Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 44

October 25, 2010

Volume 49, Issue 44

Pages 8047–8275

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Unprecedented Molecular Architectures by the Controlled Self-Assembly of a β-Peptide Foldamer (Angew. Chem. Int. Ed. 44/2010) (page 8047)

      Sunbum Kwon, Aram Jeon, Sung Hyun Yoo, Dr. Im Sik Chung and Prof. Hee-Seung Lee

      Version of Record online: 26 AUG 2010 | DOI: 10.1002/anie.201004587

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      Windmill-shaped architectures and square rods were formed by the self-assembly of a short helical β peptide in aqueous solution. In their Communication on page 8232 ff., H.-S. Lee and co-workers show how the self-assembly of these exceptional 3D shapes and their intermediate states could be guided and controlled by the addition of a surfactant.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Enantioselective Synthesis of Amines: General, Efficient Iron-Catalyzed Asymmetric Transfer Hydrogenation of Imines (Angew. Chem. Int. Ed. 44/2010) (page 8048)

      Shaolin Zhou, Steffen Fleischer, Dr. Kathrin Junge, Shoubhik Das, Daniele Addis and Prof. Dr. Matthias Beller

      Version of Record online: 3 AUG 2010 | DOI: 10.1002/anie.201004297

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      Although iron is one of the most abundant metals, its application to catalysis is still in its infancy. In their Communication on page 8121 ff., M. Beller and co-workers present the first iron-catalyzed asymmetric transfer hydrogenation of imines. Iron carbonyl complexes in the presence of a tetradentate P2N2 ligand catalyze the reduction of N-diphenylphosphinylimines with high enantioselectivity (99 %) and good yields (98 %).

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
  5. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Helmut Werner (pages 8070–8072)

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201004903

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      “My favorite subject at school was mathematics. My first experiment which I did together with a friend at the age of 11 was an oxyhydrogen gas explosion …” This and more about Helmut Werner can be found on page 8070.

  6. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Electrochemistry of Functional Supramolecular Systems. Edited by Paola Ceroni, Alberto Credi and Margherita Venturi. (pages 8073–8074)

      Anthony Harriman

      Version of Record online: 6 OCT 2010 | DOI: 10.1002/anie.201005968

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      John Wiley & Sons, Hoboken 2010. 598 pp., hardcover € 132.00.—ISBN 978-0470255575

  7. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Biological Materials Chemistry

      The Iron-Fortified Adhesive System of Marine Mussels (pages 8076–8078)

      Prof. Jonathan J. Wilker

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003171

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      Sticky business: Marine mussels (see picture) affix themselves to rocks with a system of threads and adhesive plaques. Emerging results are showing that iron–protein interactions help mussels stick by playing two roles: initiating material formation and enhancing mechanical performance.

    2. Enantioselective Catalysis

      A Bimetallic Titanium Catalyst for the Enantioselective Cyanation of Aldehydes Based on Cooperative Catalysis (pages 8079–8081)

      Prof. Michael North

      Version of Record online: 31 AUG 2010 | DOI: 10.1002/anie.201003014

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      Joined at the hip: By linking two salen ligands together with a strap of appropriate size and shape, the effectiveness of a bimetallic titanium(salen) complex as a catalyst for asymmetric cyanohydrin synthesis can be increased by up to two orders of magnitude. The optimal catalyst is active at a catalyst loading as low as 0.0005 mol % and will accept both trimethylsilyl cyanide and sodium cyanide/acetic anhydride as the cyanide source (see scheme).

  8. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Small Focused Libraries

      Factors Determining the Selection of Organic Reactions by Medicinal Chemists and the Use of These Reactions in Arrays (Small Focused Libraries) (pages 8082–8091)

      Tony W. J. Cooper, Ian B. Campbell and Dr. Simon J. F. Macdonald

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201002238

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      Helping chemists help chemists: What reactions do medicinal chemists use in drug discovery? (The pie chart shows a snapshot from one unit at GlaxoSmith-Kline.) What criteria do they use to select synthetic methodology? Why are arrays (small focused libraries) so powerful in the lead-optimization process? These questions are considered in this Minireview, which also describes attempts to expand the number of robust reactions available to medicinal chemists.

  9. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. The Ozone Layer

      Climate Change and Atmospheric Chemistry: How Will the Stratospheric Ozone Layer Develop? (pages 8092–8102)

      Prof. Dr. Martin Dameris

      Version of Record online: 4 OCT 2010 | DOI: 10.1002/anie.201001643

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      Since the industrial revolution began about 150 years ago, the concentration of greenhouse gases such as CO2 in the atmosphere has increased dramatically, with corresponding consequences for the climate. For over 25 years, destruction of the ozone layer (pink and green regions on the globe), which is caused by chlorofluorocarbons, has also been observed. The future development of the ozone layer and of the climate are closely related to each other.

  10. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Review
    8. Highlights
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Nanoparticles

      Photoswitchable Nanoassemblies by Electrostatic Self-Assembly (pages 8104–8108)

      Immanuel Willerich and Prof. Dr. Franziska Gröhn

      Version of Record online: 26 AUG 2010 | DOI: 10.1002/anie.201003271

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      Light controls size: A novel type of self-organized supramolecular nanoparticles can change their size upon irradiation with UV light (see picture). The doubly responsive system combines a light-triggered size with a pH-induced switching between nanoscale aggregates and molecular building blocks. The nano-objects form by a combination of ionic and π–π interactions between macro-ions and dye ions.

    2. Synthetic Methods

      An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes (pages 8109–8111)

      Dr. Álvaro Iglesias, Dr. Edwin G. Pérez and Prof. Dr. Kilian Muñiz

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201003653

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      Adding 2Ns: Palladium catalysis introduces two nitrogen groups in a new regio and chemoselective diamination of non-activated alkenes that proceeds under entirely intermolecular reaction control. This palladium-catalyzed reaction employs commercial nitrogen sources in combination with a hypervalent iodo(III) reagent as oxidant (see scheme; Tos=toluenesulfonyl).

    3. Enzymatic C[BOND]H Activation

      Intermediates in the Catalytic Cycle of Methyl Coenzyme M Reductase: Isotope Exchange is Consistent with Formation of a σ-Alkane–Nickel Complex (pages 8112–8115)

      Silvan Scheller, Dr. Meike Goenrich, Dr. Stefan Mayr, Prof. Rudolf K. Thauer and Prof. Bernhard Jaun

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201003214

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      The key nickel enzyme for methanogenesis (MCR) catalyzes the formation of CH3D and CH2D2 in a deuterated medium. CH2D2 is formed by an exchange of deuterium into the S-methyl group of the substrate. Deuterium is incorporated at both carbon atoms of the S-ethyl group of ethyl coenzyme M, and a 13C label is rapidly scrambled within the ethyl group (see scheme). Thus, at least one intermediate is formed and the isotope exchange pattern is consistent with formation of a σ-alkane–nickel complex.

    4. Enzyme Reactions in Microparticles

      Enzyme Reaction in the Pores of CaCO3 Particles upon Ultrasound Disruption of Attached Substrate-Filled Liposomes (pages 8116–8120)

      Dr. Alexey M. Yashchenok, Dr. Mihaela Delcea, Kristina Videnova, Prof. Elizabeth A. Jares-Erijman, Dr. Thomas M. Jovin, Dr. Manfred Konrad, Prof. Helmuth Möhwald and Dr. Andre G. Skirtach

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201003244

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      Breaking out: Liposomes that are adsorbed onto porous CaCO3 particles and that contain the peroxidase substrate Amplex Red (AR) are disrupted by ultrasonic treatment. The substrate is released and diffuses into the inner part of the multicompartment containers where the peroxidase enzyme is found, and the enzymatic reaction is triggered. This approach may be useful for the simultaneous delivery of multiple molecules into cells.

    5. Iron Catalysis

      Enantioselective Synthesis of Amines: General, Efficient Iron-Catalyzed Asymmetric Transfer Hydrogenation of Imines (pages 8121–8125)

      Shaolin Zhou, Steffen Fleischer, Dr. Kathrin Junge, Shoubhik Das, Daniele Addis and Prof. Dr. Matthias Beller

      Version of Record online: 19 JUL 2010 | DOI: 10.1002/anie.201002456

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      In the iron age: A readily accessible, active iron catalyst serves in the straightforward, catalytic transfer hydrogenation of imines (see scheme). A series of imines are converted into chiral amines in high yields and very good enantioselectivities. This method should find broad application in the search for bioactive chiral amines.

    6. Amination

      An Efficient and General Synthesis of Primary Amines by Ruthenium-Catalyzed Amination of Secondary Alcohols with Ammonia (pages 8126–8129)

      Sebastian Imm, Sebastian Bähn, Lorenz Neubert, Dr. Helfried Neumann and Prof. Dr. Matthias Beller

      Version of Record online: 2 AUG 2010 | DOI: 10.1002/anie.201002576

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      Atom efficiency and selectivity are the key features of the first homogeneously catalyzed amination of secondary alcohols with ammonia to give the corresponding primary amines (see scheme). This novel amination method relies on the commercially available catalyst [Ru3(CO)12]/cataCXium PCy and does not require any additional source of hydrogen.

    7. Direct Amination of Secondary Alcohols Using Ammonia (pages 8130–8133)

      Dennis Pingen, Dr. Christian Müller and Prof. Dr. Dieter Vogt

      Version of Record online: 29 JUL 2010 | DOI: 10.1002/anie.201002583

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      Hydrogen shuttle: For the first time secondary alcohols and ammonia can be directly converted into primary amines with a selectivity of up to 99 % by using a simple ruthenium/phosphine catalyst (see scheme; R1, R2= alkyl, aryl, alkenyl; M=[Ru3(CO)12]; and L=phosphine ligand).

    8. Gold Catalysis

      One-Pot Synthesis of Menthol Catalyzed by a Highly Diastereoselective Au/MgF2 Catalyst (pages 8134–8138)

      Dipl.-Chem. Alina Negoi, Dr. Stefan Wuttke, Prof. Dr. Erhard Kemnitz, Dr. Dan Macovei, Prof. Dr. Vasile I. Parvulescu, Dr. C. M. Teodorescu and Prof. Dr. Simona M. Coman

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201002090

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      No toxic compounds such as KCN and no thermal activation is required for the preparation of Au/MgF2 complexes by a simple and facile “incipient wetness impregnation” method in which hydrogen tetrachloroaurate (HAuCl4) is the gold precursor. One of the complexes prepared exhibits unique catalytic properties and serves as a heterogeneous catalyst for the highly diastereoselective one-pot synthesis of (±)-menthol from citronellal (see picture).

    9. P,N Compounds

      The Reaction of White Phosphorus with NO+/NO2+[Al(ORF)4]: The [P4NO]+ Cluster Formed by an Unexpected Nitrosonium Insertion (pages 8139–8143)

      Dipl.-Chem. Tobias Köchner, Dr. Sebastian Riedel, Dipl.-Chem. Anna J. Lehner, Dr. Harald Scherer, Dr. Ines Raabe, Tobias A. Engesser, Dipl.-Chem. Franziska W. Scholz, Dipl.-Chem. Urs Gellrich, Dipl.-Chem. Philipp Eiden, Dipl.-Chem. Roberto A. Paz Schmidt, Prof. Dr. Dietmar A. Plattner and Prof. Dr. Ingo Krossing

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201003031

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      An appealing couple: The unprecedented insertion of the nitrosonium cation into a tetrahedral edge of white phosphorus forms the highly reactive [P4NO]+ cation (see picture). The synthesis, characterization, and applications are discussed, and NO2[Al(OC(CF3)3)4] is presented as an easily synthesized oxidant.

    10. Rhodium Catalysis

      Rhodium-Catalyzed Asymmetric Conjugate Addition of Arylboroxines to Borylalkenes: Asymmetric Synthesis of β-Arylalkylboranes (pages 8145–8147)

      Keigo Sasaki and Prof. Dr. Tamio Hayashi

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201004980

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      Asymmetric conjugate addition of arylboroxines to borylalkenes proceed in the presence of a chiral bisphosphine/rhodium complex as a catalyst to give chiral β-arylalkylboranes with high enantioselectivities (see scheme). [O]=H2O2/NaOH.

    11. Photoreduction

      Photoinduced Catalytic Reaction by a Fluorescent Active Cryptand Containing an Anthracene Fragment (pages 8148–8151)

      Hong-Guo Hao, Xiao-Dan Zheng and Prof. Tong-Bu Lu

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201004928

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      Tripping the light fantastic: A fluorescently active cryptand containing an anthracene fragment catalyzes the photoinduced reduction of CuII to CuI with simultaneous oxidation of water to oxygen (see scheme).

    12. Dendrimers

      Click Syntheses of 1,2,3-Triazolylbiferrocenyl Dendrimers and the Selective Roles of the Inner and Outer Ferrocenyl Groups in the Redox Recognition of ATP2− and Pd2+ (pages 8152–8156)

      Rodrigue Djeda, Amalia Rapakousiou, Liyuan Liang, Nicola Guidolin, Dr. Jaime Ruiz and Prof. Didier Astruc

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201004756

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      This way and that: Triazolylbiferrocenyl dendrimers can be synthesized with up to 729 termini. Oxidation results in isolable mixed-valence dendrimers (see picture). In electrochemical studies, these species can recognize ATP2− and PdII, and they can be used to stabilize Pd nanoparticle catalysts.

    13. Synthetic Methods

      Enantioselective and Z/E-Selective Conjugate Addition of α-Substituted Cyanoacetates to Acetylenic Esters Catalyzed by Bifunctional Ruthenium and Iridium Complexes (pages 8157–8160)

      Yasuharu Hasegawa, Prof. Dr. Ilya D. Gridnev and Prof. Dr. Takao Ikariya

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201003585

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      Metal-based catalysts: The title reaction provided the chiral adducts in high yields, excellent enantiomeric excess, and high Z/E selectivity. A combined NMR/DFT study revealed a key intermediate for the stereoselective reaction and a possible reaction mechanism (see the optimized transition-state structure).

    14. Photosensitizers

      Highly Efficient N-Heterocyclic Carbene/Pyridine-Based Ruthenium Sensitizers: Complexes for Dye-Sensitized Solar Cells (pages 8161–8164)

      Wei-Chun Chang, Huei-Siou Chen, Ting-Yu Li, Nai-Mu Hsu, Yogesh S. Tingare, Chung-Yen Li, Yi-Cheng Liu, Prof. Chaochin Su and Prof. Wen-Ren Li

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201001628

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      A new generation: The incorporation of N-heterocyclic carbene/pyridine-based ruthenium sensitizers derived from benzimidazolium salts into dye-sensitized solar cells results in superior current densities, cell voltages, and photoelectric conversion efficiencies. The performance of a solar cell sensitized with CBTR (see picture) exceeded that of the traditional N719 cell.

    15. Nanostructures

      A Sinter-Resistant Catalytic System Based on Platinum Nanoparticles Supported on TiO2 Nanofibers and Covered by Porous Silica (pages 8165–8168)

      Yunqian Dai, Dr. Byungkwon Lim, Dr. Yong Yang, Claire M. Cobley, Weiyang Li, Dr. Eun Chul Cho, Dr. Benjamin Grayson, Dr. Paul T. Fanson, Prof. Charles T. Campbell, Prof. Yueming Sun and Prof. Younan Xia

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/anie.201001839

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      Holey support: The generation of a porous coating of SiO2 on Pt-decorated TiO2 nanofibers enables the preparation of a sinter-resistant catalytic system (see picture). The Pt nanoparticles could resist sintering at temperatures up to 750 °C in air, as the SiO2 coating acts as a physical barrier that slows down surface migration, but the system remained catalytically active because of the porous nature of the coating.

    16. Asymmetric Catalysis

      Asymmetric Nozaki–Hiyama Propargylation of Aldehydes: Enhancement of Enantioselectivity by Cobalt Co-Catalysis (pages 8169–8172)

      Dmitry L. Usanov and Prof. Dr. Hisashi Yamamoto

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201002751

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      It takes two to tango! A combination of partially reduced chiral H8-TBOx chromium catalyst 1 and achiral cobalt porphine co-catalyst 2 (Ar=p-anisyl) led to an enhancement in enantioselectivity by suppression of the background process that presumably proceeds through an organomanganese species.

    17. Molecular Recognition

      Small-Molecule Sensing: A Direct Enzyme-Linked Immunosorbent Assay for the Monosaccharide Kdo (pages 8173–8176)

      Dr. Karin Mannerstedt, Dr. Anita M. Jansson, Jody Weadge and Prof. Ole Hindsgaul

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201003435

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      Captured and bound! Kdo, a monosaccharide, and an immobilized capture molecule form a covalent adduct that can be detected by adduct-specific antibodies (see scheme). The recognition yields a signal that is proportional to the amount of Kdo present in solution. This small-molecule sensor should be applicable for any small molecule that can react to give an immunogenic adduct.

    18. 207Pb NMR Spectroscopy

      Probing a Homoleptic PbS3 Coordination Environment in a Designed Peptide Using 207Pb NMR Spectroscopy: Implications for Understanding the Molecular Basis of Lead Toxicity (pages 8177–8180)

      Dr. Kosh P. Neupane and Prof. Dr. Vincent L. Pecoraro

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201004429

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      The lead-inhibited active site of a zinc-binding metalloenzyme in a thiol-rich coordination environment (PbS3) has been modeled by homoleptic three-strand coiled-coil peptides and characterized using natural-abundance 207Pb NMR spectroscopy (see picture: 207Pb NMR signals from two binding sites of the same protein). 207Pb NMR spectroscopy could thus be used to identify and characterize important human proteins associated with lead toxicity.

    19. C[BOND]H Activation

      syn-Selective Rhodium(I)-Catalyzed Allylations of Ketimines Proceeding through a Directed C[BOND]H Activation/Allene Addition Sequence (pages 8181–8184)

      Duc N. Tran and Dr. Nicolai Cramer

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201004179

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      On a Rh-oll: Rhodium(I)-catalyzed C[BOND]H activations of ketimines and subsequent carborhodation of an allene led to an allyl metal species, which then allylated the imine directing group to give highly functionalized methylene dihydroindenyl amines (see scheme) with excellent regio- and diastereoselectivity.

    20. Fast Proteolysis

      Efficient Tryptic Proteolysis Accelerated by Laser Radiation for Peptide Mapping in Proteome Analysis (pages 8185–8189)

      Guoping Yao, Prof. Chunhui Deng, Prof. Xiangmin Zhang and Prof. Pengyuan Yang

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/anie.201004152

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      Back to basics: Coupled with MALDI-TOF MS, laser-assisted proteolysis (see schematic illustration) enabled rapid protein digestion and peptide mapping without the need for enzyme immobilization to increase the efficiency of tryptic digestion. Protein solutions containing trypsin were digested in less than a minute upon irradiation at 808 nm with a laser.

    21. Enzyme Models

      Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex (pages 8190–8194)

      Dr. Sarvesh C. Sawant, Xiujuan Wu, Dr. Jaeheung Cho, Dr. Kyung-Bin Cho, Dr. Sun Hee Kim, Dr. Mi Sook Seo, Dr. Yong-Min Lee, Dr. Minoru Kubo, Prof. Dr. Takashi Ogura, Prof. Dr. Sason Shaik and Prof. Dr. Wonwoo Nam

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201000819

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      The source of the problem: Experiments with isotopically labeled water can be used to unambiguously assign the source of oxygen in a nonheme manganese(IV) oxo complex. The complex, which was generated using water as an oxygen source and cerium(IV) as an oxidant (see picture), shows reactivities in the activation of C[BOND]H bonds of alkyl-functionalized aromatic molecules and the oxidation of aromatic substrates (sub) and benzyl alcohol.

    22. Glycan Imaging

      Noninvasive Imaging of Dendrimer-Type N-Glycan Clusters: In Vivo Dynamics Dependence on Oligosaccharide Structure (pages 8195–8200)

      Dr. Katsunori Tanaka, Dr. Eric R. O. Siwu, Kaori Minami, Dr. Koki Hasegawa, Dr. Satoshi Nozaki, Dr. Yousuke Kanayama, Koichi Koyama, Dr. Weihsu C. Chen, Prof. James C. Paulson, Prof. Dr. Yasuyoshi Watanabe and Prof. Dr. Koichi Fukase

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201000892

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      Body image: Self-activating Huisgen 1,3-dipolar cycloaddition and 6π azaelectrocyclization of lysine-based dendrimers (see picture) enable the in vivo dynamics and organ-specific accumulation of N-glycans to be visualized. The sugar structure and glycosyl bond linkages of N-glycans control the whole-body trafficking of the clusters in nude mice and a cancer model.

    23. Mesoporous Materials

      Chitin–Silica Nanocomposites by Self-Assembly (pages 8201–8204)

      Dr. Bruno Alonso and Dr. Emmanuel Belamie

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201002104

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      A new family of chitin–silica nanocomposites has been synthesized by using a versatile colloid-based combination of self-assembly and sol–gel chemistry (see picture). Various textures and morphologies can be obtained by adjusting the evaporation-based processes or by applying external fields. After calcination, textures and birefringence are preserved in the resulting mesoporous silicas.

    24. Cyclophanes

      Preparation and Characterization of N-Anisyl-Substituted Hexaaza[16]paracyclophane (pages 8205–8208)

      Dr. Akihiro Ito, Yuichiro Yokoyama, Ryosuke Aihara, Koji Fukui, Shoko Eguchi, Katsuyuki Shizu, Dr. Tohru Sato and Prof. Dr. Kazuyoshi Tanaka

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201002165

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      Localized or delocalized? For the first time, a cyclic oligoaniline, hexaaza[16]paracyclophane, has been prepared (see picture; carbon: gray; nitrogen: blue; hydrogen: light gray). The macrocycle exhibits a high electron-donating ability, and furthermore, the spin of the corresponding radical cation was delocalized over the macrocyclic molecular backbone.

    25. Heteroarenes

      1,5,9-Triazacoronenes: A Family of Polycyclic Heteroarenes Synthesized by a Threefold Pictet–Spengler Reaction (pages 8209–8213)

      Prof. Dr. Junfa Wei, Bo Han, Qiang Guo, Dr. Xianying Shi, Prof. Wenliang Wang and Ni Wei

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201002369

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      We are family: Triazacoronene derivatives have been synthesized in four steps from veratrole by using a threefold Pictet–Spengler reaction as the key step (see picture). They have good photophysical and electronical properties, thermal stability, and solubility, thus rendering them promising candidates as electron-transport materials.

      Corrected by:

      Corrigendum: Corrigendum: 1,5,9-Triazacoronenes: A Family of Polycyclic Heteroarenes Synthesized by a Threefold Pictet–Spengler Reaction

      Vol. 49, Issue 51, 9803, Version of Record online: 14 DEC 2010

    26. Drug Delivery

      Intracellular pH-Responsive Mesoporous Silica Nanoparticles for the Controlled Release of Anticancer Chemotherapeutics (pages 8214–8219)

      Dr. Chia-Hung Lee, Shih-Hsun Cheng, I-Ping Huang, Dr. Jeffrey S. Souris, Prof. Chung-Shi Yang, Prof. Chung-Yuan Mou and Prof. Leu-Wei Lo

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201002639

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      Cut here to cure: Doxorubicin attached to pH-sensitive mesoporous silica nanoparticles (MSN-hydrazone-Dox) shows potential in the chemotherapeutic treatment of liver cancer. Hydrolysis of the pH-sensitive hydrazone bond in the acidic environment of endosomes/lysosomes (see picture) releases Dox intracellularly from the MSN nanochannels, resulting in highly efficient apoptotic cell death.

    27. Micelles

      Pointed-Oval-Shaped Micelles from Crystalline-Coil Block Copolymers by Crystallization-Driven Living Self-Assembly (pages 8220–8223)

      Dr. Alejandro Presa Soto, Dr. Joe B. Gilroy, Prof. Mitchell A. Winnik and Prof. Ian Manners

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201003066

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      Getting in shape: Stable pointed-oval-shaped micelles of uniform size and shape (see TEM image) were prepared by extending the crystallization-driven living self-assembly method to crystalline core-forming polyferrocenylsilane diblock copolymers with corona-forming coblocks of poly(2-vinylpyridine) and polyphosphazene. The pointed-oval-shaped micelles were subsequently used as precursors to hierarchical micelle architectures.

    28. Photoisomerization

      Switching of a Single Boryl Center in π-Conjugated Photochromic Polyboryl Compounds and Its Impact on Fluorescence Quenching (pages 8224–8227)

      Dr. Chul Baik, Stephen K. Murphy and Prof. Dr. Suning Wang

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201003144

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      All for one and one for all: Molecules with multiple conjugated photochromic boryl units undergo photoisomerization on a single boryl unit only. This single boryl switching causes fluorescence quenching of the entire molecule, which is greatly amplified with increasing numbers of switchable boryl units in the molecule.

    29. Chemical Biology

      Relocation of Aurora B and Survivin from Centromeres to the Central Spindle Impaired by a Kinesin-Specific MKLP-2 Inhibitor (pages 8228–8231)

      Dr. Sergey Tcherniuk, Dr. Dimitrios A. Skoufias, Dr. Christophe Labriere, Dr. Oliver Rath, Dr. Françoise Gueritte, Dr. Catherine Guillou and Prof. Dr. Frank Kozielski

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201003254

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      Relocation, relocation: Inactivation of the mitotic kinesin MKLP-2 by a specific small-molecule inhibitor (1) leads to failure in the recruitment of the chromosome passenger protein (survivin, red) to the central spindle (microtubules, green) during anaphase chromosome segregation (DNA, blue).

    30. Self-Assembly

      Unprecedented Molecular Architectures by the Controlled Self-Assembly of a β-Peptide Foldamer (pages 8232–8236)

      Sunbum Kwon, Aram Jeon, Sung Hyun Yoo, Dr. Im Sik Chung and Prof. Hee-Seung Lee

      Version of Record online: 23 AUG 2010 | DOI: 10.1002/anie.201003302

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      Fighting against windmills: Highly homogeneous, well-defined, and finite “windmill”- and square-rod-shaped supramolecular architectures were formed by the self-assembly of a short helical β peptide in aqueous solution (see picture). The reproducible formation of the unprecedented 3D shapes could be controlled by the use of a surfactant of different concentrations.

    31. Surface Analysis

      Mesoscopic Arrays from Supramolecular Self-Assembly (pages 8237–8239)

      Sylvain Clair, Mathieu Abel and Louis Porte

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201003335

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      Well-ordered superarrays of exceptionally large period (22 nm) and involving a substantial number of hexahydroxytriphenylene molecules (20×20 superlattice) form on a Ag(111) surface. The superstructure (see picture; triangular pattern) is an intrinsic property of the system and, remarkably, it does not depend on global surface coverage (lower right: partial structure).

    32. Cell-Penetrating Compounds

      A Straightforward Approach for Cellular-Uptake Quantification (pages 8240–8243)

      Dr. David Paramelle, Dr. Gilles Subra, Lubomir L. Vezenkov, Dr. Marie Maynadier, Christophe André, Prof. Christine Enjalbal, Dr. Monique Calmès, Dr. Marcel Garcia, Prof. Jean Martinez and Dr. Muriel Amblard

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201003347

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      Putting a number on it: MALDI-TOF MS enabled direct quantification of the cellular uptake of cell-penetrating peptides (CPPs) by MDA-MB-231 breast cancer cells. This sensitive general strategy (see schematic representation), which requires no purification or separation steps, relies on the enhancement and discrimination of the MS signals of an α-cyano-4-hydroxycinnamic acid tag in a neutral α-cyano-4-hydroxycinnamic methyl ester matrix.

    33. Metal–Organic Frameworks

      Single-Crystal to Single-Crystal Cross-Linking of an Interpenetrating Chiral Metal–Organic Framework and Implications in Asymmetric Catalysis (pages 8244–8248)

      Dr. Liqing Ma, Dr. Chuan-De Wu, Marcela M. Wanderley and Prof. Wenbin Lin

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201003377

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      Support framework: Post-synthesis modification of an interpenetrating Zn-based chiral metal–organic framework with Ti(OiPr)4 results in a Lewis acidic catalyst (see picture; gray C, white H, red O, green Ti) with modest enantioselectivity in the asymmetric addition of diethylzinc to aldehydes. The Ti(OiPr)4-treated framework contains single-crystal to single-crystal cross-linking of the two interpenetrating networks.

    34. Bioinorganic Chemistry

      A {Cu2S}2+ Mixed-Valent Core Featuring a Cu[BOND]Cu Bond (pages 8249–8252)

      Dr. Stéphane Torelli, Dr. Maylis Orio, Dr. Jacques Pécaut, Dr. Hélène Jamet, Dr. Laurent Le Pape and Dr. Stéphane Ménage

      Version of Record online: 17 SEP 2010 | DOI: 10.1002/anie.201003411

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      Not so far away from me: Reductive cleavage of a disulfide ligand with CuI leads to the formation of a new mixed-valent CuIICuI complex (see picture). Combined X-ray and theoretical investigations highlight the presence of a striking Cu2S core containing a Cu[BOND]Cu bond, and solution studies also indicate a high degree of delocalization.

    35. Nanostructures

      Layered Cobalt Hydroxide Nanocones: Microwave-Assisted Synthesis, Exfoliation, and Structural Modification (pages 8253–8256)

      Dr. Xiaohe Liu, Dr. Renzhi Ma, Prof. Yoshio Bando and Prof. Takayoshi Sasaki

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201004033

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      Layered cobalt hydroxide nanocones intercalated with dodecyl sulfate (DS) ions (see scheme; OH blue, Co green dots, DS ions red) could be synthesized by the microwave-assisted rolling of lamellar structures. The cones could be exfoliated into cobalt hydroxide nanosheets and converted into CoOOH and Co3O4 nanocones.

    36. CO2 Activation

      Selective Formic Acid Synthesis from Nanoscale Electrochemistry (pages 8257–8259)

      Dipl.-Chem. Robert F. Höckendorf, Dr. Chi-Kit Siu, Dipl.-Chem. Christian van der Linde, Dr. O. Petru Balaj and Prof. Dr. Martin K. Beyer

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201004134

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      Hydrogen-atom transfer from a thiol group to the CO2 radical anion is a fast and selective downhill process in a gas-phase water cluster. This suggests that placing a thiol group near the site of electron transfer to CO2 in a nanostructured electrochemical environment allows the selective formation of formic acid (see picture; dark gray C, light gray H, red O, yellow S).

    37. Self-Assembly

      Mechanical Bond Formation by Radical Templation (pages 8260–8265)

      Hao Li, Albert C. Fahrenbach, Dr. Sanjeev K. Dey, Dr. Subhadeep Basu, Dr. Ali Trabolsi, Dr. Zhixue Zhu, Youssry Y. Botros and Prof. J. Fraser Stoddart

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201004488

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      A radical interaction has been employed as the recognition motif in the template-directed synthesis of a [2]rotaxane composed of cyclobis(paraquat-p-phenylene) and a viologen derivative. The ruthenium tris(bipyridine)/triethanolamine system is used as the electron-transfer photocatalyst to generate the necessary radical cation components that result in the formation of an inclusion complex. A stoppering reaction follows to form the mechanical bond.

    38. Mechanochemistry

      Solid-State Conversion of the Solvated Dimer [{tBuZn(μ-OtBu)(thf)}2] into a Long Overlooked Trimeric [{tBuZnOtBu}3] Species (pages 8266–8269)

      Prof. Dr. Janusz Lewiński, Michał Dutkiewicz, Michał Lesiuk, Dr. Witold Śliwiński, Dr. Karolina Zelga, Dr. Iwona Justyniak and Prof. Dr. Janusz Lipkowski

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/anie.201004504

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      Zinc links: Solid-state desolvation of the dimeric alkoxide [{tBuZn(μ-OtBu)(thf)}2] leads to a trimer [{tBuZnOtBu}3] with a unique core structure; subsequent grinding affords the tetrameric cubane [{tBuZnOtBu}4]. This approach demonstrates a new direction in the generation of metal alkoxide clusters.

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