Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 42

October 15, 2012

Volume 51, Issue 42

Pages 10419–10669

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. You have free access to this content
      Cover Picture: Multivalency as a Chemical Organization and Action Principle (Angew. Chem. Int. Ed. 42/2012) (page 10419)

      Dr. Carlo Fasting, Prof. Christoph A. Schalley, Dr. Marcus Weber, Prof. Oliver Seitz, Prof. Stefan Hecht, Prof. Beate Koksch, Dr. Jens Dernedde, Prof. Christina Graf, Prof. Ernst-Walter Knapp and Prof. Rainer Haag

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201207626

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      Multivalent binding of dendritic polyglycerolsulfate (dPGS) to the surface-exposed adhesion receptor L-selectin shields white blood cells from contacting activated vascular endothelium. In the case of overwhelming inflammation, dPGS treatment strongly inhibits leukocyte emigration and thus acts as a highly effective anti-inflammatory compound. Further information on the topic of multivalency can be found in the Review by R. Haag et al. on page 10472 ff. The cover picture was designed by Dipl.-Chem. Achim Wiedekind, with the background based on a graphic from Juan Gaertner/shutterstock.com.

    2. You have free access to this content
      Inside Cover: Thermally Assisted Photonic Inversion of Supramolecular Handedness (Angew. Chem. Int. Ed. 42/2012) (page 10420)

      Anesh Gopal, Mohamed Hifsudheen, Dr. Seiichi Furumi, Prof. Masayuki Takeuchi and Prof. Ayyappanpillai Ajayaghosh

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201207156

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      Heat and light from the sun may have a strong influence on the molecular chirality and supramolecular handedness of natural creations, such as seashells. In their Communication on page 10505 ff., A. Ajayaghosh et al. establish that the inherent helicity of a synthetic photochromic molecular self-assembly can be biased towards the opposite direction by the action of heat and light. A model for this process through a deformation–reformation pathway is shown.

    3. You have free access to this content
      Inside Back Cover: Laponite Blue: Dissolving the Insoluble (Angew. Chem. Int. Ed. 42/2012) (page 10671)

      Dr. Marina M. Lezhnina, Tobias Grewe, Dr. Hardo Stoehr and Prof. Dr. Ulrich Kynast

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201207513

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      Nanoscaled clay platelets can act as shuttles to transport even completely nonpolar molecules into aqueous solutions. In their Communication on page 10652 ff., U. Kynast et al. give an example for the formation of a colored water-soluble hybrid material composed of the well-known dye indigo, which is notoriously insoluble in its native state, and a synthetic nanoclay. Solids recovered from these solutions are reminiscent of the ancient Maya Blue pigment.

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      Back Cover: High Antitumor Activity of Highly Resistant Salan–Titanium(IV) Complexes in Nanoparticles: An Identified Active Species (Angew. Chem. Int. Ed. 42/2012) (page 10672)

      Sigalit Meker, Katrin Margulis-Goshen, Ester Weiss, Prof. Shlomo Magdassi and Prof. Edit Y. Tshuva

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201207152

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      Anticancer metallodrugs based on biologically friendly titanium(IV) offer attractive alternatives to currently used platinum-based chemotherapy. In their Communication on page 10515 ff., E. Y. Tshuva, S. Magdassi, et al. present the high anticancer activity of water-resistant salan–titanium(IV) compounds when formulated into nanoparticles. A cellular active species was also identified.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
  3. Corrigenda

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. You have free access to this content
      Corrigendum: Formal Asymmetric Synthesis of Echinopine A and B (page 10436)

      Dr. Philippe A. Peixoto, Dr. Rene Severin, Dr. Chih-Chung Tseng and Prof. Dr. David Y.-K. Chen

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201207026

      This article corrects:

      Formal Asymmetric Synthesis of Echinopine A and B1

      Vol. 50, Issue 13, 3013–3016, Version of Record online: 18 FEB 2011

    2. You have free access to this content
      Corrigendum: Polarization Rotation in the Monoclinic Perovskite BiCo1−xFexO3 (page 10436)

      Dr. Kengo Oka, Tsukasa Koyama, Tomoatsu Ozaaki, Prof. Dr. Shigeo Mori, Prof. Dr. Yuichi Shimakawa and Prof. Dr. Masaki Azuma

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201205466

      This article corrects:

      Polarization Rotation in the Monoclinic Perovskite BiCo1−xFexO31

      Vol. 51, Issue 32, 7977–7980, Version of Record online: 2 JUL 2012

  4. Addition

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. You have free access to this content
      Addition: C[BOND]H Activation in S-Alkenyl Sulfoximines: An Endo 1,5-Hydrogen Migration (page 10437)

      Xuefeng Gao, Vikram Gaddam, Erich Altenhofer, Rama Rao Tata, Zhengxin Cai, Nattawut Yongpruksa, Aswin K. Garimallaprabhakaran and Prof. Michael Harmata

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201206823

      This article corrects:

      C[BOND]H Activation in S-Alkenyl Sulfoximines: An Endo 1,5-Hydrogen Migration1

      Vol. 51, Issue 28, 7016–7019, Version of Record online: 22 JUN 2012

  5. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Noritaka Mizuno (pages 10442–10443)

      Version of Record online: 13 JUN 2012 | DOI: 10.1002/anie.201203438

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      “My mottos are ‘be naïve’ and ‘be creative’. My favorite way to spend a holiday is fishing in a mountain stream. …” This and more about Noritaka Mizuno can be found on page 10442.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
  8. Obituary

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Ivano Bertini (1940–2012) (page 10445)

      Claudio Luchinat

      Version of Record online: 7 SEP 2012 | DOI: 10.1002/anie.201205977

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  9. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Circular Dichroism and Magnetic Circular Dichroism Spectroscopy for Organic Chemists. By Nagao Kobayashi, Atsuya Muranaka, and John Mack. (page 10446)

      Babak Borhan

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201206318

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      Royal Society of Chemistry, 2011. 216 pp., hardcover, £ 99.99.—ISBN 978-1847558695

  10. Highlights

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Palladium Catalysis

      Dinuclear Palladium Complexes—Precursors or Catalysts? (pages 10448–10450)

      Dr. Robert S. Paton and Dr. John M. Brown

      Version of Record online: 11 SEP 2012 | DOI: 10.1002/anie.201205417

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      Calculations help: Recent work from Schoenebeck's group has demonstrated beyond reasonable doubt that the dimeric LPdIBr catalysts that are widely used in coupling chemistry operate through prior formal reduction to an LPd0 species. Conversely, L2Pd0 catalysts can be activated by oxidation. In other cases a binuclear species can persist through the catalytic cycle.

    2. Solar Energy

      A Solid Advancement for Dye-Sensitized Solar Cells (pages 10451–10452)

      Prof. Udo Bach and Torben Daeneke

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201205437

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      Switching to solids: Solid-state dye-sensitized solar cells are achieving efficiencies similar to those of their counterparts with liquid electrolytes. The new p-type semiconductor CsSnI3 was found to be an excellent replacement for the traditional I/I3 redox system. The picture shows a cross section of a dye-sensitized solar cell based on CsSnI3.

  11. Correspondence

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Proton Conductivity (1)

      Limits of Proton Conductivity (pages 10454–10456)

      Dr. Klaus-Dieter Kreuer and Andreas Wohlfarth

      Version of Record online: 15 AUG 2012 | DOI: 10.1002/anie.201203887

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      Parasitic current seems to be the cause for the “highest proton conductivity” of a material reported to date. Kreuer and Wohlfarth verify this hypothesis by measuring the conductivity of the same materials after preparing them in a different way. They further explain the limits of proton conductivity and comment on the problems of determining the conductivity of small objects (e.g., whiskers, see picture).

    2. Proton Conductivity (2)

      Reply: High Proton Conductivity of Water Channels in a Highly Ordered Nanowire (pages 10457–10458)

      Noah Johnson and Prof. Dr. Hai-Feng Ji

      Version of Record online: 21 AUG 2012 | DOI: 10.1002/anie.201205225

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      Nanowires of trimesic acid and melamine are shown to be proton conductive, however the magnitude of conductivity is highly dependent on the quality of the nanowire, sample preparation, and measurement conditions. These problems need to be addressed in order to obtain reproducible results for practical use of this new family of proton-conductive materials.

  12. Minireview

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Gas Chromatography

      A New Dimension in Separation Science: Comprehensive Two-Dimensional Gas Chromatography (pages 10460–10470)

      Dr. Cornelia Meinert and Prof. Dr. Uwe J. Meierhenrich

      Version of Record online: 10 SEP 2012 | DOI: 10.1002/anie.201200842

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      Dimension jump: The ability to obtain multidimensional chromatograms by passing analytes over two different stationary phases connected by a modulator led to the invention of comprehensive gas chromatography. The increased resolution offered by GC×GC techniques (see picture) compared to that of traditional GC is useful for multiple applications, including the resolution of enantiomers.

  13. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Multivalency

      Multivalency as a Chemical Organization and Action Principle (pages 10472–10498)

      Dr. Carlo Fasting, Prof. Christoph A. Schalley, Dr. Marcus Weber, Prof. Oliver Seitz, Prof. Stefan Hecht, Prof. Beate Koksch, Dr. Jens Dernedde, Prof. Christina Graf, Prof. Ernst-Walter Knapp and Prof. Rainer Haag

      Version of Record online: 5 SEP 2012 | DOI: 10.1002/anie.201201114

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      Unified strength: Multivalent structures function in a number of biological systems to generate a strong but reversible interaction between two objects. The chemical realization of this natural principle with organized multiple interactions enables, for example, the development of multivalent drugs for an effective inhibition of viral cell attachment.

  14. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigenda
    5. Addition
    6. News
    7. Author Profile
    8. News
    9. Obituary
    10. Book Review
    11. Highlights
    12. Correspondence
    13. Minireview
    14. Review
    15. Communications
    1. Photopharmacology

      Azo-Propofols: Photochromic Potentiators of GABAA Receptors (pages 10500–10504)

      Marco Stein, Simon J. Middendorp, Valentina Carta, Ervin Pejo, Douglas E. Raines, Stuart A. Forman, Erwin Sigel and Dirk Trauner

      Version of Record online: 11 SEP 2012 | DOI: 10.1002/anie.201205475

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      Shine and rise! GABAA receptors are ligand-gated chloride ion channels that respond to γ-aminobutyric acid (GABA), which is the major inhibitory neurotransmitter of the mammalian central nervous system. Azobenzene derivatives of propofol, such as compound 1 (see scheme), increase GABA-induced currents in the dark form and lose this property upon light exposure and thus function as photochromic potentiators. Compound 1 can be employed as a light-dependent general anesthetic in translucent tadpoles.

    2. Photoswitchable Helicity

      Thermally Assisted Photonic Inversion of Supramolecular Handedness (pages 10505–10509)

      Anesh Gopal, Mohamed Hifsudheen, Dr. Seiichi Furumi, Prof. Masayuki Takeuchi and Prof. Ayyappanpillai Ajayaghosh

      Version of Record online: 29 AUG 2012 | DOI: 10.1002/anie.201205332

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      Spiraling into control: A photoresponsive supramolecular assembly demonstrates that light, along with heating (Δ) and cooling (), can cause chiral communication between molecules. This effect leads to bias in the helicity of the complex, causing a reversible switching of macroscopic handedness, as shown by a reversal of sign of the circularly polarized luminescence (CPL) that is emitted.

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    3. Stereoselective Catalysis

      Counteranion-Directed Catalysis in the Tsuji–Trost Reaction: Stereocontrolled Access to 2,5-Disubstituted 3-Hydroxy-Tetrahydrofurans (pages 10510–10514)

      Dr. Martin Arthuis, Rodolphe Beaud, Prof. Dr. Vincent Gandon and Dr. Emmanuel Roulland

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201205479

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      Hydrogen bonds can play a prominent role in organometallic catalysis, as shown for the title reaction, in which a counteranion directs the cyclization through the formation of hydrogen bonds that likely involve a proton of the π-allyl/palladium species itself. The reaction allows access to four out of the eight stereoisomers of 2,5-disubstitued 3-hydroxy-tetrahydrofurans and thus fragments of complex natural products.

    4. Drug Discovery

      High Antitumor Activity of Highly Resistant Salan–Titanium(IV) Complexes in Nanoparticles: An Identified Active Species (pages 10515–10517)

      Sigalit Meker, Katrin Margulis-Goshen, Ester Weiss, Prof. Shlomo Magdassi and Prof. Edit Y. Tshuva

      Version of Record online: 7 SEP 2012 | DOI: 10.1002/anie.201205973

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      A nanoformulated trinuclear hydrolysis product of a bis(alkoxo) salan–TiIV complex shows high antitumor activity (see picture), which identifies it as an active species in cells. Additional highly stable mononuclear derivatives also show high activity, when formulated into nanoparticles, thus evincing that biologically friendly TiIV can provide high cytotoxicity with controlled biological function.

    5. Single-Molecule Imaging

      Single-Molecule Visualization of the Hybridization and Dissociation of Photoresponsive Oligonucleotides and Their Reversible Switching Behavior in a DNA Nanostructure (pages 10518–10522)

      Dr. Masayuki Endo, Yangyang Yang, Dr. Yuki Suzuki, Kumi Hidaka and Prof. Hiroshi Sugiyama

      Version of Record online: 10 SEP 2012 | DOI: 10.1002/anie.201205247

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      A framed photo of DNA: A pair of photoresponsive oligonucleotides containing azobenzene moieties was introduced into double-stranded DNA within the cavity of a DNA nanostructure (see scheme). The two dsDNAs, in contact at the center, were dissociated using UV irradiation and hybridized with visible light; this was directly observed using high-speed atomic force microscopy.

    6. Quantum Dot Biolabeling

      Conjugation of Transferrin to Azide-Modified CdSe/ZnS Core–Shell Quantum Dots using Cyclooctyne Click Chemistry (pages 10523–10527)

      Dr. Christine Schieber, Alessandra Bestetti, Dr. Jet Phey Lim, Anneke D. Ryan, Dr. Tich-Lam Nguyen, Robert Eldridge, Dr. Anthony R. White, Prof. Paul A. Gleeson, Dr. Paul S. Donnelly, Prof. Spencer J. Williams and Prof. Paul Mulvaney

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201202876

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      Twinkle twinkle quantum dot: Conjugation of biomolecules to azide-modified quantum dots (QDs) through a bifunctional linker, using strain-promoted azide–alkyne cycloaddition with the QD and a squaramide linkage to the biomolecule (see scheme). Transferrin-conjugated QDs were internalized by transferrin-receptor expressing HeLa cells.

    7. CO2 Fixation

      Picking up 30 CO2 Molecules by a Porous Metal Oxide Capsule Based on the Same Number of Receptors (pages 10528–10531)

      Somenath Garai, Dr. Erhard T. K. Haupt, Dr. Hartmut Bögge, Dr. Alice Merca and Prof. Dr. Achim Müller

      Version of Record online: 24 SEP 2012 | DOI: 10.1002/anie.201204089

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      30 receptors in waiting position: In the porous (pentagon)12(linker)30-type molybdenum oxide capsule (see picture), the 30 positively charged linkers (five unsaturated shown for illustration in green, the others contain CO32− ligands) can act as receptors for neutral and negatively charged ligands. Bubbling CO2 into the solution containing the acetate-type capsules leads to the upload of CO2 based on 30 coordinated CO32− ligands.

    8. Antibiotic Resistance

      Self-Resistance to an Antitumor Antibiotic: A DNA Glycosylase Triggers the Base-Excision Repair System in Yatakemycin Biosynthesis (pages 10532–10536)

      Dr. Hui Xu, Dr. Wei Huang, Dr. Qing-Li He, Zhi-Xiong Zhao, Feng Zhang, Prof. Dr. Renxiao Wang, Prof. Dr. Jingwu Kang and Prof. Dr. Gong-Li Tang

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201204109

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      Resistance is (not) futile: The yatakemycin biosynthetic gene cluster involves the ytkR2 gene, which encodes a protein with homology to a recently discovered bacterial DNA glycosylase. Genetic validation in vivo, biochemical assays, and in vitro mutagenesis studies revealed that YtkR2 confers resistance for the bacteria by specifically recognizing and cleaving the YTM-modified base (see scheme).

    9. Smart Materials

      A Smart Nanofiber Web That Captures and Releases Cells (pages 10537–10541)

      Young-Jin Kim, Dr. Mitsuhiro Ebara and Prof. Takao Aoyagi

      Version of Record online: 18 SEP 2012 | DOI: 10.1002/anie.201204139

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      Caught in a web: Photo-cross-linkable temperature-responsive polymer-based nanofiber webs have been synthesized that have the ability to capture, encapsulate, and release cells by dynamically transforming the fibrous structure into hydrogel-like structures by wrapping, swelling, and deswelling processes in response to external temperature changes (see picture).

    10. Metal–Organic Frameworks

      Second-Order Nonlinear Optical Activity Induced by Ordered Dipolar Chromophores Confined in the Pores of an Anionic Metal–Organic Framework (pages 10542–10545)

      Jiancan Yu, Prof. Dr. Yuanjing Cui, Prof. Dr. Chuande Wu, Dr. Yu Yang, Prof. Dr. Zhiyu Wang, Prof. Dr. Michael O'Keeffe, Prof. Dr. Banglin Chen and Prof. Dr. Guodong Qian

      Version of Record online: 18 JUL 2012 | DOI: 10.1002/anie.201204160

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      Frequency doubling: A strategy for incorporating dipolar organic chromophores into the one-dimensional channels of an anionic metal–organic framework (MOF) has been developed to generate highly active nonlinear optical materials (see picture). The resulting MOF material shows a second-harmonic generation intensity of 18.3 versus α quartz.

    11. Nanocrystal Networks

      Mesoporous Metal and Metal Alloy Particles Synthesized by Aerosol-Assisted Confined Growth of Nanocrystals (pages 10546–10550)

      Dr. Qiangfeng Xiao, Dr. Hiesang Sohn, Zheng Chen, Dr. Daniel Toso, Dr. Matthew Mechlenburg, Prof. Z. Hong Zhou, Dr. Eric Poirier, Dr. Anne Dailly, Prof. Haiqiang Wang, Prof. Zhongbiao Wu, Dr. Mei Cai and Prof. Yunfeng Lu

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201204289

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      From droplets to “spheres”: A platform technology enables the rapid and continuous synthesis of mesoporous metal and metal alloy particles (see picture). The confined growth of nanocrystals in aerosol droplets leads to the formation of these particles with defined composition.

    12. Metal–Organic Frameworks

      Organosilica-Functionalized Zeolitic Imidazolate Framework ZIF-90 Membrane with High Gas-Separation Performance (pages 10551–10555)

      Prof. Dr. Aisheng Huang, M. Sc. Nanyi Wang, Dr. Chunlong Kong and Prof. Dr. Jürgen Caro

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201204621

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      A clear separation: A post-synthetic functionalization method is reported to obtain a highly permselective zeolitic imidazolate framework (ZIF-90) membrane. The intercrystalline defects of the ZIF-90 membrane are minimized to enhance the separation selectivity while a high permeance is maintained.

    13. Drug-Carrying Nanoparticles

      Targeted Cargo Delivery in Senescent Cells Using Capped Mesoporous Silica Nanoparticles (pages 10556–10560)

      Alessandro Agostini, Dr. Laura Mondragón, Dr. Andrea Bernardos, Prof. Ramón Martínez-Máñez, Dr. M. Dolores Marcos, Dr. Félix Sancenón, Dr. Juan Soto, Prof. Ana Costero, Dr. Cristina Manguan-García, Prof. Rosario Perona, Dr. Marta Moreno-Torres, Dr. Rafael Aparicio-Sanchis and Prof. José Ramón Murguía

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201204663

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      Learning to let go with age: Intracellular controlled release of molecules within senescent cells was achieved using mesoporous silica nanoparticles (MSNs) capped with a galacto-oligosaccharide (GOS) to contain the cargo molecules (magenta spheres; see scheme). The GOS is a substrate of the senescent biomarker, senescence-associated β-galactosidase (SA-β-gal), and releases the cargo upon entry into SA-β-gal expressing cells.

    14. Materials Science

      Self-Healing Supramolecular Block Copolymers (pages 10561–10565)

      Dr. Jens Hentschel, Dr. Aaron M. Kushner, Dr. Joseph Ziller and Prof. Dr. Zhibin Guan

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201204840

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      Polymer, heal thyself! Supramolecular ABA triblock copolymers formed by dimerization of 2-ureido-4-pyrimidinone (UPy) end-functionalized polystyrene-b-poly(n-butyl acrylate) (PS-b-PBA) AB diblock copolymers have been synthesized, resulting in a self-healing material that combines the advantageous mechanical properties of thermoplastic elastomers and the dynamic self-healing features of supramolecular materials.

    15. Gel Nanocubes

      Nano- and Microsized Cubic Gel Particles from Cyclodextrin Metal–Organic Frameworks (pages 10566–10569)

      Yuki Furukawa, Takumi Ishiwata, Prof. Dr. Kouta Sugikawa, Dr. Kenta Kokado and Prof. Dr. Kazuki Sada

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201204919

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      Sweet cube o' mine: Bottom-up control of gel particles has been regarded as a great challenge. By employing internal cross-linking of cyclodextrin metal–organic frameworks, cubic sugar gels were formed with sharp edges that reflect the shape of the crystals. This enabled the fabrication of shape- and size-controlled polymer gels from porous crystals (see picture).

    16. Bionanotechnology

      Observation of Multiphoton-Induced Fluorescence from Graphene Oxide Nanoparticles and Applications in In Vivo Functional Bioimaging (pages 10570–10575)

      Dr. Jun Qian, Dan Wang, Fu-Hong Cai, Dr. Wang Xi, Li Peng, Zhen-Feng Zhu, Dr. Hao He, Prof. Ming-Lie Hu and Prof. Sailing He

      Version of Record online: 24 SEP 2012 | DOI: 10.1002/anie.201206107

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      Lightening organelles: A femtosecond laser can excite multiphoton-induced luminescence of graphene oxide nanoparticles. The flow, distributions, and clearance of intravenously injected GO-PEG nanoparticles in the blood vessel of mice could be observed clearly by two-photon imaging. The 3D distribution of microinjected GO-PEG nanoparticles in a mice brain could also be reconstructed with two-photon microscopy.

    17. Vaccine Stabilization

      Eggshell-Inspired Biomineralization Generates Vaccines that Do Not Require Refrigeration (pages 10576–10579)

      Guangchuan Wang, Xiaofeng Li, Lijuan Mo, Zhiyong Song, Wei Chen, Yongqiang Deng, Hui Zhao, Ede Qin, Prof. Dr. Chengfeng Qin and Prof. Dr. Ruikang Tang

      Version of Record online: 24 SEP 2012 | DOI: 10.1002/anie.201206154

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      We're not gonna bake it: In situ biomineralization creates an egg-like shell on vaccine particles to improve their thermostability. Different from the bare vaccine (squares), the biomineralized vaccine (red circles) can be stored at ambient temperature without refrigeration for up to a week and retain biological activity both in vitro (see graph), as well as in a mouse model.

    18. Synthetic Methods

      A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination (pages 10580–10583)

      Steven Bloom, Cody Ross Pitts, David Curtin Miller, Nathan Haselton, Maxwell Gargiulo Holl, Ellen Urheim and Prof. Thomas Lectka

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201203642

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      A group effort: Reported is the title reaction using a polycomponent catalytic system involving commercially available Selectfluor, a putative radical precursor N-hydroxyphthalimide, an anionic phase-transfer catalyst (KB(C6F5)4), and a copper(I) bis(imine). The catalyst system formed leads to monofluorinated compounds selectively (see example) without the necessity for an excess of the alkane substrate.

    19. Rare Earths

      Genuine Redox Isomerism in a Rare-Earth-Metal Complex (pages 10584–10587)

      Prof. Dr. Igor L. Fedushkin, Dr. Olga V. Maslova, Dr. Alexander G. Morozov, Dr. Sebastian Dechert, Dr. Serhiy Demeshko and Prof. Dr. Franc Meyer

      Version of Record online: 18 SEP 2012 | DOI: 10.1002/anie.201204452

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      Redox isomerism is observed for a lanthanide complex for the first time. Upon lowering the temperature, an electron of [{(dpp-bian)Yb(μ-Cl)(dme)}2] (1) is transferred from the metal to the ligand (see picture), giving rise to marked shortening of Yb[BOND]N bonds and a hysteretic jump in the magnetic moment. The crystal packing is of a crucial importance, as two other crystal modifications of 1 do not undergo this effect.

    20. Indole Synthesis

      Multicomponent Assembly of Highly Substituted Indoles by Dual Palladium-Catalyzed Coupling Reactions (pages 10588–10591)

      John M. Knapp, Jie S. Zhu, Prof. Dean J. Tantillo and Prof. Mark J. Kurth

      Version of Record online: 24 SEP 2012 | DOI: 10.1002/anie.201204633

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      Highly substituted indoles were synthesized by a palladium-catalyzed reaction involving three independent components in a one-pot reaction. Two distinct palladium-catalyzed coupling reactions occur with a single catalytic system: a Buchwald-Hartwig reaction and an arene-alkene coupling. Quantum chemical computations provide insight into the mechanism of the latter coupling step.

    21. Asymmetric Synthesis

      Regio- and Enantioselective Cobalt-Catalyzed Reductive [3+2] Cycloaddition Reaction of Alkynes with Cyclic Enones: A Route to Bicyclic Tertiary Alcohols (pages 10592–10595)

      Dr. Chu-Hung Wei, Dr. Subramaniyan Mannathan and Prof. Dr. Chien-Hong Cheng

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201205115

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      Round and round: An unusual cobalt-catalyzed regio- and enantioselective reductive [3+2] cycloaddition of cyclic enones with alkynes affording bicyclic tertiary alcohols is described. A possible mechanism involving the formation of a cobaltacyclopentene intermediate is proposed.

    22. Natural Product Synthesis

      Enantioselective Formal Total Syntheses of Didehydrostemofoline and Isodidehydrostemofoline through a Catalytic Dipolar Cycloaddition Cascade (pages 10596–10599)

      Dr. Chao Fang, Dr. Charles S. Shanahan, Dr. Daniel H. Paull and Prof. Stephen F. Martin

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201205274

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      Sweet to the core: Enantioselective formal total syntheses of the title compounds were accomplished in 24 steps from 2-deoxy-D-ribose. The synthesis features a novel cascade of reactions culminating in an intramolecular dipolar cycloaddition to form the tricyclic core of the stemofoline alkaloids from an acyclic diazo imine intermediate.

    23. Bioorthogonal Chemistry

      Genetically Encoded Cyclopropene Directs Rapid, Photoclick-Chemistry-Mediated Protein Labeling in Mammalian Cells (pages 10600–10604)

      Dr. Zhipeng Yu, Yanchao Pan, Dr. Zhiyong Wang, Prof. Dr. Jiangyun Wang and Prof. Dr. Qing Lin

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201205352

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      We just click: Genetic incorporation of a cyclopropene amino acid CpK (see scheme) site-specifically into proteins in E. coli and mammalian cells was achieved using an orthogonal aminoacyl-tRNA synthetase/tRNACUA pair (CpKRS/MbtRNACUA). Cyclopropene exhibited fast reaction kinetics in the photoclick reaction and allowed rapid (ca. 2 min) labeling of proteins.

    24. Carbenoids

      A Nonmetal Approach to α-Heterofunctionalized Carbonyl Derivatives by Formal Reductive X[BOND]H Insertion (pages 10605–10609)

      Eric J. Miller, Wei Zhao, Jonathan D. Herr and Prof. Dr. Alexander T. Radosevich

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201205604

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      Keeping it organic: A direct synthesis of α-alkoxy and α-amino ester derivatives by direct reductive coupling of widely available, stable α-keto esters and protic pronucleophiles is described (see scheme; X=OR, NR2). The method serves as a convenient nonmetal alternative to X[BOND]H insertion by diazo decomposition.

    25. Homogenous Catalysis

      Access to Sultams by Rhodium(III)-Catalyzed Directed C[BOND]H Activation (pages 10610–10614)

      Manh V. Pham, Baihua Ye and Prof. Dr. Nicolai Cramer

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201206191

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      Director's cut: The pharmaceutically relevant sulfonamide group is shown to be a competent directing group for [Cp*Rh(OAc)2]-catalyzed C[BOND]H functionalizations. Reactions of the cyclometalated intermediate with internal alkynes provide access to a wide range of sultam derivatives. The reaction is high yielding and works best under aerobic conditions with catalytic amounts of CuOAc as an oxidation mediator. Cp*=C5Me5.

    26. Membrane Fabrication

      Continuous Polycrystalline Zeolitic Imidazolate Framework-90 Membranes on Polymeric Hollow Fibers (pages 10615–10618)

      Andrew J. Brown, Dr. J. R. Johnson, Megan E. Lydon, Prof. William J. Koros, Prof. Christopher W. Jones and Prof. Sankar Nair

      Version of Record online: 26 SEP 2012 | DOI: 10.1002/anie.201206640

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      Headed for a membrane: Continuous, polycrystalline ZIF-90 membranes (picture, left) can be grown at 65 °C from methanolic precursor solutions on nanocrystal-seeded surfaces of poly(amide–imide) macroporous hollow fibers (right). The ZIF-90 membranes exhibit good separation properties for linear over cyclic hydrocarbons, as well as gas permeation selectivities higher than Knudsen values.

    27. Synthetic Methods

      Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester (pages 10619–10623)

      Bin Li, Yin-Chang Lai, Dr. Yujun Zhao, Yiu-Hang Wong, Zhi-Liang Shen and Prof. Teck-Peng Loh

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201205981

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      Cascades: An InBr3-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins–polyene cyclization as the key step.

    28. The ortho and meta Magnesiation of Functionalized Anilines and Amino-Substituted Pyridines and Pyrazines at Room Temperature (pages 10624–10627)

      M. Sc. Gabriel Monzón, Dr. Ilaria Tirotta and Prof. Dr. Paul Knochel

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201205465

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      A practical ortho,meta, (or even ortho,ortho′) magnesiation of trifluoroacetamides of anilines, aminopyridines, and aminopyrazines at room temperature was performed with TMPMgCl⋅LiCl or TMP2Mg⋅2 LiCl. These magnesiations are compatible with several carbonyl functionalities and allow access to polysubstituted anilides in satisfactory yields.

    29. Gold Fluorides

      Investigation of Gold Fluorides and Noble Gas Complexes by Matrix-Isolation Spectroscopy and Quantum-Chemical Calculations (pages 10628–10632)

      Prof. Xuefeng Wang, Prof. Dr. Lester Andrews, Knut Willmann, Dipl.-Chem. Felix Brosi and Dr. Sebastian Riedel

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201205072

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      Noble with a difference: Matrix-isolation experiments and quantum-chemical calculations have led to the characterization of two new compounds, namely first open-shell binary gold fluoride, AuF2, and a NeAuF complex. Moreover, ArAuF, AuF3, Au2F6, and monomeric AuF5 have been produced and identified under cryogenic conditions in neon and argon matrices.

    30. Dual Activation

      Gold Vinylidene Complexes: Intermolecular C(sp3)[BOND]H Insertions and Cyclopropanations Pathways (pages 10633–10637)

      Prof. Dr.  A. Stephen K. Hashmi, M. Sc. Marcel Wieteck, Dr. Ingo Braun, Dr. Matthias Rudolph and Dr. Frank Rominger

      Version of Record online: 17 SEP 2012 | DOI: 10.1002/anie.201204015

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      Highly reactive gold vinylidene species are used for intermolecular C(sp3)[BOND]H insertions into unactivated alkanes (see scheme). In addition, they can be regarded as synthons for alkylidene carbenes. Initiated by cyclopropanation of the vinylidene species/alkylidene carbenoide, cyclobutene derivatives are formed in a diastereoselective fashion by a ring-enlargement cascade in only one step.

    31. Biosynthesis

      Cooperation of Two Bifunctional Enzymes in the Biosynthesis and Attachment of Deoxysugars of the Antitumor Antibiotic Mithramycin (pages 10638–10642)

      Dr. Guojun Wang, Dr. Pallab Pahari, Dr. Madan K. Kharel, Dr. Jing Chen, Prof. Dr. Haining Zhu, Prof. Dr. Steven G. Van Lanen and Prof. Dr. Jürgen Rohr

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201205414

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      Two bifunctional enzymes cooperate in the assembly and the positioning of two sugars, D-olivose and D-mycarose, of the anticancer antibiotic mithramycin. MtmC finishes the biosynthesis of both sugar building blocks depending on which MtmGIV activity is supported. MtmGIV transfers these two sugars onto two structurally distinct acceptor substrates. The dual function of these enzymes explains two essential but previously unidentified activities.

    32. Gold(III) Hydrides

      A Thermally Stable Gold(III) Hydride: Synthesis, Reactivity, and Reductive Condensation as a Route to Gold(II) Complexes (pages 10643–10646)

      Dragoş-Adrian Roşca, Dr. Dan A. Smith, Dr. David L. Hughes and Prof. Manfred Bochmann

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201206468

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      Going for gold: The first thermally stable gold(III) hydride [(C N C)*AuH] is presented. It undergoes regioselective insertions with allenes to give gold(III) vinyl complexes, and reductive condensation with [(C N C)*AuOH] to the air-stable AuII product, [(C N C)*2Au2], with a short nonbridged gold–gold bond.

    33. Inhibitors

      Metal–Bis(2-picolyl)amine Complexes as State 1(T) Inhibitors of Activated Ras Protein (pages 10647–10651)

      Dr. Ina C. Rosnizeck, Priv.-Doz. Dr. Michael Spoerner, Tobias Harsch, Dr. Sandra Kreitner, Dr. Daniel Filchtinski, Prof. Dr. Christian Herrmann, Dr. Daniel Engel, Prof. Dr. Burkhard König and Prof. Dr. Dr. Hans Robert Kalbitzer

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201204148

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      Allosteric interactions: Metal(II) cyclens inhibit Ras–effector interactions by stabilizing a weak effector-binding state of Ras, state 1(T), and binding directly in the active site. The novel state (1T) inhibitor Zn2+–BPA (BPA=bis(2-picolyl)amine) binds outside the nucleotide binding pocket but nevertheless allosterically stabilizes state 1(T) and thus inhibits the Ras–Raf interaction.

    34. Water Solubilized Indigo

      Laponite Blue: Dissolving the Insoluble (pages 10652–10655)

      Dr. Marina M. Lezhnina, Tobias Grewe, Dr. Hardo Stoehr and Prof. Dr. Ulrich Kynast

      Version of Record online: 5 SEP 2012 | DOI: 10.1002/anie.201203236

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      The neutral organic dye indigo forms an inorganic–organic hybrid material with nanoclays (see picture; blue circles on disks symbolizing indigo, spheres indicating liberated cations) and can thus be transferred into aqueous solution. Solids recovered from these solutions resemble the ancient Maya Blue pigment. The method can also be applied to other hydrophobic species and may open the gate for novel solution chemistry, including photonic and catalytic applications.

    35. Protein–Ligand Interactions

      You have full text access to this OnlineOpen article
      Label-Free Microscale Thermophoresis Discriminates Sites and Affinity of Protein–Ligand Binding (pages 10656–10659)

      Susanne A. I. Seidel, Dr. Christoph J. Wienken, Sandra Geissler, Dr. Moran Jerabek-Willemsen, Dr. Stefan Duhr, Alwin Reiter, Prof. Dirk Trauner, Prof. Dieter Braun and Dr. Philipp Baaske

      Version of Record online: 24 SEP 2012 | DOI: 10.1002/anie.201204268

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      Look, no label! Microscale thermophoresis makes use of the intrinsic fluorescence of proteins to quantify the binding affinities of ligands and discriminate between binding sites. This method is suitable for studying binding interactions of very small amounts of protein in solution. The binding of ligands to iGluR membrane receptors, small-molecule inhibitorss to kinase p38, aptamers to thrombin, and Ca2+ ions to synaptotagmin was quantified.

    36. Enantioenriched Amines

      Kinetic Resolution of Nitrogen Heterocycles with a Reusable Polymer-Supported Reagent (pages 10660–10663)

      Imants Kreituss, Yuta Murakami, Dr. Michael Binanzer and Prof. Jeffrey W. Bode

      Version of Record online: 18 SEP 2012 | DOI: 10.1002/anie.201204991

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      Shake it up baby! Simply shaking a polymer-supported reagent and the racemic amine at room temperature kinetically resolves a broad range of N-heterocycles with good selectivity. The polymer-supported reagents are robust, easy to regenerate, and can be reused dozens of times. Cleavable acyl groups can be used to give access to both amine enantiomers in a single resolution.

    37. Combinatorial Biosynthesis

      Minimally Invasive Mutagenesis Gives Rise to a Biosynthetic Polyketide Library (pages 10664–10669)

      Dr. Susanna Kushnir, Dipl.-Ing. (FH) Uschi Sundermann, Dr. Samir Yahiaoui, Dipl.-Ing. (FH) Andreas Brockmeyer, Dr. Petra Janning and Prof. Dr. Frank Schulz

      Version of Record online: 20 SEP 2012 | DOI: 10.1002/anie.201202438

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      Not in the public domain: Site-directed mutagenesis of megasynthases was the key to the generation of a library of polyketides in bacteria. Redox derivatizations are used to change the bioactivity profile of the compounds.

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