M. Sc. Qiang Wei, M. Sc. Tobias Becherer, Dr. Stefano Angioletti-Uberti, Prof. Dr. Joachim Dzubiella, Dr. Christian Wischke, Dr. Axel T. Neffe, Prof. Dr. Andreas Lendlein, Prof. Dr. Matthias Ballauff and Prof. Rainer Haag

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201406350

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      Polymeric material coatings such as Teflon and hydrophilic polymer surfaces can prevent protein adhesion to generate protein-resistant surfaces. The Review by R. Haag et al. on page 8004 ff. describes methods and recent advances in the field of protein interactions on polymeric materials. The cover picture illustrates the adsorption of proteins (egg white) to material surfaces as exemplified by the egg in the pan. (Graphic designed by Achim Wiedekind with a background picture by Ruben Haag.)

    2. You have free access to this content
      Inside Cover: Tuning the Composition of AuPt Bimetallic Nanoparticles for Antibacterial Application (Angew. Chem. Int. Ed. 31/2014) (page 7960)

      Dr. Yuyun Zhao, Chunjie Ye, Dr. Wenwen Liu, Prof. Rong Chen and Prof. Xingyu Jiang

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201401156

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      Some metals such as Ag and Hg are well known to have intrinsic antibacterial properties, but these metals are also toxic. X. Jiang and co-workers report a new class of nontoxic AuPt bimetallic nanoparticles with potent antibacterial properties in their Communication on page 8127 ff. The antibiotic mechanism includes the rupture of the inner bacterial membrane and an increase in intracellular adenosine triphosphate (ATP) levels, but does not involve the generation of reactive oxygen species.

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      Inside Back Cover: Single-Molecule Mechanochemical Sensing Using DNA Origami Nanostructures (Angew. Chem. Int. Ed. 31/2014) (page 8251)

      Dr. Deepak Koirala, Prakash Shrestha, Tomoko Emura, Kumi Hidaka, Shankar Mandal, Prof. Dr. Masayuki Endo, Prof. Dr. Hiroshi Sugiyama and Prof. Dr. Hanbin Mao

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201406158

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      DNA origami nanotiles have been used as novel multiplex mechanochemical sensors. In their Communication on page 8137 ff., M. Endo, H. Sugiyama, H. Mao et al. show that the binding of specific target molecules to the sensor unlocks the interconnected tiles, and the global topology of the DNA nanostructure rearranges. This process is monitored as mechanochemical signals in real time using optical tweezers.

    4. You have free access to this content
      Back Cover: A Plausible Simultaneous Synthesis of Amino Acids and Simple Peptides on the Primordial Earth (Angew. Chem. Int. Ed. 31/2014) (page 8252)

      Eric T. Parker, Dr. Manshui Zhou, Dr. Aaron S. Burton, Dr. Daniel P. Glavin, Dr. Jason P. Dworkin, Prof. Dr. Ramanarayanan Krishnamurthy, Prof. Dr. Facundo M. Fernández and Prof. Dr. Jeffrey L. Bada

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201406157

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      Stanley Miller′s cyanamide experiment went unreported for over 50 years, but was recently explored to study cyanamide-mediated biomolecule polymerization under early Earth conditions. In their Communication on page 8132 ff., F. M. Fernández, J. L. Bada et al. show that the dimerization of cyanamide in the presence of amino acids and intermediates in the Strecker synthesis of amino acids yields significant levels of dipeptides, which provides evidence that cyanamide enhances polymerization under simulated prebiotic environments. (Background image provided by Ron Miller.)

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
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      Frontispiece: Size-Dependent Water Structures in Carbon Nanotubes (page 7960)

      Prof. Dr. Tomonori Ohba

      Article first published online: 29 JUL 2014 | DOI: 10.1002/anie.201483171

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      Hydrogen Bonds In his Communication on page 8032 ff., T. Ohba describes the anomalous structure of water in carbon nanotubes. In nanotubes with diameters of 2 and 3 nm, water forms clusters because of prolific hydrogen bonding.

  3. Graphical Abstract

    1. Top of page
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    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
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    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 31/2014 (pages 7963–7977)

      Article first published online: 29 JUL 2014 | DOI: 10.1002/anie.201490029

  4. Flashback

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. 50 Years Ago ... (page 7974)

      Article first published online: 29 JUL 2014 | DOI: 10.1002/anie.201406704

  5. Corrigendum

    1. Top of page
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    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
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    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
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      Corrigendum: Fluorescent Mimetics of CMP-Neu5Ac Are Highly Potent, Cell-Permeable Polarization Probes of Eukaryotic and Bacterial Sialyltransferases and Inhibit Cellular Sialylation (page 7977)

      Dr. Johannes J. Preidl, Dr. Vinayaga S. Gnanapragassam, Dr. Michael Lisurek, Dr. Jörn Saupe, Prof. Dr. Rüdiger Horstkorte and Prof. Dr. Jörg Rademann

      Article first published online: 29 JUL 2014 | DOI: 10.1002/anie.201406069

  6. News

    1. Top of page
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    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
  7. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. Flashback
    6. Corrigendum
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Nuno Maulide (page 7984)

      Article first published online: 1 APR 2014 | DOI: 10.1002/anie.201402747

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      “My greatest achievement is hopefully still to come from an unexpected observation. I lose track of time whenever I'm playing Bach …” This and more about Nuno Maulide can be found on page 7984.

  8. News

    1. Top of page
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    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
  9. Book Review

    1. Top of page
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    13. Review
    14. Communications
    1. Microwaves in Nanoparticle Synthesis. Fundamentals and Applications. Edited by Satoshi Horikoshi and Nick Serpone. (page 7986)

      Pu-Xian Gao

      Article first published online: 9 JUL 2014 | DOI: 10.1002/anie.201404498

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      Wiley-VCH, Weinheim, 2013. 352 pp., hardcover, € 129.00.—ISBN 978-3527331970

  10. Highlight

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    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Photosynthesis

      Connecting Photosynthetic Light Harvesting and Charge Separation at Higher Detail (pages 7988–7990)

      Prof. Oliver Einsle

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201405489

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      Beside the unique reaction center, efficient organismic photosynthesis requires additional arrays of chromophores to harvest photons and direct them by resonance energy transfer to the interspersed sites of charge separation. A crystal structure of the complex of a bacterial reaction center with light-harvesting complex I now reveals new details on how the storage ring interacts with and connects to the site of charge separation.

  11. Minireview

    1. Top of page
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    13. Review
    14. Communications
    1. Segmented-Flow Microfluidics

      Microfluidic Studies of Carbon Dioxide (pages 7992–8002)

      Milad Abolhasani, Prof. Axel Günther and Prof. Eugenia Kumacheva

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201403719

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      Utilizing greenhouse gas: Microfluidics offers numerous advantages in studies of CO2-related processes, including physical and chemical capturing of CO2 and its recycling into valuable products. This Minireview highlights recent progress in this area.

  12. Review

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    13. Review
    14. Communications
    1. Protein-Resistant Surfaces

      Protein Interactions with Polymer Coatings and Biomaterials (pages 8004–8031)

      M. Sc. Qiang Wei, M. Sc. Tobias Becherer, Dr. Stefano Angioletti-Uberti, Prof. Dr. Joachim Dzubiella, Dr. Christian Wischke, Dr. Axel T. Neffe, Prof. Dr. Andreas Lendlein, Prof. Dr. Matthias Ballauff and Prof. Rainer Haag

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201400546

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      The prevention of protein interactions plays a major role in everyday life, for example on common Teflon surfaces. This review focuses on recent developments in analytical, biochemical, and theoretical techniques that lead to a better understanding of polymeric biomaterials for applications as bioinert and biospecific surface coating materials in biomedical systems.

  13. Communications

    1. Top of page
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    6. Corrigendum
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    10. Book Review
    11. Highlight
    12. Minireview
    13. Review
    14. Communications
    1. Water

      Size-Dependent Water Structures in Carbon Nanotubes (pages 8032–8036)

      Prof. Dr. Tomonori Ohba

      Article first published online: 4 JUN 2014 | DOI: 10.1002/anie.201403839

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      Ice-like water clusters: Water in carbon nanotubes with a diameter of 1 nm had fewer hydrogen bonds than bulk water under ambient conditions. In carbon nanotubes with diameters of 2 and 3 nm, water formed cluster structures even under ambient conditions, because of prolific hydrogen bonding. The critical cluster size is 0.8–3.4 nm; that is, the fundamental size of a cluster is 0.8 nm.

    2. Polyvalent Inhibitors | Hot Paper

      Design of Monodisperse and Well-Defined Polypeptide-Based Polyvalent Inhibitors of Anthrax Toxin (pages 8037–8040)

      Sanket Patke, Mohan Boggara, Ronak Maheshwari, Sunit K. Srivastava, Manish Arha, Marc Douaisi, Jacob T. Martin, Ian B. Harvey, Matthew Brier, Tania Rosen, Jeremy Mogridge and Prof. Ravi S. Kane

      Article first published online: 6 APR 2014 | DOI: 10.1002/anie.201400870

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      Quantity and spacing: A protein-engineering approach was designed to develop monodisperse polyvalent molecules based on tandem-repeat polypeptide scaffolds. This approach allowed for precise control over ligand spacing and valency of the polyvalent molecules. This approach was applied to develop potent inhibitors of anthrax lethal toxin.

    3. Nanostructures

      Directed Self-Assembly of DNA Tiles into Complex Nanocages (pages 8041–8044)

      Cheng Tian, Xiang Li, Zhiyu Liu, Prof. Wen Jiang, Prof. Guansong Wang and Prof. Chengde Mao

      Article first published online: 12 MAR 2014 | DOI: 10.1002/anie.201400377

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      (Versa)tile DNA: In a directed DNA self-assembly strategy, directing tiles (yellow) and assembly tiles (red/green) were employed to control the assembly pathway of DNA nanostructures. This approach enables the rational design and assembly of a range of complex DNA nanocages, including bipyramids and Kleetopes of polyhedra. The structures produced were thoroughly characterized by gel electrophoresis and cryogenic electron microscopy.

    4. Drug Delivery

      Stimuli-Responsive Theragrippers for Chemomechanical Controlled Release (pages 8045–8049)

      Dr. Kate Malachowski, Dr. Joyce Breger, Hye Rin Kwag, Martha O. Wang, Prof. John P. Fisher, Prof. Florin M. Selaru and Prof. David H. Gracias

      Article first published online: 14 MAR 2014 | DOI: 10.1002/anie.201311047

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      Thermoresponsive polymeric grippers for controlled drug release (“theragrippers”) close spontaneously above 32 °C and grip onto tissue. They were loaded with drugs mesalamine and doxorubicin, which eluted for up to 7 days. Theragrippers show improved site-specific delivery and offer a novel strategy for sustained release with immediate applicability in the gastrointestinal tract.

    5. Macroscopic Objects | Hot Paper

      Cooperative, Reversible Self-Assembly of Covalently Pre-Linked Proteins into Giant Fibrous Structures (pages 8050–8055)

      Saadyah Averick, Orsolya Karácsony, Jacob Mohin, Dr. Xin Yong, Nicholas M. Moellers, Bradley F. Woodman, Prof. Weipu Zhu, Prof. Ryan A. Mehl, Prof. Anna C. Balazs, Prof. Tomasz Kowalewski and Prof. Krzysztof Matyjaszewski

      Article first published online: 9 JUL 2014 | DOI: 10.1002/anie.201402827

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      Protein oligomers, prepared from diazido GFP (green fluorescent protein) and dialkyne PEO (poly(ethylene oxide)), self-assemble into micrometer scale objects. The dynamics of protein assembly were elucidated and the driving force for fiber formation is the discrete interactions of hydrophobic residues on GFP.

    6. Cell Coating

      Cytoprotective Silica Coating of Individual Mammalian Cells through Bioinspired Silicification (pages 8056–8059)

      Juno Lee, Jinsu Choi, Ji Hun Park, Mi-Hee Kim, Daewha Hong, Hyeoncheol Cho, Prof. Dr. Sung Ho Yang and Prof. Dr. Insung S. Choi

      Article first published online: 4 JUN 2014 | DOI: 10.1002/anie.201402280

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      Safety glass: Several types of mammalian cells, namely HeLa cells, NIH 3T3 fibroblasts, and Jurkat cells, are individually coated with silica through bioinspired silicification. The fabrication processes are highly cytocompatible, thus leading to minimal loss of viability, and the silica coating confers protection against harmful substances, such as trypsin and poly(allylamine hydrochloride).

    7. Synthetic Methods

      Enzymatic Synthesis of Lipid II and Analogues (pages 8060–8065)

      Lin-Ya Huang, Shih-Hsien Huang, Ya-Chih Chang, Wei-Chieh Cheng, Ting-Jen R. Cheng and Chi-Huey Wong

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201402313

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      Hum with activity: Described in this study is a practical enzymatic method for the synthesis of lipid II, coupled with cofactor regeneration, to give the product in 50–70 % yield. This method was further applied to the synthesis of lipid II analogues, the activities of which were evaluated for bacterial transglycolase.

    8. Biochemical Networks | Very Important Paper

      Threshold Sensing through a Synthetic Enzymatic Reaction–Diffusion Network (pages 8066–8069)

      Dr. Sergey N. Semenov, Dr. Albert J. Markvoort, Dr. Tom F. A. de Greef and Prof. Dr. Wilhelm T. S. Huck

      Article first published online: 2 APR 2014 | DOI: 10.1002/anie.201402327

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      Mixed signals: A wet stamping method was used to precisely control the concentrations of enzymes and inhibitors in place and time inside layered gels. By coupling diffusion from spatially well-defined sources and enzymatic reactions such as autocatalysis and inhibition inside a hydrogel, a complex biochemical network that is capable of threshold sensing was constructed.

    9. Elastomeric Particles

      Nucleation and Growth Synthesis of Siloxane Gels to Form Functional, Monodisperse, and Acoustically Programmable Particles (pages 8070–8073)

      C. Wyatt Shields IV, Danping Sun, Dr. Kennita A. Johnson, Korine A. Duval, Aura V. Rodriguez, Dr. Lu Gao, Prof. Paul A. Dayton and Prof. Gabriel P. López

      Article first published online: 22 MAY 2014 | DOI: 10.1002/anie.201402471

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      Hear ye, hear ye! A class of functional, monodisperse, and acoustically programmable (FMAP) particles produced by nucleation and growth bulk synthesis is presented. This approach for synthesizing silicone gel particles enables direct programmability of properties for versatile control in acoustofluidic systems for biosensing and sorting applications.

    10. Micellization

      Chaotropic-Anion-Induced Supramolecular Self-Assembly of Ionic Polymeric Micelles (pages 8074–8078)

      Yang Li, Dr. Yiguang Wang, Dr. Gang Huang, Dr. Xinpeng Ma, Dr. Kejin Zhou and Prof. Jinming Gao

      Article first published online: 10 JUN 2014 | DOI: 10.1002/anie.201402525

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      Unexpected: The micellization of protonated polymers at low pH values is surprisingly induced by chaotropic (ClO4) instead of kosmotropic (Cl) anions. This behavior follows an anti-Hofmeister trend, as it is contrary to the effects of these anions in protein solubilization.

    11. Chirality and Surfaces

      Liquid Crystals Anchored on Mixed Monolayers of Chiral versus Achiral Molecules: Continuous Change in Orientation as a Function of Enantiomeric Excess (pages 8079–8083)

      Yiqun Bai, Reza Abbasi, Dr. Chenxuan Wang and Dr. Nicholas L. Abbott

      Article first published online: 19 MAY 2014 | DOI: 10.1002/anie.201402770

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      The orientations of liquid crystals (LCs) anchored on monolayers formed from mixtures of chiral versus achiral molecules were compared. Changes in the enantiomeric excess of mixed monolayers of chiral dipeptides gave rise to continuous changes in the orientations of nematic LCs, allowing arbitrary tuning of their azimuthal orientations. In contrast, the same LCs exhibited discontinuous changes in orientation on surfaces presenting mixtures of achiral molecules.

    12. Polymers as Antileaching Agents

      Using Soluble Polymers to Enforce Catalyst-Phase-Selective Solubility and as Antileaching Agents to Facilitate Homogeneous Catalysis (pages 8084–8087)

      Yannan Liang, Mary L. Harrell and Dr. David E. Bergbreiter

      Article first published online: 30 MAY 2014 | DOI: 10.1002/anie.201402805

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      Suppression of by-product: In biphasic heptane/CH3CN mixtures, heptane-soluble polyisobutylene (PIB)-bound RhII cyclopropanation and O[BOND]H insertion catalysts form only modest amounts of the undesired carbene dimer. It was shown that the phase isolation of these catalysts is enhanced by the addition of a polyolefin oligomer cosolvent, which acts as antileaching agent and minimizes the leaching of the PIB-bound species into the polar phase in liquid/liquid separations.

    13. Genotyping

      Measuring Fate and Rate of Single-Molecule Competition of Amplification and Restriction Digestion, and Its Use for Rapid Genotyping Tested with Hepatitis C Viral RNA (pages 8088–8092)

      Bing Sun, Dr. Jesus Rodriguez-Manzano, David A. Selck, Dr. Eugenia Khorosheva, Dr. Mikhail A. Karymov and Prof. Rustem F. Ismagilov

      Article first published online: 2 JUN 2014 | DOI: 10.1002/anie.201403035

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      Rate or fate? Competition among reverse transcription, exponential amplification, and linear degradation was monitored at the single-molecule level and used for rapid genotyping of the hepatitis C virus. End-point digital measurements were primarily sensitive to changes in “fate” of single molecules, but bulk real-time kinetic measurements were dominated by the rate of amplification of the earliest molecules.

    14. Sequential Protein Delivery

      Ordered and Kinetically Discrete Sequential Protein Release from Biodegradable Thin Films (pages 8093–8098)

      Bryan B. Hsu, Kelsey S. Jamieson, Samantha R. Hagerman, Prof. Eggehard Holler, Prof. Julia Y. Ljubimova and Prof. Paula T. Hammond

      Article first published online: 18 JUN 2014 | DOI: 10.1002/anie.201403702

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      Taking turns: Inclusion of covalent and copper-free click chemistry in layer-by-layer thin films during assembly generates sequential release behavior without modification of the protein itself. Increasingly thick barrier layers deposited on protein-containing layers delay the onset of protein release, which can be harnessed to generate well-defined sequential protein release with minimal overlap.

    15. Biomedical Imaging

      Optical-Resolution Photoacoustic Microscopy for Volumetric and Spectral Analysis of Histological and Immunochemical Samples (pages 8099–8103)

      Dr. Yu Shrike Zhang, Dr. Junjie Yao, Chi Zhang, Lei Li, Prof. Lihong V. Wang and Prof. Younan Xia

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201403812

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      Seeing not seen before: The quantitative analysis of biological samples after (immuno)histochemical staining has been achieved by optical-resolution photoacoustic microscopy. In addition to the three-dimensional imaging capability, components with different absorption spectra could be readily separated by collecting images at different wavelengths.

    16. Cancer Cell Apoptosis | Hot Paper

      Pericellular Hydrogel/Nanonets Inhibit Cancer Cells (pages 8104–8107)

      Dr. Yi Kuang, Junfeng Shi, Jie Li, Dan Yuan, Kyle A. Alberti, Prof. Qiaobing Xu and Prof. Dr. Bing Xu

      Article first published online: 12 MAY 2014 | DOI: 10.1002/anie.201402216

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      A small D-peptide derivative is reported to form fibrils and nanonets in the pericellular space. The pericellular nanonets encapsulate cancer cells, which not only prohibits cell adhesion but also selectively induces cancer cell apoptosis. This is the first example of synthetic peptides to achieve biological function through formation of nanonets.

    17. Chemical Linguistics | Hot Paper

      Organic Chemistry as a Language and the Implications of Chemical Linguistics for Structural and Retrosynthetic Analyses (pages 8108–8112)

      Dr. Andrea Cadeddu, Elizabeth K. Wylie, Prof. Dr. Janusz Jurczak, Matthew Wampler-Doty and Prof. Dr. Bartosz A. Grzybowski

      Article first published online: 10 JUL 2014 | DOI: 10.1002/anie.201403708

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      Chemistry is a language: Formal analysis confirms Lehn's analogy between chemistry and a natural language. English language patterns and the structural motifs of organic molecules follow the same statistics. The methods of computational linguistics can thus be applied to organic molecules to identify characteristic, information-rich patterns defining symmetry/repeat sub-units and bonds amenable to retrosynthetic disconnections.

    18. Fluorescent Probes

      Engineering the Stereochemistry of Cephalosporin for Specific Detection of Pathogenic Carbapenemase-Expressing Bacteria (pages 8113–8116)

      Dr. Haibin Shi, Dr. Yunfeng Cheng, Dr. Kyung Hyun Lee, Dr. Robert F. Luo, Prof. Niaz Banaei and Prof. Jianghong Rao

      Article first published online: 24 APR 2014 | DOI: 10.1002/anie.201402012

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      No more hiding: A series of fluorogenic probes based on stereochemically modified cephalosporin were developed and are specific for carbapenem-resistant Enterobacteriaceae (CRE). Data collected using recombinant β-lactamase enzymes and live bacterial species show, for the first time, that these probes can be potentially used for specific detection of carbapenemases, especially metallo-β-lactamase-active bacterial pathogens.

    19. Nanopatterns

      Controlling the Orientation of Nanowrinkles and Nanofolds by Patterning Strain in a Thin Skin Layer on a Polymer Substrate (pages 8117–8121)

      Mark D. Huntington, Clifford J. Engel and Prof. Teri W. Odom

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404483

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      Gaining the upper hand on wrinkles: In a process to create nanowrinkles with control over their amplitude and orientation, the patterning of strain distribution in the top skin layer of a polymer substrate produced ordered structures from disordered structures. Representative types of nanotextured surfaces include (clockwise from top left) 1D nanowrinkles, directed nanowrinkles, directed nanofolds, and hierarchical directed 1D nanowrinkles.

    20. Gold Complexes

      A Cyclization–Rearrangement Cascade for the Synthesis of Structurally Complex Chiral Gold(I)–Aminocarbene Complexes (pages 8122–8126)

      Dr. Filip Kolundžić, Dr. Annamalai Murali, Dr. Patricia Pérez-Galán, Dipl.-Chem. Jonathan O. Bauer, Prof. Dr. Carsten Strohmann, Dr. Kamal Kumar and Prof. Dr. Herbert Waldmann

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201403651

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      Golden opportunities: A cyclization–rearrangement cascade of different 1,7-enynes triggered by the addition of (Me2S)AuCl provides facile access to structurally unique chiral cyclic alkyl aminocarbene–gold(I) complexes in high yields. These novel complexes are catalytically active and display biologic activity against cancer cell lines.

    21. Antibiotic Nanoparticles

      You have full text access to this OnlineOpen article
      Tuning the Composition of AuPt Bimetallic Nanoparticles for Antibacterial Application (pages 8127–8131)

      Dr. Yuyun Zhao, Chunjie Ye, Dr. Wenwen Liu, Prof. Rong Chen and Prof. Xingyu Jiang

      Article first published online: 14 MAY 2014 | DOI: 10.1002/anie.201401035

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      No side-effect: Bimetallic nanoparticles of AuPt are potent antibiotic reagents with low cytotoxicity. The antibiotic mechanism includes the rupture in the bacterial inner membrane and the increase of intracellular adenosine triphosphate levels, but does not involve the generation of reactive oxygen species (see picture).

    22. Prebiotic Chemistry | Hot Paper

      A Plausible Simultaneous Synthesis of Amino Acids and Simple Peptides on the Primordial Earth (pages 8132–8136)

      Eric T. Parker, Dr. Manshui Zhou, Dr. Aaron S. Burton, Dr. Daniel P. Glavin, Dr. Jason P. Dworkin, Prof. Dr. Ramanarayanan Krishnamurthy, Prof. Dr. Facundo M. Fernández and Prof. Dr. Jeffrey L. Bada

      Article first published online: 25 JUN 2014 | DOI: 10.1002/anie.201403683

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      Prebiotic polymerization: Archived samples from Stanley Miller's previously unreported 1958 cyanamide experiment were investigated to evaluate cyanamide-mediated amino acid polymerization under prebiotic conditions. Aqueous heating experiments indicate that in the presence of an amino acid amide, the dimerization of cyanamide under the mildly basic conditions of the spark-discharge experiment significantly enhances polymerization reactions.

    23. Mechanochemical Sensing Devices

      Single-Molecule Mechanochemical Sensing Using DNA Origami Nanostructures (pages 8137–8141)

      Dr. Deepak Koirala, Prakash Shrestha, Tomoko Emura, Kumi Hidaka, Shankar Mandal, Prof. Dr. Masayuki Endo, Prof. Dr. Hiroshi Sugiyama and Prof. Dr. Hanbin Mao

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201404043

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      DNA origami nanostructures were used as expanded platforms for multiplex mechanochemical sensing with improved throughput at the single-molecule level. Topological rearrangements of the DNA origami nanoassemblies in response to the binding of specific targets were monitored in real time by using optical tweezers.

    24. Asymmetric Catalysis

      Organocatalytic Asymmetric Hydrolysis of Epoxides (pages 8142–8145)

      Mattia Riccardo Monaco, Dr. Sébastien Prévost and Prof. Dr. Benjamin List

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201400170

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      The natural strategy: Carboxylic acids were activated with chiral phosphoric acid catalysts and the mechanism of epoxide hydrolase served as a model for the asymmetric hydrolysis of meso-epoxides. This method was coupled with the Prilezhaev oxidation and the subsequent hydrolysis of the ester moiety to provide the first highly enantioselective anti-dihydroxylation of simple olefins.

    25. Interfacial Heterogeneity | Very Important Paper

      Aqueous Heterogeneity at the Air/Water Interface Revealed by 2D-HD-SFG Spectroscopy (pages 8146–8149)

      Dr. Cho-Shuen Hsieh, Dr. Masanari Okuno, Dr. Johannes Hunger, Dr. Ellen H. G. Backus, Dr. Yuki Nagata and Prof. Mischa Bonn

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201402566

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      Lonesome water: In contrast to bulk water, water molecules at the air/water interface are remarkably heterogeneous. Two-dimensional sum-frequency generation spectroscopy shows that weakly hydrogen-bonded water molecules at the interface are largely decoupled from the bulk.

    26. Pyrrolysine Analogues

      The Formation of Pyrroline and Tetrahydropyridine Rings in Amino Acids Catalyzed by Pyrrolysine Synthase (PylD) (pages 8150–8153)

      Felix Quitterer, Philipp Beck, Prof. Dr. Adelbert Bacher and Prof. Dr. Michael Groll

      Article first published online: 10 JUN 2014 | DOI: 10.1002/anie.201402595

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      PylD is the ultimate enzyme in the biosynthesis of the 22nd proteinogenic amino acid pyrrolysine. The structurally and mechanistically unique dehydrogenase exhibits broad substrate specificity, which can be exploited for the formation of pyrroline and tetrahydropyridine rings in a diverse set of amino acids. Thus, the system presents an attractive prospect for the in vivo incorporation of pyrrolysine analogues into defined target proteins.

    27. DNA Methylation

      You have full text access to this OnlineOpen article
      Direct Sensing of 5-Methylcytosine by Polymerase Chain Reaction (pages 8154–8158)

      Joos Aschenbrenner, Matthias Drum, Dr. Hüsnü Topal, Dr. Markus Wieland and Prof. Dr. Andreas Marx

      Article first published online: 12 JUN 2014 | DOI: 10.1002/anie.201403745

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      Delicate: The thermostable DNA polymerases KlenTaq and KOD exo- were found to sense 5-methylcytosine (5mC) in primer-extension experiments from mismatched primers. On this basis, a DNA polymerase mutant with advanced 5mC-detection capabilities was generated and successfully applied in a methylation-specific PCR approach directly from untreated human genomic DNA.

    28. ADP-Ribosylation

      Chain-Terminating and Clickable NAD+ Analogues for Labeling the Target Proteins of ADP-Ribosyltransferases (pages 8159–8162)

      Yan Wang, Daniel Rösner, Magdalena Grzywa and Prof. Dr. Andreas Marx

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404431

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      Stop and Click: Poly(ADP-ribosy)lation is a complex posttranslational modification of proteins that is carried out by ADP-ribosyltransferases (ARTs) with the use of NAD+. In order to tackle the complexity of the modification, which often hampers subsequent analysis, we developed new NAD+ analogues that are substrates for wild-type ARTs but act as chain terminators and allow labeling through click chemistry.

    29. C[BOND]H Amination

      Metal-Free Annulation of Arenes with 2-Aminopyridine Derivatives: The Methyl Group as a Traceless Non-Chelating Directing Group (pages 8163–8166)

      Srimanta Manna, Dr. Kiran Matcha and Dr. Andrey P. Antonchick

      Article first published online: 18 JUN 2014 | DOI: 10.1002/anie.201403712

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      Disappearing Me: A novel selective annulation between 2-aminopyridine derivatives and arenes under metal-free conditions provides the important pyrido[1,2-a]benzimidazole scaffold under mild reaction conditions. In this intermolecular reaction the methyl group of methylbenzenes serves as a traceless, non-chelating, and highly regioselective directing group.

    30. Silicon/Lithium-Centered Chirality

      From an α-Functionalized Silicon-Stereogenic N,O-Silane to a Monomeric and Tetracoordinate tBuLi Adduct with Lithium-Centered Chirality (pages 8167–8171)

      Dipl.-Chem. Jonathan O. Bauer and Prof. Dr. Carsten Strohmann

      Article first published online: 18 JUN 2014 | DOI: 10.1002/anie.201404255

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      Well-balanced reactivity is shown for a silicon-chiral tert-butyl-substituted aminomethoxysilane possessing an additional nitrogen donor function in the geminal position to silicon. This silane transfers its stereochemical information onto the lithium atom of a tBuLi molecule, forming a monomeric [methoxysilane⋅tBuLi] adduct with a tetrameric and asymmetrically coordinated lithium atom.

    31. Energetic Materials | Hot Paper

      Potassium 1,1′-Dinitramino-5,5′-bistetrazolate: A Primary Explosive with Fast Detonation and High Initiation Power (pages 8172–8175)

      Dennis Fischer, Prof. Dr. Thomas M. Klapötke and Dr. Jörg Stierstorfer

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201404790

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      Fast and furious: The picture shows the moment of detonation of the new primary explosive potassium 1,1′-dinitramino-5,5′-bistetrazolate, which can be synthesized by a safe and sustainable procedure. It shows faster detonation with greater initiation power than lead azide while simultaneously being environmentally compatible.

    32. Carbene–Antimony Adducts

      One-, Two-, and Three-Electron Reduction of a Cyclic Alkyl(amino)carbene–SbCl3 Adduct (pages 8176–8179)

      Dr. Robert Kretschmer, David A. Ruiz, Dr. Curtis E. Moore, Prof. Dr. Arnold L. Rheingold and Prof. Dr. Guy Bertrand

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201404849

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      3‥2‥1‥0: The stepwise reduction of a cyclic alkyl(amino)carbene–SbCl3 complex yields three different antimony species in the formal oxidation states of two, one, and zero. The one-electron reduction delivers the first neutral antimony-centered radical in solution. The radical and the three other compounds were characterized by EPR spectroscopy and X-ray crystallography, respectively.

    33. Radical Cyclizations

      Cyclizing Radical Carboiodination, Carbotelluration, and Carboaminoxylation of Aryl Amines (pages 8180–8183)

      Marcel Hartmann and Prof. Dr. Armido Studer

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201403968

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      Tamed radicals: The carboiodination of anilines leads to the corresponding cyclized iodides. The aryl diazonium salts generated in situ react with I ions to give the corresponding aryl radicals, which are cyclized and trapped. When the reaction is conducted in the presence of TEMPO and PhTeTePh, the respective carboaminoxylated and phenyltellurated cyclized products are obtained.

    34. Asymmetric Synthesis

      Highly Enantioselective Construction of Tricyclic Derivatives by the Desymmetrization of Cyclohexadienones (pages 8184–8189)

      Cecilia Martín-Santos, Carlos Jarava-Barrera, Sandra del Pozo, Dr. Alejandro Parra, Dr. Sergio Díaz-Tendero, Dr. Rubén Mas-Ballesté, Dr. Silvia Cabrera and Dr. José Alemán

      Article first published online: 20 JUN 2014 | DOI: 10.1002/anie.201402853

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      Breaking the mirror: In an asymmetric synthesis of tricyclic compounds containing a heterocyclic ring by the desymmetrization of cyclohexadienones, a large variety of substituents at different positions of the cyclohexadienone were tolerated, and the size of the heterocyclic ring could be varied. DFT calculations showed that the reaction proceeds through an asynchronous [4+2] cycloaddition (see scheme).

    35. Synthetic Methods

      A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides (pages 8190–8194)

      Dr. Edward I. Balmond, Dr. David Benito-Alifonso, Dr. Diane M. Coe, Prof. Roger W. Alder, Dr. Eoghan M. McGarrigle and Dr. M. Carmen Galan

      Article first published online: 20 JUN 2014 | DOI: 10.1002/anie.201403543

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      Locked in: Glucals and rhamnals are converted into disaccharides or glycoconjugates with high α-selectivity and yields using p-toluenesulfonic acid (TsOH⋅H2O) as a catalyst. The glycosylation stereoselectivity arises from conformational locking of the intermediate oxacarbenium cation by a 3,4-O-disiloxane protecting group. Glucals outperform rhamnals because the C6 side-chain conformation further augments the selectivity.

    36. Polycycles

      Dimerization of Pyramidalized 3,4,8,9-Tetramethyltetracyclo [4.4.0.03,9.04,8]dec-1(6)-ene to a Hydrocarbon Featuring Four Cyclohexane Rings in Boat Conformations (pages 8195–8199)

      Matias Rey-Carrizo, Marta Barniol-Xicota, Dr. Mercè Font-Bardia and Prof. Dr. Santiago Vázquez

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201403985

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      Rock the boat: The dimerization of a highly pyramidalized alkene led to a nonacyclic compound featuring three planar cyclobutane rings, four cyclopentane rings, and four cyclohexane rings in boat conformations. In the cyclohexane rings, very short H–H and C–C distances were found between the flagpole hydrogen atoms and also between the flagpole carbon atoms.

    37. Polyazides

      Preparation of the First Manganese(III) and Manganese(IV) Azides (pages 8200–8205)

      Prof. Dr. Ralf Haiges, Dr. Robert J. Buszek, Dr. Jerry A. Boatz and Prof. Dr. Karl O. Christe

      Article first published online: 7 JUL 2014 | DOI: 10.1002/anie.201404735

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      Put your differences azide: Mn(N3)3⋅CH3CN was obtained from MnF3 through fluoride–azide exchange with Me3SiN3 in CH3CN solution. The reaction of Mn(N3)3⋅CH3CN with PPh4N3 or 2,2′-bipyridine (bipy) resulted in disproportionation reactions and the formation of 1:1 mixtures of (bipy)2Mn(N3)2 and (bipy)Mn(N3)4 (see structure) or [PPh4]2[Mn(N3)4] and [PPh4]2[Mn(N3)6], respectively.

    38. Catalytic Mechanisms

      Substrate-Guided Front-Face Reaction Revealed by Combined Structural Snapshots and Metadynamics for the Polypeptide N-Acetylgalactosaminyltransferase 2 (pages 8206–8210)

      Erandi Lira-Navarrete, Javier Iglesias-Fernández, Dr. Wesley F. Zandberg, Ismael Compañón, Yun Kong, Dr. Francisco Corzana, Prof. B. Mario Pinto, Prof. Henrik Clausen, Prof. Jesús M. Peregrina, Prof. David J. Vocadlo, Prof. Carme Rovira and Dr. Ramon Hurtado-Guerrero

      Article first published online: 20 JUN 2014 | DOI: 10.1002/anie.201402781

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      The magic of many moments: Structural snapshots of GalNAc-T2 complexes during the catalytic cycle were combined with quantum-mechanics/molecular-mechanics metadynamics to reveal an ordered bi–bi kinetic mechanism. Critical aspects of substrate recognition were identified that dictate the specificity for acceptor Thr versus Ser residues and enforce a front-face reaction in which the substrate N-acetyl sugar coordinates glycosyl transfer.

    39. Enzyme Inhibition

      para-Nitroblebbistatin, the Non-Cytotoxic and Photostable Myosin II Inhibitor (pages 8211–8215)

      Miklós Képiró, Boglárka H. Várkuti, László Végner, Gergely Vörös, György Hegyi, Máté Varga and András Málnási-Csizmadia

      Article first published online: 20 JUN 2014 | DOI: 10.1002/anie.201403540

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      No side effects: Blebbistatin, the most popular myosin II inhibitor, is phototoxic, cytotoxic, and light sensitive. However, its C15 nitro analogue displays none of these side effects and maintains the specificity and inhibitory properties of the parent. Thus, para-nitroblebbistatin can replace blebbistatin both in vitro and in vivo.

    40. Liquid Crystals

      Bent Molecules with a 60° Central Core Angle that Form B7 and B2 Phases (pages 8216–8220)

      Eun-Woo Lee, Koji Takimoto, Prof. Dr. Masatoshi Tokita, Prof. Dr. Junji Watanabe and Prof. Dr. Sungmin Kang

      Article first published online: 24 JUN 2014 | DOI: 10.1002/anie.201403762

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      Switchable banana phases were induced by a liquid-crystal-forming molecule with a 60° angle. The molecules are effectively packed in the bent direction within the layer, irrespective of the acute shape. This system confirms the viability of ferro-switchable banana phases and also provides insights into the nature of structure–property relationships.

    41. Photodegradable Hydrogels | Hot Paper

      Photodegradable Hydrogels for Capture, Detection, and Release of Live Cells (pages 8221–8224)

      Dr. Dong-Sik Shin, Dr. Jungmok You, Ali Rahimian, Tam Vu, Christian Siltanen, Arshia Ehsanipour, Dr. Gulnaz Stybayeva, Prof. Julie Sutcliffe and Prof. Alexander Revzin

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201404323

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      Function-based cell retrieval: The function-based sorting of live cells is enabled by a photodegradable poly(ethylene glycol) hydrogel. Hydrogel-coated substrates were used to isolate T-cells from a heterogeneous mixture of immune cells, to analyze cytokine secretion on a cell-by-cell basis, and then to release cells that are actively producing cytokines. TNF=tumor necrosis factor.

    42. Coordination Polymers

      Design of Superhydrophobic Porous Coordination Polymers through the Introduction of External Surface Corrugation by the Use of an Aromatic Hydrocarbon Building Unit (pages 8225–8230)

      Dr. Koya Prabhakara Rao, Dr. Masakazu Higuchi, Dr. Kenji Sumida, Dr. Shuhei Furukawa, Dr. Jingui Duan and Prof. Susumu Kitagawa

      Article first published online: 27 JUN 2014 | DOI: 10.1002/anie.201404306

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      A strong aversion to water: In an approach to water-resistant porous materials with a superhydrophobic surface without the use of alkylation or fluorination, a porous coordination polymer was synthesized with a low-symmetry nanoscale organic linker. The material exhibited superhydrophobicity (see picture) as a result of the surface corrugation created by the aromatic hydrocarbon and displayed selective uptake of organic molecules from water.

    43. Excited-State Design

      A Strap Strategy for Construction of an Excited-State Intramolecular Proton Transfer (ESIPT) System with Dual Fluorescence (pages 8231–8235)

      Naoya Suzuki, Prof. Dr. Aiko Fukazawa, Dr. Kazuhiko Nagura, Dr. Shohei Saito, Dr. Hirotaka Kitoh-Nishioka, Prof. Dr. Daisuke Yokogawa, Prof. Dr. Stephan Irle and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201404867

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      Hold on to the strap: A new type of excited-state intramolecular proton transfer (ESIPT) chromophores has been developed by incorporation of an amine-embedded alkyl strap into an emissive boryl-substituted dithienylpyrrole skeleton. The product's dual fluorescence covers a wide range in the visible region depending on the solvent polarity. The zwitterionic ESIPT state is efficiently stabilized by the aminoalkyl strap and the terminal boryl groups.

    44. Amyloid Inhibitors | Hot Paper

      Rational Design and Identification of a Non-Peptidic Aggregation Inhibitor of Amyloid-β Based on a Pharmacophore Motif Obtained from cyclo[-Lys-Leu-Val-Phe-Phe-] (pages 8236–8239)

      Tadamasa Arai, Takushi Araya, Dr. Daisuke Sasaki, Dr. Atsuhiko Taniguchi, Dr. Takeshi Sato, Dr. Youhei Sohma and Prof. Motomu Kanai

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201405109

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      A unique pharmacophore motif for aggregation inhibitors of Alzheimer's amyloid β (Aβ), without the involvement of backbone amide moieties (see picture; right), was identified based on structure–activity relationship studies using cyclo-[KLVFF] (left). This allowed non-peptidic, small-molecule aggregation inhibitors to be designed that possess significant activity that is comparable to the parent cyclic peptides.

    45. Emulsions

      Osmotically Driven Formation of Double Emulsions Stabilized by Amphiphilic Block Copolymers (pages 8240–8245)

      Jinhye Bae, Prof. Thomas P. Russell and Prof. Ryan C. Hayward

      Article first published online: 16 JUN 2014 | DOI: 10.1002/anie.201405229

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      Water-in-oil-in-water (w/o/w) double emulsions are spontaneously generated from o/w single emulsions by the osmotic pressure provided by salt species initially dispersed in the oil phase. This phenomenon provides a simple route to tailor block copolymer self-assembly, yielding multi-vesicular structures and hierarchically structured porous films after solvent evaporation.

    46. Enzyme Models

      Catalytic Zinc Complexes for Phosphate Diester Hydrolysis (pages 8246–8250)

      Emmanuel Y. Tirel, Zoë Bellamy, Harry Adams, Vincent Lebrun, Fernanda Duarte and Prof. Nicholas H. Williams

      Article first published online: 11 JUN 2014 | DOI: 10.1002/anie.201400335

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      Taking turns: Using an acetal as a ligand-based nucleophile generates a Zn complex capable of cleaving DNA-like phosphodiesters with both turnover and unexpectedly enhanced reactivity. The proposed mechanism involves a tautomer which combines a more effective Lewis acid with a more reactive nucleophile, and suggests a new strategy for creating more efficient metal-ion-based catalysts.

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