Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 4

January 23, 2012

Volume 51, Issue 4

Pages 825–1076

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: Nanoporous Single-Crystal-Like CdxZn1−xS Nanosheets Fabricated by the Cation-Exchange Reaction of Inorganic–Organic Hybrid ZnS–Amine with Cadmium Ions (Angew. Chem. Int. Ed. 4/2012) (page 825)

      Dr. Yifu Yu, Jin Zhang, Xuan Wu, Weiwei Zhao and Prof. Dr. Bin Zhang

      Article first published online: 7 NOV 2011 | DOI: 10.1002/anie.201107508

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      Photocatalytic H2evolution from water splitting using highly active porous CdxZn1−xS nanosheets is reported by B. Zhang and co-workers in their Communication on page 897 ff. Porous CdxZn1−xS nanosheets with single-crystal-like structure, good stability, and tunable pore size and composition have been successfully fabricated by a cation-exchange reaction of a hybrid ZnS–amine nanosheet with Cd2+ ions.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Inside Cover: Light-Driven Molecular-Crystal Actuators: Rapid and Reversible Bending of Rodlike Mixed Crystals of Diarylethene Derivatives (Angew. Chem. Int. Ed. 4/2012) (page 826)

      Fumitaka Terao, Dr. Masakazu Morimoto and Prof. Dr. Masahiro Irie

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201107570

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      Light-driven actuators can be potentially used in various micro- and nanomechanical applications. In their Communication on page 901 ff., M. Irie and co-workers describe the preparation of robust molecular-crystal actuators with interesting mechanical properties. Two-component mixed crystals of photochromic diaryl ethenes exhibit rapid, reversible, and fatigue-resistant bending upon photoirradiation and carry out mechanical work, such as lifting weights and rotating gears.

  3. Inside Back Cover

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Inside Back Cover: Fragment Deconstruction of Small, Potent Factor Xa Inhibitors: Exploring the Superadditivity Energetics of Fragment Linking in Protein–Ligand Complexes (Angew. Chem. Int. Ed. 4/2012) (page 1077)

      Dr. Marc Nazaré, Dr. Hans Matter, Dr. David W. Will, Dr. Michael Wagner, Dr. Matthias Urmann, Dr. Jörg Czech, Dr. Herman Schreuder, Dr. Armin Bauer, Dr. Kurt Ritter and Dr. Volkmar Wehner

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201108620

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      The superadditivity of fragment linking on affinities was quantified by systematic deconstruction of a fXa inhibitor. In their Communication on page 905 ff., M. Nazaré, H. Matter, and co-workers show that by connecting two fragments with a single bond, a linker contribution of −14.0 kJ mol−1 results, which corresponds to an affinity improvement of about 2.5 orders of magnitude relative to the sum of fragment affinities.

  4. Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Back Cover: DNA Origami Nanopatterning on Chemically Modified Graphene (Angew. Chem. Int. Ed. 4/2012) (page 1078)

      Je Moon Yun, Kyoung Nan Kim, Ju Young Kim, Dong Ok Shin, Won Jun Lee, Sun Hwa Lee, Prof. Marya Lieberman and Prof. Sang Ouk Kim

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201107585

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      DNA origami structures are assembled from one long circular DNA strand precisely folded by lots of designed DNA staples. These ultrafine biomolecular nanopatterns are selectively and safely adsorbed on chemically modified graphene sheets. In their Communication on page 912 ff., M. Lieberman, S. O. Kim, and co-workers show that chemically modified graphene is an excellent substrate material for sublithographic bimolecular nanopatterning.

  5. Editorial

    1. Top of page
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    11. Book Reviews
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    13. Minireview
    14. Review
    15. Communications
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    1. You have free access to this content
      Editorial: Citations and Ethics (pages 828–830)

      Prof. Dr. Jan Reedijk

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201107554

  6. Graphical Abstract

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 4/2012 (pages 832–844)

      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201290005

  7. News

    1. Top of page
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    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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  8. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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    1. Hansjörg Grützmacher (pages 852–853)

      Article first published online: 30 NOV 2011 | DOI: 10.1002/anie.201107165

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      “I chose chemistry as a career because didn′t feel confident enough to study art design. In my opinion, the word “scientist” means adventurer at the edge of knowledge …” This and more about Hansjörg Grützmacher can be found on page 854.

  9. News

    1. Top of page
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    6. Editorial
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    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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  10. Book Reviews

    1. Top of page
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    6. Editorial
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    8. News
    9. Author Profile
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    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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    1. 2030. Technology That Will Change the World. By Rutger van Santen, Djan Khoe and Bram Vermeer. (pages 855–856)

      George Whitesides

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201106671

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      Oxford University Press, 2010. 304 pp., hardcover, $ 29.95.—ISBN 978-0195377170

    2. Foundations of Organic Chemistry. Unity and Diversity of Structures, Pathways, and Reactions. By David R. Dalton. (pages 856–857)

      Katarina Vazdar, Martin Holan and Ullrich Jahn

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201107776

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      John Wiley & Sons, Hoboken 2011. 1440 pp., hardcover, € 129.00.—ISBN 978-0470479087

  11. Highlight

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. News
    9. Author Profile
    10. News
    11. Book Reviews
    12. Highlight
    13. Minireview
    14. Review
    15. Communications
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    1. Solution NMR Spectroscopy

      First Solution Structures of Seven-Transmembrane Helical Proteins (pages 860–861)

      Prof. Dr. Oliver Zerbe

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201107639

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      A mastered challenge: The recent solution structures of seven-transmembrane proteins, in particular of proteorhodopsin, have been reported. The structures are a major advance in structural biology and were determined based on experimental restrains derived from nuclear Overhauser effects (NOEs), paramagnetic relaxation enhancements (PREs), and residual dipolar couplings (RDCs, see picture).

  12. Minireview

    1. Top of page
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    14. Review
    15. Communications
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    1. Nitrogen Heterocycles

      Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems (pages 862–872)

      Dr. Buddhadeb Chattopadhyay and Prof. Dr. Vladimir Gevorgyan

      Article first published online: 25 NOV 2011 | DOI: 10.1002/anie.201104807

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      One two three: Transition-metal catalyzed denitrogenative transannulation of 1,2,3-triazole rings has recently received increasing attention as a new concept for the construction of diverse nitrogen-containing heterocyclic cores in a single step (see scheme).

  13. Review

    1. Top of page
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    13. Minireview
    14. Review
    15. Communications
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    1. Single-Molecule Analysis

      Single-Molecule Analysis Using DNA Origami (pages 874–890)

      Dr. Arivazhagan Rajendran, Dr. Masayuki Endo and Prof. Dr. Hiroshi Sugiyama

      Article first published online: 25 NOV 2011 | DOI: 10.1002/anie.201102113

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      Origami for singles: Concurrent to the development of single-molecule analytical techniques has been rapid progress in nanobiotechnology and efforts at building lab-on-a-chip systems for high-throughput analytical biochemistry. The scaffolded DNA origami method is suitable for the construction of defined larger assemblies that can act as a platform for the positioning of various functionalities and their single-molecule analysis (see picture).

  14. Communications

    1. Top of page
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    15. Communications
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    1. Liquid Crystals

      Photo-Switchable Surface Topologies in Chiral Nematic Coatings (pages 892–896)

      Danqing Liu, Dr. Cees W. M. Bastiaansen, Dr. Jaap M. J. den Toonder and Dr. Dirk J. Broer

      Article first published online: 26 SEP 2011 | DOI: 10.1002/anie.201105101

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      An enlightening answer: Dynamic surface photo-responsive topologies of a polymer coating were realized by introducing azobenzene crosslinkers into liquid-crystal polymer networks (see picture). The principle of these coatings is based on breaking the molecular order in the liquid-crystal polymer networks. Under irradiation of UV light the azobenzene compound isomerizes from the trans to the cis conformation.

    2. Mesoporous Materials

      Nanoporous Single-Crystal-Like CdxZn1−xS Nanosheets Fabricated by the Cation-Exchange Reaction of Inorganic–Organic Hybrid ZnS–Amine with Cadmium Ions (pages 897–900)

      Dr. Yifu Yu, Jin Zhang, Xuan Wu, Weiwei Zhao and Prof. Dr. Bin Zhang

      Article first published online: 11 OCT 2011 | DOI: 10.1002/anie.201105786

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      Swapping ions: Nanoporous CdxZn1−xS nanosheets with single-crystal-like structure, good structural stability, and tunable pore size and composition have been successfully fabricated by the cation-exchange reaction of prepared ZnS–amine hybrid nanosheets with Cd2+ cations (see picture). The porous CdxZn1−xS nanosheets are highly active for photocatalytic H2 evolution from water splitting.

    3. Photochromic Actuators

      Light-Driven Molecular-Crystal Actuators: Rapid and Reversible Bending of Rodlike Mixed Crystals of Diarylethene Derivatives (pages 901–904)

      Fumitaka Terao, Dr. Masakazu Morimoto and Prof. Dr. Masahiro Irie

      Article first published online: 26 OCT 2011 | DOI: 10.1002/anie.201105585

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      Limber but strong: Two-component mixed crystals of diarylethene derivatives exhibit reversible, rapid, and fatigue-resistant bending upon alternate irradiation with UV and visible light (see picture). The crystals showed reversible curling into a hairpin shape while remaining crystalline.

    4. Drug Discovery

      Fragment Deconstruction of Small, Potent Factor Xa Inhibitors: Exploring the Superadditivity Energetics of Fragment Linking in Protein–Ligand Complexes (pages 905–911)

      Dr. Marc Nazaré, Dr. Hans Matter, Dr. David W. Will, Dr. Michael Wagner, Dr. Matthias Urmann, Dr. Jörg Czech, Dr. Herman Schreuder, Dr. Armin Bauer, Dr. Kurt Ritter and Dr. Volkmar Wehner

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201107091

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      More than just the sum of its parts: The superadditivity effect of fragment linking on ΔG was quantified by deconstructing two fXa inhibitors with congeneric fragments, but different linkers. By connecting both fragments with a single bond, a high linker contribution ΔGlink of −14.0 kJ mol−1 results, which corresponds to an improvement in affinity by around 2.5 orders of magnitude relative to the sum of fragment ΔG values (see picture).

    5. Surface Chemistry

      DNA Origami Nanopatterning on Chemically Modified Graphene (pages 912–915)

      Je Moon Yun, Kyoung Nan Kim, Ju Young Kim, Dong Ok Shin, Won Jun Lee, Sun Hwa Lee, Prof. Marya Lieberman and Prof. Sang Ouk Kim

      Article first published online: 27 OCT 2011 | DOI: 10.1002/anie.201106198

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      Nanoscale folding of DNA: Taking advantage of facile solution processing, pattern formation under light irradiation, and ready chemical modification of graphene oxide, various patterned films of chemically modified graphene were prepared and employed for spatial patterning of DNA origami structures (see picture). The patterning of DNA origami structures required highly selective adsorption on graphene oxide surfaces.

    6. Light Harvesting

      A DNA-Based Light-Harvesting Antenna (pages 916–919)

      M. Sc. Florian Garo and Prof. Dr. Robert Häner

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201103295

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      Shedding light on DNA: A DNA-based light-harvesting antenna has been synthesized. Light is absorbed by π-stacked phenanthrene units and efficiently transferred to a phenanthrene–pyrene exciplex. The whole system is structurally organized by a DNA scaffold. Up to eight phenanthrene units are used for light collection and the intensity of the exciplex emission is proportional to the number of light-absorbing chromophores.

    7. Double Click Chemistry

      Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi-Target Imaging (pages 920–922)

      Dr. Mark R. Karver, Prof. Ralph Weissleder and Dr. Scott A. Hilderbrand

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201104389

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      Mutually orthogonal tetrazine–trans-cyclooctene and azide–cyclooctyne cycloaddition reactions were used simultaneously for the bioorthogonal labeling of two different live cell populations in the same culture (see scheme). These small-molecule probes show good chemical reactivity and can be readily incorporated into biological systems.

    8. Asymmetric Biomineralization

      Formation of Enantiomeric Impeller-Like Helical Architectures by DNA Self-Assembly and Silica Mineralization (pages 923–927)

      Ben Liu, Dr. Lu Han and Prof. Shunai Che

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105445

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      Impeller-like helical DNA–silica complexes (see picture; green: silica) were synthesized in the presence of magnesium ions (a). DNA chiral packing and corresponding macroscopic helical morphologies are tuned by the change of reaction temperature, pH value, and molar ratio (b) of the quaternary ammonium (yellow)/phosphate group.

    9. Virus Host Recognition

      Molecular Details of the Recognition of Blood Group Antigens by a Human Norovirus as Determined by STD NMR Spectroscopy (pages 928–932)

      Brigitte Fiege, Dr. Christoph Rademacher, Jonathan Cartmell, Dr. Pavel I. Kitov, Prof. Dr. Francisco Parra and Prof. Dr. Thomas Peters

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201105719

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      Tracing the infection: The binding of human norovirus particles to blood group antigens was investigated using NMR spectroscopy. Binding epitopes were determined at atomic resolution, information on the binding specificity was obtained, and the bioactive conformation of various sugars was revealed. This provides valuable information for the design of entry inhibitors against this important class of human pathogenic viruses.

    10. Batteries

      Energetic Zinc Ion Chemistry: The Rechargeable Zinc Ion Battery (pages 933–935)

      Dr. Chengjun Xu, Baohua Li, Hongda Du and Prof. Feiyu Kang

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201106307

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      Think zinc: An ideal aqueous energy storage device, referred to as a zinc ion battery, is presented. The device is characterized by high capacity, fast charge/discharge capability, safety, and environmental friendliness. It is composed of an α-MnO2 cathode, a zinc anode, and a mild ZnSO4 or Zn(NO3)2 aqueous electrolyte (see scheme). The battery chemistry is based on the migration of Zn2+ ions between cathode and anode.

    11. Asymmetric Synthesis

      Catalytic Asymmetric Synthesis of Aromatic Spiroketals by SpinPhox/Iridium(I)-Catalyzed Hydrogenation and Spiroketalization of α,α′-Bis(2-hydroxyarylidene) Ketones (pages 936–940)

      Xiaoming Wang, Dr. Zhaobin Han, Dr. Zheng Wang and Prof. Dr. Kuiling Ding

      Article first published online: 14 DEC 2011 | DOI: 10.1002/anie.201106488

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      From spiro to spiro: An iridium(I) complex with a spiral P,N ligand (SpinPhox) is highly efficient in the catalytic asymmetric hydrogenation of α,α′-bis(2-hydroxyarylidene) ketones to afford the corresponding aromatic spiroketals in high yields with excellent diastereo- and enantioselectivities (see scheme). The complex plays a dual role in the reaction, acting as catalyst for both the hydrogenation of C[DOUBLE BOND]C bonds and the subsequent spiroketalization of bisphenolic ketones.

    12. Cancer Therapy

      A Traceless Vascular-Targeting Antibody–Drug Conjugate for Cancer Therapy (pages 941–944)

      Dr. Gonçalo J. L. Bernardes, Dr. Giulio Casi, Dr. Sabrina Trüssel, Isabelle Hartmann, Dr. Kathrin Schwager, Dr. Jörg Scheuermann and Prof. Dario Neri

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201106527

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      Right on target: A chemically defined vascular-targeting antibody–drug conjugate (ADC) that offers comprehensive tumor coverage has been developed. When injected intravenously, this ADC potently inhibited tumor growth in a syngeneic immunocompetent model of murine cancer which cannot be cured by conventional cytotoxic agents.

    13. Nanomedicine

      Anchored Proteinase-Targetable Optomagnetic Nanoprobes for Molecular Imaging of Invasive Cancer Cells (pages 945–948)

      Joseph Park, Prof. Jaemoon Yang, Eun-Kyung Lim, Eunjung Kim, Jihye Choi, Joo Kyung Ryu, Nam Hee Kim, Prof. Jin-Suck Suh, Prof. Jong In Yook, Prof. Yong-Min Huh and Prof. Seungjoo Haam

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201106758

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      Activatable nanoprobe: A dual-function nanoprobe has been developed that detects membrane type 1-matrix metalloproteinase (MT1-MMP) activity by a dual-signal increase in complementary fluorescence imaging (FI) and magnetic resonance imaging (MRI). MNCs=magnetic nanocrystals, Q=quencher, F=fluorescence dye.

    14. Nanostructured Materials

      Serial Ionic Exchange for the Synthesis of Multishelled Copper Sulfide Hollow Spheres (pages 949–952)

      Dr. Shenglin Xiong and Prof. Dr. Hua Chun Zeng

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201106826

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      Transformation in a shell: Ion exchange is used for the fabrication of multishelled inorganic hollow materials. The transformation of solid Cu2O to Cu2S hollow spheres is investigated as a model reaction (see picture; PVP=poly(vinylpyrrolidone)).

    15. Enzyme Catalysis

      Electrochemistry, AFM, and PM-IRRA Spectroscopy of Immobilized Hydrogenase: Role of a Hydrophobic Helix in Enzyme Orientation for Efficient H2 Oxidation (pages 953–956)

      Alexandre Ciaccafava, Pascale Infossi, Dr. Marianne Ilbert, Dr. Marianne Guiral, Dr. Sophie Lecomte, Dr. Marie Thérèse Giudici-Orticoni and Dr. Elisabeth Lojou

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107053

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      A transmembrane helix surrounded by detergent molecules close to the surface electron relay is shown, by electrochemical, AFM, and PM-IRRAS studies, to control the orientation of a membrane-bound [NiFe] hydrogenase on electrochemical interfaces. Hence, H2 oxidation proceeds as a mixture of direct (DET) and mediated electron transfer (MET) on hydrophilic interfaces, but by a MET process on hydrophobic interfaces (see picture).

    16. Heterogeneous Catalysis

      Chemical Probing within Catalyst Bodies by Diagonal Offset Raman Spectroscopy (pages 957–960)

      Dr. Mathijs W. Zandbergen, Dr. Simon D. M. Jacques, Prof. Dr. Bert M. Weckhuysen and Dr. Andrew M. Beale

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107175

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      A vibrational fingerprint: A Raman technique has been developed to retrieve spatiotemporal chemical information from millimeter-sized catalyst bodies under preparation. An incipient wetness impregnation of γ-Al2O3 catalysts with ammonium heptamolybdate was followed. Diagonal offset Raman spectroscopy was able to distinguish between surface, subsurface, and bulk phase of the catalyst bodies (see picture).

    17. Functional Materials

      SiO2-Surface-Assisted Controllable Synthesis of TaON and Ta3N5 Nanoparticles for Alkene Epoxidation (pages 961–965)

      Dr. Qingsheng Gao, Sinong Wang, Dr. Yuchun Ma, Prof. Yi Tang, Dr. Cristina Giordano and Prof. Markus Antonietti

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107216

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      Touching the surface: Well-defined TaON and Ta3N5 nanoparticles were fabricated by a SiO2-surface-assisted urea method, in which silica catalyzes CNx formation from urea. Such controlled nitridation endows the nanoparticles with improved activity and tunable selectivity for alkene epoxidation because of the increased electron density around Ta and surface basicity.

    18. Fluorescent Probes

      An Activity-Based Imaging Probe for the Integral Membrane Hydrolase KIAA1363 (pages 966–970)

      Jae Won Chang, Dr. Raymond E. Moellering and Prof. Dr. Benjamin F. Cravatt

      Article first published online: 7 DEC 2011 | DOI: 10.1002/anie.201107236

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      Profiling enzyme activities: A selective, activity-based imaging probe is described for the integral membrane hydrolase KIAA1363 and used to determine the subcellular localization and half-life of this enzyme in human cancer cells (see picture).

    19. Synthetic Methods

      Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A (pages 971–974)

      Giulia Bergonzini and Prof. Dr. Paolo Melchiorre

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107443

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      Taming the reactivity: Understanding the nucleophilicity of dioxindole under different reaction conditions is key to a direct and easy access to valuable spiro oxindole γ butyrolactones and 3-substituted 3-hydroxyoxindole derivatives in excellent yields and enantioselectivities (see scheme). The preparation of maremycin A serves as an example for the potential usefulness of this previously unexplored reactivity in natural product synthesis.

    20. Chemical Synthesis of Glycoproteins

      Probing the Frontiers of Glycoprotein Synthesis: The Fully Elaborated β-Subunit of the Human Follicle-Stimulating Hormone (pages 975–979)

      Dr. Pavel Nagorny, Dr. Neeraj Sane, Dr. Bernhard Fasching, Dr. Baptiste Aussedat and Prof. Dr. Samuel J. Danishefsky

      Article first published online: 9 DEC 2011 | DOI: 10.1002/anie.201107482

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      Ambitious undertaking: The β-subunit of the human follicle-stimulating hormone (hFSH) displaying a N-linked consensus sequence oligosaccharide at each of the two wild-type sites was synthesized. The glycoprotein has been designed with acetamidomethyl protected cysteine residues, anticipating folding and association with the α-subunit. This represents the largest realistically glycosylated homogeneous glycoprotein obtained by using strictly chemical methods.

    21. Peptidomimetics

      Protein Transduction Domain Mimics: The Role of Aromatic Functionality (pages 980–983)

      Dr. Abhigyan Som, Anika Reuter and Prof. Gregory N. Tew

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201104624

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      For better or worse: Protein transduction domain mimics built from synthetic polymers demonstrate that aromatic side chains provide better transduction than aliphatic groups at the same relative hydrophobicity. Similarly, a less hydrophobic aromatic side chain is more active than the corresponding aliphatic one containing the same number of carbon atoms (see picture).

    22. Nanoporous Materials

      Synthesis of Prussian Blue Nanoparticles with a Hollow Interior by Controlled Chemical Etching (pages 984–988)

      Dr. Ming Hu, Prof. Dr. Shuhei Furukawa, Ryo Ohtani, Dr. Hiroaki Sukegawa, Dr. Yoshihiro Nemoto, Dr. Julien Reboul, Prof. Dr. Susumu Kitagawa and Prof. Dr. Yusuke Yamauchi

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201105190

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      A facile route has been found to prepare Prussian blue (PB) hollow particles with a cubic shape (see picture). With PB mesocrystals used as a starting material, hollow interiors were created through controlled chemical etching in the presence of poly(vinylpyrrolidone). The hollow cavities and particle sizes could be tuned by changing the synthetic conditions, and the original PB crystallinity was preserved even after formation of interior hollows.

    23. Synthetic Methods

      Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles (pages 989–992)

      Nadine V. Hanhan, Nicolas R. Ball-Jones, Ngon T. Tran and Prof. Annaliese K. Franz

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201105739

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      Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl2(SbF6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si[BOND]C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl.

    24. Chemical Protein Synthesis

      Convergent Chemical Synthesis of [Lysine24, 38, 83] Human Erythropoietin (pages 993–999)

      Dr. Suhuai Liu, Dr. Brad L. Pentelute and Prof. Dr. Stephen B. H. Kent

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201106060

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      A new route to EPO: Nonglycosylated human erythropoietin (EPO) was prepared using a convergent chemical ligation synthetic strategy. The synthetic [Lysine24, 38, 83] EPO analogue, which was purified by HPLC and has the correct molecular weight (see picture), shows well-defined covalent structure, is correctly folded, and is biologically active in a factor-dependent cell line assay.

    25. Square-Planar Complexes

      High-Spin Square-Planar CoII and FeII Complexes and Reasons for Their Electronic Structure (pages 1000–1005)

      Stefanie A. Cantalupo, Stephanie R. Fiedler, Prof. Dr. Matthew P. Shores, Prof. Dr. Arnold L. Rheingold and Prof. Dr. Linda H. Doerrer

      Article first published online: 9 DEC 2011 | DOI: 10.1002/anie.201106091

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      It's hip to be square: Two high-spin, square-planar {MO4} complexes are prepared, including the first molecular example with M=CoII (see structure). Structural, spectroscopic, and magnetic susceptibility characterization allows a description of the ligand features required for this highly unusual electronic structure.

    26. C[BOND]H Arylation

      Transition-Metal-Free Direct Arylation of Anilines (pages 1006–1009)

      Dr. Tracey Pirali, Dr. Fengzhi Zhang, Anna H. Miller, Jenna L. Head, Donald McAusland and Prof. Michael F. Greaney

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201106150

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      Aryne arylation: A new method of direct arylation is reported for aniline substrates. The reaction uses benzyne to synthesize a variety of aminobiaryls under mild conditions (see scheme), requiring no stoichiometric metalation or transition-metal catalysis. An ene mechanism is implicated, and conveys excellent functional group tolerance relative to metal-mediated processes.

    27. Selective Cycloaddition

      Three-Component [2+2+2] Cycloaddition of Carboryne, Unactivated Alkene, and Alkyne via Zirconacyclopentane Mediated by Nickel: One-Pot Synthesis of Dihydrobenzocarboranes (pages 1010–1013)

      Dr. Shikuo Ren, Dr. Zaozao Qiu and Prof. Dr. Zuowei Xie

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201106212

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      Mix three—get one: The complexation of a transition-metal center to an olefin or alkyne can significantly modify its reactivity, which makes the selective coupling of different alkenes or alkynes to carboryne possible. An example of a three-component [2+2+2] cycloaddition reaction of carboryne with unactivated alkene (see scheme, blue) and alkyne (red) mediated by zirconium and nickel complexes is described.

    28. Chemoselective Hydrogenation

      Iridium-Catalyzed Chemoselective and Enantioselective Hydrogenation of (1-Chloro-1-Alkenyl) Boronic Esters (pages 1014–1018)

      Dr. Ivana Gazić Smilović, Dr. Eva Casas-Arcé, Dr. Stephen J. Roseblade, Dr. Ulrike Nettekoven, Dr. Antonio Zanotti-Gerosa, Dr. Miroslav Kovačevič and Dr. Zdenko Časar

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201106262

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      Persistent chlorine: Hydrogenation of borolane-substituted vinylic chlorides catalyzed by Ir[BOND]P N complexes greatly preserved the chlorine substituent on the hydrogenated product, with only 3–19 % of dechlorinated byproducts present after hydrogenation. The α-chloro boronic ester products are ideal precursors for proteasome-inhibitor-type anti-cancer drugs, a fact which demonstrates the utility of this hydrogenation method.

    29. Medicinal Chemistry

      The Tuberculosis Drug Streptomycin as a Potential Cancer Therapeutic: Inhibition of miR-21 Function by Directly Targeting Its Precursor (pages 1019–1023)

      Debojit Bose, Gopal Jayaraj, Hemant Suryawanshi, Prachi Agarwala, Subrata Kumar Pore, Dr. Rajkumar Banerjee and Dr. Souvik Maiti

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201106455

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      No dice: MicroRNAs (miRNAs) fine-tune gene expression, deregulation of which has been causally associated with a number of debilitating conditions. Streptomycin, a well-known aminoglycoside drug, binds to RNA secondary structures and is shown to inhibit miR-21 function by direct binding to its precursor, thus presumably interfering with the processing by the Dicer enzyme (see scheme).

    30. Total Synthesis

      Enantioselective Total Synthesis of (−)-Stenine (pages 1024–1027)

      Dr. Jingbo Chen, Jingchao Chen, Yan Xie and Prof. Dr. Hongbin Zhang

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201106587

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      In control: (−)-Stenine has been synthesized in 14 steps from commercially available compounds with an overall yield of 5.9 % by using a method that is based on double Michael addition. In the key step, the stereogenic centers that are required for (−)-stenine are generated in a highly stereocontrolled, asymmetric, one-pot cyclization to give a densely substituted cyclohexane core.

    31. Reaction Mechanisms

      Copper(I) Enolate Complexes in α-Arylation Reactions: Synthesis, Reactivity, and Mechanism (pages 1028–1032)

      Dr. Zheng Huang and Prof. Dr. John F. Hartwig

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201106719

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      Copper is all bound up: The copper-catalyzed α-arylation of carbonyl compounds occurs through oxidative addition of iodoarenes to the C-bound CuI enolate species 1 to form an aryl–CuIII intermediate (see scheme). Computational results provide insight into the origins of the relative reactivity of various CuI enolate complexes in the reactions with iodoarenes.

    32. C[BOND]C Coupling

      Palladium-Catalyzed 2,2,2-Trifluoroethylation of Organoboronic Acids and Esters (pages 1033–1036)

      Yanchuan Zhao and Prof. Dr. Jinbo Hu

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201106742

      Thumbnail image of graphical abstract

      Trifluoroethylation: Aryl boronic acids can be catalytically trifluoroethylated with the readily available reagent CF3CH2I (see scheme, dba=dibenzylideneacetone). The reaction tolerates a variety of functional groups and can be extended to the trifluoroethylation of aryl or alkenyl boronic esters. The method is also suitable for the late-stage installation of the CF3CH2 group into target molecules.

    33. Supramolecular Chemistry

      A Supramolecular Protecting Group Strategy Introduced to the Organic Solid State: Enhanced Reactivity through Molecular Pedal Motion (pages 1037–1041)

      Elizabeth Elacqua, Dr. Poonam Kaushik, Prof. Ryan H. Groeneman, Dr. Joseph C. Sumrak, Dr. Dejan-Krešimir Bučar and Prof. Leonard R. MacGillivray

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201106842

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      A supramolecular protecting group strategy has been applied to achieve solid-state photodimerizations of olefins lined with a combination of hydrogen-bond-donor and -acceptor groups. Esters were used as protecting groups to generate head-to-head photodimers that were readily converted into diacids. A protected olefin equipped with a stilbene unit exhibits enhanced reactivity that is ascribed to pedal motions in the solid state (orange hexagons: template: blur circles: recognition sites).

    34. Homogeneous Catalysis

      From Olefin Metathesis Catalyst to Alcohol Racemization Catalyst in One Step (pages 1042–1045)

      Simone Manzini, César A. Urbina-Blanco, Dr. Albert Poater, Prof. Alexandra M. Z. Slawin, Prof. Luigi Cavallo and Prof. Dr. Steven P. Nolan

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201106915

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      Easy as π: An unusual indenylidene to η5-indenyl rearrangement of a ruthenium catalyst has been observed. The resulting complex is the formal decomposition product of an olefin metathesis precatalyst that displays exceptional activity in the racemization of chiral alcohols at very low catalyst loadings.

    35. Synthetic Methods

      Core-Structure-Oriented Asymmetric Organocatalytic Substitution of 3-Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)-Folicanthine (pages 1046–1050)

      Chang Guo, Jin Song, Jian-Zhou Huang, Peng-Hao Chen, Shi-Wei Luo and Prof. Liu-Zhu Gong

      Article first published online: 7 DEC 2011 | DOI: 10.1002/anie.201107079

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      Something constructive: The title reaction involving 3-hydroxyoxindoles gives 3,3′-disubstituted oxindoles with concomitant generation of an all-carbon quaternary stereogenic center in high yield and excellent enantioselectivity. This reaction enabled the enantioselective construction of hexahydropyrroloindole skeletons and the first catalytic enantioselective total synthesis of (+)-folicanthine.

    36. Regio- and Stereoselective Carbobismuthination of Alkynes (pages 1051–1054)

      Dr. Yoshihiro Nishimoto, Midori Takeuchi, Dr. Makoto Yasuda and Prof. Dr. Akio Baba

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107127

      Thumbnail image of graphical abstract

      Three become one: The first carbobismuthination of alkynes has been accomplished by the simple reaction of an alkyne, BiBr3, and a ketene silyl acetal to produce an alkenylbismuth with high stereo- and regioselectivity (see scheme). X-ray crystallographic analysis of the alkenylbismuth product and control experiments using α-bismuthino ester revealed the reaction mechanism.

    37. Asymmetric Catalysis

      Enyne Chlorides: Substrates for Copper-Catalyzed Asymmetric Allylic Alkylation (pages 1055–1058)

      Hailing Li and Prof. Dr. Alexandre Alexakis

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201107129

      Thumbnail image of graphical abstract

      A select few: Several prochiral enyne chlorides were employed as substrates in the title reaction using Grignard reagents as the alkylation reagents (see scheme; CuTC=copper(I) thiophenecarboxylate). Excellent 1,3 substitution regioselectivities and good to excellent enantioselectivities were obtained. The substrate scope is additionally extended to diene chlorides.

    38. One-Pot Syntheses

      Multistep One-Pot Synthesis of Enantioenriched Polysubstituted Cyclopenta[b]indoles (pages 1059–1062)

      Biao Xu, Zhi-Lei Guo, Wan-Yan Jin, Zhi-Ping Wang, Prof. Yun-Gui Peng and Prof. Qi-Xiang Guo

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201107308

      Thumbnail image of graphical abstract

      Simple steps, complex result: Consecutive organo-catalyzed reactions of 3-indolylmethanol compounds with aldehydes and N-protected indoles lead to the formation of structurally complex cyclopenta[b]indoles (see scheme, Bn=benzyl). These one-pot multistep reactions have a broad substrate scope and give the products in high yields, and with excellent diastereoselectivities and enantioselectivities.

    39. Total Synthesis

      Total Synthesis of Carolacton, a Highly Potent Biofilm Inhibitor (pages 1063–1066)

      Thomas Schmidt and Prof. Dr. Andreas Kirschning

      Article first published online: 9 DEC 2011 | DOI: 10.1002/anie.201106762

      Thumbnail image of graphical abstract

      Metals are the key players in the synthesis of caralacton, a strong inhibitor of bacterial biofilms. The total synthesis is based on several metal-mediated key transformations such as the Ley and the Duthaler–Hafner aldol reactions, the Marshall reaction and Breit's substitution, as well as the Nozaki–Hiyama–Kishi and Negishi–Fu C[BOND]C coupling reactions.

    40. Cage Effect

      Change of the Fe Configuration in Chiral Half-Sandwich Complexes Within the Solvent Cage (pages 1067–1070)

      Prof. Henri Brunner, Manfred Muschiol, Prof. Takashi Tsuno, Hyato Ike, Takaki Kurosawa and Kazuhito Koyama

      Article first published online: 13 DEC 2011 | DOI: 10.1002/anie.201104960

      Thumbnail image of graphical abstract

      Change before exchange: Cross-over experiments with chiral half-sandwich complexes [Cp′Fe(Prophos)NCR]X (Cp′=C5H5, MeC5H4; X=I, PF6), in which change of configuration at the metal atom and RCN ligand exchange compete, show that the change of the Fe configuration within the solvent cage is faster than ligand exchange (see scheme).

    41. Clickable Surfaces

      Adding Spatial Control to Click Chemistry: Phototriggered Diels–Alder Surface (Bio)functionalization at Ambient Temperature (pages 1071–1074)

      Thomas Pauloehrl, Dr. Guillaume Delaittre, Volker Winkler, Dr. Alexander Welle, Dr. Michael Bruns, Prof. Dr. Hans G. Börner, Dr. Alexandra M. Greiner, Prof. Dr. Martin Bastmeyer and Prof. Dr. Christopher Barner-Kowollik

      Article first published online: 9 DEC 2011 | DOI: 10.1002/anie.201107095

      Thumbnail image of graphical abstract

      A photoconjugation strategy based on light-triggered Diels–Alder addition of o-quinodimethanes is compatible with biomolecules and proceeds rapidly at ambient temperature without the need of a catalyst. Spatial control was confirmed by photopatterning of a small-molecule ATRP initiator, a polymer, and a peptide in a time-of-flight secondary-ion mass spectrometry investigation.

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      Article first published online: 17 JAN 2012 | DOI: 10.1002/anie.201290004

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