Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

December 3, 2010

Volume 49, Issue 49

Pages 9295–9537

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Cover Picture: Organic Sol–Gel Synthesis: Solution-Processable Microporous Organic Networks (Angew. Chem. Int. Ed. 49/2010) (page 9295)

      Su-Young Moon, Jae-Sung Bae, Eunkyung Jeon and Prof. Ji-Woong Park

      Article first published online: 17 SEP 2010 | DOI: 10.1002/anie.201005442

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      Microporous networks of rigid organic building blocks can be solution-processed by using an organic sol–gel method. In their Communication on page 9504 ff., J.-W. Park and co-workers describe how organic molecular networks grow by the formation of stable organic sols comprising nanoparticle dispersions. This method enables processing of three-dimensional microporous molecular networks into unprecedented forms such as nanoparticles, membranes, or nanocomposites.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Inside Cover: Adhesive Vesicles through Adaptive Response of a Biobased Surfactant (Angew. Chem. Int. Ed. 49/2010) (page 9296)

      Dr. Vijai S. Balachandran, Swapnil R. Jadhav, Dr. Padmanava Pradhan, Prof. Dr. Sacha De Carlo and Prof. Dr. George John

      Article first published online: 16 SEP 2010 | DOI: 10.1002/anie.201005439

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      Life is a dynamic self-assembly process driven by response to stimuli such as touch, temperature, and light. This is fundamental to all forms of life—as exemplified by the venus flytrap (Dionaea muscipula), which executes a specific function in response to a short-term stimulus—and also for tropism and homeostasis. G. John and co-workers describe in their Communication on page 9509 ff. functional materials that are responsive to stimuli which have been synthesized by using the lessons learned from nature.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 49/2010 (pages 9299–9311)

      Article first published online: 1 DEC 2010 | DOI: 10.1002/anie.201090153

  4. Retraction

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    4. Graphical Abstract
    5. Retraction
    6. News
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    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    15. Preview
    1. You have free access to this content
      Retraction: Stable Aziridinium Salts as Versatile Intermediates: Isolation and Regio- and Stereoselective Ring-Opening and Rearrangement (page 9311)

      Hyun A. Song, Mamta Dadwal, Yeseul Lee, Emily Mick and Hyun-Soon Chong

      Article first published online: 1 DEC 2010 | DOI: 10.1002/anie.201090154

      This article corrects:
  5. News

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
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    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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  6. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. François P. Gabbaï (page 9318)

      Article first published online: 9 NOV 2010 | DOI: 10.1002/anie.201005522

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      “When I wake up I go to our kitchen and prepare the lunches of my daughters. The biggest problem that scientists face is the increasing pressure put on our planet by humanity …” This and more about François P. Gabbaï can be found on page 9318.

  7. News

    1. Top of page
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    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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  8. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Model Systems in Catalysis. Single Crystals to Supported Enzyme Mimics. Edited by Robert M. Rioux. (page 9320)

      Cynthia Friend

      Article first published online: 17 NOV 2010 | DOI: 10.1002/anie.201005956

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      Springer Verlag, Heidelberg 2010. 526 pp., hardcover € 171.15.—ISBN 978-0387980416

  9. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Retraction
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Cross-Coupling

      Transition-Metal-Catalyzed Trifluoromethylation of Aryl Halides (pages 9322–9324)

      Rylan J. Lundgren and Prof. Dr. Mark Stradiotto

      Article first published online: 28 SEP 2010 | DOI: 10.1002/anie.201004051

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      Making inroads into ArCF3: Recent advances in the copper- and palladium-catalyzed cross-coupling of aryl halides and the trifluoromethyl anion, derived from (trifluoromethyl)silanes, are highlighted.

    2. Nanoparticle SERS

      The Next Generation of Advanced Spectroscopy: Surface Enhanced Raman Scattering from Metal Nanoparticles (pages 9325–9327)

      Prof. Duncan Graham

      Article first published online: 7 OCT 2010 | DOI: 10.1002/anie.201002838

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      Shining light: Surface enhanced Raman scattering (SERS) offers much in terms of molecularly specific information at ultrasensitive levels. Two recent breakthroughs have occured in this field. First, a new surface was developed that provides SERS information previously inaccessible, and second, a nanoparticle SERS label was introduced to image antigens relating to cancer in tissue.

    3. Surface Modifications

      Small, Minimally Invasive, Direct: Electrons Induce Local Reactions of Adsorbed Functional Molecules on the Nanoscale (pages 9328–9330)

      Dr. Ivo Utke and Prof. Armin Gölzhäuser

      Article first published online: 30 SEP 2010 | DOI: 10.1002/anie.201002677

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      Double duty: Apart from imaging and analysis purposes, modern electron microscopes can be exploited for focused electron beam induced processing (FEBIP) on the nanometer scale using adsorbed functional volatile molecules. Depending on the nature of injected molecules and substrates, the electron-impact dissociation products form solid deposits (metals, dielectrics, semiconductors, nanocomposites) or remove substrate material locally.

  10. Essay

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    5. Retraction
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    9. Book Review
    10. Highlights
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Graphene Research

      Graphene—How a Laboratory Curiosity Suddenly Became Extremely Interesting (pages 9332–9335)

      Prof. Dr. Hanns-Peter Boehm

      Article first published online: 23 SEP 2010 | DOI: 10.1002/anie.201004096

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      Thanks to its unusual electronic properties graphene has received considerable attention in recent years. It is less known, however, that research in this area goes much further back: At the start of the 1960s H.-P. Boehm et al. reduced graphite oxide with formation of thin films, which today, on account of their content of foreign atoms, would be called “chemically modified graphenes” (figure: electron microscopy image from that time).

  11. Minireview

    1. Top of page
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    4. Graphical Abstract
    5. Retraction
    6. News
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    9. Book Review
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    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Genealogy of Graphene

      From Conception to Realization: An Historial Account of Graphene and Some Perspectives for Its Future (pages 9336–9344)

      Daniel R. Dreyer, Prof. Rodney S. Ruoff and Prof. Christopher W. Bielawski

      Article first published online: 25 NOV 2010 | DOI: 10.1002/anie.201003024

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      A transformation for the ages: There has been a surge in interest in graphene in recent years; however, graphene-like materials derived from graphite oxide were reported in 1962, and related chemical modifications of graphite were described as early as 1840. This account reveals that the rich history of graphene chemistry, the development of its synthesis and characterization, has laid the foundation for research that continues to this day.

  12. Review

    1. Top of page
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    4. Graphical Abstract
    5. Retraction
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    11. Essay
    12. Minireview
    13. Review
    14. Communications
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    1. Salinosporamides

      Salinosporamide Natural Products: Potent 20 S Proteasome Inhibitors as Promising Cancer Chemotherapeutics (pages 9346–9367)

      Dr. Tobias A. M. Gulder and Prof. Dr. Bradley S. Moore

      Article first published online: 6 OCT 2010 | DOI: 10.1002/anie.201000728

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      A young family: The salinosporamides (picture: salinosporamide A), γ-lactam-β-lactone marine natural products isolated from Salinispora tropica, are irreversible proteasome inhibitors and constitute a potent new class of small molecules for cancer drugs. This Review highlights the impressive achievements of recent multidisciplinary research on the discovery, biosynthesis, bioengineering, total synthesis, and biomedical evaluation of this young natural product family.

  13. Communications

    1. Top of page
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    10. Highlights
    11. Essay
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    13. Review
    14. Communications
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    1. Core/Shell Nanoparticles

      Synthesis and Characterization of Multimetallic Pd/Au and Pd/Au/FePt Core/Shell Nanoparticles (pages 9368–9372)

      Vismadeb Mazumder, Dr. Miaofang Chi, Dr. Karren L. More and Prof. Shouheng Sun

      Article first published online: 17 SEP 2010 | DOI: 10.1002/anie.201003903

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      Multimetallic dreamcoat: Core/shell nanoparticles of Pd/Au and Pd/Au/FePt were synthesized with palladium (5 nm diameter), a gold shell (1–2 nm), and a FePt shell (2 nm). The synthetic control allowed the Pd/Au catalytic properties to be tuned by the shell thickness. The synthesis provides an indication for future development of multicomponent nanoparticles for advanced catalytic applications.

    2. Molecular Recognition

      Supramolecular Porous Network Formed by Molecular Recognition between Chemically Modified Nucleobases Guanine and Cytosine (pages 9373–9377)

      Prof. Wei Xu, Prof. Jian-guo Wang, Dr. Mikkel F. Jacobsen, Dr. Manuela Mura, Dr. Miao Yu, Dr. Ross E. A. Kelly, Qiang-qiang Meng, Prof. Erik Lægsgaard, Prof. Ivan Stensgaard, Prof. Trolle R. Linderoth, Prof. Jørgen Kjems, Prof. Lev N. Kantorovich, Prof. Kurt V. Gothelf and Prof. Flemming Besenbacher

      Article first published online: 9 NOV 2010 | DOI: 10.1002/anie.201003390

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      In a stable relationship: Watson–Crick hydrogen bonding plays a key role in stabilizing the highly ordered supramolecular porous structure formed by co-deposition of biomimetically modified nucleobases cytosine and guanine onto a Au(111) surface under ultrahigh vacuum conditions. A combination of high-resolution STM imaging and density functional theory has been used to determine the structure of the network (see picture).

    3. DNA Nanotechnology

      Orthogonal Protein Decoration of DNA Origami (pages 9378–9383)

      Dr. Barbara Saccà, Dipl.-Chem. Rebecca Meyer, Dipl.-Biotechnol. Michael Erkelenz, M. Sc. Kathrin Kiko, Andreas Arndt, Dr. Hendrik Schroeder, Dr. Kersten S. Rabe and Prof. Christof M. Niemeyer

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201005931

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      If the face fits: Self-labeling fusion proteins have been used for the site-specific decoration of DNA origami. This method even allows individual faces of the quasi-two-dimensional plane of the nanostructure to be specifically decorated (see picture), thereby enabling directional immobilization and thus control over the accessibility of distinct proteins presented on the structure.

    4. Iron Catalysis

      Asymmetric Iron-Catalyzed Hydrosilane Reduction of Ketones: Effect of Zinc Metal upon the Absolute Configuration (pages 9384–9387)

      Tomohiko Inagaki, Akihiro Ito, Dr. Jun-ichi Ito and Prof. Hisao Nishiyama

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201005363

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      Just a little bit: The 1/FeCl2 complex was activated in the presence of Zn and exhibited catalytic activity for the hydrosilane reduction of ketones to give the S-configured alcohol. In contrast, the mixed-catalyst system of 1 and Fe(OAc)2 provides the R enantiomer. This approach provides both enantiomers from a single chiral source by the addition of a small amount of Zn.

    5. Organometallic Reagents

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      Structurally Engineered Deprotonation/Alumination of THF and THTP with Retention of Their Cycloanionic Structures (pages 9388–9391)

      Elaine Crosbie, Dr. Pablo García-Álvarez, Dr. Alan R. Kennedy, Dr. Jan Klett, Prof. Robert E. Mulvey and Dr. Stuart D. Robertson

      Article first published online: 26 OCT 2010 | DOI: 10.1002/anie.201005119

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      Engagement ring: α-Metalated by a lithium bisamido-bisalkylaluminate base, the sensitive cycloanionic ring of THF or THTP remains intact by engaging with both metal centers of the base residue (see structure; X=O, S).

    6. Fullerene Synthesis

      Towards the Isomer-Specific Synthesis of Higher Fullerenes and Buckybowls by the Surface-Catalyzed Cyclodehydrogenation of Aromatic Precursors (pages 9392–9396)

      Dr. Konstantin Amsharov, Nasiba Abdurakhmanova, Dr. Sebastian Stepanow, Dr. Stephan Rauschenbach, Prof. Martin Jansen and Prof. Klaus Kern

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201005000

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      Fullerenes on a plate: A surface-catalyzed cyclodehydrogenation reaction enabled selective fullerene-cage formation from polycyclic organic precursors. As no C[BOND]C bond rearrangement occurred during the reaction, only specifically designed precursors gave the desired fullerene (see picture). This efficient and selective condensation process opens new horizons in the directed synthesis of fullerenes and related structures.

    7. Nanorods

      The Crystalline Structure of Gold Nanorods Revisited: Evidence for Higher-Index Lateral Facets (pages 9397–9400)

      Enrique Carbó-Argibay, Dr. Benito Rodríguez-González, Sergio Gómez-Graña, Dr. Andrés Guerrero-Martínez, Dr. Isabel Pastoriza-Santos, Dr. Jorge Pérez-Juste and Prof. Luis M. Liz-Marzán

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201004910

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      A new face of nanorod crystallinity: The structure of single-crystal gold nanorods is reinterpreted on the basis of high-resolution transmission electron microscopy on standing rods. The studies provided evidence for eight identical higher-index {250} lateral facets (see picture for TEM image and proposed model).

    8. Surface Modification

      One-Step Modification of Superhydrophobic Surfaces by a Mussel-Inspired Polymer Coating (pages 9401–9404)

      Dr. Sung Min Kang, Inseong You, Dr. Woo Kyung Cho, Hyun Kyong Shon, Dr. Tae Geol Lee, Prof. Dr. Insung S. Choi, Prof. Dr. Jeffery M. Karp and Prof. Dr. Haeshin Lee

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004693

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      Science MIMIC-king nature: Hydrophilic conversion of superhydrophobic surfaces can be easily achieved through a bioinspired approach to produce an alternating superhydrophobic–hydrophilic surface by using established soft-lithographic techniques, such as micromolding in capillaries (MIMIC). The resulting patterned surface showed high water adhesion properties as well as superhydrophobic properties.

    9. Biocomposites

      A Molecular Rationale of Shock Absorption and Self-Healing in a Biomimetic Apatite–Collagen Composite under Mechanical Load (pages 9405–9407)

      Prof. Dr. Dirk Zahn

      Article first published online: 27 OCT 2010 | DOI: 10.1002/anie.201002663

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      Once bitten: Compression along the c axis of apatite–collagen composites (see picture), such as that on tooth enamel during biting, reveals a molecular mechanism that accounts for the steel-like characteristics of these composites. Simulations reveal that before eventual failure, inelastic deformation is initiated near the collagen molecules followed by pseudo-elastic deformation. The composite may undergo self-healing after release of the mechanical load.

    10. Drug Polymorphism

      Cisplatin: Polymorphism and Structural Insights into an Important Chemotherapeutic Drug (pages 9408–9411)

      Dr. Valeska P. Ting, Dr. Marc Schmidtmann, Prof. Chick C. Wilson and Prof. Mark T. Weller

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201003185

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      The changing face of cisplatin: The complete crystal structures, including the details of extensive intermolecular hydrogen bonding in two enantiotropic polymorphs of the chemotherapeutic drug cisplatin, have been elucidated. A massive thermal hysteresis effect exists between the two polymorphs, α and β, that are active at ambient temperatures.

    11. Single-Enzyme Analysis

      A Versatile DNA Nanochip for Direct Analysis of DNA Base-Excision Repair (pages 9412–9416)

      Dr. Masayuki Endo, Yousuke Katsuda, Kumi Hidaka and Prof. Dr. Hiroshi Sugiyama

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201003604

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      Repair kit: The single DNA-repair enzymes 8-oxoguanine glycosylase and T4 pyrimidine dimer glycosylase were analyzed by a nanoscale DNA chip containing two double-stranded DNA molecules (see picture). Dynamic movement of the enzymes and the single DNA-repair reaction on the DNA nanochip was visualized by fast-scanning atomic force microscopy.

    12. Protein Chemistry

      A Highly Efficient Strategy for Modification of Proteins at the C Terminus (pages 9417–9421)

      Long Yi, Dr. Hongyan Sun, Dr. Yao-Wen Wu, Dr. Gemma Triola, Prof. Herbert Waldmann and Prof. Roger S. Goody

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201003834

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      A new linker: In a facile, chemoselective, and potentially general method for protein modification at the C terminus oxyamino-modified proteins obtained from protein thioesters react rapidly with ketones under mild conditions. This strategy was used for fluorescence labeling, for example with modified coumarin and fluorescein (see scheme).

    13. Bimolecular Imaging

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      Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells (pages 9422–9425)

      Jan Dommerholt, Samuel Schmidt, Rinske Temming, Linda J. A. Hendriks, Floris P. J. T. Rutjes, Jan C. M. van Hest, Dirk J. Lefeber, Peter Friedl and Floris L. van Delft

      Article first published online: 20 SEP 2010 | DOI: 10.1002/anie.201003761

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      I can see clearly now: Bicyclo[6.1.0]non-4-yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain-promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular-resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three-dimensional collagen lattices.

    14. Amphiphilic Graphene

      Amphiphilic Graphene Composites (pages 9426–9429)

      Xiaoying Qi, Kan-Yi Pu, Dr. Hai Li, Dr. Xiaozhu Zhou, Shixin Wu, Prof. Qu-Li Fan, Prof. Bin Liu, Prof. Freddy Boey, Prof. Wei Huang and Prof. Hua Zhang

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004497

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      Both kinds of solubility: An amphiphilic reduced graphene oxide (rGO) composite is synthesized by using a novel coil-rod-coil conjugated triblock copolymer as the π–π binding stabilizer. Such a graphene-based composite can be dissolved not only in organic solvents with low polarity (such as toluene and chloroform) but also in water-miscible solvents with high polarity (for example methanol).

    15. Natural Products

      Maradolipids: Diacyltrehalose Glycolipids Specific to Dauer Larva in Caenorhabditis elegans (pages 9430–9435)

      Sider Penkov, Fanny Mende, Vyacheslav Zagoriy, Cihan Erkut, Dr. René Martin, Ulrike Pässler, Kai Schuhmann, Dr. Dominik Schwudke, Dr. Margit Gruner, Jana Mäntler, Dr. Thomas Reichert-Müller, Dr. Andrej Shevchenko, Prof. Dr. Hans-Joachim Knölker and Prof. Dr. Teymuras V. Kurzchalia

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201004466

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      Don't stress: Maradolipids (see picture; red O, grey C, white H) are the first diacyltrehaloses found to be produced in animal organisms. The nematode Caenorhabditis elegans synthesizes maradolipids for the highly stress-resistant dauer larvae. Genetic knockout studies result in the improper morphology of the gut lumen of dauer larvae. Maradolipids might be important for understanding the chemical basis for the resistance of dauer larvae to extreme environmental stress.

    16. Polymer Dots

      Ultrabright and Bioorthogonal Labeling of Cellular Targets Using Semiconducting Polymer Dots and Click Chemistry (pages 9436–9440)

      Changfeng Wu, Yuhui Jin, Thomas Schneider, Daniel R. Burnham, Polina B. Smith and Prof. Daniel T. Chiu

      Article first published online: 26 OCT 2010 | DOI: 10.1002/anie.201004260

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      All aboard! A facile conjugation method allows covalent linking of functional molecules to semiconducting polymer dots for bioorthogonal labeling of cellular targets. Targeting of the polymer dots to newly synthesized proteins and glycoproteins in mammalian cells by click chemistry is highly efficient and specific.

    17. Superresolution Imaging

      Superresolution Optical Fluctuation Imaging with Organic Dyes (pages 9441–9443)

      Dr. Thomas Dertinger, Dr. Mike Heilemann, Robert Vogel, Prof. Markus Sauer and Prof. Shimon Weiss

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004138

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      SOFI′s choice: Amongst the variety of superresolution far-field microscopy techniques, the most recently established method is superresolution optical fluctuation imaging, SOFI. SOFI can be quickly performed on samples labeled with conventional organic dyes.

    18. Carbenes

      Activation of Si[BOND]H, B[BOND]H, and P[BOND]H Bonds at a Single Nonmetal Center (pages 9444–9447)

      Dr. Guido D. Frey, Dr. Jason D. Masuda, Bruno Donnadieu and Prof. Guy Bertrand

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201005698

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      Carbenes more than measure up: Singlet stable carbenes compete with transition metals in the activation of enthalpically strong bonds, as shown by the cleavage of the E[BOND]H bonds of silanes, boranes, and phosphanes (see scheme). However, in contrast with the electrophilic mode of activation observed with metals, carbenes act as nucleophiles towards these substrates. Dipp=2,6-diisopropylphenyl.

    19. Prefibrillar Aggregates

      Characterizing Early Aggregates Formed by an Amyloidogenic Peptide by Mass Spectrometry (pages 9448–9451)

      Harriet L. Cole, Dr. Jason M. D. Kalapothakis, Guy Bennett, Dr. Perdita E. Barran and Dr. Cait E. MacPhee

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201003373

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      What floats in the soup? Time-course and ion-mobility nano-electrospray ionization (nESI) mass spectrometry probes the early aggregation states of an amyloidogenic endecapeptide derived from amino acid residues 105–115 of the human plasma protein transthyretin. A wide range of densely packed prefibrillar oligomers 1≤n≤13 are observed in dynamic populations over 8 h.

    20. P Ligands

      Primary and Secondary Aminophosphines as Novel P-Stereogenic Building Blocks for Ligand Synthesis (pages 9452–9455)

      Marc Revés, Dr. Catalina Ferrer, Thierry León, Sean Doran, Dr. Pablo Etayo, Dr. Anton Vidal-Ferran, Prof. Antoni Riera and Prof. Xavier Verdaguer

      Article first published online: 26 OCT 2010 | DOI: 10.1002/anie.201004041

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      Set the N free! The reactivity of the amino group of P-stereogenic aminophosphines allows the further elaboration of the aminophosphine unit whilst preserving the original chirality of the phosphorus atom (see picture; Rh green). P-stereogenic aminodiphosphine ligands can easily be prepared in optically pure forms, feature distinct structural and electronic characteristics, and can be used in asymmetric hydrogenation reactions.

    21. Glycerol Oxidation

      Selective Catalytic Oxidation of Glycerol to Dihydroxyacetone (pages 9456–9459)

      Ron M. Painter, David M. Pearson and Prof. Dr. Robert M. Waymouth

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004063

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      High selectivity and high yield characterize the oxidation of glycerol into dihydroxyacetone using catalyst 1, with benzoquinone or air as the oxidant. The mechanism proposed involves reversible palladium-alkoxide formation with the turnover-limiting reoxidation of the palladium complex.

    22. Organocatalysis

      Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxyindolin-2-ones (pages 9460–9464)

      Dr. Qunsheng Guo, Dr. Mayur Bhanushali and Prof. Dr. Cong-Gui Zhao

      Article first published online: 29 OCT 2010 | DOI: 10.1002/anie.201004161

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      New catalysis mechanism! The asymmetric aldol reaction of unactivated ketones and activated carbonyl compounds is realized with a quinidine-derived thiourea catalyst (see scheme), and involves an enolate mechanism instead of the widely used enamine mechanism. With isatins as the substrate, the reaction can be applied to the enantioselective synthesis of biologically active 3-hydroxyindolin-2-ones.

    23. Heterocycle Synthesis

      Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues (pages 9465–9468)

      Dr. Denis S. Ermolat'ev, Dr. Jitender B. Bariwal, Hans P. L. Steenackers, Dr. Sigrid C. J. De Keersmaecker and Prof. Dr. Erik V. Van der Eycken

      Article first published online: 20 OCT 2010 | DOI: 10.1002/anie.201004256

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      Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)-catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds. Boc=tert-butoxycarbonyl, Cbz=carbobenzyloxy.

    24. Continuous Flow

      Packed-Bed Reactors for Continuous-Flow C[BOND]N Cross-Coupling (pages 9469–9474)

      John R. Naber and Prof. Stephen L. Buchwald

      Article first published online: 29 OCT 2010 | DOI: 10.1002/anie.201004425

      Thumbnail image of graphical abstract

      Take a C[BOND]N bond and make it better: The optimized conditions for continuous-flow palladium-catalyzed C[BOND]N bond-forming reactions have been determined. They require the use of aqueous KOH, toluene as the solvent, tetrabutylammonium bromide as a phase-transfer catalyst, and a packed-bed microreactor (see scheme; TBAB=tetrabutylammonium bromide). In some cases, peforming these reactions under harsh conditions led to greatly enhanced reaction rates.

    25. Asymmetric Hydrogenation

      Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs (pages 9475–9478)

      Dianjun Chen, Dr. Yutian Wang and Prof. Dr. Jürgen Klankermayer

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004525

      Thumbnail image of graphical abstract

      No subsequent frustration: Frustrated Lewis pairs (FLPs) have been recently introduced as an unprecedented possibility to activate hydrogen. On the basis of this concept the first example of highly enantioselective catalytic hydrogenation of imines using chiral FLPs has been demonstrated (see scheme).

    26. Synthetic Methods

      Enantioselective, Organocatalyzed, Intramolecular Aldol Lactonizations with Keto Acids Leading to Bi- and Tricyclic β-Lactones and Topology-Morphing Transformations (pages 9479–9483)

      Dr. Carolyn A. Leverett, Dr. Vikram C. Purohit and Prof. Dr. Daniel Romo

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201004671

      Thumbnail image of graphical abstract

      Quickly emerging complexity characterizes the asymmetric, nucleophile-catalyzed aldol lactonization (NCAL) process with keto acid substrates and subsequent topology-altering reactions. The utility of chiral cyclic isothiourea catalysts as nucleophilic promoters (Lewis bases) for desymmetrization reactions through scaleable NCAL processes is demonstrated (see picture; HBTM=homobenzotetramisole).

    27. Rearrangement Reactions

      Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement (pages 9484–9487)

      Gesine K. Veits, Donald R. Wenz and Prof. Javier Read de Alaniz

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201005131

      Thumbnail image of graphical abstract

      A sweet dysprosition: A dysprosium(III) trifluoromethanesulfonate catalyzed rearrangement of furylcarbinols into 4-aminocyclopentenones by a 4π electrocyclization has been developed. The aza-Piancatelli rearrangement affords a single trans diastereomer from both aryl- and alkyl-substituted furylcarbinols.

    28. Aromaticity

      Redox-Induced Palladium Migrations that Allow Reversible Topological Changes between Palladium(II) Complexes of Möbius Aromatic [28]Hexaphyrin and Hückel Aromatic [26]Hexaphyrin (pages 9488–9491)

      Mitsunori Inoue and Prof. Dr. Atsuhiro Osuka

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201005334

      Thumbnail image of graphical abstract

      Plane twisted: A twisted Möbius aromatic [28]hexaphyrin/PdII complex and a planar Hückel aromatic [26]hexaphyrin/PdII complex are reversibly interconvertible by an unprecedented palladium migration through oxidation and reduction (see scheme). The [26]hexaphyrin/PdII complex is a precursor to [26]hexaphyrin hetero-bis(metal) complexes having PdII/CuIII or PdII/AgIII centers. C gray, N blue, H white, F green, Pd yellow.

    29. Synthetic Methods

      Total Synthesis of Jadomycin A and a Carbasugar Analogue of Jadomycin B (pages 9492–9495)

      Mingde Shan, Ehesan U. Sharif and Prof. George A. O'Doherty

      Article first published online: 26 OCT 2010 | DOI: 10.1002/anie.201005329

      Thumbnail image of graphical abstract

      One's trash is another one's treasure: The first syntheses of jadomycin A and the carbasugar analogue of jadomycin B have been achieved in 6 and 20 longest linear steps, respectively. The key ring system of the aglycone was prepared by a 6π-electron electrocyclic ring closure and subsequent hemiaminal ring closure. Acid sensitivity of the glycosidic bond in jadomycin B (see structure; X=O) precluded its synthesis but led to the carbasugar analogue (X=CH2).

    30. Nanomaterials

      Alkyne-Stabilized Ruthenium Nanoparticles: Manipulation of Intraparticle Charge Delocalization by Nanoparticle Charge States (pages 9496–9499)

      Xiongwu Kang, Nathaniel B. Zuckerman, Prof. Joseph P. Konopelski and Prof. Shaowei Chen

      Article first published online: 28 OCT 2010 | DOI: 10.1002/anie.201004967

      Thumbnail image of graphical abstract

      Particles in charge: Ruthenium nanoparticles passivated by Ru[BOND]C[TRIPLE BOND] interfacial bonding interactions exhibit apparent intraparticle charge delocalization, which can be manipulated by the nanoparticle charge state. Control of the back-bonding occurs by interactions between ruthenium core electrons and sp-hybridized carbon atoms of the alkynyl ligands (see picture: Csp 1s binding energy (BE): •••• reduced, - - - - oxidized form, — as-prepared nanoparticles).

    31. Peptide Coupling

      Insights into the Finer Issues of Native Chemical Ligation: An Approach to Cascade Ligations (pages 9500–9503)

      Dr. Zhongping Tan, Dr. Shiying Shang and Prof. Samuel J. Danishefsky

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201005513

      Thumbnail image of graphical abstract

      Maximizing by minimizing: An efficient and broadly useful two-step ligation protocol was developed. Important mechanistic issues of ligation were probed from competition studies on the formation of diastereomeric ligation products. This study provides a valuable approach to facilitate polypeptide synthesis by minimizing protecting group manipulations and intermediate isolations.

    32. Organic Sol–Gel Process

      Organic Sol–Gel Synthesis: Solution-Processable Microporous Organic Networks (pages 9504–9508)

      Su-Young Moon, Jae-Sung Bae, Eunkyung Jeon and Prof. Ji-Woong Park

      Article first published online: 30 AUG 2010 | DOI: 10.1002/anie.201002609

      Thumbnail image of graphical abstract

      Concentration is critical: Amine/isocyanate polycondensation below the critical gelation concentration cg affords a sol of growing microporous molecular-network nanoparticles rather than a gelated network (see picture, for model of particle: NCO red, NH2 blue, tetrahedral cross-link point gray). Further growth to form monolithic networks occurs on solvent evaporation, analogous to sol–gel synthesis of inorganic oxide networks.

    33. Vesicular Adhesion

      Adhesive Vesicles through Adaptive Response of a Biobased Surfactant (pages 9509–9512)

      Dr. Vijai S. Balachandran, Swapnil R. Jadhav, Dr. Padmanava Pradhan, Prof. Dr. Sacha De Carlo and Prof. Dr. George John

      Article first published online: 28 SEP 2010 | DOI: 10.1002/anie.201002260

      Thumbnail image of graphical abstract

      Chemist's caviar: Stimuli-responsive fusogenic vesicles from a cardanol-taurine surfactant are reported. The thermo-responsive behavior of the unsaturations in the alkyl chains, reminiscent of homeoviscous alterations, lead to a micelle-to-vesicle transformation and to the formation of caviar-like adhesive vesicles (see photograph).

    34. Indole Synthesis

      Fischer Indole Synthesis with Organozinc Reagents (pages 9513–9516)

      Benjamin A. Haag, Zhi-Guang Zhang, Prof. Dr. Jin-Shan Li and Prof. Dr. Paul Knochel

      Article first published online: 26 OCT 2010 | DOI: 10.1002/anie.201005319

      Thumbnail image of graphical abstract

      Updated classic: Primary and secondary alkylzinc reagents add to various aryldiazonium salts leading regioselectively to polyfunctional indoles by means of a [3,3]-sigmatropic shift and subsequent aromatization. This organometallic variation of the Fischer indole synthesis tolerates a wide range of functional groups and displays absolute regioselectivity.

    35. Bis(borylene) Complexes

      Towards Homoleptic Borylene Complexes: Incorporation of Two Borylene Ligands into a Mononuclear Iridium Species (pages 9517–9520)

      Stefanie Bertsch, Prof. Dr. Holger Braunschweig, Bastian Christ, Dr. Melanie Forster, Katrin Schwab and Dr. Krzysztof Radacki

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201004103

      Thumbnail image of graphical abstract

      Place two B: The isolation of the first terminal, mononuclear bis(borylene) complex (see structure) represents a significant step towards the synthesis of homoleptic borylene complexes, and also provides deeper insight into the bonding characteristics of borylene complexes in general. A preliminary elucidation of the question of how two terminal BR ligands affect each other when bound to the same metal center is presented.

    36. Oxygen Reduction

      Theoretical Studies of Potential-Dependent and Competing Mechanisms of the Electrocatalytic Oxygen Reduction Reaction on Pt(111) (pages 9521–9525)

      Dr. John A. Keith and Dr. Timo Jacob

      Article first published online: 29 OCT 2010 | DOI: 10.1002/anie.201004794

      Thumbnail image of graphical abstract

      This way ORR that: Theoretical investigations on the oxygen reduction reaction (ORR) mechanism using first-principles quantum chemistry are presented. Explicit analysis of potential-dependent mechanisms shows how subtle changes in conditions alter ORR reaction processes. Importantly, a kinetics-based model reproduces experimental observations for products and quantitative potential ranges.

    37. Organocatalysis

      Kinetic Evidence for the Formation of Oxazolidinones in the Stereogenic Step of Proline-Catalyzed Reactions (pages 9526–9529)

      Tanja Kanzian, Dr. Sami Lakhdar and Prof. Dr. Herbert Mayr

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201004344

      Thumbnail image of graphical abstract

      Neighboring-group participation: Anchimeric assistance of the carboxylate group accelerates the attack of the electrophiles at the double bond of the proline-derived enamine A by a factor of about 50.

    38. Hybrid Interfaces

      Microscopic Mechanism of Specific Peptide Adhesion to Semiconductor Substrates (pages 9530–9533)

      Dr. Michael Bachmann, Dr. Karsten Goede, Prof. Annette G. Beck-Sickinger, Prof. Marius Grundmann, Prof. Anders Irbäck and Prof. Wolfhard Janke

      Article first published online: 4 NOV 2010 | DOI: 10.1002/anie.201000984

      Thumbnail image of graphical abstract

      On the surface of it: Experimental and computational analyses for a hybrid peptide–substrate system showed that changing the position of a proline residue in synthetic peptides changes their adsorption onto semiconductors substantially and predictably (see picture with a Si(100) surface). Such information is essential for the formation of novel peptide–solid interfaces for nanotechnological applications.

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      Article first published online: 1 DEC 2010 | DOI: 10.1002/anie.201090155

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