Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 5

January 27, 2012

Volume 51, Issue 5

Pages 1079–1280

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: Prediction of a Ligand-Binding Niche within a Human Olfactory Receptor by Combining Site-Directed Mutagenesis with Dynamic Homology Modeling (Angew. Chem. Int. Ed. 5/2012) (page 1079)

      Dr. Lian Gelis, Dr. Steffen Wolf, Prof. Dr. Hanns Hatt, Prof. Dr. Eva M. Neuhaus and Prof. Dr. Klaus Gerwert

      Article first published online: 7 DEC 2011 | DOI: 10.1002/anie.201107509

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      Ligand recognition in olfaction depends on the formation of a defined dynamic receptor–ligand hydrogen-bond pattern. Like two dancers, the odorant moves steadily within the binding site, while the receptor offers changing side chains for bonding. In their Communication on page 1274 ff., K. Gerwert and co-workers elucidate this dynamic pattern for the human olfactory receptor hOR2 AG1 through a combination of dynamic homology modeling, site-directed mutagenesis, and Ca2+ imaging. Dancers: Laila and Leandro Oliver.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Inside Cover: Sub-Micrometer Vaterite Containers: Synthesis, Substance Loading, and Release (Angew. Chem. Int. Ed. 5/2012) (page 1080)

      Dr. Bogdan V. Parakhonskiy, Dr. Albrecht Haase and Prof. Renzo Antolini

      Article first published online: 7 NOV 2011 | DOI: 10.1002/anie.201107543

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      The loading and storage of various payloads is possible in the porous structure of sub-micrometer-sized vaterite particles. These particles can be synthesized by modifying the crystal-growth parameters. As B. V. Parakhonskiy et al. report in their Communication on page 1195 ff., the recystallization of vaterite into calcite in aqueous solutions acts as a release mechanism. Thus, the payload release can be controlled by the immersion medium, thus offering a simple, cost-effective, and versatile system for drug-delivery applications.

  3. Inside Back Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Inside Back Cover: Remarkable Adsorption Capacity of CuCl2-Loaded Porous Vanadium Benzenedicarboxylate for Benzothiophene (Angew. Chem. Int. Ed. 5/2012) (page 1281)

      Nazmul Abedin Khan and Prof.Dr. Sung Hwa Jhung

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201108254

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      Metal–organic frameworks loaded with cupric chloride have been applied for adsorptive desulfurization. In their Communication on page 1198 ff., S. H. Jhung and N. A. Khan report the remarkable adsorptive performance of CuCl2/V–benzenedicarboxylate (V-BDC) arising from the facile reduction of CuII to CuI by VIII in V-BDC. This approach provides new insights into redox reactions in metal–organic framework materials and can find application in the adsorptive desulfurization of liquid fuels.

  4. Back Cover

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Back Cover: Single-Particle and Ensemble Diffusivities—Test of Ergodicity (Angew. Chem. Int. Ed. 5/2012) (page 1282)

      M. Sc. Florian Feil, Dr. Sergej Naumov, Prof. Dr. Jens Michaelis, Dr. Rustem Valiullin, Prof. Dr. Dirk Enke, Prof. Dr. Jörg Kärger and Prof. Dr. Christoph Bräuchle

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201108621

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      Coincidence between the mean-squared displacements determined for the same molecule over sequential time intervals and for all molecules over the same time interval follows as a consequence of the ergodic theorem. In their Communication on page 1152 ff., C. Bräuchle et al. confirm experimentally this fundamental principle of thermodynamics by diffusion studies using fluorescence microscopy and NMR spectroscopy with pulsed field gradients.

  5. Graphical Abstract

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 5/2012 (pages 1083–1094)

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201290006

  6. Flashback

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. 50 Years Ago... (page 1092)

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201108796

  7. News

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  8. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Bas de Bruin (page 1102)

      Article first published online: 6 DEC 2011 | DOI: 10.1002/anie.201107429

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      “The most significant scientific advance of the last 100 years has been quantum mechanics. The greatest scientific advance in the next decade will be the discovery of a wireless interface between our brains and the internet …” This and more about Bas de Bruin can be found on page 1102.

  9. News

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  10. Book Review

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Periodic Tales. A Cultural History of the Elements, from Arsenic to Zinc. By Hugh Aldersey-Williams. (pages 1104–1105)

      Matthias Driess

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201108295

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      HarperCollins, New York, 2011. 448 pp., hardcover, $ 29.99.—ISBN 978-0061824722

  11. Highlights

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. Flashback
    8. News
    9. Author Profile
    10. News
    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Radiochemistry

      Novel Strategies for Fluorine-18 Radiochemistry (pages 1106–1109)

      Dr. Ryan Littich and Dr. Peter J. H. Scott

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106785

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      Radiotracers: The growing demand for novel radiopharmaceuticals can only be met through the development of new approaches to isotopic labeling. Effective strategies and reagents for nucleophilic and electrophilic 18F-radiolabeling are highlighted (see picture).

    2. Self-Assembly

      Design Rules: A Net and Archimedean Polyhedra Score Big for Self-Assembly (pages 1110–1112)

      Prof. Leonard R. MacGillivray

      Article first published online: 2 JAN 2012 | DOI: 10.1002/anie.201107282

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      Caged: Taking its origin in recent work by Ward and co-workers, an overview is given on the synthesis of Archimedean and Platonic bodies (see picture) by different approaches, such as hydrogen-bonded self-assembly and coordination chemistry.

  12. Minireview

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Synthetic Chemistry

      Lead-Oriented Synthesis: A New Opportunity for Synthetic Chemistry (pages 1114–1122)

      Dr. Alan Nadin, Dr. Channa Hattotuwagama and Dr. Ian Churcher

      Article first published online: 3 JAN 2012 | DOI: 10.1002/anie.201105840

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      Leading the way: Lead-oriented synthesis (LOS) is a new but simple concept describing reactions that allow the efficient preparation of diverse sets of small, polar molecules to act as starting points for drug discovery. Much existing synthetic methodology cannot easily deliver this, and a huge opportunity exists for developers of new reactions to help the search for new medicines by developing more syntheses that are lead-oriented in nature.

  13. Review

    1. Top of page
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Terpenes

      Terpene Biosynthesis: Modularity Rules (pages 1124–1137)

      Prof. Dr. Dr. Eric Oldfield and Dr. Fu-Yang Lin

      Article first published online: 21 NOV 2011 | DOI: 10.1002/anie.201103110

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      Natural building blocks: Recent progress has been achieved in determining the structure, function, and inhibition of the enzymes responsible for the formation of terpenes and isoprenoids. Most of these enzymes contain combinations of α-, β-, γ-, δ-, ε-, and/or ζ-domain structures that in many cases are fused to form modular proteins. Gene fusion, exon loss, and recombination are thought to play major roles in the genesis of these enzymes.

  14. Communications

    1. Top of page
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    6. Graphical Abstract
    7. Flashback
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    9. Author Profile
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    11. Book Review
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Self-Healing Materials

      Self-Healing of Chemical Gels Cross-Linked by Diarylbibenzofuranone-Based Trigger-Free Dynamic Covalent Bonds at Room Temperature (pages 1138–1142)

      Keiichi Imato, Dr. Masamichi Nishihara, Takeshi Kanehara, Dr. Yoshifumi Amamoto, Prof. Atsushi Takahara and Prof. Hideyuki Otsuka

      Article first published online: 3 NOV 2011 | DOI: 10.1002/anie.201104069

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      Linked: Polymers cross-linked with diarylbibenzofuranone units have been prepared by polyaddition. The exchange of bonds of the gels and their macroscopic self-healing were accomplished under air at room temperature in the dark. The macroscopic fusion of completely separated parts was successful (see picture).

    2. Gene Delivery

      Reactive and Bioactive Cationic α-Helical Polypeptide Template for Nonviral Gene Delivery (pages 1143–1147)

      Dr. Nathan P. Gabrielson, Dr. Hua Lu, Dr. Lichen Yin, Dr. Dong Li, Prof. Dr. Fei Wang and Prof. Dr. Jianjun Cheng

      Article first published online: 7 DEC 2011 | DOI: 10.1002/anie.201104262

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      At every turn: Poly(γ-(4-vinylbenzyl)-L-glutamate) (PVBLG) is a bioactive and reactive template for a library of cationic α-helical polypeptides (PVBLGn-X) for gene delivery. The top-performing PVBLGn-X outperformed polyethyleneimine (PEI) by 12-fold. Preliminary data indicate that the helicity of the polypeptides is essential for their performance, and enhanced membrane disruption is a likely source of their transfection efficiency. RLU=relative light unit.

    3. Nanomaterials

      Controlled Doping of MS2 (M=W, Mo) Nanotubes and Fullerene-like Nanoparticles (pages 1148–1151)

      Lena Yadgarov, Dr. Rita Rosentsveig, Dr. Gregory Leitus, Dr. Ana Albu-Yaron, Dr. Alexey Moshkovich, Dr. Vladislav Perfilyev, Dr. Relja Vasic, Prof. Anatoly I. Frenkel, Dr. Andrey N. Enyashin, Prof. Dr. Gotthard Seifert, Prof. Lev Rapoport and Prof. Reshef Tenne

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105324

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      Lubricating nanoparticles: The effect of doping semiconductor hollow closed-fullerene-like nanoparticles of MoS2 and WS2 has been overlooked to date. Rhenium doping of these nanoparticles leads to a marked increase in the nanoparticle's conductivity, reduced agglomeration, and a great reduction in friction and wear (see picture) that approaches superlubricity.

    4. Single-Molecule Spectroscopy

      Single-Particle and Ensemble Diffusivities—Test of Ergodicity (pages 1152–1155)

      M. Sc. Florian Feil, Dr. Sergej Naumov, Prof. Dr. Jens Michaelis, Dr. Rustem Valiullin, Prof. Dr. Dirk Enke, Prof. Dr. Jörg Kärger and Prof. Dr. Christoph Bräuchle

      Article first published online: 18 OCT 2011 | DOI: 10.1002/anie.201105388

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      To prove the ergodic theorem experimentally the diffusivities of guest molecules inside a nanostructured porous glass were measured by using two conceptually different approaches under identical conditions. The data obtained through the direct observation of dye-molecule diffusion by single-molecule tracking experiments (red circles) was in perfect agreement with the ensemble value obtained in pulsed-field gradient NMR experiments (black squares).

    5. Mesoporous Organosilica

      Mesoporous Organosilica Hybrids Consisting of Silica-Wrapped π–π Stacking Columns (pages 1156–1160)

      Dr. Norihiro Mizoshita, Dr. Takao Tani, Prof. Hiroshi Shinokubo and Dr. Shinji Inagaki

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105394

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      A new class of periodic mesoporous organosilica (PMO) materials with a columnar π-stacking arrangement of the framework organic groups has been prepared from disklike precursors with hydrophobic perylene bisimide (PBI) cores (see picture). The PBI-bridged PMOs exhibit exciton coupling and efficient formation of mobile radical spins by electron doping within the pore walls.

    6. Cutting Graphene

      Strain-Induced Orientation-Selective Cutting of Graphene into Graphene Nanoribbons on Oxidation (pages 1161–1164)

      Liang Ma, Prof. Jinlan Wang and Dr. Feng Ding

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105920

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      Cut to ribbons: Making atomically well-controlled graphene nanoribbons (GNRs) is prerequisite for many graphene applications. Ab initio calculations reveal that, on applying a uniaxial external tensile strain, O atoms adsorbed on graphene form parallel epoxy chains, and subsequent cutting by oxygen attack gives GNRs instead of the quantum dots that are obtained from unstrained graphene (see picture).

    7. Molecular Devices

      A Photon-Fueled DNA Nanodevice that Contains Two Different Photoswitches (pages 1165–1168)

      Dr. Hidenori Nishioka, Prof. Dr. Xingguo Liang, Tomohiro Kato and Prof. Dr. Hiroyuki Asanuma

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201106093

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      DNA seesaw: Photoswitchable azobenzenecarboxylic acid 1 reversibly photoisomerizes between the trans form and the thermally stable cis form upon irradiation with visible light. A photon-fueled DNA nanodevice that moves like a seesaw in response to irradiation with different wavelengths of light was made by modifying DNA oligonucleotides with a combination of 1 and a conventional azobenzene (see picture).

    8. Nanoconjugates

      ImmunoPods: Polymer Shells with Native Antibody Cross-Links (pages 1169–1172)

      Dr. Ke Zhang, Dan Zheng, Liangliang Hao, Joshua I. Cutler, Evelyn Auyeung and Prof. Chad A. Mirkin

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201106313

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      Nanopods functionalized with anti-HER2 antibodies (ImmunoPods, see scheme) have been synthesized by adsorbing the proteins onto gold nanoparticles and catalytically cross-linking them with a coadsorbed polymer through pendant propargyl ether groups. Upon dissolution of the gold template, the hollow polymer nanopod–protein conjugates remain. ImmunoPods are bioactive and can target cancer cells that express the HER2 antigen.

    9. Vesicles

      Polymersomes in Polymersomes: Multiple Loading and Permeability Control (pages 1173–1176)

      Maïté Marguet, Lise Edembe and Prof. Sébastien Lecommandoux

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201106410

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      Capsules in capsules: An emulsion–centrifugation method allows polymersomes in polymersomes “PiPs” (see picture) or polymer vesosomes to be prepared. This simple approach to generate biomimetic compartmentalized structures offers a way to encapsulate several different and even mutually incompatible active substances, thereby opening avenues in combinatory drug release and providing exquisite control of permeation properties.

    10. Molecular Devices

      Fine-Tuning Conformational Motion of a Self-Assembled Metal–Organic Macrocycle by Multiple C[BOND]H⋅⋅⋅Anion Hydrogen Bonds (pages 1177–1181)

      Ting-Zheng Xie, Cheng Guo, Prof. Dr. Shu-Yan Yu and Prof. Dr. Yuan-Jiang Pan

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106504

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      Anion switches: A bistable self-assembled metal–organic macrocycle undergoes intramolecular conformational motion that is switched reversibly with anions by multiple hydrogen-bonding interactions (see picture; Pd orange, N blue, O red). The molecular bowl fixed with a nitrate anion could be freed to a partial chair by adding a tetraphenylborate anion.

    11. Annulation

      Triptycene Diols: A Strategy for Synthesizing Planar π Systems through Catalytic Conversion of a Poly(p-phenylene ethynylene) into a Poly(p-phenylene vinylene) (pages 1182–1186)

      Brett VanVeller, Dale Robinson and Prof. Timothy M. Swager

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106985

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      At level best: A strategic synthesis of a new class of poly(p-phenylene vinylene)-bearing annulated alkene units from a parent poly(p-phenylene ethynylene) is described (see scheme). The gold-mediated cycloisomerization reaction of alkynes with appended hydroxy-group reacting partners delivers products having a stark increase in chain rigidity and planarity, as evidenced by pronounced photophysical changes.

    12. Organocatalysis

      An Achiral-Acid-Induced Switch in the Enantioselectivity of a Chiral cis-Diamine-Based Organocatalyst for Asymmetric Aldol and Mannich Reactions (pages 1187–1190)

      Dr. Shin A. Moteki, Jianwei Han, Satoru Arimitsu, Dr. Matsujiro Akakura, Dr. Keiji Nakayama and Prof. Dr. Keiji Maruoka

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201107239

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      Pick and choose: The asymmetric synthesis of two different enantiomeric products has been achieved through the use of a single organocatalyst with or without achiral organic acid additives (see scheme). These additives may assist in altering the substrate orientations at the catalytic center, leading to efficient enantiomeric inversions in both aldol and Mannich products.

    13. Highly Diastereo- and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts (pages 1191–1194)

      Dr. Taichi Kano, Sunhwa Song, Dr. Yasushi Kubota and Prof. Keiji Maruoka

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107375

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      High selectivity: A highly diastereo- and enantioselective Mannich reaction between a synthetically flexible ketimine and aldehydes has been developed. The syn- or anti-Mannich products contain tetrasubstituted chiral carbon centers and were obtained with almost complete stereoselectivity by using either L-proline or an axially chiral aminosulfonamide, respectively, as the catalyst (see scheme, Tf=trifluoromethanesulfonyl).

    14. Nanocontainers

      Sub-Micrometer Vaterite Containers: Synthesis, Substance Loading, and Release (pages 1195–1197)

      Dr. Bogdan V. Parakhonskiy, Dr. Albrecht Haase and Prof. Renzo Antolini

      Article first published online: 6 OCT 2011 | DOI: 10.1002/anie.201104316

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      Simply smaller: Sub-micrometer vaterite particles (see picture) were synthesized by modifying the crystal growth parameters. Their porous structure allows the loading and storage of various payloads. The recystallization to calcite in aqueous solutions can be used as a release mechanism. The release can be controlled by the properties of the immersion medium, thereby creating a simple, cost-effective, and versatile system for drug-delivery applications.

    15. Metal–Organic Frameworks

      Remarkable Adsorption Capacity of CuCl2-Loaded Porous Vanadium Benzenedicarboxylate for Benzothiophene (pages 1198–1201)

      Nazmul Abedin Khan and Prof.Dr. Sung Hwa Jhung

      Article first published online: 25 NOV 2011 | DOI: 10.1002/anie.201105113

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      A molecular sieve: A metal–organic framework (MOF) MIL-47 loaded with CuCl2 shows the highest adsorption capacity for benzothiophene because of the presence of CuI ions derived from CuII ions and porous MIL-47. The CuI ions were obtained by reduction of CuII with VIII ions in MIL-47. The modified MOF could be successfully used for the desulfurization of a liquid fuel (see picture).

    16. Oligodeoxynucleotides

      Polyvalent Immunostimulatory Nanoagents with Self-Assembled CpG Oligonucleotide-Conjugated Gold Nanoparticles (pages 1202–1206)

      Min Wei, Dr. Nan Chen, Dr. Jiang Li, Min Yin, Le Liang, Prof. Yao He, Prof. Haiyun Song, Prof. Chunhai Fan and Prof. Qing Huang

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201105187

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      Delivery vehicles: Gold nanoparticles (AuNPs) have been used as a nanocarrier to non-invasively deliver synthetic cytosine–phosphate–guanosine (CpG) oligodeoxynucleotides (ODNs) into cells. Compared to unconjugated single-stranded CpG ODNs, self-assembled polyvalent CpG-AuNP conjugates enhance the efficiency of cellular uptake and stimulate secretion of cytokines (see picture).

    17. Homogeneous Catalysis

      The Deformability of Polymers: The Role of Disordered Mesomorphic Crystals and Stress-Induced Phase Transformations (pages 1207–1211)

      Prof. Claudio De Rosa and Prof. Finizia Auriemma

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201105289

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      Crystals in polymers: The γ form of isotactic polypropylene shows an unexpected better ductility than the mesophase because of the occurrence of a stress-induced transition from the γ form to the mesophase. This provides a mechanism of conversion of mechanical energy into latent heat of fusion that induces local melting of the crystals followed by recrystallization at high deformation in the mesophase (see picture).

    18. Structure Elucidation

      Two Different Packing Arrangements of Antiparallel Polyalanine (pages 1212–1215)

      Prof. Dr. Tetsuo Asakura, Michi Okonogi, Kumiko Horiguchi, Dr. Akihiro Aoki, Dr. Hazime Saitô, Dr. David P. Knight and Prof. Dr. Mike P. Williamson

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105356

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      Two β-sheet arrangements: Polyalanines have been shown to adopt two different antiparallel crystal-packing arrangements, depending on the length of the polymers. Short polymers that contain six alanine residues or fewer adopt a rectangular packing arrangement, whereas longer polymers are packed in a staggered pattern (see scheme). The elucidation of these structures may help to explain the physical and biological properties of polyalanines.

    19. Biosynthesis

      Enzymatic Total Synthesis of Defucogilvocarcin M and Its Implications for Gilvocarcin Biosynthesis (pages 1216–1220)

      Dr. Pallab Pahari, Prof. Dr. Madan K. Kharel, Dr. Micah D. Shepherd, Prof. Dr. Steven G. van Lanen and Prof. Dr. Jürgen Rohr

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201105882

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      Teamwork: Defucogilvocarcin M (1, see scheme) was synthesized in a one-pot, enzymatic reaction from acetyl-CoA and malonyl-CoA by a combination of 15 enzymes obtained from E. coli as well as the gilvocarcin, jadomycin, and ravidomycin biosynthetic pathways. The mixture of enzymes was systematically reduced and varied to further delineate the sequence of reactions in the complex, post-polyketide steps of gilvocarcin biosynthesis.

    20. Water Oxidation Catalysis

      The Mechanism of O[BOND]O Bond Formation in Tanaka’s Water Oxidation Catalyst (pages 1221–1224)

      Soumya Ghosh and Prof. Dr. Mu-Hyun Baik

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106337

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      Oh-oh! The mechanism of water oxidation by Tanaka's catalyst (shown schematically in the picture) has been studied by using quantum chemical methods. The formation of the O[BOND]O bond between the two terminal oxo moieties of the catalyst lacks any thermodynamic driving force. The redox-active quinone ligand, however, assists in the addition of a water molecule to one of the Ru centers, thus facilitating the release of dioxygen.

    21. Cascade Reactions

      One-Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes (pages 1225–1227)

      Zhou Li and Prof. Vladimir Gevorgyan

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201106969

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      A one-pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br+ and PFP in this highly efficient, easily scaled-up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

    22. α-Chiral Allylsilanes

      Nickel-Catalyzed Enantio- and Diastereoselective Three-Component Coupling of 1,3-Dienes, Aldehydes, and a Silylborane Leading to α-Chiral Allylsilanes (pages 1228–1231)

      Dr. Nozomi Saito, Ayami Kobayashi and Prof. Dr. Yoshihiro Sato

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107360

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      Three-in-one: The nickel-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and a silylborane in the presence of a chiral phosphoroamidite ligand has been realized. The reaction proceeds by σ-bond metathesis of an oxanickelacycle intermediate with the silylborane to afford the corresponding α-chiral allylsilane derivative in a highly diastereo- and enantioselective manner.

    23. Synthetic Methods

      Stereoarrays with an All-Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes (pages 1232–1235)

      Dr. Bruno Linclau, Elena Cini, Catherine S. Oakes, Dr. Solen Josse, Dr. Mark Light and Dr. Victoria Ironmonger

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201107370

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      Tamed by chelation: The MgBr2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS=tert-butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center.

    24. DNA Detection

      Distinguishing DNA by Analog-to-Digital-like Conversion by Using Optofluidic Lasers (pages 1236–1239)

      Dr. Yuze Sun and Prof. Dr. Xudong Fan

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201107381

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      Laser precision: A highly sensitive technique based on laser emission for differentiating a target DNA strand from strands that contain single base mismatches has been developed. Laser emission is used to amplify the small difference in signals that are generated by the different strands after hybridization with a molecular beacon (MB, see picture) in a conversion that is similar to analog-to-digital.

    25. Enzyme Catalysis

      Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to β-Nitrostyrenes Catalyzed by a Promiscuous Proline-Based Tautomerase (pages 1240–1243)

      Ellen Zandvoort, Dr. Edzard M. Geertsema, Bert-Jan Baas, Prof. Dr. Wim J. Quax and Dr. Gerrit J. Poelarends

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201107404

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      Non-natural beauty: The enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously (i.e., with non-natural activity) catalyzes the Michael-type addition of acetaldehyde to nitrostyrene. Catalysis likely proceeds via enamine formation of the amino-terminal proline residue of 4-OT with acetaldehyde (see picture), reminiscent of organocatalysis. High stereoselectivity, low catalyst loading, and water as reaction medium characterize this methodology.

    26. Synthetic Methods

      Highly Regioselective Copper-Catalyzed Benzylic C[BOND]H Amination by N-Fluorobenzenesulfonimide (pages 1244–1247)

      Zhikun Ni, Prof. Dr. Qian Zhang, Tao Xiong, Yiying Zheng, Yan Li, Hongwei Zhang, Prof. Dr. Jingping Zhang and Prof. Dr. Qun Liu

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107427

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      Primary target: A practical and effective copper-catalyzed amination strategy for synthesizing various benzylic amines from benzylic hydrocarbons is described (see scheme; DCE=1,2-dichloroethane). Xylene substrates can undergo diamination reactions using this method. The remarkable preference for primary over secondary benzylic C[BOND]H bonds has been observed for the first time.

    27. Asymmetric Catalysis

      A Highly Diastereo- and Enantioselective Reaction for Constructing Functionalized Cyclohexanes: Six Contiguous Stereocenters in One Step (pages 1248–1251)

      Dengjian Shi, Yinjun Xie, Han Zhou, Prof. Dr. Chungu Xia and Prof. Dr. Hanmin Huang

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201107495

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      Just mix to get six: Six contiguous stereocenters, including one quaternary stereocenter, and three C[BOND]C bonds are created by a new copper-catalyzed tandem reaction (see scheme). Rigid chiral diamine ligands enabled this asymmetric tandem reaction to proceed with excellent stereoselectivity (complete diastereoselectivity and high enantioselectivity) and high yield under mild reaction conditions.

    28. Gold Catalysis

      A Highly Efficient Gold-Catalyzed Oxidative C[BOND]C Coupling from C[BOND]H Bonds Using Air as Oxidant (pages 1252–1255)

      Jin Xie, Huamin Li, Jiecong Zhou, Prof. Yixiang Cheng and Prof. Chengjian Zhu

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107605

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      A breath of fresh air: The title reaction has been developed for the coupling of amines with nitroalkanes and different unmodified ketones using air as the sole oxidant under mild reaction conditions. The safe, convenient, and environmentally benign process, as well as the low catalyst loading, short reaction time, and good yields make this protocol very practical (see scheme).

    29. Natural Products

      Isolation and Total Synthesis of Icumazoles and Noricumazoles—Antifungal Antibiotics and Cation-Channel Blockers from Sorangium cellulosum (pages 1256–1260)

      Jenny Barbier, Dr. Rolf Jansen, Dr. Herbert Irschik, Dr. Stefan Benson, Dr. Klaus Gerth, Bettina Böhlendorf, Prof. Dr. Gerhard Höfle, Prof. Dr. Hans Reichenbach, Jens Wegner, Dr. Carsten Zeilinger, Prof. Dr. Andreas Kirschning and Prof. Dr. Rolf Müller

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106435

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      Joint efforts: The antifungal icumazole A, the potassium-ion-channel inhibitor noricumazole A, and their glycosylated derivatives are new, structurally related secondary metabolites isolated from Sorangium cellulosum. Their structures have been fully assigned by a joint strategy that relied on spectroscopy, derivatization, fragmentation, and finally the first total synthesis of noricumazole A.

    30. Natural Product Synthesis

      Total Synthesis of (+)-Lactiflorin by an Intramolecular [2+2] Photocycloaddition (pages 1261–1264)

      Dr. Ping Lu and Prof. Dr. Thorsten Bach

      Article first published online: 21 DEC 2011 | DOI: 10.1002/anie.201106889

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      Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1[RIGHTWARDS ARROW]2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.

    31. C[BOND]H Bond Functionalization

      Aerobic Palladium(II)-Catalyzed 5-endo-trig Cyclization: An Entry into the Diastereoselective C-2 Alkenylation of Indoles with Tri- and Tetrasubstituted Double Bonds (pages 1265–1269)

      Sandeep R. Kandukuri, Dr. Julia A. Schiffner and Prof. Dr. Martin Oestreich

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201106927

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      Theendotrick: An endo ring closure onto the trigonal β carbon atom of α,β-unsaturated acceptors that are tethered to the indole nitrogen atom followed by amide cleavage enables the diastereoselective C-2 alkenylation of indoles with fully substituted double bonds. The carboxy group functions as a synthetically useful temporary tether (see scheme).

    32. Synthetic Methods

      Up the Hill: Selective Double-Bond Isomerization of Terminal 1,3-Dienes towards Z-1,3-Dienes or 2Z,4E-Dienes (pages 1270–1273)

      Dipl.-Chem. Florian Pünner, Dipl.-Chem. Anastasia Schmidt and Prof. Dr. Gerhard Hilt

      Article first published online: 15 DEC 2011 | DOI: 10.1002/anie.201107512

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      Against all odds: Two different cobalt catalyst systems led to the selective isomerization of 1,3-dienes. In the case of the [CoBr2(py-imine)]-catalyzed reaction, the Z-1,3-diene was formed in a highly selective manner (see scheme). When the catalyst precursor [CoBr2(dpppMe2)] was applied, a double-bond migration and selective isomerization towards the 2Z,4E-configured 2,4-dienes were observed

    33. Structural Biology

      Prediction of a Ligand-Binding Niche within a Human Olfactory Receptor by Combining Site-Directed Mutagenesis with Dynamic Homology Modeling (pages 1274–1278)

      Dr. Lian Gelis, Dr. Steffen Wolf, Prof. Dr. Hanns Hatt, Prof. Dr. Eva M. Neuhaus and Prof. Dr. Klaus Gerwert

      Article first published online: 5 DEC 2011 | DOI: 10.1002/anie.201103980

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      Reprogramming a smell receptor: The ligand-binding niche within a three-dimensional model of a human olfactory receptor has been predicted by dynamic homology modeling and confirmed experimentally by functional studies of site-directed receptor mutants. Even a proposed reprogramming of the receptor's binding and activation properties was experimentally confirmed.

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      Preview: Angew. Chem. Int. Ed. 6/2012 (page 1280)

      Article first published online: 24 JAN 2012 | DOI: 10.1002/anie.201290007

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