Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 22

May 17, 2010

Volume 49, Issue 22

Pages 3699–3847

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Cover Picture: Which Is the Actual Catalyst: Chiral Phosphoric Acid or Chiral Calcium Phosphate? (Angew. Chem. Int. Ed. 22/2010) (page 3699)

      Manabu Hatano, Katsuhiko Moriyama, Toshikatsu Maki and Kazuaki Ishihara

      Article first published online: 29 APR 2010 | DOI: 10.1002/anie.201002202

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      Both are active, the chiral phosphoric acid and the chiral calcium phosphate. K. Ishihara and co-workers describe in their Communication on page 3823 ff. a highly enantioselective direct Mannich-type reaction of aldimines with a wide range of 1,3-dicarbonyl compounds. The catalyst, a chiral phosphoric acid, is used in the presence or absence of CaII. The absolute stereoselectivity of the products without CaII is the opposite of that obtained with the calcium phosphate catalyst.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Inside Cover: Iridium Complex with Antiangiogenic Properties (Angew. Chem. Int. Ed. 22/2010) (page 3700)

      Alexander Wilbuer, Danielle H. Vlecken, Daan J. Schmitz, Katja Kräling, Klaus Harms, Christoph P. Bagowski and Eric Meggers

      Article first published online: 30 APR 2010 | DOI: 10.1002/anie.201001646

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      Organoiridium complexes are noteworthy scaffolds for the design of enzyme inhibitors. As described by E. Meggers and co-workers in their Communication on page 3839 ff., a nanomolar and selective iridium-based inhibitor for the receptor protein kinase VEGFR3 (Flt4) has been discovered. This nontoxic octahedral iridium(III) complex, which is synthesized through stereoselective oxidative addition starting from a suitable square-planar iridium(I) precursor, is revealed to interfere with the development of blood vessels in vivo in two different zebrafish angiogenesis models.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 22/2010 (pages 3703–3711)

      Article first published online: 10 MAY 2010 | DOI: 10.1002/anie.201090065

  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    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 Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Lutz Ackermann (page 3716)

      Article first published online: 19 APR 2010 | DOI: 10.1002/anie.201000968

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      “The secret of being a successful scientist is curiosity and dedication. A good work day begins with exciting new experimental results …” This and more about Lutz Ackermann can be found on page 3716.

  6. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Amino Acids, Peptides and Proteins in Organic Chemistry. Volume 1 – Origins and Synthesis of Amino Acids. Edited by Andrew B. Hughes. (pages 3717–3718)

      Katja Schmitz

      Article first published online: 10 MAY 2010 | DOI: 10.1002/anie.201001553

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      Wiley-VCH, Weinheim 2009. 714 pp., hardcover € 159.00.—ISBN 978-3527320967

  7. Highlights

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

      Building Addressable Libraries as Platforms for Biological Assays by an Electrochemical Method (pages 3720–3722)

      Jun-ichi Yoshida and Aiichiro Nagaki

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.201000046

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      A well-stocked toolbox is available for the site-selective arrangement of molecules on microelectrode arrays to form addressable libraries thanks to a combination of electrochemistry with a variety of organometallic reactions, such as the Suzuki reaction (see scheme; TBAB=tetrabutylammonium bromide). A diblock copolymer formed an advantageous electrode coating in place of conventional agarose and sucrose.

    2. Hydrogen Production

      Electrochemical Hydrogen Production: Bridging Homogeneous and Heterogeneous Catalysis (pages 3723–3725)

      Marc T. M. Koper and Elisabeth Bouwman

      Article first published online: 26 APR 2010 | DOI: 10.1002/anie.201000629

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      Beyond platinum: A recently reported nickel-based molecular catalyst stands out as one of the best non-platinum-based catalysts developed for the electrochemical evolution of hydrogen. These findings are discussed within the framework of a simple theory for this reaction that has evolved from the Sabatier principle (see volcano plot in the picture, η is the thermodynamic overpotential, ΔG(H) is the binding energy of H to the catalyst) and recent DFT calculations.

  8. Essay

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. Plastic Banknotes

      Australia’s Plastic Banknotes: Fighting Counterfeit Currency (pages 3726–3736)

      Emma L. Prime and David H. Solomon

      Article first published online: 31 MAR 2010 | DOI: 10.1002/anie.200904538

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      More security: The world's first banknote printed on clear plastic film and using optically variable devices (OVDs) was issued in Australia in 1988 (see picture) after twenty years of research and development. In the course of this, a great deal of technical as well as logistic issues had to be solved. Shown is the Australian Bicentennial $10 note released in 1988.

  9. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
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    1. The Origin of Life

      On the Origin of Primitive Cells: From Nutrient Intake to Elongation of Encapsulated Nucleotides (pages 3738–3750)

      Uwe J. Meierhenrich, Jean-Jacques Filippi, Cornelia Meinert, Pierre Vierling and Jason P. Dworkin

      Article first published online: 30 APR 2010 | DOI: 10.1002/anie.200905465

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      A primitive cell remodeled: Bilayer membrane vesicles (see picture) provide a multifaceted microenvironment in which protometabolic reactions could have been triggered. This Review summarizes experiments carried out to form vesicles by the aggregation of amphiphiles. The addition of nucleotides to the extravesicular medium results in them being taken up and their participation in non-enzymatic elongation of the DNA primer within the vesicular interior.

  10. Communications

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

      Reversible Thermally and Photoinduced Electron Transfer in a Cyano-Bridged {Fe2Co2} Square Complex (pages 3752–3756)

      Yuanzhu Zhang, Dongfeng Li, Rodolphe Clérac, Marguerite Kalisz, Corine Mathonière and Stephen M. Holmes

      Article first published online: 21 APR 2010 | DOI: 10.1002/anie.201000765

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      Flip to be square: Structural, spectroscopic, magnetic, and photomagnetic studies conclusively demonstrate that a tetranuclear cyanometalate {Fe2Co2} complex undergoes reversible thermally and light-induced changes in its optical and magnetic properties. This bistability is induced by an intramolecular electron transfer, as observed in three-dimensional Co/Fe Prussian blue compounds (see picture).

    2. Micropatterning

      Micromolding of a Highly Fluorescent Reticular Coordination Polymer: Solvent-Mediated Reconfigurable Polymerization in a Soft Lithographic Mold (pages 3757–3761)

      Youngmin You, Hoichang Yang, Jong Won Chung, Jong H. Kim, Yunoh Jung and Soo Young Park

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.201000096

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      The fluorescent stripes: Coordination polymerization of pyridine-based ligands and zinc or silver ions was controlled by soft lithographic micromolding in capillaries. The polymer patterns (see picture) that are produced are highly fluorescent and supramolecularly structured.

    3. Designed Stereoselectivity

      Building Stereoselectivity into a Chemoselective Ring-Opening Metathesis Polymerization Catalyst for Alternating Copolymerization (pages 3762–3766)

      Sebastian Torker, Andre Müller and Peter Chen

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.200906846

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      This way and that: Ruthenium complexes with asymmetric bidentate phosphine ligands bearing two substituents that differ in size (green spheres) produce a totally alternating copolymer of norbornene and cyclooctene by ring-opening metathesis polymerization (ROMP). The E/Z ratio can be influenced systematically by changing the bulkiness of the aryl sulfonate ligand (blue rectangles).

    4. Nanotechnology

      Elucidation of Peptide Effects that Control the Activity of Nanoparticles (pages 3767–3770)

      Ryan Coppage, Joseph M. Slocik, Manish Sethi, Dennis B. Pacardo, Rajesh R. Naik and Marc R. Knecht

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.200906949

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      A lot of pep: Simple changes to the sequence of peptide nanostructures were found to maintain stability and enhance the activity of peptide-based palladium nanocatalysts. A histidine to alanine substitution in the peptide chain afforded an increase in turnover frequency from 2234 to 5224, which suggests that the peptide modulates the functionality of bio-inspired nanomaterials.

    5. Nanoparticles

      Nanoparticles for Drug Delivery Prepared from Amphiphilic PLGA Zwitterionic Block Copolymers with Sharp Contrast in Polarity between Two Blocks (pages 3771–3776)

      Zhiqiang Cao, Qiuming Yu, Hong Xue, Gang Cheng and Shaoyi Jiang

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.200907079

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      In sharp contrast: Poly(carboxybetaine) (PCB)–poly(lactic-co-glycolic acid) (PLGA) block copolymers were obtained by inclusion of tBu groups onto the PCB monomers. The resulting self-assembled PLGA core/PCB shell nanoparticles have extraordinary stability and a high potential for functionalization because of the COO groups on the PCB shell (see picture; EDC=1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; NHS=N-hydroxysuccinimide).

    6. Nanotechnology

      Photothermal Effects of Supramolecularly Assembled Gold Nanoparticles for the Targeted Treatment of Cancer Cells (pages 3777–3781)

      Shutao Wang, Kuan-Ju Chen, Ting-Hsiang Wu, Hao Wang, Wei-Yu Lin, Minori Ohashi, Pei-Yu Chiou and Hsian-Rong Tseng

      Article first published online: 9 APR 2010 | DOI: 10.1002/anie.201000062

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      Laser-triggered nanobomb: Size-controlled gold supramolecular nanoparticles (Au-SNPs) were synthesized from 2 nm gold colloids by a supramolecular self-assembly approach. These Au-SNPs exhibited significantly enhanced photothermal effects and could be used in conjunction with laser irradiation for the selective destruction of cancer cells (see picture) after the incorporation of a target-specific ligand.

    7. Photochemistry

      Remote-Control Photorelease of Caged Compounds Using Near-Infrared Light and Upconverting Nanoparticles (pages 3782–3785)

      Carl-Johan Carling, Farahnaz Nourmohammadian, John-Christopher Boyer and Neil R. Branda

      Article first published online: 14 APR 2010 | DOI: 10.1002/anie.201000611

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      Cage fighter: Lanthanide-doped upconverting nanoparticles convert near-infrared light into ultraviolet light, which drives the photoinduced release of a “caged” species on the nanoparticle surface. This approach overcomes the problem that low-energy light is necessary for penetrating deeper into tissue without damage but cannot be used to directly trigger important organic photochemical reactions.

    8. Magnetic Particles

      Magnetoresponsive Microparticles with Nanoscopic Surface Structures for Remote-Controlled Locomotion (pages 3786–3790)

      Shin-Hyun Kim, Jae Young Sim, Jong-Min Lim and Seung-Man Yang

      Article first published online: 14 APR 2010 | DOI: 10.1002/anie.201001031

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      Rock and roll: The rotational and translational motion of magnetic Janus particles with nanoscopic surface structure can be controlled by an external magnetic field (see picture). The nanoscopic surface pattern enhances the microscopic motion of the microspheres by inducing strong coupling between rotation and translation. The separation of individual microspheres from the mixture in a microfluidic device is also demonstrated.

    9. Selective C[BOND]O Cleavage

      Non-Oxidative Vanadium-Catalyzed C[BOND]O Bond Cleavage: Application to Degradation of Lignin Model Compounds (pages 3791–3794)

      Sunghee Son and F. Dean Toste

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.201001293

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      New direction: Changes in the ligand structure divert the reactivity of vanadium(V) oxo complexes from alcohol oxidation to a novel non-oxidative C[BOND]O bond cleavage. Thus, highly functionalized aryl enones can be selectively generated from lignin model compounds by vanadium-catalyzed cleavage of the β-O-4 linkage (see scheme; N blue, O red).

    10. Asymmetric Catalysis

      Rhodium-Catalyzed Asymmetric Synthesis of Spirocarbocycles: Arylboron Reagents as Surrogates of 1,2-Dimetalloarenes (pages 3795–3798)

      Ryo Shintani, Shingo Isobe, Momotaro Takeda and Tamio Hayashi

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.201000937

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      Revolutionary Rh-oad: A rhodium/diene-catalyzed addition of sodium tetraarylborates to alkyne-tethered 2-cycloalken-1-ones has been developed for the synthesis of spirocarbocycles. The tetraarylborates catalytically form two new carbon–carbon bonds. A chiral diene ligand also asymmetrically creates quaternary spirocarbon stereocenters with high enantiomeric purity.

    11. Asymmetric Three-Component Inverse Electron-Demand Aza-Diels–Alder Reaction: Efficient Synthesis of Ring-Fused Tetrahydroquinolines (pages 3799–3802)

      Mingsheng Xie, Xiaohong Chen, Yin Zhu, Bo Gao, Lili Lin, Xiaohua Liu and Xiaoming Feng

      Article first published online: 14 APR 2010 | DOI: 10.1002/anie.201000590

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      Diels or no Diels: The titled reaction of aldehydes, anilines, and cyclopentadiene, promoted by 0.5–5 mol % of an N,N′-dioxide scandium complex, afforded ring-fused tetrahydroquinolines that contained three contiguous stereocenters. The one-pot reaction delivers the products with good yields and excellent diastereo- and enantioselectivities.

    12. Concerted Proton–Electron Transfer

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      Inserting a Hydrogen-Bond Relay between Proton Exchanging Sites in Proton-Coupled Electron Transfers (pages 3803–3806)

      Cyrille Costentin, Marc Robert, Jean-Michel Savéant and Cédric Tard

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.200907192

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      Take the “H-bond” train: Introduction of a hydrogen-bond relay efficiently mediates the electron-transfer triggered exchange of protons between two sites over large distances (see picture). Thanks to this concerted proton–electron transfer mechanism, protonation of the relay group is avoided.

    13. Chiral Catalysts

      Integrating the Schrock and Grubbs Catalysts: Ruthenium–Binaphtholate Catalysts for Olefin Metathesis (pages 3807–3810)

      Johanna M. Blacquiere, Robert McDonald and Deryn E. Fogg

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.200906635

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      The best of both worlds: Direct incorporation of the atropisomeric binaphtholate ligand into the Grubbs class ruthenium metathesis catalysts is described. Chiral Ru–bino complexes are accessible in good to excellent yields by reaction of K2(bino) with [RuCl2(NHC)(py)2([DOUBLE BOND]CHPh)] in pyridine (see scheme; bino=1,1′-binaphthyl-2,2′-diolate, py=pyridine, NHC=IMes, H2IMes; IMes=N,N′-bis(mesityl)imidazol-2-ylidene; L=PCy3 or (py)2).

    14. Actinides

      Solving the Hydration Structure of the Heaviest Actinide Aqua Ion Known: The Californium(III) Case (pages 3811–3815)

      Elsa Galbis, Jorge Hernández-Cobos, Christophe den Auwer, Claire Le Naour, Dominique Guillaumont, Eric Simoni, Rafael R. Pappalardo and Enrique Sánchez Marcos

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.200906129

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      Wish they all could be californium: X-ray absorption spectroscopy (black points) and Monte Carlo simulations (blue line) of CfIII in aqueous solutions have been combined to determine the ligand distance and coordination number (CN) of the CfIII aqua ion (see picture), the heaviest cation measured and simulated to date. The results confirm that a contraction takes place in the actinide series as in the lanthanide series.

    15. Cheminformatics

      Structure–Activity Relationships through Sequencing (StARTS) Defines Optimal and Suboptimal RNA Motif Targets for Small Molecules (pages 3816–3818)

      Sai Pradeep Velagapudi, Steven J. Seedhouse and Matthew D. Disney

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.200907257

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      Hitting the target: A combined computational and experimental approach defines optimal and suboptimal RNA motifs as targets for small molecules through two-dimensional combinatorial screening. The method, termed structure–activity relationships through sequencing (StARTS), uses information from the sequences of the RNA motifs selected to bind a ligand.

    16. Fluorine Chemistry

      Activation of C[BOND]F Bonds in Preference to C[BOND]I Bonds: Difluoromethylation of Lithium Enolates with Trifluoromethyl Iodide (pages 3819–3822)

      Koichi Mikami, Yuichi Tomita and Yoshimitsu Itoh

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.201000435

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      The I's have it: A conceptually new C[BOND]F activation/C[BOND]C formation and its mechanism are described. Surprisingly, a reaction with Li-enolates and trifluoromethyl iodide gave (alpha)-difluoromethyl product via C[BOND]F bond cleavage in preference to the weaker C[BOND]I bond of trifluoromethyliodide. This reaction proceeds without the use of any late transition-metal catalyst (see scheme; LHMDS=lithium hexamethyldisilaxide).

    17. Asymmetric Catalysis

      Which Is the Actual Catalyst: Chiral Phosphoric Acid or Chiral Calcium Phosphate? (pages 3823–3826)

      Manabu Hatano, Katsuhiko Moriyama, Toshikatsu Maki and Kazuaki Ishihara

      Article first published online: 20 APR 2010 | DOI: 10.1002/anie.201000824

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      Both catalysts work: A highly enantioselective direct Mannich-type reaction of N-Boc-protected aldimines with 1,3-dicarbonyl compounds has been developed with the use of a chiral phosphoric acid in the presence or absence of CaII. The absolute stereoselectivity of the phosphoric acid catalysis was found to be opposite to that of the calcium phosphate catalysis (see scheme; Boc=tert-butoxycarbonyl).

    18. Asymmetric C[BOND]H Addition

      Nickel-Catalyzed Asymmetric Addition of Alkyne C[BOND]H Bonds across 1,3-Dienes Using Taddol-Based Chiral Phosphoramidite Ligands (pages 3827–3829)

      Masamichi Shirakura and Michinori Suginome

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.201001188

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      Enantioenriched 3-methyl-1,4-enynes are the products of the title reaction. The terminal α-siloxy-sec-alkyl groups were then converted into γ-oxoalkyl groups by rhodium-catalyzed conjugate alkynyl addition to α,β-unsaturated ketones through cleavage of the alkynyl C[BOND]C bond.

    19. Inhibitors

      Stabilizing a Weak Binding State for Effectors in the Human Ras Protein by Cyclen Complexes (pages 3830–3833)

      Ina C. Rosnizeck, Thorsten Graf, Michael Spoerner, Jens Tränkle, Daniel Filchtinski, Christian Herrmann, Lothar Gremer, Ingrid R. Vetter, Alfred Wittinghofer, Burkhard König and Hans Robert Kalbitzer

      Article first published online: 16 APR 2010 | DOI: 10.1002/anie.200907002

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      En route to new inhibitors: The binding of Zn2+ cyclen to the human Ras protein stabilizes a protein conformation that has a weak affinity for effectors. Consequently this complex is a lead structure for inhibition studies on the Ras–effector interaction. The picture shows the NMR structure of Ras⋅Mg2+⋅GppNHp complexed to Zn2+ cyclen.

    20. Mass-Spectrometry-Based Histology

      Histology by Mass Spectrometry: Label-Free Tissue Characterization Obtained from High-Accuracy Bioanalytical Imaging (pages 3834–3838)

      Andreas Römpp, Sabine Guenther, Yvonne Schober, Oliver Schulz, Zoltan Takats, Wolfgang Kummer and Bernhard Spengler

      Article first published online: 15 APR 2010 | DOI: 10.1002/anie.200905559

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      Next-generation imaging mass spectrometry of biological tissue on the cellular level shows excellent agreement with histochemical evaluation whilst providing a much higher discrimination capacity based on label-free molecular information (see image of a mouse urinary bladder section).

    21. Bioorganometallic Chemistry

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      Iridium Complex with Antiangiogenic Properties (pages 3839–3842)

      Alexander Wilbuer, Danielle H. Vlecken, Daan J. Schmitz, Katja Kräling, Klaus Harms, Christoph P. Bagowski and Eric Meggers

      Article first published online: 30 APR 2010 | DOI: 10.1002/anie.201000682

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      Identified as nanomolar and selective inhibitor of receptor protein kinase VEGFR3 (Flt4), the nontoxic and octahedrally coordinated IrIII complex 1 was synthesized by a stereoselective oxidative addition to a square-planar coordinated IrI precursor. The arrows in the image indicate positions at which the blood vessel formation in a zebrafish model of angiogenesis has been hampered by 1.

  11. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. Book Reviews
    8. Highlights
    9. Essay
    10. Review
    11. Communications
    12. Preview
    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 23/2010 (page 3847)

      Article first published online: 10 MAY 2010 | DOI: 10.1002/anie.201090067

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