Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 50

December 7, 2012

Volume 51, Issue 50

Pages 12377–12625

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. You have free access to this content
      Cover Picture: Muscle-like Supramolecular Polymers: Integrated Motion from Thousands of Molecular Machines (Angew. Chem. Int. Ed. 50/2012) (page 12377)

      Guangyan Du, Dr. Emilie Moulin, Dr. Nicolas Jouault, Prof. Dr. Eric Buhler and Prof. Dr. Nicolas Giuseppone

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201208497

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      Artificial muscles can be created by using a bottom-up approach that involves coupling the controlled motions of a very high number of molecular machines. The cover picture shows a muscular fiber from which a single-chain supramolecular polymer made of thousands of telescopic rotaxanes emerges. In their Communication on page 12504 ff., N. Giuseppone and co-workers show how the integrated functioning of these rotaxanes results in amplified motion. (Graphics by Mathieu Lejeune.)

    2. You have free access to this content
      Inside Cover: In Situ Probing of Newly Synthesized Peptidoglycan in Live Bacteria with Fluorescent D-Amino Acids (Angew. Chem. Int. Ed. 50/2012) (page 12378)

      Erkin Kuru, H. Velocity Hughes, Dr. Pamela J. Brown, Edward Hall, Srinivas Tekkam, Prof. Felipe Cava, Prof. Miguel A. de Pedro, Prof. Yves V. Brun and Prof. Michael S. VanNieuwenhze

      Version of Record online: 23 NOV 2012 | DOI: 10.1002/anie.201209051

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      The lack of a global strategy for direct imaging of sites of active peptidoglycan (PG) synthesis in live cells has until now limited our knowledge of PG synthesis and dynamics. In their Communication on page 12519 ff., M. VanNieuwenhze, Y. V. Brun, and co-workers report a method that utilizes fluorescently modified D-amino acids for rapid and covalent incorporation and detection of fluorescently derivatized PG during cell-wall synthesis in real time, and in live bacterial cells.

    3. You have free access to this content
      Inside Back Cover: Quantum Soldering of Individual Quantum Dots (Angew. Chem. Int. Ed. 50/2012) (page 12627)

      Dr. Xavier Roy, Christine L. Schenck, Dr. Seokhoon Ahn, Prof. Roger A. Lalancette, Prof. Latha Venkataraman, Prof. Colin Nuckolls and Dr. Michael L. Steigerwald

      Version of Record online: 3 DEC 2012 | DOI: 10.1002/anie.201209203

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      Single quantum-dot electronic circuits are fabricated by wiring atomically precise metal chalcogenide clusters with conjugated molecular connectors. In their Communication on page 12473 ff., L. Venkataraman, C. Nuckolls, M. L. Steigerwald et al. report a method for the preparation of structurally and electronically discrete quantum dots on the molecular scale that connect reliably to nanoscale electrodes. The picture shows a caricature of Schroedinger soldering a molecule into a computer chip.

    4. You have free access to this content
      Back Cover: Medication Detection by a Combinatorial Fluorescent Molecular Sensor (Angew. Chem. Int. Ed. 50/2012) (page 12628)

      Dr. Bhimsen Rout, Linor Unger, Gad Armony, Dr. Mark A. Iron and Dr. David Margulies

      Version of Record online: 23 NOV 2012 | DOI: 10.1002/anie.201209049

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      A fluorescent molecular sensor can mimic the function of optical cross-reactive sensor arrays. In their Communication on page 12477 ff., D. Margulies et al. show how a series of nonspecific, fluorescent receptors can be “arrayed” on a single molecular platform. The resulting analytical device can generate unique optical fingerprints for different medications, as well as analyze drug combinations and concentrations in human urine in a high-throughput manner.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
  3. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
  4. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Shu-Hong Yu (page 12402)

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201205545

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      “If I were not a scientist, I would be a fisherman or a farmer. What I look for first in a publication is its graphical abstract …” This and more about Shu-Hong Yu can be found on page 12402.

  5. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
  6. Obituary

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Heinz A. Staab (19262012) (pages 12404–12405)

      Matthias W. Haenel

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201208180

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  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. The Pauson–Khand Reaction. Scope, Variations and Applications. Edited by Ramon Rios Torres. (page 12406)

      Nina Kann

      Version of Record online: 4 DEC 2012 | DOI: 10.1002/anie.201207470

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      John Wiley & Sons, Hoboken, 2012. 328 S., hardcover, € 129.00.—ISBN 978-0470970768

  8. Highlights

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Nanoparticle Chains

      Self-Assembly and Colloidal Polymerization of Polymer–Nanoparticle Hybrids into Mesoscopic Chains (pages 12408–12409)

      Prof. Jeffrey Pyun

      Version of Record online: 19 NOV 2012 | DOI: 10.1002/anie.201206245

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      No, it's not frogspawn! Polymer-coated gold nanoparticles can be assembled into extended mesoscopic chains with precise dimensional control. Here, the conditions can be adjusted to promote the fusion of polymeric ligands into cylindrical micellar aggregates. This type of colloidal polymerization offers a new and versatile route to a variety of mesoscopic assemblies of nanoparticles.

    2. Photocatalysis

      A Highly Efficient Photocatalyst—Hydrogenated Black TiO2 for the Photocatalytic Splitting of Water (pages 12410–12412)

      Prof. Yun Hang Hu

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201206375

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      In black and white: The hydrogenation of TiO2 can extend its optical absorption into the visible and infrared region and change its color from white to black. Furthermore, the hydrogenated black TiO2 exhibits excellent photocatalytic activity for the splitting of water to yield H2.

  9. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Total Synthesis

      How Thiostrepton Was Made in the Laboratory (pages 12414–12436)

      K. C. Nicolaou

      Version of Record online: 3 DEC 2012 | DOI: 10.1002/anie.201205576

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      An adventurous undertaking: The synthetic conquest of thiostrepton was achieved in 2004. In this vivid account the author describes the laboratory odyssey with its many intriguing twists and turns that led to this memorable total synthesis.

  10. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlights
    10. Review
    11. Communications
    1. Metabolomics

      Complex Small-Molecule Architectures Regulate Phenotypic Plasticity in a Nematode (pages 12438–12443)

      Neelanjan Bose, Dr. Akira Ogawa, Dr. Stephan H. von Reuss, Joshua J. Yim, Dr. Erik J. Ragsdale, Prof. Ralf J. Sommer and Prof. Frank C. Schroeder

      Version of Record online: 19 NOV 2012 | DOI: 10.1002/anie.201206797

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      Chemistry the worm's way: The nematode Pristionchus pacificus constructs elaborate small molecules from modified building blocks of primary metabolism, including an unusual xylopyranose-based nucleoside (see scheme). These compounds act as signaling molecules to control adult phenotypic plasticity and dauer development and provide examples of modular generation of structural diversity in metazoans.

    2. E/Z-Alkene Synthesis

      Diastereodivergent Synthesis of Trisubstituted Alkenes through Protodeboronation of Allylic Boronic Esters: Application to the Synthesis of the Californian Red Scale Beetle Pheromone (pages 12444–12448)

      Matthew J. Hesse, Dr. Craig P. Butts, Prof. Christine L. Willis and Prof. Varinder K. Aggarwal

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201207312

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      E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF⋅3 H2O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF2/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle.

    3. Ligand Design

      Single-Round, Multiplexed Antibody Mimetic Design through mRNA Display (pages 12449–12453)

      Dr. C. Anders Olson, Jeff Nie, Jonathan Diep, Dr. Ibrahim Al-Shyoukh, Prof. Terry T. Takahashi, Dr. Laith Q. Al-Mawsawi, Jennifer M. Bolin, Angela L. Elwell, Scott Swanson, Dr. Ron Stewart, Prof. James A. Thomson, Prof. H. Tom Soh, Prof. Richard W. Roberts and Prof. Ren Sun

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207005

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      In a single round: By combining the high-efficiency enrichment through the continuous-flow magnetic separation (CFMS) technique with the analytical power of next-generation sequencing, the generation of antibody mimetics with a single round of mRNA display is made possible. This approach eliminates iterative selection cycles and provides a path to fully automated ligand generation (see picture).

    4. Bioreduction

      Tracking the Bioreduction of Disulfide-Containing Cationic Dendrimers (pages 12454–12458)

      Lorine Brülisauer, Nadia Kathriner, Mark Prenrecaj, Dr. Marc A. Gauthier and Prof. Dr. Jean-Christophe Leroux

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201207070

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      Disulfides enhance the transfection efficacy and reduce the toxicity of cationic gene delivery polymers. A quantitative analysis is provided of the bioreduction of a dynamic bioreducible dendritic polycationic probe in four cell lines. Such knowledge is indispensible for understanding and optimizing bioreducible drug and gene delivery systems.

    5. Porphyrinoids

      Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen-Bonding Interactions of meso-Imidazolyl Groups (pages 12459–12463)

      Hirotaka Mori, Young Mo Sung, Byung Sun Lee, Prof. Dr. Dongho Kim and Prof. Dr. Atsuhiro Osuka

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207212

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      Stable antiaromatic expanded porphyrins were designed by the judicious implementation of meso-imidazolyl groups, which cause stabilization through the creation of a hydrogen-bonding network (see structures) that overcomes antiaromatic electronic destabilization. Both the [28]hexaphyrin 1 and the [36]octaphyrin 2, which contain imidazolyl groups at two opposite meso positions, are shown to be stable Hückel antiaromatic species.

    6. Protein Conformations

      Real-Time Monitoring of Protein Conformational Dynamics in Solution Using Kinetic Capillary Electrophoresis (pages 12464–12468)

      Dr. Christopher M. Clouthier, Gleb G. Mironov, Dr. Victor Okhonin, Prof. Maxim V. Berezovski and Prof. Jeffrey W. Keillor

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/anie.201205575

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      Conformational analysis: Capillary electrophoresis (CE) allows for the rapid separation of slowly interconverting protein conformers. Kinetic analysis (kopen, kclosed, and Kd) of electropherograms in the presence and absence of effector ligands allows the measurement of kinetic and thermodynamic constants associated with conformational changes and ligand binding.

    7. Smart Materials

      Engineering of Complex Order and the Macroscopic Deformation of Liquid Crystal Polymer Networks (pages 12469–12472)

      Laurens T. de Haan, Dr. Carlos Sánchez-Somolinos, Dr. Cees M. W. Bastiaansen, Dr. Albertus P. H. J. Schenning and Prof. Dr. Dirk J. Broer

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201205964

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      Rise or fall: Complex-structured freestanding polymer films with molecular order in three dimensions were prepared through photoalignment of polymerizable liquid crystals. The resulting films deform into cone and saddle shapes upon heating.

    8. Molecular Electronics

      Quantum Soldering of Individual Quantum Dots (pages 12473–12476)

      Dr. Xavier Roy, Christine L. Schenck, Dr. Seokhoon Ahn, Prof. Roger A. Lalancette, Prof. Latha Venkataraman, Prof. Colin Nuckolls and Dr. Michael L. Steigerwald

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/anie.201206301

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      Making contact to a quantum dot: Single quantum-dot electronic circuits are fabricated by wiring atomically precise metal chalcogenide clusters with conjugated molecular connectors. These wired clusters can couple electronically to nanoscale electrodes and be tuned to control the charge-transfer characteristics (see picture).

    9. Molecular-Scale Diagnostics

      Medication Detection by a Combinatorial Fluorescent Molecular Sensor (pages 12477–12481)

      Dr. Bhimsen Rout, Linor Unger, Gad Armony, Dr. Mark A. Iron and Dr. David Margulies

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/anie.201206374

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      Working together to uncover the truth: A molecule-sized diagnostic system combining several recognition elements and four fluorescence-emission channels enabled the identification of a wide range of pharmaceuticals on the basis of distinct photophysical processes. The molecular sensor (see simplified representation; ID=identification) was also used to analyze drug concentrations and combinations in urine samples in a high-throughput manner.

    10. Synergistic Apoptosis

      Double-Effector Nanoparticles: A Synergistic Approach to Apoptotic Hyperthermia (pages 12482–12485)

      Dr. Dongwon Yoo, Heeyeong Jeong, Christian Preihs, Dr. Jin-sil Choi, Tae-Hyun Shin, Prof. Jonathan L. Sessler and Prof. Jinwoo Cheon

      Version of Record online: 8 NOV 2012 | DOI: 10.1002/anie.201206400

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      Highly efficient apoptotic hyperthermia is achieved using a double-effector nanoparticle that can generate reactive oxygen species (ROS) and heat. ROS render cancer cells more susceptible to subsequent heat treatment, which remarkably increases the degree of apoptotic cell death. Xenograft tumors (100 mm3) in mice are completely eliminated within 8 days after a single mild magnetic hyperthermia treatment at 43 °C for 30 min.

    11. Targeted Drug Delivery

      Enzyme-Responsive Controlled Release of Covalently Bound Prodrug from Functional Mesoporous Silica Nanospheres (pages 12486–12489)

      Dr. Amirali Popat, Dr. Benjamin P. Ross, Dr. Jian Liu, Siddharth Jambhrunkar, Prof. Freddy Kleitz and Prof. Shi Zhang Qiao

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201206416

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      I want to break free: Mesoporous silica nanoparticles are functionalized with sulfasalazine (SZ; see scheme), a prodrug of 5-aminosalicylic acid (5-ASA) and sulfapyridine, to generate enzyme-responsive nanocarriers. In the presence of the colon-specific enzyme azo-reductase (orange), 5-ASA and sulfapyridine are efficiently released.

    12. Metal–Organic Frameworks

      Spectroscopic Evidence for the Structure Directing Role of the Solvent in the Synthesis of Two Iron Carboxylates (pages 12490–12494)

      Tadeja Birsa Čelič, Dr. Mojca Rangus, Dr. Károly Lázár, Prof. Venčeslav Kaučič and Prof. Nataša Zabukovec Logar

      Version of Record online: 13 NOV 2012 | DOI: 10.1002/anie.201204573

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      Crystal engineering: The synthesis of the known compounds MIL-100(Fe) and MIL-45(Fe) is characterized by spectroscopy. The products are obtained under identical conditions by varying the solvent from pure water to a mixture of water and acetone. The starting solution, the gel, and the final reaction product were characterized by X-ray absorption spectroscopy (see picture).

    13. Electrochemistry

      Enhancing the Alkaline Hydrogen Evolution Reaction Activity through the Bifunctionality of Ni(OH)2/Metal Catalysts (pages 12495–12498)

      Dr. N. Danilovic, Dr. Ram Subbaraman, Dr. D. Strmcnik, Dr. Kee-Chul Chang, Dr. A. P. Paulikas, Dr. V. R. Stamenkovic and Dr. Nenad M. Markovic

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201204842

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      Active in alkaline environment: The activity of nickel, silver, and copper catalysts for the electrochemical transformation of water to molecular hydrogen in alkaline solutions was enhanced by modification of the metal surfaces by Ni(OH)2 (see picture; I=current density and η=overpotential). The hydrogen evolution reaction rate on a Ni electrode modified by Ni(OH)2 nanoclusters is about four times higher than on a bare Ni surface.

    14. Soft Matter

      Photo- and Thermoresponsive Polymersomes for Triggered Release (pages 12499–12503)

      Dr. Esther Amstad, Prof. Dr. Shin-Hyun Kim and Prof. Dr. David A. Weitz

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201206531

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      Microfluidics: Thermo- and photoresponsive polymersomes are assembled using capillary microfluidic devices. Encapsulants can be selectively released from the thermoresponsive polymersomes if they are incubated at and above temperatures of 40 °C, whereas the photoresponsive polymersomes selectively release encapsulants if illuminated with laser light (see picture; NP=nanoparticle).

    15. Nanotechnology

      Muscle-like Supramolecular Polymers: Integrated Motion from Thousands of Molecular Machines (pages 12504–12508)

      Guangyan Du, Dr. Emilie Moulin, Dr. Nicolas Jouault, Prof. Dr. Eric Buhler and Prof. Dr. Nicolas Giuseppone

      Version of Record online: 18 OCT 2012 | DOI: 10.1002/anie.201206571

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      Pumping iron: Double-threaded rotaxanes can be linked to coordination units and polymerized in the presence of iron or zinc ions. pH modulation triggers cooperative contractions (or extensions) of the individual rotaxanes, thus resulting in an amplified motion of the muscle-like supramolecular chains with changes of their contour lengths of several micrometers (see picture).

    16. Pluripotency

      A Novel Small Molecule Facilitates the Reprogramming of Human Somatic Cells into a Pluripotent State and Supports the Maintenance of an Undifferentiated State of Human Pluripotent Stem Cells (pages 12509–12513)

      Dr. Jungwoon Lee, Yan Xia, Mi-Young Son, Guanghai Jin, Binna Seol, Min-Jeong Kim, Dr. Myung Jin Son, Misol Do, Minho Lee, Prof. Dongsup Kim, Prof. Kyeong Lee and Dr. Yee Sook Cho

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201206691

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      Booster of pluripotency: RSC133, a new synthetic derivative of indoleacrylic acid/indolepropionic acid, exhibits dual activity by inhibiting histone deacetylase and DNA methyltransferase. Furthermore it potently improves the reprogramming of human somatic cells into a pluripotent state and aids the growth and maintenance of human pluripotent stem cells (hPSCs).

    17. Bond Theory

      Confirmation of an Early Postulate: B[BOND]C[BOND]B Two-Electron–Three-Center Bonding in Organo(hydro)boranes (pages 12514–12518)

      Alexander Hübner, Dr. Martin Diefenbach, Dr. Michael Bolte, Dr. Hans-Wolfram Lerner, Prof. Dr. Max C. Holthausen and Prof. Dr. Matthias Wagner

      Version of Record online: 14 NOV 2012 | DOI: 10.1002/anie.201207335

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      Finally, boron did it too: The first example of a dimeric organyl(hydro)borane with a B-B-bridging aryl ring has been elucidated (see picture; B green/blue, C black/gray). It features a B[BOND]C[BOND]B two-electron–three-center bond and a largely unperturbed aromatic π-electron system.

    18. Fluorescence Imaging

      In Situ Probing of Newly Synthesized Peptidoglycan in Live Bacteria with Fluorescent D-Amino Acids (pages 12519–12523)

      Erkin Kuru, H. Velocity Hughes, Dr. Pamela J. Brown, Edward Hall, Srinivas Tekkam, Prof. Felipe Cava, Prof. Miguel A. de Pedro, Prof. Yves V. Brun and Prof. Michael S. VanNieuwenhze

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201206749

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      Tracking a bug's life: Peptidoglycan (PG) of diverse bacteria is labeled by exploiting the tolerance of cells for incorporating different non-natural D-amino acids. These nontoxic D-amino acids preferably label the sites of active PG synthesis, thereby enabling fine spatiotemporal tracking of cell-wall dynamics in phylogenetically and morphologically diverse bacteria. HCC=7-hydroxycoumarin, NBD=7-nitrobenzofurazan, TAMRA=carboxytetramethylrhodamine.

    19. Alloys

      A Strategy for Designing a Concave Pt–Ni Alloy through Controllable Chemical Etching (pages 12524–12528)

      Yuen Wu, Dingsheng Wang, Zhiqiang Niu, Pengcheng Chen, Gang Zhou and Prof. Yadong Li

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/anie.201207491

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      This corrosion: Octahedral Pt–Ni alloy nanoparticles (NPs) are converted into concave Pt3Ni NPs by a coordination-assisted chemical-etching process (see scheme). The corroded concave Pt–Ni NPs have a higher density of low-coordinate atoms in steps sites, a decisive property in heterogeneous catalysis.

    20. Enzyme Labeling

      Novel Activity-Based Probes for Broad-Spectrum Profiling of Retaining β-Exoglucosidases In Situ and In Vivo (pages 12529–12533)

      Wouter W. Kallemeijn, Kah-Yee Li, Dr. Martin D. Witte, André R. A. Marques, Dr. Jan Aten, Saskia Scheij, Jianbing Jiang, Lianne I. Willems, Tineke M. Voorn-Brouwer, Cindy P. A. A. van Roomen, Roelof Ottenhoff, Dr. Rolf G. Boot, Hans van den Elst, Marthe T. C. Walvoort, Dr. Bogdan I. Florea, Dr. Jeroen D. C. Codée, Prof. Dr. Gijsbert A. van der Marel, Prof. Dr. Johannes M. F. G. Aerts and Prof. Dr. Herman S. Overkleeft

      Version of Record online: 8 NOV 2012 | DOI: 10.1002/anie.201207771

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      A high-end label: Cyclophellitol aziridine-type activity-based probes allow for ultra-sensitive visualization of mammalian β-glucosidases (GBA1, GBA2, GBA3, and LPH) as well as several non-mammalian β-glucosidases (see picture). These probes offer new ways to study β-exoglucosidases, and configurational isomers of the cyclophellitol aziridine core may give activity-based probes targeting other retaining glycosidase families.

    21. Multifunctional Organic Materials

      A Multifunctional Porous Organic Schottky Barrier Diode (pages 12534–12537)

      Sasanka Dalapati, Rajat Saha, Sankar Jana, Astam K. Patra, Dr. Asim Bhaumik, Dr. Sanjay Kumar and Dr. Nikhil Guchhait

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201205439

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      Mesoporous materials: A multifunctional porous organic material (ANPPIT; see picture) has been synthesized and characterized. Multifunctionality of the compound has been determined from nitrogen adsorption, guest-dependent luminescence, and electrical conductivity measurements.

    22. Cross-Coupling Reactions

      Organocatalytic Amidation and Esterification of Aldehydes with Activating Reagents by a Cross-Coupling Strategy (pages 12538–12541)

      Dr. Bin Tan, Dr. Narihiro Toda and Prof. Dr. Carlos F. Barbas III

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/anie.201205921

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      Formation on demand: An organocatalytic cross-coupling reaction of aldehydes with N-hydroxyimides, hexafluoroisopropyl alcohol, and sulfonimides has been developed. The resulting active intermediates can be directly converted into amides or esters in one pot. This simple method makes use of readily available starting materials, and the newly discovered activating reagents should find broad application in the synthesis of amides and esters.

    23. Radical Reactions

      Transition-Metal-Free Alkoxycarbonylation of Aryl Halides (pages 12542–12545)

      Hua Zhang, Renyi Shi, Anxing Ding, Lijun Lu, Borui Chen and Prof. Aiwen Lei

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201206518

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      Transitions: The title reaction has been developed for the synthesis of a variety of tert-butyl benzoates by employing 1,10-phenanthroline as an additive. Various functional groups were tolerated and heteroaryl iodides were also suitable substrates. Preliminary mechanism studies were conducted and indicate the participation of radical intermediates.

    24. Indole Chemistry

      FeCl3-Mediated Friedel–Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines (pages 12546–12550)

      Rodolphe Beaud, Dr. Régis Guillot, Prof.Dr. Cyrille Kouklovsky and Dr. Guillaume Vincent

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201206611

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      IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl3 features a rare example of the electrophilic reactivity of the indole core in a Friedel–Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.

    25. Cross-Coupling Reactions

      Copper-Promoted Trifluoromethylation of Primary and Secondary Alkylboronic Acids (pages 12551–12554)

      Jun Xu, Bin Xiao, Chuan-Qi Xie, Dong-Fen Luo, Prof. Lei Liu and Prof. Yao Fu

      Version of Record online: 9 NOV 2012 | DOI: 10.1002/anie.201206681

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      New couple: The Cu-promoted trifluoromethylation of primary and secondary alkylboronic acids with TMSCF3 extends the scope of transition-metal-catalyzed trifluoromethylation reactions to sp3-hybridized carbon centers. It also represents one of the first examples for Cu-catalyzed C[BOND]C cross-coupling reactions of alkylboronic acid derivatives.

    26. Boron Compounds

      Synthesis of Boron-Substituted Diaryliodonium Salts and Selective Transformation into Functionalized Aryl Boronates (pages 12555–12558)

      Dr. Motoki Ito, Itsuki Itani, Yosuke Toyoda, Dr. Koji Morimoto, Dr. Toshifumi Dohi and Prof. Dr. Yasuyuki Kita

      Version of Record online: 8 NOV 2012 | DOI: 10.1002/anie.201206917

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      Dormant boron awaits its true destiny in diaryliodonium salts synthesized from aryl boronate derivatives according to two alternative general methods with hypervalent iodine(III) reagents and fluoroalcohol solvents: transformation of an aryl C[BOND]H bond and boron–iodine(III) exchange (see scheme; FG=functional group). The salts could be functionalized by both catalyst-free and metal-catalyzed reactions without loss of the boron functionality.

    27. Hydrides

      Zirconocene Dichloride Catalyzed Hydrodefluorination of Cmath image[BOND]F bonds (pages 12559–12563)

      Dr. Shuhui Yow, Sarah J. Gates, Dr. Andrew J. P. White and Dr. Mark R. Crimmin

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/anie.201207036

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      A two-metal job: Four-coordinate aluminum dihydrides such as 1 are reported as terminal reductants for the selective title reaction. The heterobimetallic complex 2 has been isolated and shown to be catalytically competent.

    28. Oxygenation Chemistry

      Hydrogenation of a Rhodium Peroxido Complex by Formate Derivatives: Mechanistic Studies and the Catalytic Formation of H2O2 from O2 (pages 12564–12569)

      Gregor Meier and Prof. Dr. Thomas Braun

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207073

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      Hydrogenation of dioxygen: The rhodium peroxido complex 1, which can be prepared from 2 and dioxygen, can be reduced with dihydrogen sources to yield hydrogen peroxide. In a catalytic experiment, hydrogen peroxide is produced from dioxygen and ammonium formate under ambient conditions in the presence of 1 (see scheme).

    29. Synthetic Methods

      Transition-Metal-Free Aerobic Oxidative Cleavage of C[BOND]C Bonds in α-Hydroxy Ketones and Mechanistic Insight to the Reaction Pathway (pages 12570–12574)

      Hui Liu, Chao Dong, Zeguang Zhang, Peiyu Wu and Prof. Dr. Xuefeng Jiang

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201207206

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      Clear cut: For the title reaction, O2, the ideal oxidant, was used as the only oxidizing reagent. The dimer intermediate (see scheme) and isotopic labeling control experiments with 18O2 partially disclosed the reaction mechanism.

    30. Membranes

      Reversible Sensing of the Anticoagulant Heparin with Protamine Permselective Membranes (pages 12575–12578)

      Gastón A. Crespo, Majid Ghahraman Afshar and Prof. Eric Bakker

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207444

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      A permselective membrane electrode allows the rapid and operationally reversible detection of the polycationic polypeptide protamine in physiological samples. Anticoagulant levels of heparin can be measured in undiluted whole blood by adding a known excess of its antidote protamine to discrete blood samples.

    31. Boolean Logic

      Using Thermally Regenerable Cerium Oxide Nanoparticles in Biocomputing to Perform Label-free, Resettable, and Colorimetric Logic Operations (pages 12579–12583)

      Youhui Lin, Can Xu, Prof. Dr. Jinsong Ren and Prof. Dr. Xiaogang Qu

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/anie.201207587

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      A label-free, resettable, and colorimetric logic network has been realized by utilizing thermally regenerable cerium oxide nanoparticles and biocatalytic reactions. Coupling switchable CeO2 nanoparticles with biocomputing would convert molecular recognition events into colorimetric outputs and make logic gates feasible to reset.

    32. Uranyl Complexes

      Controlled Deprotection and Reorganization of Uranyl Oxo Groups in a Binuclear Macrocyclic Environment (pages 12584–12587)

      Guy M. Jones, Prof. Polly L. Arnold and Dr. Jason B. Love

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/anie.201207609

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      Switching on uranium(V) reactivity: The silylated uranium(V) dioxo complex [(Me3SiOUO)2(L)2] (A) is inert to oxidation, but after two-electron reduction to [(Me3SiOUO)2(L)]2− (1), it can be desilylated to form [OU(μ-O)2UO(L)2]2− (2) with reinstated uranyl character. Removal of the silyl group uncovers new redox and oxo rearrangement chemistry for uranium, thus reforming the uranyl motif and involving the UVI/V couple in dioxygen reduction.

    33. Nanoparticle Gradient

      A Simple Route to Hierarchically Assembled Micelles and Inorganic Nanoparticles (pages 12588–12592)

      Dr. Wei Han, Dr. Myunghwan Byun, Bo Li, Dr. Xinchang Pang and Prof. Zhiqun Lin

      Version of Record online: 7 NOV 2012 | DOI: 10.1002/anie.201207902

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      Earning their stripes: A hierarchical assembly of micelles composed of an amphiphilic diblock copolymer, poly(styrene)-block-poly(4-vinylpyridine) (PS-b-P4VP), were made by combining controlled evaporative self-assembly of the confined PS-b-P4VP toluene solution in a cylinder-on-Si geometry with spontaneous self-assembly of micelles. This method gave microscopic stripes of nanometer-sized PS-b-P4VP micelles within the stripes (see pictures).

    34. RNA Recognition

      Triple-Helical Recognition of RNA Using 2-Aminopyridine-Modified PNA at Physiologically Relevant Conditions (pages 12593–12596)

      Thomas Zengeya, Dr. Pankaj Gupta and Dr. Eriks Rozners

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207925

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      Peptide nucleic acids containing thymidine and 2-aminopyridine (M) nucleobases form stable and sequence-selective triple helices with double-stranded RNA at physiologically relevant conditions. The M-modified PNA showed unique RNA selectivity by having two orders of magnitude higher affinity for the double-stranded RNAs than for the same DNA sequences.

    35. Spin Transitions

      Cooperative Spin Transition in a Mononuclear Manganese(III) Complex (pages 12597–12601)

      Dr. Paulo N. Martinho, Brendan Gildea, Michelle M. Harris, Dr. Tibebe Lemma, Dr. Anil D. Naik, Dr. Helge Müller-Bunz, Prof. Tia E. Keyes, Prof. Dr. Yann Garcia and Dr. Grace G. Morgan

      Version of Record online: 5 NOV 2012 | DOI: 10.1002/anie.201205573

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      Mind the gap: A complete, cooperative spin transition for a mononuclear MnIII complex is reported with an 8 K hysteresis window. Raman spectra collected at a single temperature in warming and cooling modes confirm the electronic bistability within the hysteresis loop. The source of the cooperativity is a disconnection in the hydrogen-bonded 1D chains that connect adjacent cations owing to an order–disorder transition in the PF6 counterion.

    36. Peptide Structures

      Analysis of Peptide Secondary Structures by Photoactivatable Amino Acid Analogues (pages 12602–12605)

      Dr. Knut Kölbel, Dr. Christian H. Ihling and Prof. Dr. Andrea Sinz

      Version of Record online: 26 OCT 2012 | DOI: 10.1002/anie.201205308

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      Photochemical cross-linking was applied to trap intramolecular interactions in peptides. The incorporation of diazirine-labeled amino acid analogues in combination with high-resolution mass spectrometry made it possible to catch reverse-turn conformations within peptides, exactly map their self-interacting surfaces, and discriminate between stable and transient interactions.

    37. Photoionization

      Counterintuitive Influence of Protonation on Radical-Anion Photoionization (pages 12606–12608)

      Prof. Dr. Martin Goez and Christoph Kerzig

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201206605

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      Protonation of a radical anion M.− greatly facilitates its green-light photoionization despite much less favorable energetics for the resulting ketyl radical MH.. The state symmetry of the radical species absorbing the ionizing photon might provide an explanation.

    38. Asymmetric Catalysis

      Organocatalytic, Highly Enantioselective Vinylogous Mukaiyama–Michael Reaction of Acyclic Dienol Silyl Ethers (pages 12609–12612)

      Vaishali Gupta, Dr. Sai Sudhir V., Dr. Tanmay Mandal and Prof. Dr. Christoph Schneider

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/anie.201207058

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      Now also acyclic: The first catalytic, enantioselective, vinylogous Michael reaction of linear, acyclic dienol silyl ethers was achieved. The reaction, based upon the principle of iminium ion catalysis, delivered 1,7-dioxo compounds in one step with good yields, complete regio-, and excellent enantioselectivity. γ-Substituted dienol silyl ethers furnished products with two new stereogenic centers with good diastereoselectivity. Ms=mesityl, PNBA=para-nitrobenzoic acid.

    39. Platinum Dissolution

      You have full text access to this OnlineOpen article
      Dissolution of Platinum: Limits for the Deployment of Electrochemical Energy Conversion? (pages 12613–12615)

      Angel A. Topalov, Dr. Ioannis Katsounaros, Dr. Michael Auinger, Dr. Serhiy Cherevko, Josef C. Meier, Dr. Sebastian O. Klemm and Dr. Karl J. J. Mayrhofer

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201207256

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      Platinum stability: Dissolution of Pt, which is one major degradation mechanism in, for example, hydrogen/air fuel cells, was monitored under potentiodynamic and potentiostatic conditions. The highly sensitive and time-resolving dissolution monitoring enables the distinction between anodic and cathodic dissolution processes during potential transient and chronoamperometric experiments, and the precise quantification of the amount of dissolved Pt.

    40. Surface Patterning

      Immobilization of Liposomes and Vesicles on Patterned Surfaces by a Peptide Coiled-Coil Binding Motif (pages 12616–12620)

      Dr. Jens Voskuhl, Dr. Christian Wendeln, M. Sc. Frank Versluis, M. Sc. Eva-Corinna Fritz, M. Sc. Oliver Roling, M. Sc. Harshal Zope, Dr. Christian Schulz, Dipl.-Phys. Stefan Rinnen, Prof. Dr. Heinrich F. Arlinghaus, Prof. Dr. Bart Jan Ravoo and Dr. Alexander Kros

      Version of Record online: 26 SEP 2012 | DOI: 10.1002/anie.201204836

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      Patchy surfaces: An azide-terminated self-assembled monolayer was patterned with the peptide sequence (EIAALEK)3 by using microcontact printing. This sequence forms stable coiled-coil heterodimers with the complementary peptide (KIAALKE)3. By introducing this peptide to the surface of phospholipid liposomes and cyclodextrin vesicles, liposomes and vesicles can be immobilized at the patterned surface.

    41. Amyloids

      Solid-State NMR Spectroscopy of Functional Amyloid from a Fungal Hydrophobin: A Well-Ordered β-Sheet Core Amidst Structural Heterogeneity (pages 12621–12625)

      Vanessa K. Morris, Rasmus Linser, Karyn L. Wilde, Anthony P. Duff, Margaret Sunde and Ann H. Kwan

      Version of Record online: 4 NOV 2012 | DOI: 10.1002/anie.201205625

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      GrEASy fibrils: Hydrophobins are fungal proteins that assemble into an amphipathic fibrillar monolayer with amyloid properties and a hydrophobic face as water-resistant as Teflon. Solid-state NMR studies on EAS hydrophobin fibrils reveal direct evidence of a partial molecular rearrangement on assembly and an ordered β-sheet-rich core in the context of a whole protein in this functional amyloid.

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