Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 23

May 25, 2010

Volume 49, Issue 23

Pages 3849–3989

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
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    1. Cover Picture: Highly Active Chiral Ruthenium-Based Metathesis Catalysts through a Monosubstitution in the N-Heterocyclic Carbene (Angew. Chem. Int. Ed. 23/2010) (page 3849)

      Sascha Tiede, Anke Berger, David Schlesiger, Daniel Rost, Anja Lühl and Siegfried Blechert

      Article first published online: 5 MAY 2010 | DOI: 10.1002/anie.201001706

      Thumbnail image of graphical abstract

      One handed is very efficient not only for fiddler crabs, but also for chiral ruthenium metathesis (pre)catalysts that contain a monosubstituted carbon center in the N-heterocyclic ligand. In their Communication on page 3972 ff. S. Blechert and co-workers show that through the combination of ligands a highly stable catalyst is formed that rapidly initiates the asymmetric ring-opening cross-metathesis and delivers high E-isomer selectivity and high enantioselectivity. (Photo: Thorsten Stegmann.)

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
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    1. Inside Cover: Chemical Proteomics Discloses Petrosapongiolide M, an Antiinflammatory Marine Sesterterpene, as a Proteasome Inhibitor (Angew. Chem. Int. Ed. 23/2010) (page 3850)

      Luigi Margarucci, Maria Chiara Monti, Alessandra Tosco, Raffaele Riccio and Agostino Casapullo

      Article first published online: 29 APR 2010 | DOI: 10.1002/anie.201002028

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      Petrosaspongiolide M, a marine natural product with anti-inflammatory properties, has an intriguing pharmacological profile. In their Communication on page 3960 ff. Casapullo and co-workers identified the macromolecular targets of this potential drug candidate; the 20S proteasome was found to be its most important target.

  3. Graphical Abstract

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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
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    8. Book Review
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 23/2010 (pages 3853–3860)

      Article first published online: 17 MAY 2010 | DOI: 10.1002/anie.201090068

  4. Corrigendum

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    10. Minireview
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      Corrigendum: A Single Residue Influences the Reaction Mechanism of Ammonia Lyases and Mutases (page 3860)

      Sebastian Bartsch and Uwe T. Bornscheuer

      Article first published online: 17 MAY 2010 | DOI: 10.1002/anie.201090069

      This article corrects:

      A Single Residue Influences the Reaction Mechanism of Ammonia Lyases and Mutases1

      Vol. 48, Issue 18, 3362–3365, Article first published online: 2 APR 2009

  5. News

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
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  6. Author Profile

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    1. David Milstein (page 3866)

      Article first published online: 29 APR 2010 | DOI: 10.1002/anie.201001386

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      “The biggest problem that scientists face is funding and public recognition of the importance of basic research. If I could be anyone for a day, I would be the finance minister of our country. This would be a marvelous opportunity to be very generous towards the universities in our country …” This and more about David Milstein can be found on page 3866.

  7. Book Review

    1. Top of page
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    1. From Enzyme Models to Model Enzymes. By Anthony J. Kirby and Florian Hollfelder. (page 3867)

      Wolf-D. Woggon

      Article first published online: 17 MAY 2010 | DOI: 10.1002/anie.201001260

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      Royal Society of Chemistry, Cambridge 2009. 286 pp., hardcover £ 69.95.—ISBN 978-0854041756

  8. Highlight

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    4. Graphical Abstract
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    1. Bioinorganic Chemistry

      An Engineered Metalloprotein as a Functional and Structural Bioinorganic Model System (pages 3868–3869)

      Takafumi Ueno

      Article first published online: 30 APR 2010 | DOI: 10.1002/anie.201000337

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      How best to mimic a protein: Rational design based on the use of a metalloprotein as the molecular scaffold led to a structural (see picture) and functional model of a metalloenzyme that is difficult to obtain in high yield and for which no crystal structure has been determined. This approach will be useful for the preparation of models of sophisticated functional metal centers that are difficult to prepare by chemical synthesis.

  9. Minireview

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    1. Asymmetric Catalysis

      DNA-Based Hybrid Catalysts for Asymmetric Organic Synthesis (pages 3870–3878)

      Soyoung Park and Hiroshi Sugiyama

      Article first published online: 7 MAY 2010 | DOI: 10.1002/anie.200905382

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      The best of both worlds: The helical chirality of DNA has been exploited in asymmetric catalysis through the use of hybrid catalysts self-assembled from DNA and a metal complex. These catalysts promote a range of asymmetric carbon–carbon and carbon–heteroatom bond-forming reactions in aqueous media. The use of DNA in Lewis acid catalyzed reactions, such as Michael addition reactions (see scheme), led to high stereoselectivity and rate enhancement.

  10. Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    8. Book Review
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    11. Review
    12. Communications
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    1. Ultrasmall-Scale Analysis

      Analytical Chemistry on the Femtoliter Scale (pages 3880–3895)

      Hans H. Gorris and David R. Walt

      Article first published online: 23 APR 2010 | DOI: 10.1002/anie.200906417

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      Smaller than small: Reducing the volume of containers leads to the rational limit at which on average one molecule is present per container (solid line in the plot). For femtoliter containers this concentration limit is in the picomolar range. Lower concentrations (dotted line) can be used to increase the probability of observing single-molecule events.

  11. Communications

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

      Controlled Hydrogen-Bond Breaking in a Rotaxane by Discrete Solvation (pages 3896–3900)

      Anouk M. Rijs, Nadja Sändig, Martine N. Blom, Jos Oomens, Jeffrey S. Hannam, David A. Leigh, Francesco Zerbetto and Wybren J. Buma

      Article first published online: 29 APR 2010 | DOI: 10.1002/anie.201001231

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      Controlling a molecular brake: Binding interactions between the thread and the macrocycle of a [2]rotaxane can be tuned in a quasi-continuous manner by adding hydrogen-bond-forming solvent molecules one at a time to an isolated [2]rotaxane molecule. Conformational changes that detach the thread from the macrocycle can be induced controllably, and the system resembles a molecular version of applying and releasing a brake.

    2. 1H NMR without Couplings

      Pure Shift 1H NMR: A Resolution of the Resolution Problem? (pages 3901–3903)

      Juan A. Aguilar, Stephen Faulkner, Mathias Nilsson and Gareth A. Morris

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.201001107

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      Suppressing multiplet structure in 1H NMR spectra offers a large improvement in spectral resolution (see picture), equivalent to the use of a spectrometer in the GHz range. Such “pure shift” techniques are readily extended to multidimensional methods, for example DOSY.

    3. Protein Aggregates

      Multidimensional Structure–Activity Relationship of a Protein in Its Aggregated States (pages 3904–3908)

      Lei Wang, David Schubert, Michael R. Sawaya, David Eisenberg and Roland Riek

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.201000068

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      The same, but very different: Diverse chemical, physical, and biological conditions induced the aggregation of a single protein into five structurally distinct protein aggregates (see electron micrographs, scale bars: 500 nm), all of which contained the cross-β-sheet motif. The aggregates differed in their affinity for adenosine-5′-triphosphate, thioflavin T, DNA, and membrane mimics, and in their interference with cell viability.

    4. Imaging Techniques

      A Secreted Enzyme Reporter System for MRI (pages 3909–3911)

      Gil G. Westmeyer, Yves Durocher and Alan Jasanoff

      Article first published online: 22 APR 2010 | DOI: 10.1002/anie.200906712

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      Let′s see what comes out: An extracellular enzymatic gene-reporter system for magnetic resonance imaging (MRI) yields strong, reversible contrast changes in response to the expression of secreted alkaline phosphatase (SEAP; see picture). Products of SEAP activity were specifically detected using an iron-oxide-based sensor. The contrast agent is not used up by the enzyme, cell delivery is not required, and multimodal detection is possible.

    5. Pump–Probe Spectroscopy

      Observation of Terahertz Vibrations in the Nitrogenase FeMo Cofactor by Femtosecond Pump–Probe Spectroscopy (pages 3912–3915)

      Ines Delfino, Giulio Cerullo, Salvatore Cannistraro, Cristian Manzoni, Dario Polli, Christie Dapper, William E. Newton, Yisong Guo and Stephen P. Cramer

      Article first published online: 21 APR 2010 | DOI: 10.1002/anie.200906787

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      Pump it up! The FeMo cofactor (see picture) has resisted characterization by resonance Raman spectroscopy. Impulsive coherent vibrational spectroscopy may be an alternative probe of its dynamics. A 15 fs visible laser pulse pumped the sample to an excited electronic state, and a second <10 fs pulse probed the change in transmission as a function of the time delay.

    6. Mechanochemistry

      High Reactivity of Metal–Organic Frameworks under Grinding Conditions: Parallels with Organic Molecular Materials (pages 3916–3919)

      Wenbing Yuan, Tomislav Friščić, David Apperley and Stuart L. James

      Article first published online: 26 APR 2010 | DOI: 10.1002/anie.200906965

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      Interconversion made easy: Metal–organic frameworks (MOFs) are surprisingly reactive under grinding conditions and can perform various rearrangements (see picture). In this respect, the results reveal clear parallels between MOFs and organic molecular materials.

    7. Functionalized Nanotubes

      Giant Nanotubes Loaded with Artificial Peroxidase Centers: Self-Assembly of Supramolecular Amphiphiles as a Tool To Functionalize Nanotubes (pages 3920–3924)

      Yong Tang, Lipeng Zhou, Jiaxi Li, Quan Luo, Xin Huang, Ping Wu, Yongguo Wang, Jiayun Xu, Jiacong Shen and Junqiu Liu

      Article first published online: 29 APR 2010 | DOI: 10.1002/anie.200907036

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      Test tubes: Large-diameter nanotubes have been obtained by direct self-assembly of cyclodextrin-based host–guest superamphiphiles (see picture). By manipulating the surface of the nanotubes with a combination of a molecular-imprinting strategy and self-assembly, the main catalytic components of glutathione peroxidase were fabricated on the nanotube scaffold.

    8. Interfacial Synthesis

      Luminescent Ag7 and Ag8 Clusters by Interfacial Synthesis (pages 3925–3929)

      T. Udaya Bhaskara Rao and T. Pradeep

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.200907120

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      Interfacial etching of silver nanoparticles and separation of the products by polyacrylamide gel electrophoresis afforded Ag8 and Ag7 clusters with red and blue-green fluorescence emission, respectively (see picture). The strongly temperature-dependent emission of the clusters suggests potential applications, whilst their facile phase transfer to organic media facilitates further studies.

    9. Porphyrinoids

      One-Pot Synthesis of Indene-Expanded Porphyrins (pages 3930–3933)

      Geneva R. Peterson and Nick Bampos

      Article first published online: 10 MAY 2010 | DOI: 10.1002/anie.200906580

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      An in situ annulation has been added to the typical reactions which comprise aldehyde–dipyrromethane porphyrinoid syntheses. This reaction provides a novel route to fully conjugated aromatic-expanded porphyrins. The fast stepwise metalation with Zn(OAc)2 provides monometalated and dimetalated species according to the stoichiometry see (picture; N blue, Zn magenta, O red).

    10. Proteasome Inhibition

      Elucidation of the Structure and Intermolecular Interactions of a Reversible Cyclic-Peptide Inhibitor of the Proteasome by NMR Spectroscopy and Molecular Modeling (pages 3934–3938)

      Benjamin Stauch, Bernd Simon, Teodora Basile, Gisbert Schneider, Nisar P. Malek, Markus Kalesse and Teresa Carlomagno

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.201000140

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      Complex considerations: The proteasome plays a key role in diseases and is thus an appealing drug target. A structural model (see picture) of the proteasome as a complex with argyrin, a cyclic heptapeptide with antitumoral activity, provides a rationale for the high biological activity of this natural product. The structure–activity-relationship data available for the drug are discussed on the basis of this model.

    11. Porphyrin Aggregation

      Dilution-Induced Self-Assembly of Porphyrin Aggregates: A Consequence of Coupled Equilibria (pages 3939–3942)

      Floris Helmich, Cameron C. Lee, Marko M. L. Nieuwenhuizen, Jeroen C. Gielen, Peter C. M. Christianen, Antje Larsen, George Fytas, Philippe E. L. G. Leclère, Albertus P. H. J. Schenning and E. W. Meijer

      Article first published online: 8 APR 2010 | DOI: 10.1002/anie.201000162

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      Piggy-back porphyrins: The presence of a Lewis base remarkably affects the cooperative self-assembly of zinc porphyrins. Driven by the susceptibility of the monomer towards the axial ligand, monomer scavenging caused depolymerization of porphyrin aggregates, and dilution caused aggregation by a re-entrant phase transition. Model predictions were validated by dilution experiments.

    12. Light-Switchable Proteins

      Photocontrol of Coiled-Coil Proteins in Living Cells (pages 3943–3946)

      Fuzhong Zhang, Katharina A. Timm, Katja M. Arndt and G. Andrew Woolley

      Article first published online: 23 APR 2010 | DOI: 10.1002/anie.201000909

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      Light switching of the activity of a coiled-coil protein, the AP-1 transcription factor, in living cells was made possible by the introduction of a designed azobenzene-cross-linked dominant negative peptide, XAFosW (red and yellow in the picture). In the dark, XAFosW showed decreased helical content and decreased affinity for target Jun proteins (green); irradiation at 365 nm enhanced helicity and target affinity.

    13. Boryl Complexes

      A Highly Reactive Rhodium(I)–Boryl Complex as a Useful Tool for C[BOND]H Bond Activation and Catalytic C[BOND]F Bond Borylation (pages 3947–3951)

      Michael Teltewskoi, Julien A. Panetier, Stuart A. Macgregor and Thomas Braun

      Article first published online: 23 APR 2010 | DOI: 10.1002/anie.201001070

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      C[BOND]F bond borylation: A 16-electron rhodium(I)–boryl complex was synthesized by borylation of a rhodium(I)–fluorine complex. The former reacts with benzene or 2,3,5,6-tetrafluoropyridine by C[BOND]H activation. A catalytic C[BOND]F borylation reaction of pentafluoropyridine was also developed, which uses [Rh(Bpin)(PEt3)3] as a catalyst and Me3SiSiMe3 as a solvent. pin=pinacol.

    14. Silicon Chemistry

      Convenient Access to Monosilicon Epoxides with Pentacoordinate Silicon (pages 3952–3955)

      Rajendra S. Ghadwal, Sakya S. Sen, Herbert W. Roesky, Markus Granitzka, Daniel Kratzert, Sebastian Merkel and Dietmar Stalke

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.201000835

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      From intermediate to stable molecule: Stable monosilicon epoxides with pentacoordinate silicon were prepared for the first time by [2+1] cycloaddition reactions of Lewis base stabilized chlorosilylenes with ketones. Molecular structures of these compounds with SiOC three-membered rings were established by X-ray diffraction studies (e.g., see picture; N blue, O red, Cl green).

    15. Mesoporous Materials

      A High-Speed Passive-Matrix Electrochromic Display Using a Mesoporous TiO2 Electrode with Vertical Porosity (pages 3956–3959)

      Wu Weng, Tetsuya Higuchi, Masao Suzuki, Toshimi Fukuoka, Takeshi Shimomura, Masatoshi Ono, Logudurai Radhakrishnan, Hongjing Wang, Norihiro Suzuki, Hamid Oveisi and Yusuke Yamauchi

      Article first published online: 21 APR 2010 | DOI: 10.1002/anie.200907008

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      On display: A high-speed and high-quality passive-matrix electrochromic display (ECD) is constructed from a leuco dye and a TiO2 nanoporous electrode (see picture). The vertical pores prevent the drifting of the colored dye molecules, leading to a clear image at high driving speeds. With full-color features, this kind of ECD promises to be a competitive candidate for a reflective electric display.

    16. Chemical Biology

      Chemical Proteomics Discloses Petrosapongiolide M, an Antiinflammatory Marine Sesterterpene, as a Proteasome Inhibitor (pages 3960–3963)

      Luigi Margarucci, Maria Chiara Monti, Alessandra Tosco, Raffaele Riccio and Agostino Casapullo

      Article first published online: 7 APR 2010 | DOI: 10.1002/anie.200907153

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      Gone fishing: Petrosaspongiolide M (PM), a marine γ-hydroxybutenolide sesterterpenoid, was efficiently immobilized on a solid support to selectively bind its macromolecular targets in a macrophage cell lysate. The proteasome machinery was identified as its most important partner.

    17. C[BOND]H Insertion

      Remote C[BOND]H Functionalization: Using the N[BOND]O Moiety as an Atom-Economical Tether to Obtain 1,5- and the Rare 1,7-C[BOND]H Insertions (pages 3964–3968)

      Jingxin Wang, Bogdan Stefane, Deana Jaber, Jacqueline A. I. Smith, Christopher Vickery, Mouhamed Diop and Herman O. Sintim

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.201000160

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      Dr. N[BOND]O: Rhodium-catalyzed intramolecular C[BOND]H insertion with diazocompounds, which are tethered by alkoxyamines, afforded 1,5- and the rare 1,7-insertion products (see scheme; Bn=benzyl). The resulting N[BOND]O tether is unaffected under the C[BOND]H insertion reaction conditions and it can be readily cleaved or transformed into various functionalities. The reduction of the N[BOND]O moiety controls acyclic stereochemistry.

    18. Asymmetric Catalysis

      Chiral Tetrafluorobenzobarrelenes as Effective Ligands for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboroxines to β,β-Disubstituted α,β-Unsaturated Ketones (pages 3969–3971)

      Ryo Shintani, Momotaro Takeda, Takahiro Nishimura and Tamio Hayashi

      Article first published online: 13 APR 2010 | DOI: 10.1002/anie.201000467

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      Lock, Stock and Two Smoking Barrelenes: The rhodium-catalyzed 1,4-addition of readily available arylboronic acid anhydrides to simple β,β-disubstituted α,β-unsaturated ketones creates quaternary carbon stereocenters with high enantiomeric excesses using a chiral tetrafluorobenzobarrelene ligand.

    19. Highly Active Chiral Ruthenium-Based Metathesis Catalysts through a Monosubstitution in the N-Heterocyclic Carbene (pages 3972–3975)

      Sascha Tiede, Anke Berger, David Schlesiger, Daniel Rost, Anja Lühl and Siegfried Blechert

      Article first published online: 5 MAY 2010 | DOI: 10.1002/anie.201000940

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      Single (substitution) is better: New chiral ruthenium metathesis (pre)catalysts with a monosubstituted carbon atom in the N-heterocyclic carbene ligand are highly stable in solution, initiate easily, show very high enantioselectivity and excellent E selectivity in asymmetric ring-opening cross-metathesis (see scheme).

    20. Functional Nanomaterials

      Au@MnO Nanoflowers: Hybrid Nanocomposites for Selective Dual Functionalization and Imaging (pages 3976–3980)

      Thomas D. Schladt, Mohammed Ibrahim Shukoor, Kerstin Schneider, Muhammad Nawaz Tahir, Filipe Natalio, Irene Ament, Jan Becker, Florian D. Jochum, Stefan Weber, Oskar Köhler, Patrick Theato, Laura Maria Schreiber, Carsten Sönnichsen, Heinz C. Schröder, Werner E. G. Müller and Wolfgang Tremel

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.200906689

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      Flower power: A convenient strategy for preparing core-tunable multicomponent Au@MnO nanocrystals has been developed. The magnetic nanoflowers are not only efficient as cargo-specific carriers but also have excellent fluorescent properties resulting from fluorophors bound to the Au and MnO domains.

    21. Water Splitting

      Photochemical Fate: The First Step Determines Efficiency of H2 Formation with a Supramolecular Photocatalyst (pages 3981–3984)

      Stefanie Tschierlei, Michael Karnahl, Martin Presselt, Benjamin Dietzek, Julien Guthmuller, Leticia González, Michael Schmitt, Sven Rau and Jürgen Popp

      Article first published online: 21 APR 2010 | DOI: 10.1002/anie.200906595

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      The color of the incident light determines the efficiency of the hydrogen evolution mediated by a supramolecular photocatalyst. This finding demonstrates the importance of the Franck–Condon point in artificial photosynthesis systems and should have an impact on their design.

  12. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 24/2010 (page 3989)

      Article first published online: 17 MAY 2010 | DOI: 10.1002/anie.201090071

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