Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 8

February 20, 2012

Volume 51, Issue 8

Pages 1731–1976

  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. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Cover Picture: Dynamics and Multiple Stable Binding Modes of DNA Intercalators Revealed by Single-Molecule Force Spectroscopy (Angew. Chem. Int. Ed. 8/2012) (page 1731)

      Dr. D. Hern Paik and Prof. Thomas T. Perkins

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108162

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      Intercalation of YOYO a bisintercalating DNA dye, was studied by using single-molecule force spectroscopy. In their Communication on page 1811 ff., D. H. Paik and T. T. Perkins show that force-enhanced intercalation, traditionally ascribed to the dye in solution binding to the DNA, can occur from a reservoir of bound dye that remained out of equilibrium with the free dye for long periods of time (>2 hours). Hence, binding/unbinding and intercalation/de-intercalation are distinct processes that can occur on very different time scales.

  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. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Inside Cover: Molecular Engineering of Zinc Phthalocyanines with Phosphinic Acid Anchoring Groups (Angew. Chem. Int. Ed. 8/2012) (page 1732)

      Dr. Ismael López-Duarte, Dr. Mingkui Wang, Dr. Robin Humphry-Baker, Mine Ince, Dr. M. Victoria Martínez-Díaz, Prof. Mohammad K. Nazeeruddin, Prof. Tomás Torres and Prof. Michael Grätzel

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/anie.201200228

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      Zinc phthalocyanine sensitizers that contain phosphinic acid anchoring groups have an overall conversion efficiency of 3.24 % under 1 sun in a dye-sensitized solar cell (DSSC). M. K. Nazeeruddin, T. Torres, M. Grätzel, and co-workers demonstrate in their Communication on page 1895 ff. that the phosphinic acid groups provide a stronger binding affinity relative to carboxylic acid anchoring groups, which improves the durability of DSSCs.

  3. Inside Back Cover

    1. Top of page
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    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
    1. Inside Back Cover: Fine-tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine (Angew. Chem. Int. Ed. 8/2012) (page 1977)

      Pablo Martín-Gago, Dr. Marc Gomez-Caminals, Dr. Rosario Ramón, Prof. Xavier Verdaguer, Pau Martin-Malpartida, Eric Aragón, Dr. Jimena Fernández-Carneado, Dr. Berta Ponsati, Prof. Pilar López-Ruiz, Maria Alicia Cortes, Prof. Begoña Colás, Prof. Maria J. Macias and Prof. Antoni Riera

      Version of Record online: 5 JAN 2012 | DOI: 10.1002/anie.201108928

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      The π–π aromatic interactions between amino acids 6, 7, and 11 in the natural hormone somatostatin are crucial for conformational stability. In their Communication on page 1820 ff., M. J. Macias, A. Riera, and co-workers describe that peptidic analogues obtained by replacing each phenylalanine with mesitylalanine are conformationally more rigid than the parent hormone. This strategy has yielded the first 3D structures of 14-amino-acid somatostatin analogues.

  4. Back Cover

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    6. Editorial
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    8. Corrigendum
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    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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    1. Back Cover: Photoreversible Patterning of Biomolecules within Click-Based Hydrogels (Angew. Chem. Int. Ed. 8/2012) (page 1978)

      Dr. Cole A. DeForest and Prof. Kristi S. Anseth

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108165

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      Reversible biomolecular patterning in hydrogels can direct cell function in a user-defined manner. In their Communication on page 1816 ff., K. S. Anseth and C. A DeForest report 4D spatiotemporal control over the presentation of bioligands by using a thiol–ene photoconjugation reaction, which is initiated by visible light, combined with the photocleavage of an o-nitrobenzyl ether, which is controlled by UV light. This method allows cell functions to be probed dynamically.

  5. Editorial

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    8. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
    17. Preview
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  6. Graphical Abstract

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    5. Back Cover
    6. Editorial
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    8. Corrigendum
    9. News
    10. Author Profile
    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
    16. Communications
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  7. Corrigendum

    1. Top of page
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      Corrigendum: Editorial: Fundamental Research Needs Excellent Scientists and its Own Space (page 1750)

      Dr. Daniela Kneißl and Prof. Dr. Helmut Schwarz

      Version of Record online: 14 FEB 2012 | DOI: 10.1002/anie.201109227

      This article corrects:

      Editorial: Fundamental Research Needs Excellent Scientists and its Own Space1

      Vol. 50, Issue 52, 12370–12371, Version of Record online: 8 DEC 2011

  8. News

    1. Top of page
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    8. Corrigendum
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    11. News
    12. Book Review
    13. Highlights
    14. Minireview
    15. Review
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  9. Author Profile

    1. Top of page
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    4. Inside Back Cover
    5. Back Cover
    6. Editorial
    7. Graphical Abstract
    8. Corrigendum
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    12. Book Review
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    14. Minireview
    15. Review
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    1. Manfred Scheer (pages 1756–1757)

      Version of Record online: 10 JAN 2012 | DOI: 10.1002/anie.201107657

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      “If I could be anyone for a day, I would be Leonardo da Vinci. My favorite way to spend a holiday is to hike on an alpine ‘via ferrata’ …” This and more about Manfred Scheer can be found on page 1756.

  10. News

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    12. Book Review
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    14. Minireview
    15. Review
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  11. Book Review

    1. Top of page
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    1. Chemical Synthetic Biology. Edited by Pier Luigi Luisi and Cristiano Chiarabelli. (page 1759)

      Susanne Brakmann

      Version of Record online: 14 FEB 2012 | DOI: 10.1002/anie.201108847

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      John Wiley & Sons, Hoboken, 2011. 384 pp., hardcover, € 249.00.—ISBN 978-0470713976

  12. Highlights

    1. Top of page
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    6. Editorial
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    8. Corrigendum
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    1. Molecular Gels

      Flexible Optics: Recent Developments in Molecular Gels (pages 1760–1762)

      Prof. George John, Swapnil R. Jadhav, Prof. Vinod M. Menon and Prof. Vijay T. John

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201107167

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      Get smart: Organogels based on sugar ketals have been prepared with a unique combination of properties suitable for the development of flexible optical devices and potential applications as smart materials for the fabrication of microphotonic systems. Key features in the self-assembly of these gelators were conformational restrictions and interaction affinities.

    2. Palladium(II) Catalysis

      A New Direction in C[BOND]H Alkenylation: Silanol as a Helping Hand (pages 1763–1765)

      Marius Mewald, Dr. Julia A. Schiffner and Prof. Dr. Martin Oestreich

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201107859

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      Director's cut: Not only conventional alcohols but also silanols can act as directing groups in oxidative palladium(II)-catalyzed C[BOND]H alkenylations. The silicon-tethered hydroxy groups are “traceless”, thereby facilitating the regioselective C[BOND]H activation of toluene derivitives as well as phenols (see scheme).

  13. Minireview

    1. Top of page
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    1. Materials Science

      Self-Assembled Gelators for Organic Electronics (pages 1766–1776)

      Dr. Sukumaran Santhosh Babu, Seelam Prasanthkumar and Dr. Ayyappanpillai Ajayaghosh

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/anie.201106767

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      All gelled together: Solvent-assisted gelation of functional organic molecules leading to one-dimensional fibers is an area of great interest. Recent developments in molecular self-assembly-assisted gelation of π systems into soft functional materials and their potential application in organic electronic devices, such as organic field-effect transistors and organic solar cells, are reviewed (see picture).

  14. Review

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    1. Backbone Binding

      Enhancing Protein Backbone Binding—A Fruitful Concept for Combating Drug-Resistant HIV (pages 1778–1802)

      Dr. Arun K. Ghosh, David D. Anderson, Dr. Irene T. Weber and Dr. Hiroaki Mitsuya

      Version of Record online: 31 JAN 2012 | DOI: 10.1002/anie.201102762

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      Impeding the evolution of drug resistance: HIV protease inhibitors are critical to antiretroviral treatment regimens. However, the rapid onset of drug resistance limits the effectiveness of most approved inhibitors. The structure-based design of inhibitors targeting atoms in the protein backbone is an attractive strategy for maintaining drug efficacy. This approach limits the enzyme's ability to evolve resistance without sacrificing its catalytic activity.

  15. Communications

    1. Top of page
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    1. Alzheimer’s Therapeutics

      Inhibition of Beta-Amyloid Peptide Aggregation by Multifunctional Carbazole-Based Fluorophores (pages 1804–1810)

      Wanggui Yang, Yi Wong, Dr. Olivia T. W. Ng, Dr. Li-Ping Bai, Prof. Daniel W. J. Kwong, Prof. Ya Ke, Prof. Zhi-Hong Jiang, Prof. Hung-Wing Li, Prof. Ken K. L. Yung and Prof. Man Shing Wong

      Version of Record online: 15 NOV 2011 | DOI: 10.1002/anie.201104150

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      Stopping aggregation: Carbazole-based cyanine fluorophores bind selectively to the Aβ(1–40) peptide and its aggregates which are responsible for causing Alzheimer's disease. One of these fluorophores, SLOH, exerts a strong inhibitory effect on Aβ(1–40) fibrillogenesis (see scheme) and can pass through the blood-brain barrier making it a potential therapeutic agent for Alzheimer's disease.

    2. DNA Intercalation

      Dynamics and Multiple Stable Binding Modes of DNA Intercalators Revealed by Single-Molecule Force Spectroscopy (pages 1811–1815)

      Dr. D. Hern Paik and Prof. Thomas T. Perkins

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/anie.201105540

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      Lights off, but someone is home: Single-molecule force spectroscopy was used to investigate DNA intercalation in the presence and absence of unbound dye (see picture). Force-induced intercalation, traditionally ascribed to dye from solution binding to the DNA, occured approximately two hours after the removal of the free dye. The results show that binding/unbinding and intercalation/deintercalation are distinct processes that occur on very different time scales.

    3. Hydrogels

      You have full text access to this OnlineOpen article
      Photoreversible Patterning of Biomolecules within Click-Based Hydrogels (pages 1816–1819)

      Dr. Cole A. DeForest and Prof. Kristi S. Anseth

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201106463

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      Lighting the way: Biochemical cues have been reversibly patterned into hydrogels with full spatiotemporal control by using two photochemical reactions. The hydrogel is conjugated with a peptide by a thiol-ene photoaddition reaction that is initiated by visible light. Subsequent, selective photocleavage of an o-nitrobenzyl ether with UV light enables dynamic presentation of the peptide to cells with control in three dimensions.

    4. Noncovalent Interactions

      Fine-tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine (pages 1820–1825)

      Pablo Martín-Gago, Dr. Marc Gomez-Caminals, Dr. Rosario Ramón, Prof. Xavier Verdaguer, Pau Martin-Malpartida, Eric Aragón, Dr. Jimena Fernández-Carneado, Dr. Berta Ponsati, Prof. Pilar López-Ruiz, Maria Alicia Cortes, Prof. Begoña Colás, Prof. Maria J. Macias and Prof. Antoni Riera

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/anie.201106406

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      Going through the motions: Somatostatin analogues having greater conformational rigidity than somatostatin have been prepared by substituting Phe residues in the native sequence with mesityl alanine (Msa; see structure). The analogues show high affinity for SSTR receptors, thus showing that fine-tuning of noncovalent interactions between amino acid side chains can modulate peptide affinity and selectivity.

    5. CO2 Capture Materials

      Competition and Cooperativity in Carbon Dioxide Sorption by Amine-Functionalized Metal–Organic Frameworks (pages 1826–1829)

      Dr. Ramanathan Vaidhyanathan, Dr. Simon S. Iremonger, Prof. George K. H. Shimizu, Peter G. Boyd, Dr. Saman Alavi and Prof. Tom K. Woo

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201105109

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      Molecular insights into the roles of amine functionalization and cooperative CO2 interactions into enhancing (and diminishing) CO2 binding by metal-organic frameworks are shown both experimentally and computationally. Contrary to popular thinking, higher amination decreases CO2 binding in this system. This loss is compensated by cooperativity between CO2 triads that enhances binding by over 7 kJ mol−1.

    6. Bionanotechnology

      Graphene Oxide Nanoparticles as a Nonbleaching Optical Probe for Two-Photon Luminescence Imaging and Cell Therapy (pages 1830–1834)

      Dr. Jing-Liang Li, Dr. Hong-Chun Bao, Xue-Liang Hou, Lu Sun, Prof. Xun-Gai Wang and Prof. Min Gu

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201106102

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      Lasting glow: Under femtosecond laser irradiation, graphene oxide nanoparticles (GONs) give strong two-photon luminescence (TPL; see picture). The presence of GONs also induces microbubbling, which causes cell death at an order of magnitude lower laser power than when cells are not labeled. The results show that GONs can be used for TPL-based imaging and photothermal cancer therapy.

    7. Protein Modifications

      Conversion of Cysteine into Dehydroalanine Enables Access to Synthetic Histones Bearing Diverse Post-Translational Modifications (pages 1835–1839)

      Justin M. Chalker, Lukas Lercher, Dr. Nathan R. Rose, Prof. Christopher J. Schofield and Prof. Benjamin G. Davis

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201106432

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      Six for the price of one: From a single precursor, dehydroalanine, six distinct post-translational modifications can be site-selectively installed on histone proteins (see figure), including the first site-selective phosphorylation and glycosylation of histones. Direct observation of histone deacetylase activity on a full-length modified histone as well as its interactions with both chromatin reader and writer/eraser proteins are reported.

    8. Caged Compounds

      Water-Soluble, Donor–Acceptor Biphenyl Derivatives in the 2-(o-Nitrophenyl)propyl Series: Highly Efficient Two-Photon Uncaging of the Neurotransmitter γ-Aminobutyric Acid at λ=800 nm (pages 1840–1843)

      Loïc Donato, Dr. Alexandre Mourot, Dr. Christopher M. Davenport, Dr. Cyril Herbivo, David Warther, Dr. Jérémie Léonard, Dr. Frédéric Bolze, Prof. Dr. Jean-François Nicoud, Prof. Dr. Richard H. Kramer, Prof. Dr. Maurice Goeldner and Dr. Alexandre Specht

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/anie.201106559

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      Rattling the cage: The two γ-aminobutyric acid (GABA) derivatives 1 and 2 exhibit efficient and rapid (<5×10−6 s) GABA photorelease upon one-photon excitation combined with two-photon uncaging cross-section at λ=800 nm. Compounds 1 and 2 were successfully used for two-photon GABA release in intact brain tissue, thus offering attractive perspectives in chemical neurosciences.

    9. Supramolecular Chemistry

      Self-Assembly of Amphiphilic Molecules in Droplet Compartments: An Approach Toward Discrete Submicrometer-Sized One-Dimensional Structures (pages 1844–1848)

      Prof. Munenori Numata, Daiki Kinoshita, Nobuko Taniguchi, Prof. Hitoshi Tamiaki and Prof. Akio Ohta

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/anie.201106632

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      Self-assembly in a droplet: A supramolecular system that governs self-assembly events over hierarchies from the nano- to the micrometer range has been developed by combining a bottom-up strategy based on molecular programming with top-down droplet microscience. Discrete 1D tubular structures were created by exploiting the compartment effect of the droplet, induced during dynamic shrinking under non-equilibrium conditions (see picture).

    10. Surface Modification

      Surface Modification by Electrostatic Self-Assembly Followed by Covalent Fixation (pages 1849–1852)

      Dr. Marcus Foston, Dr. Christopher Hubbell, Doh-Yeon Park, Prof. Fred Cook, Prof. Yasuyuki Tezuka and Prof. Haskell W. Beckham

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201106968

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      Sticks and bonds: Surface-modifying agents can be functionalized with ionic groups that enable high exhaustion from a processing bath through electrostatic self-assembly. Using cyclic oniums as the ionic functional groups, thermally induced ring-opening converts the ionic bonds to covalent bonds, thus lending permanency to the modification of the surface.

    11. Lithium Batteries

      Double-Structured LiMn0.85Fe0.15PO4 Coordinated with LiFePO4 for Rechargeable Lithium Batteries (pages 1853–1856)

      Seung-Min Oh, Prof. Seung-Taek Myung, Jin Bum Park, Prof. Bruno Scrosati, Dr. Khalil Amine and Prof. Yang-Kook Sun

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201107394

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      A new coat: LiMn1−xFexPO4 materials with a LiFePO4 outer layer of varying thickness and a LiMn0.85Fe0.15PO4 bulk were prepared. The physical characteristics such as tap density, porosity, and spherical morphology were fine-tuned. The double-structured micron-sized LiMn0.85Fe0.15PO4/LiFePO4 material (see picture) shows properties which make this material an ideal candidate for rechargeable lithium batteries.

    12. Metal-Organic Frameworks

      High Propene/Propane Selectivity in Isostructural Metal–Organic Frameworks with High Densities of Open Metal Sites (pages 1857–1860)

      Prof. Youn-Sang Bae, Dr. Chang Yeon Lee, Dr. Ki Chul Kim, Prof. Omar K. Farha, Dr. Peter Nickias, Prof. Joseph T. Hupp, Prof. SonBinh T. Nguyen and Prof. Randall Q. Snurr

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201107534

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      Two go in, one comes out: A series of isostructural M-MOF-74 materials (M=Co, Mn, and Mg) with high densities of open metal sites have been examined for the selective adsorption of propene over propane. Co-MOF-74 exhibits the highest thermodynamic C3H6/C3H8 selectivity (ca. 45) reported for any MOF to date.

    13. Multicopper Oxidases

      An O-Centered Structure of the Trinuclear Copper Center in the Cys500Ser/Glu506Gln Mutant of CueO and Structural Changes in Low to High X-Ray Dose Conditions (pages 1861–1864)

      Prof. Hirofumi Komori, Ryosuke Sugiyama, Prof. Kunishige Kataoka, Prof. Yoshiki Higuchi and Prof. Takeshi Sakurai

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201107739

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      Right on CueO: The O-centered structure of the trinuclear copper center in a multicopper oxidase (CueO) was shown to be an intermediate of the four-electron reduction of dioxygen (see picture). This structure was determined by in situ data collection of X-ray diffractions and copper K-edge spectra at low to high X-ray dose conditions.

    14. β-Lactam Antibiotics

      Ratiometric Fluorescence Detection of Pathogenic Bacteria Resistant to Broad-Spectrum β-Lactam Antibiotics (pages 1865–1868)

      Dr. Junxiang Zhang, Yang Shen, Sarah L. May, Prof. Daniel C. Nelson and Prof. Shuwei Li

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201107810

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      Identification of bacteria: A methoxyimino cephalosporin derivative containing a pair of fluorescence resonance energy transfer (FRET) fluorophores was synthesized. This probe displays selective cleavage toward different types of β-lactamases, thereby providing a rapid assay to distinguish bacterial cells that are either sensitive or resistant to broad-spectrum β-lactam antibiotics (see picture).

    15. Actinides

      Curium(III) Borate Shows Coordination Environments of Both Plutonium(III) and Americium(III) Borates (pages 1869–1872)

      Matthew J. Polinski, Shuao Wang, Prof. Dr. Evgeny V. Alekseev, Prof. Dr. Wulf Depmeier, Dr. Guokui Liu, Dr. Richard G. Haire and Prof. Dr. Thomas E. Albrecht-Schmitt

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201107956

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      The two faces of curium: The first curium borate has been prepared showing a complex structure with coordination environments for CmIII that are found in both PuIII and AmIII borates (see picture). Time-resolved laser-induced photoluminescence studies as well as X-ray diffraction experiments show two distinct CmIII sites with different coordination environments.

    16. Lithium Diazenide

      High-Pressure Synthesis and Characterization of the Alkali Diazenide Li2N2 (pages 1873–1875)

      Sebastian B. Schneider, Rainer Frankovsky and Prof. Dr. Wolfgang Schnick

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201108252

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      Diazenide surprise: The synthesis of an alkali diazenide, Li2N2, is presented. Lithium diazenide adopts an unprecedented structure type for compounds with A2B2 composition (see picture). Spectroscopic analysis shows a significant feature at 1328 cm−1 which is assigned to the stretching vibration of the [N2]2− ion. Electronic structure calculations underline the metallic character and confirm the 50 % occupation of the antibonding π states in [N2]2−.

    17. Halogen Bonding

      A Halogen-Bonding Catenane for Anion Recognition and Sensing (pages 1876–1880)

      Dr. Antonio Caballero, Dr. Fabiola Zapata, Nicholas G. White, Dr. Paulo J. Costa, Prof. Vítor Félix and Prof. Paul D. Beer

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201108404

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      The anion-templated synthesis of a halogen-bonding catenane, which recognizes chloride and bromide ions solely by halogen bonding, is described. The catenane's ability to optically sense halide anions using fluorescence spectroscopy is demonstrated.

    18. Host–Guest Systems

      Transformative Binding and Release of Gold Guests from a Self-Assembled Cu8L4 Tube (pages 1881–1884)

      Wenjing Meng, Dr. Jack K. Clegg and Dr. Jonathan R. Nitschke

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201108450

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      Totally tubular: A linear M8L48+ receptor, which binds tightly and selectively to the dicyanoaurate anion, was assembled from simple organic subcomponents and copper(I) ions. The guest complex is not bound unchanged, but instead is transformed into a longer linear complex where two dicyanogold units are bridged by a central cation of copper/silver (see scheme). This complex optimally fills the cavity of the receptor but is not observed in the absence of the host.

    19. Covalent Organic Frameworks

      Internal Functionalization of Three-Dimensional Covalent Organic Frameworks (pages 1885–1889)

      David N. Bunck and Prof. Dr. William R. Dichtel

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201108462

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      Thinking inside the COF: Internally functionalized, boroxine-linked, three-dimensional, covalent organic frameworks (COFs) can be synthesized by co-crystallizing a truncated, trifunctional monomer with the parent tetrafunctional building block. The functionalized COFs possess accessible functional groups and a distinct interior microenvironment. In the picture the orange sphere corresponds to an alkyl chain or an allyl group in the pore interior.

    20. Peptide Design

      Bio-Inspired Design and Potential Biomedical Applications of a Novel Class of High-Affinity Peptides (pages 1890–1894)

      Sunghyun Kim, Daejin Kim, Hyun Ho Jung, In-Hyun Lee, Prof. Jae IL Kim, Prof. Jeong-Yong Suh and Prof. Sangyong Jon

      Version of Record online: 24 JAN 2012 | DOI: 10.1002/anie.201107894

      Thumbnail image of graphical abstract

      Two arms to hold: Inspired by the structure of basic leucine-zipper proteins, high-affinity peptides, named aptides, were designed that contain a stabilizing scaffold (tryptophan zipper) and two target-binding regions (orange and blue in picture). A fluorescently labeled aptide that binds to a tumor-specific protein was used for fluorescence imaging in vivo.

    21. Photosensitizers

      Molecular Engineering of Zinc Phthalocyanines with Phosphinic Acid Anchoring Groups (pages 1895–1898)

      Dr. Ismael López-Duarte, Dr. Mingkui Wang, Dr. Robin Humphry-Baker, Mine Ince, Dr. M. Victoria Martínez-Díaz, Prof. Mohammad K. Nazeeruddin, Prof. Tomás Torres and Prof. Michael Grätzel

      Version of Record online: 9 NOV 2011 | DOI: 10.1002/anie.201105950

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      Anchors away! Two zinc phthalocyanine photosensitizers with different phosphinic acid anchor groups were synthesized (see scheme). Solar cells sensitized with these compounds have a short-circuit photocurrent density of 7.6±0.2 mA cm−2, an open-circuit voltage of 559±30 mV, and a fill factor of 0.76±0.03, which corresponds to an overall conversion efficiency of 3.24 % under 1 sun.

    22. Organocatalysis

      The Direct Asymmetric α Alkylation of Ketones by Brønsted Acid Catalysis (pages 1899–1902)

      Liu Song, Prof. Qi-Xiang Guo, Xing-Cheng Li, Juan Tian and Prof. Yun-Gui Peng

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/anie.201106275

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      Being direct: A Brønsted acid catalyzed α alkylation of ketones is described. The phosphoric acid 1 promotes this reaction to afford the desired products with high yields, high diastereoselectivities, and good to excellent enantioselectivites.

    23. Protein-Based Force Probe

      A Nanoscale Force Probe for Gauging Intermolecular Interactions (pages 1903–1906)

      Dr. Minkyu Kim, Dr. Chien-Chung Wang, Fabrizio Benedetti and Prof. Piotr E. Marszalek

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201107210

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      Into low force regime: A universal molecular force probe for measuring by AFM the strength of receptor–ligand and protein–protein complexes was developed. The protein-based force probe has the sensitivity on the order of piconewtons and provides a single-molecule fingerprint for identifying mechanical rupture events of individual complexes (see picture).

    24. Water Splitting

      A Porphyrin-Doped Polymer Catalyzes Selective, Light-Assisted Water Oxidation in Seawater (pages 1907–1910)

      Dr. Jun Chen, Dr. Pawel Wagner, Lei Tong, Prof. Dr. Gordon G. Wallace, Prof. Dr. David L. Officer and Prof. Dr. Gerhard F. Swiegers

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/anie.201107355

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      A flexible polymer for selective seawater splitting: Incorporation of a monomeric Mn-porphyrin that is normally catalytically inactive, into a flexible poly(terthiophene) film yields a remarkable light-assisted water oxidation catalyst with an apparent overpotential for water oxidation of a mere 0.09 V. The catalyst generates exclusively O2 and no Cl2 in seawater at 0.9 V versus Ag/AgCl.

    25. C[BOND]C Cleavage

      Facile Access to Chiral Ketones through Metal-Free Oxidative C[BOND]C Bond Cleavage of Aldehydes by O2 (pages 1911–1914)

      Dr. Bhoopendra Tiwari, Dr. Junmin Zhang and Prof. Dr. Yonggui Robin Chi

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201107473

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      Giving the metal the boot: The title reaction provides facile access to functionalized chiral ketones from chiral α,α′-disubstituted aldehydes in the presence of molecular oxygen (see scheme). The C[BOND]C bond-cleavage approach offers an alternative or better method relative to the typical bond-forming strategies used in synthesizing chiral ketones.

    26. Homogeneous Catalysis

      Rapid Access to Chroman-3-ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers (pages 1915–1918)

      Yanzhao Wang, Dr. Kegong Ji, Sylvester Lan and Prof. Dr. Liming Zhang

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201107561

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      The two-step: Chroman-3-ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold-catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme).

    27. Biomimetic Chemistry

      Reversible Protonation of a Thiolate Ligand in an [Fe]-Hydrogenase Model Complex (pages 1919–1921)

      Dr. Dafa Chen, Dr. Rosario Scopelliti and Prof. Dr. Xile Hu

      Version of Record online: 10 JAN 2012 | DOI: 10.1002/anie.201107634

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      What is the channel? The thiolate ligand in the five-coordinate model complex 1 of [Fe]-hydrogenase is preferentially and reversibly protonated, even in the presence of an acyl ligand. The results suggest that the Cys176 thiolate ligand in [Fe]-hydrogenase can serve as the internal base to accept the proton after heterolytic splitting of H2.

    28. Asymmetric Catalysis

      Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents (pages 1922–1925)

      Dr. Martín Fañanás-Mastral, Dr. Manuel Pérez, Pieter H. Bos, Dr. Alena Rudolph, Dr. Syuzanna R. Harutyunyan and Prof. Dr. Ben L. Feringa

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/anie.201107840

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      An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.

    29. C[BOND]H Functionalization

      Combined Oxypalladation/C[BOND]H Functionalization: Palladium(II)-Catalyzed Intramolecular Oxidative Oxyarylation of Hydroxyalkenes (pages 1926–1929)

      Rong Zhu and Prof. Dr. Stephen L. Buchwald

      Version of Record online: 11 JAN 2012 | DOI: 10.1002/anie.201108129

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      An efficient protocol has been developed for the intramolecular oxidative oxyarylation using a PdII-catalyzed tandem oxypalladation/C[BOND]H functionalization strategy. This methodology allows rapid access to tetrahydro-2H-indeno-[2,1-b]furan frameworks from simple hydroxyalkenes. The reactivity of this process is orthogonal to that of Pd0-catalyzed transformations, enabling the divergent modification of a single molecule.

    30. Cluster Compounds

      A Hydrocarbon-Soluble Lithium Hydride Complex (pages 1930–1933)

      Dr. Andreas Stasch

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201108134

      Thumbnail image of graphical abstract

      LiH-ghtweight: The title complex having a central (LiH)4 cube has been prepared and structurally characterized (see picture). The compound is stable towards LiH elimination at room temperature in solution, and can be employed for hydrolithiation reactivity as has been demonstrated by its reaction with benzophenone.

    31. C(sp3)[BOND]Si Activation

      Palladium-Catalyzed Intermolecular Coupling of 2-Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene-Fused Siloles by Catalytic Cleavage of the C(sp3)[BOND]Si Bond (pages 1934–1937)

      Dr. Yun Liang, Weizhi Geng, Junnian Wei and Prof. Dr. Zhenfeng Xi

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201108154

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      Unusual split: A wide variety of benzosiloles and derivatives are obtained by the Pd-catalyzed intermolecular coupling of 2-silylaryl bromides and alkynes and the accompanying selective cleavage of the C(sp3)[BOND]Si bonds as a key step (see scheme). The product spectrum includes benzosiloles, benzothiophene-fused siloles, ladder-type π-conjugated benzosiloles, and thiophene-bridged 2,5-bisbenzosiloles.

    32. Synthetic Methods

      Efficient Synthesis of Thiopyrans Using a Sulfur-Enabled Anionic Cascade (pages 1938–1941)

      Fang Li, David Calabrese, Matthew Brichacek, Ivy Lin and Prof. Jon T. Njardarson

      Version of Record online: 10 JAN 2012 | DOI: 10.1002/anie.201108261

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      The fifth element: An efficient new synthetic method for accessing 3,6-dihydro-2H-thiopyrans 1 in one pot has been developed. This method employs an anionic cascade, which is triggered by the addition of a vinyl nucleophile to a carbonyl group followed by S to O thiophosphate migration and an intramolecular thiolate displacement. The scope is demonstrated for a range of ketone and ester substrates.

    33. Rapid and Stereochemically Flexible Synthesis of Polypropionates: Super-Silyl-Governed Aldol Cascades (pages 1942–1946)

      Patrick B. Brady and Prof. Dr. Hisashi Yamamoto

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201108325

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      Polypropionates made EZ: The E/Z geometry of tris(trimethylsilyl)silyl super silyl enol ethers derived from propionaldehyde controls diastereoselectivity in the aldehyde crossed-aldol reaction. These silyl enol ethers can participate in polyaldol cascade reactions, thus allowing the one-pot synthesis of four different dipropionate stereotetrads (see scheme), and polyketides bearing up to five contiguous stereocenters.

    34. Biocatalysis

      ATP-Independent Formation of Hydrocarbons Catalyzed by Isolated Nitrogenase Cofactors (pages 1947–1949)

      Chi Chung Lee, Dr. Yilin Hu and Prof. Dr. Markus W. Ribbe

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201108916

      Thumbnail image of graphical abstract

      Reduce to produce: Molybdenum- and vanadium-nitrogenase cofactors have been isolated and shown to reduce carbon monoxide and cyanide ions to a mixture of alkanes and alkenes in the presence of a strong reductant, europium(II) diethylenetriaminepentaacetate (see scheme). Various hydrocarbons of up to seven carbon atoms in length are detected as products in these ATP-free reactions.

    35. Redox Reactions

      Intramolecular Redox-Triggered C[BOND]H Functionalization (pages 1950–1953)

      Dr. Igor D. Jurberg, Dr. Bo Peng, Eckhard Wöstefeld, Maximilian Wasserloos and Dr. Nuno Maulide

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/anie.201108639

      Thumbnail image of graphical abstract

      Sacrifice for the team: A one-pot method achieves remote functionalization at the α-position of an amine moiety through the sacrificial reduction of a neighboring group. The process takes advantage of an intramolecular redox reaction, thereby avoiding the need for any external oxidants. This method was applied to a concise five-step total synthesis of indolizidine 167B.

    36. Phosphorus Heterocycles

      The 1,1-Carboboration of Bis(alkynyl)phosphanes as a Route to Phosphole Compounds (pages 1954–1957)

      Juri Möbus, Quentin Bonnin, Kirika Ueda, Dr. Roland Fröhlich, Prof. Kenichiro Itami, Dr. Gerald Kehr and Gerhard Erker

      Version of Record online: 13 JAN 2012 | DOI: 10.1002/anie.201107398

      Thumbnail image of graphical abstract

      Neat and tidy: B(C6F5)3 efficiently converts a series of bis(alkynyl)phosphanes into highly substituted 3-borylphospholes through a twofold 1,1-carboboration reaction sequence. The boron substituted phospholes were also used as substrates in Suzuki–Miyaura type cross-coupling reactions (see scheme).

    37. Heterocycle Synthesis

      Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers (pages 1958–1961)

      M. Sc. Thomas Kunz and Prof. Dr. Paul Knochel

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201106734

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      Highly functional: A copper(I)-catalyzed intramolecular carbomagnesiation under mild conditions transforms readily available alkynyl(aryl)thioethers into magnesiated benzothiophenes. Subsequent reaction with various electrophiles (acid chlorides, allyl bromides, aryl halides) provides polyfunctional benzo[b]thiophenes (see scheme). Further modification of the cyclization products affords highly diversified benzothiophene derivatives and new heterocyclic scaffolds.

    38. Zeolites

      Assemblies of Mesoporous FAU-Type Zeolite Nanosheets (pages 1962–1965)

      Alexandra Inayat, Dr. Isabel Knoke, Prof. Erdmann Spiecker and Prof. Wilhelm Schwieger

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201105738

      Thumbnail image of graphical abstract

      Holey sheets: Nanosheet assemblies of FAU-type zeolite X with intracrystalline mesopores are prepared (see picture). This material is synthesized by soft-templating and combines micro, meso, and macropores in a hierarchically interconnected manner.

    39. Thiolate Dynamics on Surfaces

      Thiolate-Induced Metal Adatom Trapping at Solid–Liquid Interfaces (pages 1966–1969)

      Dr. Yaw-Chia Yang, Andriy Taranovskyy and Prof. Olaf M. Magnussen

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201106584

      Thumbnail image of graphical abstract

      Dynamic trapping: Scanning tunneling microscopy video imaging of methyl thiolates on copper surfaces reveal the formation of defined metastable dimers with fluctuations on subsecond timescales, indicating short-term trapping of copper surface atoms (see picture). This transient stabilization of metal adatoms has important implications for applications of organosulfur species as additives and in nanoscience.

    40. Halogen Azides

      Solid-State Structure of Bromine Azide (pages 1970–1974)

      Benjamin Lyhs, Dieter Bläser, Dr. Christoph Wölper, Prof. Stephan Schulz and Prof. Georg Jansen

      Version of Record online: 16 JAN 2012 | DOI: 10.1002/anie.201108092

      Thumbnail image of graphical abstract

      A new twist: The single-crystal structural analysis of BrN3 is described. In contrast to IN3, which forms chains, BrN3 forms a helical structure in the solid state (see picture). Such a structural feature has not been previously observed in covalent p-block azide chemistry.

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