Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 30

July 22, 2013

Volume 52, Issue 30

Pages 7607–7885

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. You have free access to this content
      Cover Picture: Light-Regulated Stapled Peptides to Inhibit Protein–Protein Interactions Involved in Clathrin-Mediated Endocytosis (Angew. Chem. Int. Ed. 30/2013) (page 7607)

      Dr. Laura Nevola, Andrés Martín-Quirós, Dr. Kay Eckelt, Dr. Núria Camarero, Dr. Sébastien Tosi, Dr. Artur Llobet, Prof. Dr. Ernest Giralt and Prof. Dr. Pau Gorostiza

      Article first published online: 1 JUL 2013 | DOI: 10.1002/anie.201304975

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      Remote control of membrane traffic is described by E. Giralt, P. Gorostiza, et al. in their Communication on page 7704 ff. Photoswitchable inhibitors of protein–protein interactions have been applied to photoregulate clathrin-mediated endocytosis in living cells. Traffic light peptides constitute a new tool to control cell signaling in spatiotemporally defined patterns and can be used to dissect the role of clathrin-mediated endocytosis in receptor internalization and in cell growth, division, and differentiation.

    2. You have free access to this content
      Inside Cover: A Chemo-Enzymatic Approach for Site-Specific Modification of the RNA Cap (Angew. Chem. Int. Ed. 30/2013) (page 7608)

      Daniela Schulz, Josephin Marie Holstein and Dr. Andrea Rentmeister

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304978

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      Targeting the mRNA cap by a chemo-enzymatic approach opens up new possibilities in mRNA isolation and visualization. In their Communication on page 7874 ff. A. Rentmeister and co-workers present a novel two-step approach for the regiospecific labeling of the m7G cap, a hallmark of eukaryotic mRNAs. They make use of a trimethylguanosine variant capable of transferring reactive groups from AdoMet analogues to the cap. The transferred residues are amenable to click reactions.

    3. You have free access to this content
      Inside Back Cover: Shaping Micelles: The Interplay Between Hydrogen Bonds and Dispersive Interactions (Angew. Chem. Int. Ed. 30/2013) (page 7887)

      Dr. Iker León, Dr. Judith Millán, Dr. Emilio J. Cocinero, Prof. Alberto Lesarri and Dr. José A. Fernández

      Article first published online: 27 JUN 2013 | DOI: 10.1002/anie.201304979

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      Unraveling the inverse micelle structure of propofol, a potent general anesthetic, through a combination of mass-resolved laser-based spectroscopic techniques and high-level quantum-mechanical calculations is presented by J. A. Fernández et al. in their Communication on page 7772 ff. In propofol, highly directional hydrogen bonds impose a framework on which the rest of the noncovalent interactions are built to give the micelle its final shape, leaving a characteristic signature in the infrared spectrum.

    4. You have free access to this content
      Back Cover: Highly Conductive Aluminum Textile and Paper for Flexible and Wearable Electronics (Angew. Chem. Int. Ed. 30/2013) (page 7888)

      Dr. Hye Moon Lee, Dr. Si-Young Choi, Areum Jung and Prof. Seung Hwan Ko

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304984

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      Wearable electronics require highly conductive fibrous materials, which can now be fabricated at room temperature. In their Communication on page 7718 ff., H. M. Lee, S. H. Ko, and co-workers demonstrate that cotton or paper fibers can be impregnated and coated with Al atoms from the precursor Al{O(C4H9)2}. The fibrous materials exhibit excellent electrical conductivity, as well as enduring mechanical strength, which is indicative of their potential applications for flexible and wearable electronics.

  2. Editorial

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. You have free access to this content
  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 30/2013 (pages 7613–7628)

      Article first published online: 17 JUL 2013 | DOI: 10.1002/anie.201390030

  4. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. You have free access to this content
      Corrigendum: Dendritic Luminescent Gold(III) Complexes for Highly Efficient Solution-Processable Organic Light-Emitting Devices (page 7628)

      Man-Chung Tang, Daniel Ping-Kuen Tsang, Dr. Maggie Mei-Yee Chan, Dr. Keith Man-Chung Wong and Prof. Dr. Vivian Wing-Wah Yam

      Article first published online: 17 JUL 2013 | DOI: 10.1002/anie.201304585

      This article corrects:
  5. News

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
  6. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Janine Cossy (pages 7634–7635)

      Article first published online: 2 APR 2013 | DOI: 10.1002/anie.201300417

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      “What I look for first in a publication is the abstract and schemes. The most important thing I learned from my parents is to work hard. …” This and more about Janine Cossy can be found on page 7634–7635.

  7. News

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
  8. Book Review

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Acids and Bases. Solvent Effects on Acid–Base Strength. By Brian G. Cox. (page 7638)

      Robin A. Cox

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201304650

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      Oxford University Press, 2013. 160 pp., softcover, $ 45.00.—ISBN 978-0199670529

  9. Highlights

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Energy Harvesting

      Nanofluidics for Giant Power Harvesting (pages 7640–7641)

      Dr. Li Zhang and Prof. Xiaodong Chen

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201302707

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      Nanochannels for power generation: The confinement of fluid motion in a single boron nitride nanotube can provide an efficient means of power harvesting owing to the osmotically driven streaming current under a salt concentration difference (see picture). Devices based on this principle may open a new avenue in the exploration for new sources of renewable energy.

    2. Sustainable Chemistry

      More Sustainable Formation of C[BOND]N and C[BOND]C Bonds for the Synthesis of N-Heterocycles (pages 7642–7644)

      Johannes Schranck, Dr. Anis Tlili and Prof. Dr. Matthias Beller

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201303015

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      Heterocycles made green: New methodologies for the synthesis of pyrroles were recently developed based on domino Ir- and Ru-catalyzed amination and alkylations of alcohols. The concept provides a greener approach to interesting N-heterocyclic compounds.

  10. Minireview

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Total Synthesis

      The Winding Pathway to Erythropoietin Along the Chemistry–Biology Frontier: A Success At Last (pages 7646–7665)

      Rebecca M. Wilson, Dr. Suwei Dong, Dr. Ping Wang and Prof. Samuel J. Danishefsky

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201301666

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      Going native: The total synthesis of a homogeneous erythropoietin, possessing the native amino acid sequence and chitobiose glycans at each of the three wild-type sites of N glycosylation, has been accomplished. Herein is an account of the decade-long research effort en route to this formidable target compound.

  11. Review

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Bioorganometallic Chemistry

      Bioactive Luminescent Transition-Metal Complexes for Biomedical Applications (pages 7666–7682)

      Dr. Dik-Lung Ma, Hong-Zhang He, Ka-Ho Leung, Daniel Shiu-Hin Chan and Dr. Chung-Hang Leung

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201208414

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      Metal-based theranostics: This Review highlights recent examples of biologically active luminescent metal complexes that can target and probe a specific biomolecule, and offers insight into the future potential of luminescent metal-based therapeutics for the investigation and treatment of human diseases.

  12. Communications

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    1. Bioorganic Chemistry

      Polymer Nanomicelles for Efficient Mucus Delivery and Antigen-Specific High Mucosal Immunity (pages 7684–7689)

      Young-Woock Noh, Ji Hyun Hong, Sang-Mu Shim, Hye Sun Park, Hee Ho Bae, Eun Kyoung Ryu, Jung Hwan Hwang, Dr. Chul-Ho Lee, Seong Hun Cho, Dr. Moon-Hee Sung, Dr. Haryoung Poo and Prof. Dr. Yong Taik Lim

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201302881

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      Micelles for mucosal immunity: A mucosal vaccine system based on γ-PGA nanomicelles and viral antigens was synthesized. The intranasal administration of the vaccine system induces a high immune response both in the humoral and cellular immunity (see picture).

    2. Bioorganometallics

      The Ferroquine Antimalarial Conundrum: Redox Activation and Reinvasion Inhibition (pages 7690–7693)

      Dr. Faustine Dubar, Dr. Christian Slomianny, Dr. Jamal Khalife, Dr. Daniel Dive, Hadidjatou Kalamou, Dr. Yann Guérardel, Prof. Philippe Grellier and Prof. Christophe Biot

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201303690

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      Metal health: Ferroquine is a ferrocene-based analogue of the antimalarial drug chloroquine. In addition to the primary mechanism of quinoline action, fluorescent probe studies in infected red blood cells show another mechanism is at work. It is based on the production of HO. in the acidic and oxidizing environment of the digestive vacuole of the malaria parasite and implies that, with ferroquine, reinvasion can be inhibited.

    3. Enantioselective Catalysis

      Combining NHC–Cu and Brønsted Base Catalysis: Enantioselective Allylic Substitution/Conjugate Additions with Alkynylaluminum Reagents and Stereospecific Isomerization of the Products to Trisubstituted Allenes (pages 7694–7699)

      Jennifer A. Dabrowski, Dr. Fredrik Haeffner and Prof. Amir H. Hoveyda

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201303501

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      All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC=N-heterocyclic carbene).

    4. Asymmetric Synthesis

      Remarkable Configurational Stability of Magnesiated Nitriles (pages 7700–7703)

      Dr. Graeme Barker, Madeha R. Alshawish, Melanie C. Skilbeck and Prof. Iain Coldham

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201303442

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      Quaternary stereocenters: Chiral α-magnesiated nitriles can be formed by deprotonation and are configurationally stable at low temperature, even for acyclic examples. These can be trapped with electrophiles to give enantiomerically enriched quaternary substituted products (see scheme; TMP=2,2,6,6-tetramethylpiperidine).

    5. Optopharmacology

      Light-Regulated Stapled Peptides to Inhibit Protein–Protein Interactions Involved in Clathrin-Mediated Endocytosis (pages 7704–7708)

      Dr. Laura Nevola, Andrés Martín-Quirós, Dr. Kay Eckelt, Dr. Núria Camarero, Dr. Sébastien Tosi, Dr. Artur Llobet, Prof. Dr. Ernest Giralt and Prof. Dr. Pau Gorostiza

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201303324

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      Control of membrane traffic: Photoswitchable inhibitors of protein–protein interactions were applied to photoregulate clathrin-mediated endocytosis (CME) in living cells. Traffic light (TL) peptides acting as “stop” and “go” signals for membrane traffic can be used to dissect the role of CME in receptor internalization and in cell growth, division, and differentiation.

    6. Demethylases/Hydroxylases

      You have full text access to this OnlineOpen article
      Is JmjC Oxygenase Catalysis Limited to Demethylation? (pages 7709–7713)

      Dr. Richard J. Hopkinson, Louise J. Walport, Dr. Martin Münzel, Dr. Nathan R. Rose, Tristan J. Smart, Dr. Akane Kawamura, Dr. Timothy D. W. Claridge and Prof. Christopher J. Schofield

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303282

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      Jobs on the side: Substrate selectivity studies indicate that members of the biomedically important JmjC demethylase family of histone Nε-methyllysine demethylases are capable of catalyzing the de-N-alkylation of groups other than N-methyl and can catalyze reactions that form stable hydroxylated products. The differences in binding preferences in this set of enzymes may be helpful in the design of selective inhibitors.

    7. Protein–Ligand Binding

      The Binding of Benzoarylsulfonamide Ligands to Human Carbonic Anhydrase is Insensitive to Formal Fluorination of the Ligand (pages 7714–7717)

      Dr. Matthew R. Lockett, Dr. Heiko Lange, Dr. Benjamin Breiten, Dr. Annie Heroux, Dr. Woody Sherman, Dr. Dmitrij Rappoport, Patricia O. Yau, Dr. Philip W. Snyder and Prof. Dr. George M. Whitesides

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301813

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      It's the water that matters. Pairs of benzo- and perfluorobenzoarylsulfonamide ligands bind to human carbonic anhydrase with a conserved binding geometry, an enthalpy-driven binding, and indistinguishable binding affinities (see picture). These data support the pervasive theory that the lock-and-key model disregards an important component of binding: the water, which fills the binding pocket of the protein and surrounds the ligand.

    8. Conductive Fibrous Materials

      Highly Conductive Aluminum Textile and Paper for Flexible and Wearable Electronics (pages 7718–7723)

      Dr. Hye Moon Lee, Dr. Si-Young Choi, Areum Jung and Prof. Seung Hwan Ko

      Article first published online: 7 JUN 2013 | DOI: 10.1002/anie.201301941

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      Light to wear: Aluminum coated fibrous materials with excellent electrical conductivity and mechanical endurance are fabricated at room temperature by a chemical solution process. The resulting aluminum-coated conductive papers and threads can be used in electric circuits for flexible and wearable electronics.

    9. Asymmetric Fluorination

      Enantioselective Fluoroamination: 1,4-Addition to Conjugated Dienes Using Anionic Phase-Transfer Catalysis (pages 7724–7727)

      Hunter P. Shunatona, Natalja Früh, Yi-Ming Wang, Dr. Vivek Rauniyar and Prof. Dr. F. Dean Toste

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201302002

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      Chiral-anion phase-transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3-dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents outperformed Selectfluor in the desired transformation.

    10. 3D Metallomacrocycles

      Self-Assembly of a Supramolecular, Three-Dimensional, Spoked, Bicycle-like Wheel (pages 7728–7731)

      Xiaocun Lu, Prof. Xiaopeng Li, Dr. Yan Cao, Dr. Anthony Schultz, Dr. Jin-Liang Wang, Dr. Charles N. Moorefield, Prof. Chrys Wesdemiotis, Prof. Stephen Z. D. Cheng and Prof. George R. Newkome

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201302362

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      Where there′s a wheel, there′s a way: The terpyridine-based title system has been synthesized through a facile self-assembly process. Two tris(terpyridine) ligands possessing angles of either 120° or 60° between adjacent tpy units were mixed with a stoichiometric amount of Zn2+ (2:6:12) to generate the desired coordination-driven bicycle-like wheel (90 % yield).

    11. Hierarchical Assembly

      Simulation-Assisted Self-Assembly of Multicomponent Polymers into Hierarchical Assemblies with Varied Morphologies (pages 7732–7736)

      Chunhua Cai, Yongliang Li, Prof. Jiaping Lin, Liquan Wang, Shaoliang Lin, Dr. Xiao-Song Wang and Tao Jiang

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201210024

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      As you like it: The synthesis of supramolecular hierarchical nanostructures with designed morphologies has been realized through computer-simulation-guided multicomponent assembly of polypeptide-based block copolymers and homopolymers. By adjusting the attraction between hydrophobic polypeptide rods, as well as other parameters such as the molar ratio of copolymers and the rigidity of polymers, a variety of morphologies were obtained.

    12. Supported Catalysts

      Rationalization of Interactions in Precious Metal/Ceria Catalysts Using the d-Band Center Model (pages 7737–7741)

      Dr. N. Acerbi, Prof. S. C. Edman Tsang, Dr. G. Jones, Prof. S. Golunski and Dr. P. Collier

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201300130

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      A correlation between ceria reducibility and the precious-metal d-band center is reported for ceria-supported precious-metal catalysts. The results could provide the missing link to fully explain the occurrence of strong metal–support interaction (SMSI) and hydrogen spillover in catalysts that consist of dispersed metals in contact with reducible metal oxides.

    13. Quadruplex Formation

      Combination of i-Motif and G-Quadruplex Structures within the Same Strand: Formation and Application (pages 7742–7746)

      Dr. Jun Zhou, Dr. Samir Amrane, Dursun Nizam Korkut, Dr. Anne Bourdoncle, Hong-Zhang He, Prof. Dik-Lung Ma and Dr. Jean-Louis Mergny

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201301278

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      Peaceful coexistence: A double quadruplex composed of an i-motif and a G-quadruplex was constructed within one oligonucleotide strand (see picture). The defined double-quadruplex structure can serve as a NOTIF logic gate on the basis of the fluorescence of crystal violet.

    14. Biosensors

      DNA Origami as a DNA Repair Nanosensor at the Single-Molecule Level (pages 7747–7750)

      Maria Tintoré, Dr. Isaac Gállego, Dr. Brendan Manning, Dr. Ramon Eritja and Dr. Carme Fàbrega

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201301293

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      The folding of DNA molecules by DNA origami is used in a nanosensor to analyze enzymatic DNA repair activity of hAGT. The method uses conformational changes that condition α-thrombin interaction with DNA aptamers, and illustrates the use of DNA origami as a proteinrecognition biosensor.

    15. Organic Semiconductors

      Doping of Organic Semiconductors: Impact of Dopant Strength and Electronic Coupling (pages 7751–7755)

      Henry Méndez, Georg Heimel, Andreas Opitz, Katrein Sauer, Patrick Barkowski, Martin Oehzelt, Junshi Soeda, Toshihiro Okamoto, Jun Takeya, Jean-Baptiste Arlin, Jean-Yves Balandier, Yves Geerts, Norbert Koch and Ingo Salzmann

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201302396

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      Molecular doping: The standard model for molecular p-doping of organic semiconductors (OSCs) assumes integer charge transfer between OSC and dopant. This is in contrast to an alternative model based on intermolecular complex formation instead. By systematically varying the acceptor strength it was possible to discriminate the two models. The latter is clearly favored, suggesting strategies for the chemical design of more efficient molecular dopants.

    16. Luminescent Probes

      Activatable Probes Based on Distance-Dependent Luminescence Associated with Cerenkov Radiation (pages 7756–7760)

      Dr. Nalinikanth Kotagiri, Dr. Dariusz M. Niedzwiedzki, Kohtaro Ohara and Prof. Dr. Samuel Achilefu

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201302564

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      Let me get my nanoruler: Activatable probes based on radionuclide and quantum dots (QDs) were constructed using DNA as a linker. Cerenkov radiation from 64Cu was used to excite the QDs in a distance-dependent manner. The luminescence was lowest nearest to the QD and increased with distance.

    17. Supramolecular Catalysis

      Supramolecular Assemblies of Amphiphilic L-Proline Regulated by Compressed CO2 as a Recyclable Organocatalyst for the Asymmetric Aldol Reaction (pages 7761–7765)

      Long Qin, Dr. Li Zhang, Dr. Qingxian Jin, Prof. Jianling Zhang, Prof. Buxing Han and Prof. Minghua Liu

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201302662

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      Compressed CO2 triggers the formation of amphiphilic proline supramolecular assemblies in water, which catalyze the asymmetric aldol reaction without any additives. Compressed CO2 can dynamically regulate the size of the assemblies and subsequently the catalyst activity and selectivity. Furthermore, CO2 provides the merit of easy separation and purification, making the process sustainable and recyclable.

    18. DNA Nanotechnology

      You have full text access to this OnlineOpen article
      Rigid DNA Beams for High-Resolution Single-Molecule Mechanics (pages 7766–7771)

      Emanuel Pfitzner, Christian Wachauf, Fabian Kilchherr, Benjamin Pelz, William M. Shih, Matthias Rief and Prof. Dr. Hendrik Dietz

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302727

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      Bridging the gap: Rigid DNA linkers (blue, see picture) between microspheres (green) for high-resolution single-molecule mechanical experiments were constructed using DNA origami. The resulting DNA helical bundles greatly reduce the noise generated in studies of conformation changes using optical tweezers and were applied to study small DNA secondary structures.

    19. Supramolecular Chemistry

      Shaping Micelles: The Interplay Between Hydrogen Bonds and Dispersive Interactions (pages 7772–7775)

      Dr. Iker León, Dr. Judith Millán, Dr. Emilio J. Cocinero, Prof. Alberto Lesarri and Dr. José A. Fernández

      Article first published online: 10 JUN 2013 | DOI: 10.1002/anie.201303245

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      A subtle interplay: In the formation of a 1.6 nm micelle containing up to six molecules of propofol, a hydrogen-bond network is shown to influence the structure of the micelle, whereas the nonpolar groups arrange in such a way that the remaining noncovalent interactions are maximized. Such globular structures present a characteristic signature in the IR spectrum that will allow their identification in more complex media.

    20. Sensor Materials

      Electric Current Test Paper Based on Conjugated Polymers and Aligned Carbon Nanotubes (pages 7776–7780)

      Xuemei Sun, Zhitao Zhang, Xin Lu, Guozhen Guan, Houpu Li and Prof. Huisheng Peng

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201303209

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      Making sense: A novel polyacetylene composite material with incorporated aligned carbon nanotubes shows rapid changes in both fluorescent intensity and color appearance in response to applied electric currents, and these electrochromatic transitions remain reversible even after a thousand cycles. The composite material is anticipated to be suitable for various other sensing applications.

    21. Self-Assembly

      Switchable Catalytic Activity: Selenium-Containing Peptides with Redox-Controllable Self-Assembly Properties (pages 7781–7785)

      Xiaoming Miao, Wei Cao, Wenting Zheng, Jingyu Wang, Xiaoli Zhang, Jie Gao, Chengbiao Yang, Prof. Deling Kong, Prof. Huaping Xu, Dr. Ling Wang and Prof. Zhimou Yang

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201303199

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      Mimicking nature: The reversible formation of self-assembled nanostructures of selenium-containing peptides can be controlled by redox triggers (see scheme, VC=vitamin C). As a consequence, the catalytic activity of these peptides is switchable. These results should lead to the development of nature-mimicking smart materials with promising properties.

    22. Polymer Receptors

      Rationally Designed Polymer Hosts of Fullerene (pages 7786–7790)

      Dr. Mihaiela C. Stuparu

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201303032

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      A class of its own: A new class of fullerene C60 hosts—polymeric in nature—has been developed by careful design of the molecular structure of the polymer repeat unit and the mode of interaction between the repeat unit and C60 (see picture). As these hosts are synthesized by free-radical polymerization, polymer hosts with various chemical compositions and architectures can be constructed readily by appropriate design of the receptor monomer.

    23. [8]Circulenes

      Synthesis, Structural Analysis, and Properties of [8]Circulenes (pages 7791–7794)

      Chieh-Ning Feng, Prof. Ming-Yu Kuo and Prof. Yao-Ting Wu

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201303875

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      Polygons: [8]Circulenes were easily prepared by Pd-catalyzed annulations of tetraiodotetraphenylenes with alkynes. Their saddle-shaped structure with an [8]radialene character was identified by X-ray crystallography. Similar to 1,3,5,7-cyclooctatetraene, they have a tub-shaped eight-membered ring, but all of the bond lengths and bond angles are almost equal. Variable-temperature NMR investigations showed interesting dynamic behavior.

    24. Homogeneous Catalysis

      Gold-Catalyzed Cyclizations of cis-Enediynes: Insights into the Nature of Gold–Aryne Interactions (pages 7795–7799)

      Youliang Wang, Akop Yepremyan, Dr. Subir Ghorai, Dr. Robert Todd, Prof. Dr. Donald H. Aue and Prof. Dr. Liming Zhang

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301057

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      Golden aryne? Gold aryne complexes are inferred as transition states in dual gold-catalyzed cyclizations of cis-enediynes (see scheme; DCE=1,2-dichloroethane). They are better described as ortho-aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp3)[BOND]H bonds. Indanes, fused heteroarenes, and phenol derivatives are readily prepared using this method.

    25. Quantum Dots

      Carbon-Based Dots Co-doped with Nitrogen and Sulfur for High Quantum Yield and Excitation-Independent Emission (pages 7800–7804)

      Dr. Yongqiang Dong, Dr. Hongchang Pang, Dr. Hong Bin Yang, Dr. Chunxian Guo, Prof. Jingwei Shao, Prof. Yuwu Chi, Prof. Chang Ming Li and Prof. Ting Yu

      Article first published online: 11 JUN 2013 | DOI: 10.1002/anie.201301114

      Thumbnail image of graphical abstract

      Helpful elements: A facile bottom-up method using citric acid and L-cysteine as a precursor has been developed to prepare graphene quantum dots (GQDs) co-doped with nitrogen and sulfur. A new type and high density of surface state of GQDs arises, leading to high yields (more than 70 %) and excitation-independent emission. FLQY=fluorescence quantum yield.

    26. Complex Ceramic Structures

      Designing Smart Particles for the Assembly of Complex Macroscopic Structures (pages 7805–7808)

      Dr. Esther Garcia-Tunon, Dr. Suelen Barg, Robert Bell, Dr. Jonathan V. M. Weaver, Dr. Claudia Walter, Lidia Goyos and Prof. Eduardo Saiz

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201301636

      Thumbnail image of graphical abstract

      Particle get-together: Surface functionalization with a branched copolymer surfactant is used to create responsive inorganic particles that can self-assemble in complex structures. The assembly process is triggered by a pH switch that reversibly activates multiple hydrogen bonds between ceramic particles (see picture; yellow) and soft templates (n-decane; green).

    27. Synthetic Methods

      Catalytic Regioselective Oxidation of Glycosides (pages 7809–7812)

      Manuel Jäger, Marcel Hartmann, Prof. Dr. Johannes G. de Vries and Prof. Dr. Adriaan J. Minnaard

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201301662

      Thumbnail image of graphical abstract

      Discrimination among equals: A catalytic method for the selective oxidation of unprotected glycosides, both monosaccharides and disaccharides, has been developed. The resulting ketosaccharides are isolated in moderate to excellent yields. This approach provides a basis for protecting-group-free synthetic transformations of carbohydrates.

    28. Metal Clusters

      Ion Exchange of Protons by Coinage Metals to Give Gold and Silver Encapsulation within a Pseudo-D2d Distorted Face-Capped Pd14 Cubic Kernel: [(μ14-M)Pd22(CO)20(PEt3)8]+ (M=Au, Ag) (pages 7813–7817)

      Dr. Evgueni G. Mednikov and Prof. Lawrence F. Dahl

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201301982

      Thumbnail image of graphical abstract

      Heart of gold (or silver): The pseudo-D2d distorted MPd14 cubic kernel of [(μ14-M)Pd22(CO)20(PEt3)8]+ cations, with M=Au (1), Ag (2), has an encapsulated M atom (see picture; yellow) coordinated to eight cubic corner (black) and six face-capping Pd atoms (gray). Compounds 1 and 2 were obtained (28–60 % yields) from two-step/one-pot reactions of a Pd10 precursor with CF3CO2H followed by coinage-metal ion exchange of protons.

    29. Natural Products

      Total Synthesis and Stereochemical Assignment of Baringolin (pages 7818–7821)

      Xavier Just-Baringo, Dr. Paolo Bruno, Dr. Lars K. Ottesen, Dr. Librada M. Cañedo, Prof. Fernando Albericio and Prof. Mercedes Álvarez

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201302372

      Thumbnail image of graphical abstract

      The thiopeptide antibiotic baringolin has been synthesized, and its structure and stereochemistry have been confirmed. The use of a strategy based on palladium-catalyzed cross-couplings permitted a modular construction of this natural product.

    30. Anthracimycin, a Potent Anthrax Antibiotic from a Marine-Derived Actinomycete (pages 7822–7824)

      Dr. Kyoung Hwa Jang, Dr. Sang-Jip Nam, Dr. Jeffrey B. Locke, Christopher A. Kauffman, Deanna S. Beatty, Lauren A. Paul and Prof. Dr. William Fenical

      Article first published online: 17 JUN 2013 | DOI: 10.1002/anie.201302749

      Thumbnail image of graphical abstract

      Licensed to kill: A new antibiotic, anthracimycin (see scheme), produced by a marine-derived actinomycete in saline culture, shows significant activity toward Bacillus anthracis, the bacterial pathogen responsible for anthrax infections. Chlorination of anthracimycin gives a dichloro derivative that retains activity against Gram-positive bacteria, such as anthrax, but also shows activity against selected Gram-negative bacteria.

      Corrected by:

      Corrigendum: Corrigendum: Anthracimycin, a Potent Anthrax Antibiotic from a Marine-Derived Actinomycete

      Vol. 53, Issue 3, 621, Article first published online: 8 JAN 2014

    31. Arenes

      Domino Synthesis of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons: 1,1-Difluoroallenes as Synthetic Platforms (pages 7825–7828)

      Dr. Kohei Fuchibe, Yuka Mayumi, Nan Zhao, Shumpei Watanabe, Dr. Misaki Yokota and Prof. Dr. Junji Ichikawa

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201302740

      Thumbnail image of graphical abstract

      Rather crafty: 1,1-Difluoroallenes bearing an aryl group and a cyclopentene moiety undergo indium(III)-catalyzed Friedel–Crafts-type cyclization with subsequent ring expansion and dehydrogenation to afford fluorinated polycyclic aromatic hydrocarbons in high yields. The introduction of an Ar group was effected by in situ halogenation of the intermediary indium species and a subsequent Suzuki–Miyaura reaction.

    32. Radiochemistry

      Nickel-Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging (pages 7829–7832)

      Dr. Alastair A. Cant, Dr. Sue Champion, Dr. Rajiv Bhalla, Dr. Sally L. Pimlott and Dr. Andrew Sutherland

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201302800

      Thumbnail image of graphical abstract

      Rapid and efficient radioiodination of aryl and heteroaryl bromides has been achieved using a nickel(0)-mediated halogen-exchange reaction. This transformation gives direct access to [123I]- and [125I]-imaging agents for single photon emission computed tomography (SPECT), such as 5-[123I]-A85380 (see scheme, Boc=tert-butyloxycarbonyl, cod=1,5-cyclooctadiene, TFA=trifluoroacetic acid).

    33. Asymmetric Catalysis

      Catalytic Asymmetric Hydrogenation of δ-Ketoesters: Highly Efficient Approach to Chiral 1,5-Diols (pages 7833–7836)

      Xiao-Hui Yang, Prof. Jian-Hua Xie, Wei-Peng Liu and Prof. Qi-Lin Zhou

      Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201303011

      Thumbnail image of graphical abstract

      High turnover: An highly efficient catalytic asymmetric hydrogenation of δ-aryl-δ-ketoesters has been realized by using the chiral spiroiridium catalyst (R)-1. Chiral 1,5-diol products are obtained with excellent enantioselectivity and turnover numbers (TONs) as high as 100 000. TOF=turnover frequency.

    34. Oxidative Cross-Coupling

      Palladium(II)-Catalyzed Dehydrogenative Cross-Coupling between Two Cmath image[BOND]H Bonds: Unexpected C[DOUBLE BOND]C Bond Formation (pages 7837–7840)

      Gaocan Li, Shengyou Qian, Chunxia Wang and Prof. Dr. Jingsong You

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201303099

      Thumbnail image of graphical abstract

      C[DOUBLE BOND]C bond construction: A palladium-catalyzed oxidative Cmath image[BOND]H/Cmath image[BOND]H cross-coupling is shown to forge C[DOUBLE BOND]C bonds rather than Cmath image[BOND]Cmath image bonds through reactions of indolin-2-ones or benzofuran-2-ones with O-benzoyl hydroxylamines in the absence of an added oxidant.

    35. Trifluoromethylation

      Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines (pages 7841–7844)

      Dr. Hiromichi Egami, Dr. Shintaro Kawamura, Dr. Ayako Miyazaki and Prof. Dr. Mikiko Sodeoka

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201303350

      Thumbnail image of graphical abstract

      A multitalented system: N-Migratory oxytrifluoromethylation and one-pot three-component reactions of allylamines as well as the aminotrifluoromethylation of alkenyl amines all proceeded efficiently in the presence of the Togni reagent (1) and CuI to afford a variety of β-trifluoromethylamine derivatives (see scheme).

    36. Synthetic Methods

      Carbonylation of Propargyl Carbamates with Palladium(II) Bisoxazoline Catalysts: Efficient Synthesis of 5-Methoxy-3(2H)-furanones (pages 7845–7849)

      Dr. Taichi Kusakabe, Takeo Takahashi, Rong Shen, Ayumi Ikeda, Yogesh Daulat Dhage, Dr. Yuichro Kanno, Prof. Dr. Yoshio Inouye, Prof. Dr. Hiroaki Sasai, Prof. Dr. Tomoyuki Mochida and Prof. Dr. Keisuke Kato

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201303684

      Thumbnail image of graphical abstract

      Palladium and CO: Carbonylation of 1 with [Pd(tfa)2(±)-L1] (tfa=trifluoroacetate) affords the spirofuranone 2 with inversion of the stereochemistry at C17 in 96 % yield. C17-epi-1 also gave the same product 2 with retention of the stereochemistry at C17. Labelling studies show that 13CO was incorporated into the C5′ position of the furanone ring. The first asymmetric version of this new reaction was achieved.

    37. C[BOND]C Bond Cleavage

      Selective Cmath image[BOND]Csp Bond Cleavage: The Nitrogenation of Alkynes to Amides (pages 7850–7854)

      Chong Qin, Peng Feng, Yang Ou, Tao Shen, Teng Wang and Dr. Ning Jiao

      Article first published online: 26 JUN 2013 | DOI: 10.1002/anie.201303376

      Thumbnail image of graphical abstract

      Breakthrough: A novel catalyzed direct highly selective Cmath image[BOND]Csp bond functionalization of alkynes to amides has been developed. Nitrogenation is achieved by the highly selective Cmath image[BOND]Csp bond cleavage of aryl-substituted alkynes. The oxidant-free and mild conditions and wide substrate scope make this method very practical.

    38. Synthesis Design

      Chemical Synthesis of Biologically Active Monoglycosylated GM2-Activator Protein Analogue Using N-Sulfanylethylanilide Peptide (pages 7855–7859)

      Kohei Sato, Prof. Dr. Akira Shigenaga, Keisuke Kitakaze, Ken Sakamoto, Prof. Dr. Daisuke Tsuji, Prof. Dr. Kohji Itoh and Prof. Dr. Akira Otaka

      Article first published online: 13 JUN 2013 | DOI: 10.1002/anie.201303390

      Thumbnail image of graphical abstract

      Going to SEA(lide): Total chemical synthesis of a 162-residue glycoprotein analogue of the monoglycosylated human GM2-activator protein (GM2AP) was achieved. Key steps were the use of N-sulfanylethylanilide (SEAlide) peptides in the kinetic chemical ligation synthesis of a large peptide fragment, and a convergent native chemical ligation for final fragment assembly.

    39. Photoredox Catalysis

      A Mild, One-Pot Stadler–Ziegler Synthesis of Arylsulfides Facilitated by Photoredox Catalysis in Batch and Continuous-Flow (pages 7860–7864)

      Dr. Xiao Wang, Prof. Dr. Gregory D. Cuny and Dr. Timothy Noël

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201303483

      Thumbnail image of graphical abstract

      Visible advance: A mild, one-pot Stadler–Ziegler process for C[BOND]S bond formation has been developed. The method employs the photoredox catalyst [Ru(bpy)3Cl2]⋅6 H2O irradiated with visible light. A variety of aryl–alkyl and diaryl sulfides were prepared from readily available arylamines and aryl/alkylthiols in good yields. The use of a photo microreactor led to a significant improvement with respect to safety and efficiency.

    40. C[BOND]H Activation

      Enantioselective C[BOND]H Arylation Strategy for Functionalized Dibenzazepinones with Quaternary Stereocenters (pages 7865–7868)

      Tanguy Saget and Prof. Dr. Nicolai Cramer

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201303816

      Thumbnail image of graphical abstract

      Tada! Highly functionalized chiral dibenzazepinones are obtained by a mild palladium(0)-catalyzed enantioselective C[BOND]H arylation with excellent selectivities by using simple taddol phosphoramidite ligands. The amide tether allows exclusive regioselectivity through a rare eight-membered palladacycle intermediate.

    41. Asymmetric Catalysis

      Catalytic Enantioselective Difluoroalkylation of Aldehydes (pages 7869–7873)

      Peng Zhang and Dr. Christian Wolf

      Article first published online: 18 JUN 2013 | DOI: 10.1002/anie.201303551

      Thumbnail image of graphical abstract

      Copper-catalyzed bond scission of pentafluorobutane-1,3-diones generates difluoroenolates that react with aldehydes to give a wide range of chiral α,α-difluoro-β-hydroxy ketones within a few hours in up to 99 % yield and 92 % ee. The synthetic utility of this reaction is demonstrated with the stereoselective synthesis of a chiral anti-1,3-diol exhibiting a central difluoromethylene unit and efficient conversion to a 2,2-difluoro-3-hydroxy carboxylic acid.

    42. Messenger RNA

      A Chemo-Enzymatic Approach for Site-Specific Modification of the RNA Cap (pages 7874–7878)

      Daniela Schulz, Josephin Marie Holstein and Dr. Andrea Rentmeister

      Article first published online: 21 JUN 2013 | DOI: 10.1002/anie.201302874

      Thumbnail image of graphical abstract

      Capped and gowned: A two-step approach can be used to site-specifically modify the 5′-cap of eukaryotic mRNAs. First, a trimethylguanosinesynthase variant recognizes the m7G cap structure and introduces bioorthogonal groups using S-adenosyl-L-methionine-based cosubstrates. Then, the enzymatically introduced reporter groups are further modified by thiol–ene or CuAAC click chemistry (see scheme).

    43. Molecular Switches

      An Azobenzene Unit Embedded in a Cyclopeptide as a Type-Specific and Spatially Directed Switch (pages 7879–7882)

      Prof. Dr. Gebhard Haberhauer, M.Sc. Christine Kallweit, Dr. Christoph Wölper and Dieter Bläser

      Article first published online: 19 JUN 2013 | DOI: 10.1002/anie.201301516

      Thumbnail image of graphical abstract

      By embedding an azobenzene unit into a chiral scaffold, switching of azobenzene from the trans-(P) isomer to the cis-(P) isomer and back was achieved (black arrows in picture). The embedding leads to a flipping process in which the phenyl rings can only move directly towards one another in the switching process.

    44. Electrochemistry

      Why Silver Deposition is so Fast: Solving the Enigma of Metal Deposition (pages 7883–7885)

      Leandro M. C. Pinto, Prof. Eckhard Spohr, Dr. Paola Quaino, Dr. Elizabeth Santos and Prof. Wolfgang Schmickler

      Article first published online: 20 JUN 2013 | DOI: 10.1002/anie.201301998

      Thumbnail image of graphical abstract

      A perfect match: Silver deposition is one of the fastest electrochemical reactions, even though the Ag+ ion loses more than 5 eV solvation energy in the process. This phenomenon, an example of the enigma of metal deposition, was investigated by a combination of MD simulations, DFT, and specially developed theory. At the surface, the Ag+ ion experiences a strong interaction with the sp band of silver, which catalyzes the reaction.

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