Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 22

May 18, 2009

Volume 48, Issue 22

Pages 3883–4077

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Photoprogrammable Organic Light-Emitting Diodes (Angew. Chem. Int. Ed. 22/2009) (page 3883)

      Philipp Zacharias, Malte C. Gather, Anne Köhnen, Nina Rehmann and Klaus Meerholz

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200990111

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      Programmable organic light-emitting diodes: UV irradiation converts an oxetane-functionalized dithienylethene derivative from its colorless open form into a dark blue closed form, while visible light reverses the reaction. In the Communication on page 4038 ff., K. Meerholz and co-workers describe a reversibly switchable organic light-emitting diode based on this principle.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
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    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. Inside Cover: Switching the Chirality of Single Adsorbate Complexes (Angew. Chem. Int. Ed. 22/2009) (page 3884)

      Manfred Parschau, Daniele Passerone, Karl-Heinz Rieder, Hans J. Hug and Karl-Heinz Ernst

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200990112

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      Wrong handedness? No problem! K.-H. Ernst et al. describe in their Communication on page 4065 ff. how the chirality of single adsorbates can be switched into the opposite enantiomeric state. By using inelastically tunneling electrons from the tip of a scanning tunneling microscope in an ultra-high vacuum, certain molecular vibrations are excited that, in turn, cause different actions such as hopping, rotation, and chirality conversion at the surface.

  3. Graphical Abstract

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    5. Corrigendum
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    10. Highlights
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    12. Review
    13. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 22/2009 (pages 3887–3896)

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200990113

  4. Corrigendum

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
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    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. You have free access to this content
      Pseudo-Bridging Silanols as Versatile Brønsted Acid Sites of Amorphous Aluminosilicate Surfaces (page 3896)

      Céline Chizallet and Pascal Raybaud

      Article first published online: 14 MAY 2009 | DOI: 10.1002/anie.200990114

      This article corrects:

      Pseudo-Bridging Silanols as Versatile Brønsted Acid Sites of Amorphous Aluminosilicate Surfaces

      Vol. 48, Issue 16, 2891–2893, Article first published online: 19 JAN 2009

  5. News

    1. Top of page
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    5. Corrigendum
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    11. Minireview
    12. Review
    13. Communications
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  6. Author Profile

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
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    9. Book Reviews
    10. Highlights
    11. Minireview
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    13. Communications
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    1. Benjamin G. Davis (page 3900)

      Article first published online: 30 APR 2009 | DOI: 10.1002/anie.200901068

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      „When I wake up I row. When I was eighteen I wanted to be Morrissey. …“ This and more about Benjamin G. Davis can be found on page 3900.

  7. News

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    5. Corrigendum
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  8. Book Reviews

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    5. Corrigendum
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    1. Highlights in Colloid Science.Edited by D. Platikanov and D. Exerowa. (page 3902)

      Jürgen-Hinrich Fuhrhop

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200900361

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      Wiley-VCH, Weinheim 2009. 306 pp., hardcover, 129.00 €.—ISBN 978-3527320370

    2. Metal Oxide Catalysis.1+2. Edited by S. David Jackson and Justin S. J. Hargreaves. (pages 3902–3903)

      Geoff Thornton

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200901285

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      Wiley-VCH, Weinheim 2008. 866 pp., hardcover € 279.00.—ISBN 978-3527318155

  9. Highlights

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
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    13. Communications
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    1. Heterogeneous Catalysis

      Probing Solid Catalysts under Operating Conditions: Electrons or X-rays? (pages 3904–3907)

      John Meurig Thomas and Juan-Carlos Hernandez-Garrido

      Article first published online: 9 APR 2009 | DOI: 10.1002/anie.200805994

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      Seeing is believing: In light of recent advances, the pros and cons of using electrons and X-rays for in situ studies of catalysts are analyzed: by using X-rays the structure of bound reactants at steady state are obtained from extended X-ray adsorption fine structure spectroscopy (EXAFS) data (see graph), thereby affording mechanistic insights.

    2. Single-Molecule Studies

      Light at the End of the Tunnel (pages 3908–3910)

      Mike Heilemann

      Article first published online: 7 APR 2009 | DOI: 10.1002/anie.200900696

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      Turn the light on: The synthesis, folding and maturation kinetics of individual green fluorescent protein (GFP) molecules have been studied using a cell-free transcription–translation system and single-molecule fluorescence. Ribosomes, which were labeled with a red fluorophore and tethered to a glass surface, were used to synthesize GFP Emerald molecules that become fluorescent after maturation.

    3. Conducting Oligomers

      High Electrical Conductance of Single Molecules: A Challenge in the Series of Conjugated Oligomers (pages 3911–3913)

      Herbert Meier

      Article first published online: 25 MAR 2009 | DOI: 10.1002/anie.200900568

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      En route to molecular electronics: As extended, conjugated oligomers are desirable for molecular electronics, their electrical conductance should display a low attenuation factor. Zinc-complexed oligo(ethynyleneporphyrindiylethynylene)s have been prepared that are distinguished by ultralow attenuation factors in single-molecule conductance.

  10. Minireview

    1. Top of page
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    5. Corrigendum
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    12. Review
    13. Communications
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    1. Biopolymers

      Chemical and Structural Diversity in Eumelanins: Unexplored Bio-Optoelectronic Materials (pages 3914–3921)

      Marco d'Ischia, Alessandra Napolitano, Alessandro Pezzella, Paul Meredith and Tadeusz Sarna

      Article first published online: 17 MAR 2009 | DOI: 10.1002/anie.200803786

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      A black whole: The black insoluble biopolymer eumelanin is prepared through the oxidative polymerization of 5,6-dihydroxyindoles (see scheme). It has a largely unknown heterogeneous structure and unique optoelectronic properties. Current structural models are presented and possible applications are discussed.

  11. Review

    1. Top of page
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    5. Corrigendum
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    13. Communications
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    1. Supramolecular Chemistry

      Binding Mechanisms in Supramolecular Complexes (pages 3924–3977)

      Hans-Jörg Schneider

      Article first published online: 4 MAY 2009 | DOI: 10.1002/anie.200802947

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      Forces to reckon with: Supramolecular complexes, such as the one shown, are normally based on a combination of different interactions such as ion pairing, hydrogen bonds, and stacking interactions. The not always simple characterization of the nature and strength of intermolecular forces provides assistance to the understanding of biomimetic systems, as well as for the design of synthetic receptors, drugs, and intelligent materials.

  12. Communications

    1. Top of page
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    1. Emulsions

      The Colloidal Suprastructure of Smart Microgels at Oil–Water Interfaces (pages 3978–3981)

      Bastian Brugger, Stephan Rütten, Kim-Ho Phan, Martin Möller and Walter Richtering

      Article first published online: 27 MAR 2009 | DOI: 10.1002/anie.200900239

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      Oil on troubled waters: Stimuli-sensitive emulsions have been used to prepare temperature- and pH-responsive microgels. The emulsion stability at oil–water interfaces is not governed by the particle packing density, and structural changes induced by the interface lead to connections between the individual microgels (see picture; scale bar 1 μm), which behave very differently compared to solid-particle-stabilized emulsions.

    2. Heterogeneous Catalysis

      Direct C[BOND]C Cross-Coupling of Secondary and Primary Alcohols Catalyzed by a γ-Alumina-Supported Silver Subnanocluster (pages 3982–3986)

      Ken-ichi Shimizu, Ryosuke Sato and Atsushi Satsuma

      Article first published online: 25 APR 2009 | DOI: 10.1002/anie.200901057

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      Let's drink to that! Two alcohols (one primary and one secondary) can be coupled in an atom-efficient process by a hydrogen-autotransfer catalytic system in the form of silver subnanoclusters supported on γ-Al2O3. The recyclable heterogeneous catalyst promoted the one-pot C[BOND]C cross-coupling in the presence of a catalytic amount of the weak base Cs2CO3 (see reaction mechanism).

    3. Biofuels

      Highly Selective Catalytic Conversion of Phenolic Bio-Oil to Alkanes (pages 3987–3990)

      Chen Zhao, Yuan Kou, Angeliki A. Lemonidou, Xuebing Li and Johannes A. Lercher

      Article first published online: 29 APR 2009 | DOI: 10.1002/anie.200900404

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      Oil and water: A new energy-efficient and atom-economical catalytic route for the production of alkanes and methanol by upgrading the phenolic fraction of bio-oil has been developed. The one-pot aqueous-phase hydrodeoxygenation process is based on two catalysts facilitating consecutive hydrogenation, hydrolysis, and dehydration reactions.

    4. Nanostructures

      One-Step Synthesis and Characterization of Gold–Hollow PbSx Hybrid Nanoparticles (pages 3991–3995)

      Jian Yang, JunJun Peng, Qingbo Zhang, Feng Peng, Hongjuan Wang and Hao Yu

      Article first published online: 17 APR 2009 | DOI: 10.1002/anie.200806036

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      Turing lead into gold: Hollow hybrid PbSx–Au nanostructures of about 10 nm in diameter were synthesized using a one-step reaction under mild experimental conditions. The redox reaction of gold precursors with PbS nanocrystals in the presence of dodecylamine leads to the hollow feature of hybrid nanostructures (see picture).

    5. Lead Sensors

      Development of a Fluorescent Pb2+ Sensor (pages 3996–3998)

      Lauren Marbella, Barbara Serli-Mitasev and Partha Basu

      Article first published online: 30 APR 2009 | DOI: 10.1002/anie.200806297

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      A real turn-on: The emission intensity of heterocycle 1 increases upon binding to Pb2+. Thus, 1 acts as a small-molecule “turn-on” fluorescent sensor for lead. The sensor is highly selective and is functional over a wide range of pH values.

    6. C[BOND]H Activation

      Platinum(II)-Catalyzed Intramolecular Cyclization of o-Substituted Aryl Alkynes through sp3 C[BOND]H Activation (pages 3999–4001)

      Shangdong Yang, Zigang Li, Xing Jian and Chuan He

      Article first published online: 28 APR 2009 | DOI: 10.1002/anie.200900368

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      Ring leader: PtCl2 catalyzes intramolecular cyclization of o-isopropyl or o-benzyl aryl alkynes to give substituted indene derivatives with good yields and high selectivity. This reaction appears to proceed through an sp3 C[BOND]H activation and 1,4-hydrogen migration pathway (see scheme).

    7. Phospholes

      A Convenient Method for the Synthesis of α-Ethynylphospholes and Modulation of Their π-Conjugated Systems (pages 4002–4005)

      Yoshihiro Matano, Makoto Nakashima and Hiroshi Imahori

      Article first published online: 28 APR 2009 | DOI: 10.1002/anie.200900542

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      Mind the (narrow) gap: α-Ethynylphospholes generated in situ from the corresponding silyl-capped precursors were converted into a series of α-(arylethynyl) phospholes bearing functional substituents as well as an α,α′-linked terphosphole (see scheme). The terphosphole has a narrow HOMO–LUMO gap owing to efficient π conjugation over the three phosphole rings.

    8. Diazonium Chemistry

      In Situ Formation of Diazonium Salts from Nitro Precursors for Scanning Electrochemical Microscopy Patterning of Surfaces (pages 4006–4008)

      Charles Cougnon, Frédéric Gohier, Daniel Bélanger and Janine Mauzeroll

      Article first published online: 24 APR 2009 | DOI: 10.1002/anie.200900498

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      Give me a tip: In situ production of diazonium salts from nitro compounds allows the use of diazonium chemistry for microelectrochemical patterning of surfaces by scanning electrochemical microscopy. The nitro precursor is reduced at the tip to the amine, which is diazotized in the interelectrode space as it diffuses (see picture). The tip acts as a source of diazonium salts, allowing sample derivatization just beneath the tip.

    9. Boron Heterocycles

      9-Boraanthracene Derivatives Stabilized by N-Heterocyclic Carbenes (pages 4009–4012)

      Thomas K. Wood, Warren E. Piers, Brian A. Keay and Masood Parvez

      Article first published online: 28 APR 2009 | DOI: 10.1002/anie.200901217

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      2009: A boraanthracene odyssey: General routes to boraanthracene derivatives—long proposed, but never observed—are disclosed, along with the structural and photophysical properties of these compounds and their remarkable reactivity towards oxygen.

    10. Cluster Chemistry

      A Hydride-Rich Magnesium Cluster (pages 4013–4016)

      Merle Arrowsmith, Michael S. Hill, Dugald J. MacDougall and Mary F. Mahon

      Article first published online: 29 APR 2009 | DOI: 10.1002/anie.200900878

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      High-de-hydride! A straightforward reaction between a magnesium silylamido/N-heterocyclic carbene adduct and phenylsilane provides a {Mg4H6} cluster molecule that may be regarded as a combination of two magnesium dihydride and two magnesium monohydride moieties.

    11. Continuous-Flow Synthesis

      Multistep Synthesis Using Modular Flow Reactors: Bestmann–Ohira Reagent for the Formation of Alkynes and Triazoles (pages 4017–4021)

      Ian R. Baxendale, Steven V. Ley, Andrew C. Mansfield and Christopher D. Smith

      Article first published online: 22 APR 2009 | DOI: 10.1002/anie.200900970

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      Multistep in flow: The Seyferth–Gilbert reagent 1 has been applied in a flow system to rapidly synthesize terminal alkynes. The system has been further applied to synthesize triazole 3 from alcohol 2 in a three-step oxidation/homologation/copper(I)-catalyzed azide–alkyne cycloaddition sequence without isolation of intermediates (see scheme).

    12. Organic Electronics

      Interactive Radical Dimers in Photoconductive Organic Thin Films (pages 4022–4024)

      Akito Iwasaki, Laigui Hu, Rie Suizu, Kenji Nomura, Hirofumi Yoshikawa, Kunio Awaga, Yukiko Noda, Kaname Kanai, Yukio Ouchi, Kazuhiko Seki and Hiroshi Ito

      Article first published online: 25 APR 2009 | DOI: 10.1002/anie.200900472

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      Fully interactive: Overlap between extended unoccupied molecular orbitals leads to the high photoconductivity of interactive radical dimers. Sandwich-type cells (see picture; ITO=indium tin oxide) comprising highly oriented thin films of a disjoint diradical, 4,4′-bis(1,2,3,5-dithiadiazolyl) (BDTDA) exhibit a photocurrent with a high on/off ratio at reverse bias voltages and photovoltaic behavior at zero bias voltage.

    13. Self-Assembled Cages

      Computer-Aided Design of a Sulfate-Encapsulating Receptor (pages 4025–4029)

      Radu Custelcean, Jerome Bosano, Peter V. Bonnesen, Vilmos Kertesz and Benjamin P. Hay

      Article first published online: 17 APR 2009 | DOI: 10.1002/anie.200900108

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      Custom built: A promising new approach towards more efficient self-assembled cage receptors through computer-aided design is demonstrated. The resulting M4L6 tetrahedral cage, internally functionalized with accurately positioned urea hydrogen-bonding groups (see structure; yellow: predicted, blue: experimental, space-filling: SO42−), proved to be a remarkably strong sulfate receptor in water.

    14. Glycobiology

      Metabolic Labeling of Sialic Acids in Living Animals with Alkynyl Sugars (pages 4030–4033)

      Pamela V. Chang, Xing Chen, Chris Smyrniotis, Alexander Xenakis, Tianshun Hu, Carolyn R. Bertozzi and Peng Wu

      Article first published online: 22 APR 2009 | DOI: 10.1002/anie.200806319

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      Sialome sweet sialome: As sialic acids are involved in many host–pathogen recognition events and are markers of embryonic and malignant tissues, there is great interest in methods for the enrichment and identification of sialylated glycoproteins from complex tissues. Now N-(4-pentynoyl)mannosamine can be used to metabolically label sialylated glycoproteins in living animals, enabling future identification of new biomarkers.

    15. Fluorescent Probes

      A Highly Sensitive Fluorescence Probe for Fast Thiol-Quantification Assay of Glutathione Reductase (pages 4034–4037)

      Long Yi, Heyang Li, Lu Sun, Liangliang Liu, Caihong Zhang and Zhen Xi

      Article first published online: 22 APR 2009 | DOI: 10.1002/anie.200805693

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      Fast detection of cellular thiols in aqueous medium was achieved using a newly developed fluorescence probe (see picture). Based on this probe, a high-throughput fluorescence assay for glutathione reductase was developed.

    16. OLEDs

      Photoprogrammable Organic Light-Emitting Diodes (pages 4038–4041)

      Philipp Zacharias, Malte C. Gather, Anne Köhnen, Nina Rehmann and Klaus Meerholz

      Article first published online: 16 FEB 2009 | DOI: 10.1002/anie.200805969

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      Enlightening the memory: The integration of a crosslinkable photochromic dithienylperfluorocyclopentene (DTE) into organic light-emitting diodes (OLED) allows for the individualization of the emissive area of the OLED device, for example, for signage applications. The operation principle is based on switching the injection barrier for holes (positive charge carriers). Very large ON/OFF ratios of up to 3000 for current as well as electroluminescence have been achieved.

    17. Organic–Inorganic Materials

      Light Harvesting by a Periodic Mesoporous Organosilica Chromophore (pages 4042–4046)

      Shinji Inagaki, Osamu Ohtani, Yasutomo Goto, Kentaro Okamoto, Masamichi Ikai, Ken-ichi Yamanaka, Takao Tani and Tadashi Okada

      Article first published online: 24 APR 2009 | DOI: 10.1002/anie.200900266

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      Light aqueduct: Periodic mesoporous organosilica exhibits strong light absorption due to densely packed organic chromophores within the pore walls. Light energy absorbed by 125 biphenyl groups in the pore walls is funneled into a single coumarin 1 molecule in the mesochannels with almost 100 % quantum efficiency, and results in significant enhancement of emission from the coumarin 1 dye.

    18. DNA Binding

      “On-Off” Multivalent Recognition: Degradable Dendrons for Temporary High-Affinity DNA Binding (pages 4047–4051)

      Daniel J. Welsh, Simon P. Jones and David K. Smith

      Article first published online: 28 APR 2009 | DOI: 10.1002/anie.200900401

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      Now you bind it—now you don't! Chemical degradation of a dendritic scaffold allows multivalent interactions with DNA to be “switched off” as the multivalent array of ligands breaks down into smaller fragments, offering an approach by which a molecule can be temporarily endowed with high affinity for a biological target—an important concept in the development of new synthetic systems to intervene in biological pathways.

    19. Expanded Genetic Code

      A Facile System for Encoding Unnatural Amino Acids in Mammalian Cells (pages 4052–4055)

      Peng R. Chen, Dan Groff, Jiantao Guo, Weijia Ou, Susan Cellitti, Bernhard H. Geierstanger and Peter G. Schultz

      Article first published online: 17 APR 2009 | DOI: 10.1002/anie.200900683

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      A shuttle system has been developed to genetically encode unnatural amino acids in mammalian cells using aminoacyl-tRNA synthetases (aaRSs) evolved in E. coli. A pyrrolysyl-tRNA synthetase (PylRS) mutant was evolved in E. coli that selectively aminoacylates a cognate nonsense suppressor tRNA with a photocaged lysine derivative. Transfer of this orthogonal tRNA–aaRS pair into mammalian cells made possible the selective incorporation of this unnatural amino acid into proteins.

    20. RNA–Peptide Conjugates

      Non-Hydrolyzable RNA–Peptide Conjugates: A Powerful Advance in the Synthesis of Mimics for 3′-Peptidyl tRNA Termini (pages 4056–4060)

      Holger Moroder, Jessica Steger, Dagmar Graber, Katja Fauster, Krista Trappl, Viter Marquez, Norbert Polacek, Daniel N. Wilson and Ronald Micura

      Article first published online: 24 APR 2009 | DOI: 10.1002/anie.200900939

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      Translation of specific small peptides on the ribosome can confer resistance to macrolide antibiotics. To reveal the molecular details of this and related phenomena, stable RNA–peptide conjugates that mimic peptidyl-tRNA would be desirable, especially for ribosome structural biology. A flexible solid-phase synthesis strategy now allows efficient access to these highly requested derivatives without restriction on the RNA and peptide sequences.

    21. Single-Molecule Manipulation

      Chirality Change of Chloronitrobenzene on Au(111) Induced by Inelastic Electron Tunneling (pages 4061–4064)

      Violeta Simic-Milosevic, Jörg Meyer and Karina Morgenstern

      Article first published online: 30 MAR 2009 | DOI: 10.1002/anie.200805551

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      Chirality chameleon: Inelastic electron tunneling manipulation can be used to change a single chloronitrobenzene (ClNB) molecule, randomly adsorbed on Au(111), into its desired enantiomeric form (r or l, see STM images and ball-and-stick representation) and to vary its rotational orientation. The different threshold voltages for chirality change (260 mV) and rotation (380 mV) allow these processes to be induced separately.

    22. Chirality

      Switching the Chirality of Single Adsorbate Complexes (pages 4065–4068)

      Manfred Parschau, Daniele Passerone, Karl-Heinz Rieder, Hans J. Hug and Karl-Heinz Ernst

      Article first published online: 10 FEB 2009 | DOI: 10.1002/anie.200805740

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      Pumped up: Propene molecules form chiral complexes when adsorbed on a copper surface. Inelastically scattered tunneling electrons from the tip of a scanning tunneling microscope induce rotation or diffusion of the adsorbate on the surface. Higher tunneling currents can lead to conversion of the adsorbate into the opposite enantiomer.

    23. Silaselenones

      A Bis(silaselenone) with Two Donor-Stabilized Si[DOUBLE BOND]Se Bonds from an Unexpected Stereoconvergent Hydrolysis of a Diselenadisiletane (pages 4069–4072)

      Amitabha Mitra, Joseph P. Wojcik, Daniel Lecoanet, Thomas Müller and Robert West

      Article first published online: 28 APR 2009 | DOI: 10.1002/anie.200806389

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      SiSe matters: Diselenadisiletane 2, formed from direct reaction of a racemic silylene 1 with elemental selenium, gives the first bis(silaselenone) upon hydrolysis with water (3; see picture, C gray, H white, N blue, O red, Se purple, Si green; d(Si[DOUBLE BOND]Se)=215 pm). The reaction is stereoconvergent: only racemic forms of 3 are obtained from a mixture of racemic and meso forms of 2.

  13. Preview

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
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    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. Preview: Angew. Chem. Int. Ed. 23/2009 (page 4077)

      Article first published online: 12 MAY 2009 | DOI: 10.1002/anie.200990116

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