Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 39

September 22, 2014

Volume 53, Issue 39

Pages 10253–10544

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Editorial
    5. Graphical Abstract
    6. Flashback
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlight
    12. Minireview
    13. Reviews
    14. Communications
    1. You have free access to this content
      Cover Picture: Aerogels with 3D Ordered Nanofiber Skeletons of Liquid-Crystalline Nanocellulose Derivatives as Tough and Transparent Insulators (Angew. Chem. Int. Ed. 39/2014) (page 10253)

      Yuri Kobayashi, Assoc. Prof. Tsuguyuki Saito and Prof. Akira Isogai

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201406635

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      Aerogels with 3D-ordered nanofiber skeletons of liquid-crystalline nanocellulose are described by T. Saito et al. in their Communication on page 10394 ff. The nanocellulose is composed of mechanically strong, surface-carboxylated cellulose nanofibers dispersed in a nematic order, which were prepared from abundant wood biomass through a water-based process. These aerogels display good insulation properties, optical transparency, and mechanical toughness.

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      Inside Cover: Integrating Perovskite Solar Cells into a Flexible Fiber (Angew. Chem. Int. Ed. 39/2014) (page 10254)

      Longbin Qiu, Jue Deng, Xin Lu, Zhibin Yang and Prof. Huisheng Peng

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201406844

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      Wearable perovskite solar cells with a fiber structure are synthesized according to a procedure that is described by H. Peng et al. in their Communication on page 10425 ff. and entails continuously winding an aligned carbon nanotube sheet onto a stainless steel wire; photoactive materials are incorporated in between them through a solution process. The fiber-shaped perovskite solar cells exhibit an energy conversion efficiency of 3.3 % that is not affected by bending.

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      Inside Back Cover: Plasmon-Assisted Water Splitting Using Two Sides of the Same SrTiO3 Single-Crystal Substrate: Conversion of Visible Light to Chemical Energy (Angew. Chem. Int. Ed. 39/2014) (page 10545)

      Yuqing Zhong, Prof. Kosei Ueno, Yuko Mori, Dr. Xu Shi, Dr. Tomoya Oshikiri, Prof. Kei Murakoshi, Prof. Haruo Inoue and Prof. Hiroaki Misawa

      Article first published online: 8 JUL 2014 | DOI: 10.1002/anie.201406609

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      A plasmon-induced water splitting system that operates under irradiation by visible light is described by H. Misawa et al. in their Communication on page 10350 ff. The system uses both sides of the same strontium titanate single-crystal substrate to separate hydrogen and oxygen. The chemical bias is substantially reduced by plasmonic effects because of efficient water oxidation.

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      Back Cover: Maximum Noble-Metal Efficiency in Catalytic Materials: Atomically Dispersed Surface Platinum (Angew. Chem. Int. Ed. 39/2014) (page 10546)

      Dr. Albert Bruix, Dr. Yaroslava Lykhach, Dr. Iva Matolínová, M. Sc. Armin Neitzel, Dr. Tomáš Skála, Dr. Nataliya Tsud, Dr. Mykhailo Vorokhta, M. Sc. Vitalii Stetsovych, M. Sc. Klára Ševčíková, Dr. Josef Mysliveček, M. Sc. Roman Fiala, M. Sc. Michal Václavů, Dr. Kevin C. Prince, Dr. Stéphanie Bruyère, Dr. Valérie Potin, Prof. Dr. Francesc Illas, Prof. Dr. Vladimír Matolín, Prof. Dr. Jörg Libuda and Prof. Dr. Konstantin M. Neyman

      Article first published online: 17 JUL 2014 | DOI: 10.1002/anie.201406634

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      Low-cost platinum-based catalysts Cooperation of researchers from five European countries allowed Pt-CeO2 materials with the highest possible noble-metal dispersion to be prepared and characterized. As V. Matolín, J. Libuda, K. M. Neyman, and co-workers show in their Communication on page 10525 ff., surface atomic Pt2+ species are stabilized in {100} “nanopockets” of CeO2, decreasing the amount of platinum required for catalysis, thus lowering the cost of their implementation for applications, such as in fuel-cell devices.

  2. Frontispiece

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    13. Reviews
    14. Communications
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      Frontispiece: Mild and Versatile Nitrate-Promoted C[BOND]H Bond Fluorination

      Dr. Shao-Jie Lou, Prof. Dan-Qian Xu and Prof. Zhen-Yuan Xu

      Article first published online: 17 SEP 2014 | DOI: 10.1002/anie.201483971

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      Fluorination In their Communication on page 10329 ff., D.-Q. Xu, Z.-Y. Xu, and co-workers describe the fluorination of aromatic and olefinic C(sp2)[BOND]H bonds in the presence of a catalytic amount of inexpensive and nontoxic nitrate.

  3. Editorial

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      C[BOND]H Functionalization: Collaborative Methods to Redefine Chemical Logic (pages 10256–10258)

      Prof. Huw M. L. Davies and Dr. Daniel Morton

      Article first published online: 11 SEP 2014 | DOI: 10.1002/anie.201406633

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  4. Graphical Abstract

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    1. Graphical Abstract: Angew. Chem. Int. Ed. 39/2014 (pages 10260–10275)

      Article first published online: 17 SEP 2014 | DOI: 10.1002/anie.201490037

  5. Flashback

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    14. Communications
    1. 50 Years Ago ... (page 10270)

      Article first published online: 17 SEP 2014 | DOI: 10.1002/anie.201483914

  6. News

    1. Top of page
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    14. Communications
  7. Author Profile

    1. Top of page
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    14. Communications
    1. Eric Meggers (page 10280)

      Article first published online: 6 MAY 2014 | DOI: 10.1002/anie.201403996

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      “My favorite food is anything with curry. My favorite place on earth is San Diego, closely followed by Xiamen …” This and more about Eric Meggers can be found on page 10280.

  8. News

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  9. Book Review

    1. Top of page
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    1. The Last Alchemist in Paris. & other curious tales from chemistry. By Lars Öhrström. (page 10283)

      Gerald Linti

      Article first published online: 28 AUG 2014 | DOI: 10.1002/anie.201407853

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      Oxford University Press, Oxford, 2013. 272 pp., hardcover, £ 16.99.—ISBN 978-0199661091

  10. Highlight

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    14. Communications
    1. Membranes

      Graphene Oxide: A New Platform for High-Performance Gas- and Liquid-Separation Membranes (pages 10286–10288)

      Dr. Zachary P. Smith and Prof. Benny D. Freeman

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201404407

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      Depending on size: Graphene oxide can be deposited into thin layers having defects and inter-layer structures with dimensions that are appropriate for separating molecules based on size differences and enable rapid transport through these structures. The picture illustrates the pathway of two differently sized molecules through the graphene oxide layers.

  11. Minireview

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    1. Photomechanics

      Photomobile Polymer Materials with Crosslinked Liquid-Crystalline Structures: Molecular Design, Fabrication, and Functions (pages 10290–10299)

      Dr. Toru Ube and Prof. Dr. Tomiki Ikeda

      Article first published online: 4 SEP 2014 | DOI: 10.1002/anie.201400513

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      The macroscopic deformation of photomobile polymer materials upon irradiation with light is a result of cooperative effects of crosslinked liquid-crystalline polymers. This review describes recent advances in the molecular design, fabrication methods, and composite structures of such materials for their application in various fields, such as soft robotics and microfluidics.

  12. Reviews

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    1. Bioanalytical Methods

      In-Cell NMR and EPR Spectroscopy of Biomacromolecules (pages 10300–10314)

      Robert Hänsel, Laura M. Luh, Ivan Corbeski, Lukáš Trantirek and Prof. Volker Dötsch

      Article first published online: 28 JUL 2014 | DOI: 10.1002/anie.201311320

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      Magnets that attract cell biology: Magnetic resonance spectroscopy has been applied to cellular systems and tissues for a long time. The development of in-cell NMR and EPR spectroscopy now enables direct investigation of the conformation, dynamics, binding events, and posttranslational modifications of biological macromolecules in living cells. This Review summarizes the main techniques and applications to different cellular systems and macromolecules.

    2. Glycation Reactions

      Baking, Ageing, Diabetes: A Short History of the Maillard Reaction (pages 10316–10329)

      Dr. Michael Hellwig and Prof. Dr. Thomas Henle

      Article first published online: 9 JUL 2014 | DOI: 10.1002/anie.201308808

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      Food for thought: The reaction of reducing carbohydrates with amino compounds described by Louis-Camille Maillard in 1912 is responsible for the aroma, taste, and appearance of thermally processed food. Corresponding reactions occur in the body and are important in diabetes and ageing processes. A historical overview of the most important findings is given in this Review.

  13. Communications

    1. Top of page
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    1. Fluorination | Hot Paper

      Mild and Versatile Nitrate-Promoted C[BOND]H Bond Fluorination (pages 10330–10335)

      Dr. Shao-Jie Lou, Prof. Dan-Qian Xu and Prof. Zhen-Yuan Xu

      Article first published online: 14 JUL 2014 | DOI: 10.1002/anie.201404423

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      Nitrate makes it possible: A novel and facile method for C[BOND]H bond fluorination entails remarkably mild reaction conditions (close to room temperature in most cases). Both aromatic and olefinic C(sp2)[BOND]H bonds were selectively fluorinated in the presence of a catalytic amount of inexpensive and nontoxic nitrate as the promoter.

    2. Platinum-Free Fuel Cell

      Anode Catalysts for Direct Hydrazine Fuel Cells: From Laboratory Test to an Electric Vehicle (pages 10336–10339)

      Dr. Alexey Serov, Monica Padilla, Aaron J. Roy, Prof. Dr. Plamen Atanassov, Tomokazu Sakamoto, Dr. Koichiro Asazawa and Dr. Hirohisa Tanaka

      Article first published online: 12 AUG 2014 | DOI: 10.1002/anie.201404734

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      Enjoy the ride: Highly active electrocatalysts for hydrazine hydrate fuel cells were developed, synthesized, and integrated into a vehicle prototype. The materials show the highest activity ever measured with a peak current density of 16 000 A g−1 and a power density of 450 mW cm−2 under operation in air.

    3. Collagen

      Switchable Proline Derivatives: Tuning the Conformational Stability of the Collagen Triple Helix by pH Changes (pages 10340–10344)

      Christiane Siebler, Dr. Roman S. Erdmann and Prof. Dr. Helma Wennemers

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201404935

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      Small proton, big impact: (4S)-Aminoproline is introduced as a pH-sensitive probe for tuning the conformational properties of peptides and proteins. The pH-triggered flip of the ring puckering and the formation/release of a transannular H bond were used to switch the formation of collagen triple helices on and off reversibly.

    4. Protein Interactions

      Characterizing Methyl-Bearing Side Chain Contacts and Dynamics Mediating Amyloid β Protofibril Interactions Using 13Cmethyl-DEST and Lifetime Line Broadening (pages 10345–10349)

      Dr. Nicolas L. Fawzi, Dr. David S. Libich, Dr. Jinfa Ying, Dr. Vitali Tugarinov and Dr. G. Marius Clore

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201405180

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      Amyloid β assemblies: Amyloid β plays a key role in the etiology of Alzheimer's disease. Solution NMR 13Cmethyl lifetime line broadening and dark-state exchange saturation transfer spectroscopy (DEST) is used to probe the transient interactions of methyl groups of monomeric amyloid β exchanging on the surface of very large (2–80 MDa) protofibril assemblies.

    5. Water Splitting | Hot Paper

      Plasmon-Assisted Water Splitting Using Two Sides of the Same SrTiO3 Single-Crystal Substrate: Conversion of Visible Light to Chemical Energy (pages 10350–10354)

      Yuqing Zhong, Prof. Kosei Ueno, Yuko Mori, Dr. Xu Shi, Dr. Tomoya Oshikiri, Prof. Kei Murakoshi, Prof. Haruo Inoue and Prof. Hiroaki Misawa

      Article first published online: 2 JUL 2014 | DOI: 10.1002/anie.201404926

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      Photochemistry: A plasmon-induced water splitting system that operates under irradiation by visible light using both sides of the same SrTiO3 substrate is reported (see picture). The hydrogen-evolution action spectrum closely corresponds to the plasmon resonance spectrum, indicating that the plasmon-induced charge separation at the Au/SrTiO3 interface promotes water oxidation and the reduction of protons.

    6. Supramolecular Chemistry

      Harnessing the Liquid-Phase Exfoliation of Graphene Using Aliphatic Compounds: A Supramolecular Approach (pages 10355–10361)

      Dr. Artur Ciesielski, Sébastien Haar, Dr. Mirella El Gemayel, Huafeng Yang, Joseph Clough, Georgian Melinte, Dr. Marco Gobbi, Dr. Emanuele Orgiu, Dr. Marco V. Nardi, Giovanni Ligorio, Dr. Vincenzo Palermo, Prof. Norbert Koch, Prof. Ovidiu Ersen, Dr. Cinzia Casiraghi and Prof. Paolo Samorì

      Article first published online: 15 JUL 2014 | DOI: 10.1002/anie.201402696

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      Graphene dispersions: A simple method is reported for producing homogenous dispersions of unfunctionalized and non-oxidized graphene nanosheets in 1-methyl-2-pyrrolidinone (see picture). Simple molecular modules are used, which act as dispersion-stabilizing compounds during a liquid-phase exfoliation process, leading to an increase in the concentration of graphene dispersions.

    7. Polyoxometalates

      Time-Resolved Assembly of Cluster-in-Cluster {Ag12}-in-{W76} Polyoxometalates under Supramolecular Control (pages 10362–10366)

      Caihong Zhan, Jamie M. Cameron, Jing Gao, Jamie W. Purcell, De-Liang Long and Leroy Cronin

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201402932

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      Cluster-in-cluster: Polyoxometalate clusters [H(10+m)Ag18Cl(Te3W38O134)2]n with n=1 and m=0, n=2 and m=3, and n=∞ and m=5 were isolated after 4, 10, and 14 days from the same reaction mixture. The proposed mechanism for the formation of the clusters was confirmed by ESI-MS studies and control experiments, which demonstrate the crucial role that TeO32−, Cl, and Ag+ play in the self-assembly of these compounds.

    8. Protein Design | Very Important Paper

      A Designed Conformational Shift To Control Protein Binding Specificity (pages 10367–10371)

      Dr. Servaas Michielssens, Dr. Jan Henning Peters, Dr. David Ban, Supriya Pratihar, Dr. Daniel Seeliger, Monika Sharma, Karin Giller, Dr. Thomas Michael Sabo, Dr. Stefan Becker, Dr. Donghan Lee, Prof. Dr. Christian Griesinger and Prof. Dr. Bert L. de Groot

      Article first published online: 12 AUG 2014 | DOI: 10.1002/anie.201403102

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      Since protein dynamics is inextricably linked to protein function, protein functionality can be altered by manipulating protein dynamics. The specificity of protein–protein binding can be altered solely by a designed change in conformational preference, while leaving the binding interface untouched. This mechanism, which nature utilizes to control binding specificity, provides a novel route to designing protein function.

    9. DNA Rotaxane Shuttles

      Logic Gating by Macrocycle Displacement Using a Double-Stranded DNA [3]Rotaxane Shuttle (pages 10372–10376)

      Finn Lohmann, Johannes Weigandt, Dr. Julián Valero and Prof. Michael Famulok

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201405447

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      Shuttling on a DNA track: A cascade macrocycle-displacement and -dethreading reaction triggered by light and toehold release oligodeoxynucleotides is used to assemble a logic AND gate on a double-stranded DNA [3]rotaxane. Such structures may find applications in nanoengineering, DNA computing, and even nanomedicine.

    10. Chromium Oxyhydride

      Direct Synthesis of Chromium Perovskite Oxyhydride with a High Magnetic-Transition Temperature (pages 10377–10380)

      Dr. Cédric Tassel, Yoshihiro Goto, Yoshinori Kuno, Dr. James Hester, Prof. Mark Green, Dr. Yoji Kobayashi and Prof. Hiroshi Kageyama

      Article first published online: 12 AUG 2014 | DOI: 10.1002/anie.201405453

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      Performing better under pressure: A high-pressure, high-temperature route gives the first chromium oxyhydride, SrCrO2H. It has a perovskite structure and the highest antiferromagnetic ordering temperature (TN) among chromium oxides, which is remarkable given non-bonding nature of its Cr-H-Cr interaction. The high TN arises from decreased octahedral tilting that enhances the Cr-O-Cr antiferromagnetic coupling and reduces the competition between nearest and next-nearest neighbor interactions.

    11. Carbohydrates

      Furanosyl Oxocarbenium Ion Stability and Stereoselectivity (pages 10381–10385)

      Erwin R. van Rijssel, Dr. Pieter van Delft, Dr. Gerrit Lodder, Prof. Herman S. Overkleeft, Prof. Gijsbert A. van der Marel, Dr. Dmitri V. Filippov and Dr. Jeroen D. C. Codée

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201405477

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      Mapping the landscape: The energy landscape of the complete conformational space of the oxocarbenium ions of the four pentofuranosides, ribose, arabinose, xylose, and lyxose, have been mapped. The free energy surfaces (FESs) provide a very detailed picture of the stability of the oxocarbenium ion conformers and the influence of the ring substituents on these. The FES maps can be used to account for the stereochemistry in condensations of furanosyl acetate donors.

    12. Glycoprotein Assay

      A Boronate Affinity Sandwich Assay: An Appealing Alternative to Immunoassays for the Determination of Glycoproteins (pages 10386–10389)

      Jin Ye, Yang Chen and Dr. Zhen Liu

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201405525

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      A specific and sensitive approach has been developed to detect trace levels of glycoproteins in complex samples. A target glycoprotein is specifically captured by a boronate-affinity molecular-imprinted polymer array and then labeled with boronate-affinity silver nanoparticles. The surface-enhanced Raman scattering of the resulting complex (see picture) is then measured.

    13. Protein Folding

      Misfolding of Luciferase at the Single-Molecule Level (pages 10390–10393)

      Dr. Alireza Mashaghi, Samaneh Mashaghi and Prof. Dr. Ir. Sander J. Tans

      Article first published online: 14 AUG 2014 | DOI: 10.1002/anie.201405566

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      Use the force: When stretched from its ends, a single molecule of luciferase unfolds in a multistep process and visits multiple conformational intermediates (I) on the way to the fully unfolded state (U). When allowed to relax, the chain can refold to a misfolded state (X), which has a long lifetime and high mechanical stability, and suppresses formation of the fully folded state (C).

    14. Ordered Aerogels

      Aerogels with 3D Ordered Nanofiber Skeletons of Liquid-Crystalline Nanocellulose Derivatives as Tough and Transparent Insulators (pages 10394–10397)

      Yuri Kobayashi, Assoc. Prof. Tsuguyuki Saito and Prof. Akira Isogai

      Article first published online: 1 JUL 2014 | DOI: 10.1002/anie.201405123

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      A structurally new type of aerogel was prepared from a multi-domain nematic liquid-crystalline dispersion of mechanically strong, surface-carboxylated cellulose nanofibers through acid-induced gelation and supercritical drying. This aerogel displays good insulation properties, optical transparency, and mechanical toughness.

    15. Zeolite Structures

      High-Silica Zeolite SSZ-61 with Dumbbell-Shaped Extra-Large-Pore Channels (pages 10398–10402)

      Stef Smeets, Dr. Dan Xie, Dr. Christian Baerlocher, Dr. Lynne B. McCusker, Dr. Wei Wan, Prof. Xiaodong Zou and Dr. Stacey I. Zones

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201405658

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      Molecular sieves: By combining several structure analysis techniques, the complex structure of the first high-silica zeolite with 18-ring channels (SSZ-61; see picture) could be derived. The material is stable to calcination, and the unusual dumbbell shape of the pore with terminal O atoms pointing into the channel offers the tantalizing possibility of inserting catalytically active centers between them.

    16. Cobalt-Oxo Complexes

      Spectroscopic Capture and Reactivity of a Low-Spin Cobalt(IV)-Oxo Complex Stabilized by Binding Redox-Inactive Metal Ions (pages 10403–10407)

      Seungwoo Hong, Florian F. Pfaff, Eunji Kwon, Yong Wang, Mi-Sook Seo, Eckhard Bill, Dr. Kallol Ray and Prof. Dr. Wonwoo Nam

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201405874

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      What is the metal's role? Cobalt(IV)-oxo complexes binding redox-inactive metal ions, such as Sc3+, Ce3+, Y3+, and Zn2+, are investigated in oxygenation reactions. Theory predicts that the binding of metal ions to the cobalt-oxo core increases the electrophilicity of the oxygen atom. This result supports the role of redox-inactive metal ions in facilitating the formation of high-valent metal-oxo cores as a necessary step for oxygen evolution in chemistry and biology. CAN=cerium ammonium nitrate.

    17. Boron–Carbon Clusters

      Extensive Structural Rearrangements upon Reduction of 9H-9-Borafluorene (pages 10408–10411)

      M. Sc. Alexander Hübner, Dr. Michael Bolte, Dr. Hans-Wolfram Lerner and Prof. Dr. Matthias Wagner

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201405957

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      What a difference an electron can make: Extensive rearrangements of the 9H-9-borafluorene scaffold occur upon injection of electrons into the system using Li metal. Two major reduction products are a [B3H8] cluster analogue and a graphene flake with a central B[DOUBLE BOND]B bond (see picture; C black, H white, B green).

    18. Metal Nitrides

      Two-Electron Reductive Carbonylation of Terminal Uranium(V) and Uranium(VI) Nitrides to Cyanate by Carbon Monoxide (pages 10412–10415)

      Peter A. Cleaves, Dr. David M. King, Dr. Christos E. Kefalidis, Prof. Laurent Maron, Dr. Floriana Tuna, Prof. Eric J. L. McInnes, Dr. Jonathan McMaster, Dr. William Lewis, Prof. Alexander J. Blake and Prof. Stephen T. Liddle

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201406203

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      Exploiting U: A reductive f-block carbonylation of terminal uranium(V) and uranium(VI) nitrides affords cyanates, which can be retained at uranium or expelled. This method effects denitrification and the closure of a remarkably simple synthetic cycle for the conversion of azide to nitride to cyanate, exploiting a two-electron UIII/V redox couple.

    19. Temporary Protecting Groups | Hot Paper

      Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds (pages 10416–10419)

      Victor Laserna, Dr. Giulia Fiorani, Dr. Christopher J. Whiteoak, Dr. Eddy Martin, Eduardo Escudero-Adán and Prof. Dr. Arjan W. Kleij

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201406645

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      Protective Carbon: Aminotriphenolate complexes of FeIII and AlIII are highly efficient and selective catalysts for the conversion of functional (multi)cyclic oxiranes into the corresponding cis carbonates. Basic hydrolysis of the latter provides a series of useful cyclic cis-diol scaffolds in high yield. In this process, CO2 acts as both a temporary protecting group and an oxygen donor.

    20. 1,2,3-Triazoles

      An Organocatalytic Azide–Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles (pages 10420–10424)

      Prof. Dr. Dhevalapally B. Ramachary, Adluri B. Shashank and S. Karthik

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201406721

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      Metal-free click: A variety of commercially available aldehydes was used in the metal-free organo-click reaction with aryl azides to obtain 1,4-disubstituted 1,2,3-triazoles. The method constitutes an alternative to previously known metal-catalyzed azide–alkyne cycloaddition reactions (AAC), such as CuAAC, RuAAC, and IrAAC. DBU=1,8-diazabicyclo[5.4.0]undec-7-ene; DMSO=dimethyl sulfoxide.

    21. Solar Cells | Very Important Paper

      Integrating Perovskite Solar Cells into a Flexible Fiber (pages 10425–10428)

      Longbin Qiu, Jue Deng, Xin Lu, Zhibin Yang and Prof. Huisheng Peng

      Article first published online: 22 JUL 2014 | DOI: 10.1002/anie.201404973

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      Wearable perovskite solar cells with a fiber structure are synthesized by continuously winding an aligned carbon nanotube (CNT) sheet onto a stainless-steel wire; photoactive materials are incorporated in between them through a solution process. The fiber-shaped perovskite solar cell exhibits an energy conversion efficiency of 3.3 % and may be woven into electronic textiles.

    22. Hydrates

      Antifreezes Act as Catalysts for Methane Hydrate Formation from Ice (pages 10429–10433)

      Graham McLaurin, Dr. Kyuchul Shin, Dr. Saman Alavi and Dr. John A. Ripmeester

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201403638

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      Catalytic methane hydrate formation: When powdered frozen water/methanol or water/ammonia solutions are exposed to methane gas at pressures of 30–125 bar and a temperature of 253 K (see picture), hydrate forms at greatly accelerated rates as compared to powdered ice without antifreeze added. The process gave near-complete conversion of ice to hydrate as shown by powder X-ray diffraction and Raman spectroscopy.

    23. Synthetic Methods

      Efficient and Selective Formation of Unsaturated Carboxylic and Phenylacetic Acids from Diketene (pages 10434–10438)

      Takamichi Mori, Yusuke Akioka, Hisaho Kawahara, Ryo Ninokata, Dr. Gen Onodera and Prof. Dr. Masanari Kimura

      Article first published online: 5 AUG 2014 | DOI: 10.1002/anie.201404816

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      Have it three ways: A nickel catalyst promotes the multicomponent coupling reaction of diketene, an alkyne, and Me2Zn to provide 3-methylene-4-hexenoic acids in excellent yields. Under similar conditions, the combination of the nickel catalyst and Et2Al(OEt) promotes a cycloaddition reaction involving dimerization of an alkyne to furnish phenylacetic acids. In the presence of PPh3, a formal [2+2+1+1] cycloaddition reaction proceeds to afford regioisomeric phenylacetic acids.

    24. C[BOND]H Activation

      Exceedingly Fast Copper(II)-Promoted ortho C[BOND]H Trifluoromethylation of Arenes using TMSCF3 (pages 10439–10442)

      Ming Shang, Shang-Zheng Sun, Dr. Hong-Li Wang, Dr. Brian N. Laforteza, Prof. Dr. Hui-Xiong Dai and Prof. Dr. Jin-Quan Yu

      Article first published online: 5 AUG 2014 | DOI: 10.1002/anie.201404822

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      CF3 installation: The direct ortho-trifluoromethylation of arenes including heteroarenes with TMSCF3 has been accomplished by a copper(II)-promoted C[BOND]H activation reaction. Mechanistic investigations are consistent with the involvement of C[BOND]H activation rather than a simple electrophilic aromatic substitution as the key step. DG=directing group, TMS=trimethylsilyl.

    25. Total Synthesis

      Total Synthesis of Δ12-Prostaglandin J3, a Highly Potent and Selective Antileukemic Agent (pages 10443–10447)

      Prof. Dr. K. C. Nicolaou, Dr. Philipp Heretsch, Dr. Abdelatif ElMarrouni, Christopher R. H. Hale, Dr. Kiran K. Pulukuri, Dr. Avinash K. Kudva, Dr. Vivek Narayan and Prof. Dr. K. Sandeep Prabhu

      Article first published online: 5 AUG 2014 | DOI: 10.1002/anie.201404917

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      Leukemia ablator: The naturally occurring and highly potent and selective antileukemic agent Δ12-prostaglandin J312-PGJ3) has been assembled through a catalytic, asymmetric, and convergent strategy. The total synthesis renders this precious but rare substance readily available for thorough biological investigations and opens the way for analogue design, synthesis, and biological evaluation.

    26. Small-Molecule Activation

      Tuning Lanthanide Reactivity Towards Small Molecules with Electron-Rich Siloxide Ligands (pages 10448–10452)

      Julie Andrez, Dr. Jacques Pécaut, Pierre-Alain Bayle and Dr. Marinella Mazzanti

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201405031

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      Yb and Eu can do it! The sterically demanding and electron-rich coordination environment of EuII and YbII in homoleptic siloxide complexes leads to the reduction of azobenzene, carbon disulfide, and carbon dioxide, and the ready release of the reduction products.

    27. Glycosylation

      Hydrogen Bond Mediated Aglycone Delivery: Synthesis of Linear and Branched α-Glucans (pages 10453–10456)

      Jagodige P. Yasomanee and Prof. Alexei V. Demchenko

      Article first published online: 12 AUG 2014 | DOI: 10.1002/anie.201405084

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      Special delivery: O-Picoloyl groups at remote positions can mediate the course of glycosylation reactions by providing high facial selectivity for the hydrogen bond mediated attack of the glycosyl acceptor. A new practical method for the stereoselective synthesis of oligosaccharides containing multiple 1,2-cis glucose residues is presented. 1,2-DCE=1,2-dichloroethane, DMTST=dimethyl(methylthio)sulfonium triflate, M.S.=molecular sieves.

    28. Difluoroalkylation

      Synthesis of α,α-Difluoromethylene Alkynes by Palladium-Catalyzed gem-Difluoropropargylation of Aryl and Alkenyl Boron Reagents (pages 10457–10461)

      Yan-Bo Yu, Guo-Zhen He and Prof. Dr. Xingang Zhang

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201405204

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      gem-Difluoropropargylation: A palladium-catalyzed gem-difluoropropargylation of aryl and alkenyl boronic acids and boronates with gem-difluoropropargyl bromides has been developed (see Scheme). This cross-coupling process represents an attractive approach for the synthesis of complex fluorinated molecules, in particular for drug discovery and development.

    29. Asymmetric Catalysis

      PyBidine/Copper Catalyst: Asymmetric exo′-Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole (pages 10462–10465)

      Dr. Atsuko Awata and Prof. Dr. Takayoshi Arai

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201405223

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      Under attack: An electrophilic indole undergo nucleophilic attack at C2 and electrophilic functionalization at C3. The PyBidine/Cu catalyst promoted highly enantio- and exo′-selective [3+2] cycloaddition using imino esters and 3-nitroindoles. This reaction can provide diverse chiral pyrroloindoline compounds.

    30. Methanol Formation

      Efficient Disproportionation of Formic Acid to Methanol Using Molecular Ruthenium Catalysts (pages 10466–10470)

      Solène Savourey, Dr. Guillaume Lefèvre, Dr. Jean-Claude Berthet, Dr. Pierre Thuéry, Dr. Caroline Genre and Dr. Thibault Cantat

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201405457

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      The search for selectivity: Methanol is efficiently produced in >50 % yield by the disproportionation of formic acid using molecular ruthenium catalysts. Mechanistic experimental and DFT investigations have unveiled different pathways involving transient ruthenium hydride species.

    31. Asymmetric Catalysis

      Highly Enantioselective [3+2] Coupling of Indoles with Quinone Monoimines Promoted by a Chiral Phosphoric Acid (pages 10471–10475)

      Dr. Lihua Liao, Dr. Chang Shu, Dr. Minmin Zhang, Dr. Yijun Liao, Dr. Xiaoyan Hu, Dr. Yonghong Zhang, Dr. Zhijun Wu, Prof. Dr. Weicheng Yuan and Prof. Dr. Xiaomei Zhang

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201405689

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      Benzofuroindolines: The title reaction has been realized. A wide variety of benzofuroindolines have been prepared with moderate to good yields in moderate to excellent enantioselectivities. Ts=4-toluenesulfonyl.

    32. Heterocycles

      Catalytic Methylation of C[BOND]H Bonds Using CO2 and H2 (pages 10476–10480)

      Dr. Yuehui Li, Tao Yan, Dr. Kathrin Junge and Prof. Dr. Matthias Beller

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201405779

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      Capturing: Carbon dioxide in the presence of H2 is shown to be an efficient methylating reagent for carbon nucleophiles such as 2-substituted indoles, pyrroles, and electron-rich arenes. Experimental data support the formal capture of formaldehyde. acac=acetylacetonate, triphos=1,1,1-tris(diphenylphosphinomethyl)ethane.

    33. Molecular Devices

      Sequential Logic Operations with a Molecular Keypad Lock with Four Inputs and Dual Fluorescence Outputs (pages 10481–10484)

      Dr. Xiong-Jie Jiang and Prof. Dennis K. P. Ng

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201406002

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      A coumarin–rhodamine conjugate serves as a ratiometric and highly selective fluorescent sensor for Hg2+ ions. Its metal-responsive spectral properties were utilized to construct an advanced molecular keypad lock with a high security level.

    34. Photoanodes

      In Situ Preparation of a Ti3+ Self-Doped TiO2 Film with Enhanced Activity as Photoanode by N2H4 Reduction (pages 10485–10489)

      Chengyu Mao, Dr. Fan Zuo, Dr. Yang Hou, Prof. Xianhui Bu and Prof. Pingyun Feng

      Article first published online: 1 AUG 2014 | DOI: 10.1002/anie.201406017

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      Ti time: A new method enables the fabrication of highly stable Ti3+-modified TiO2 photoanodes for H2O oxidation. With Ti foil as the substrate and the Ti3+/Ti4+ source, blue Ti3+/TiO2 crystals were grown by a one-step hydrothermal reaction. The Ti3+ concentration was increased by N2H4 reduction, leading to a greater activity. This method is also effective in improving other photoanodes.

    35. Hypervalent Compounds

      Selective CH Functionalization of Methane, Ethane, and Propane by a Perfluoroarene Iodine(III) Complex (pages 10490–10494)

      Dr. Michael M. Konnick, Dr. Brian G. Hashiguchi, Dr. Deepa Devarajan, Nicholas C. Boaz, Prof. T. Brent Gunnoe, Prof. John T. Groves, Niles Gunsalus, Prof. Daniel H. Ess and Prof. Roy A. Periana

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201406185

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      Gas up: Direct partial oxidation of methane, ethane, and propane to their respective trifluoroacetate (TFA) esters is achieved by a homogeneous hypervalent iodine(III) complex in non-superacidic solvent (HTFA). The reaction is highly selective, and for ethane, greater than 0.5 M Et[BOND]TFA can be achieved. Preliminary kinetic analysis and density functional calculations support a nonradical electrophilic CH activation and iodine alkyl functionalization mechanism.

    36. C[BOND]N Bond Formation

      Dehydrogenative N-Incorporation: A Direct Approach to Quinoxaline N-Oxides under Mild Conditions (pages 10495–10499)

      Feng Chen, Xiaoqiang Huang, Xinyao Li, Tao Shen, Miancheng Zou and Prof. Dr. Ning Jiao

      Article first published online: 5 AUG 2014 | DOI: 10.1002/anie.201406479

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      The dehydrogenative incorporation of a nitrogen atom for the synthesis of quinoxaline N-oxides through the functionalization of one C(sp2)[BOND]H bond and two C(sp3)[BOND]H bonds in imines proceeds under transition-metal-free conditions. Simple and readily available tert-butyl nitrite (TBN) was employed as the NO source. TBAB=tetrabutylammonium bromide.

    37. Asymmetric Synthesis

      Enantioselective and Regioselective Pyrone Diels–Alder Reactions of Vinyl Sulfones: Total Synthesis of (+)-Cavicularin (pages 10500–10503)

      Peng Zhao and Prof. Dr. Christopher M. Beaudry

      Article first published online: 31 JUL 2014 | DOI: 10.1002/anie.201406621

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      The total synthesis of (+)-cavicularin features an enantio- and regioselective Diels–Alder reaction of a pyrone with a vinyl sulfone. The substrate for this transformation is prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene.

    38. Bioconjugation

      Double-Clicking Peptides onto Phosphorothioate Oligonucleotides: Combining Two Proapoptotic Agents in One Molecule (pages 10504–10509)

      Frank Abendroth and Prof. Dr. Oliver Seitz

      Article first published online: 19 AUG 2014 | DOI: 10.1002/anie.201406674

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      A stone for two birds is accessed through a combination of oxime ligation and strain-promoted [2+3] cycloaddition. This method was used to conjugate phosphorothioate antisense oligonucleotides (PSAOs) with peptide-based drugs. The activity of a PSAO sequence targeted against mRNA from c-Flip can be enhanced by conjugation with a peptide mimetic designed to inhibit the X-linked inhibitor of apoptosis protein (XIAP).

    39. Synthetic Methods

      Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids (pages 10510–10514)

      Guojiao Wu, Yifan Deng, Chaoqiang Wu, Dr. Yan Zhang and Prof. Dr. Jianbo Wang

      Article first published online: 12 AUG 2014 | DOI: 10.1002/anie.201406765

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      Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

    40. NHC Organocatalysis

      Conjugate Umpolung of β,β-Disubstituted Enals by Dual Catalysis with an N-Heterocyclic Carbene and a Brønsted Acid: Facile Construction of Contiguous Quaternary Stereocenters (pages 10515–10519)

      Dr. Jun-Long Li, Basudev Sahoo, Dr. Constantin-G. Daniliuc and Prof. Dr. Frank Glorius

      Article first published online: 14 AUG 2014 | DOI: 10.1002/anie.201405178

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      Hey neighbor! A previously unreported conjugate umpolung of β,β-disubstituted enals through NHC catalysis has been discovered, allowing the formation of products containing contiguous quaternary centers. Densely substituted spirocyclic oxindoles were readily prepared using a dual activation strategy.

    41. Zigzag Ribbons

      Synthesis of Nitrogen-Doped ZigZag-Edge Peripheries: Dibenzo-9a-azaphenalene as Repeating Unit (pages 10520–10524)

      Reinhard Berger, Angelos Giannakopoulos, Prince Ravat, Dr. Manfred Wagner, Dr. David Beljonne, Prof. Dr. Xinliang Feng and Prof. Dr. Klaus Müllen

      Article first published online: 11 AUG 2014 | DOI: 10.1002/anie.201403302

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      Having the edge: The unprecedented dibenzo-9a-azaphenalene has been used as a core motif in a bottom-up approach toward stable and monodisperse segments of graphenes with a nitrogen-doped zigzag edges. The goal of the approach is the synthesis of larger nitrogen-doped zigzag nanographenes and graphene nanoribbons.

    42. Heterogeneous Catalysis

      Maximum Noble-Metal Efficiency in Catalytic Materials: Atomically Dispersed Surface Platinum (pages 10525–10530)

      Dr. Albert Bruix, Dr. Yaroslava Lykhach, Dr. Iva Matolínová, M. Sc. Armin Neitzel, Dr. Tomáš Skála, Dr. Nataliya Tsud, Dr. Mykhailo Vorokhta, M. Sc. Vitalii Stetsovych, M. Sc. Klára Ševčíková, Dr. Josef Mysliveček, M. Sc. Roman Fiala, M. Sc. Michal Václavů, Dr. Kevin C. Prince, Dr. Stéphanie Bruyère, Dr. Valérie Potin, Prof. Dr. Francesc Illas, Prof. Dr. Vladimír Matolín, Prof. Dr. Jörg Libuda and Prof. Dr. Konstantin M. Neyman

      Article first published online: 11 JUN 2014 | DOI: 10.1002/anie.201402342

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      Platinum stuck in my pocket: Pt-CeO2 materials with highest possible noble-metal dispersion can be prepared by stabilizing surface Pt2+ species in {100} “nanopockets” of nanostructured CeO2 (see picture). Such materials can dramatically decrease the amount of noble metal required for catalysts.

    43. Lithium-Ion Batteries

      Spatiotemporal Changes of the Solid Electrolyte Interphase in Lithium-Ion Batteries Detected by Scanning Electrochemical Microscopy (pages 10531–10535)

      M. Sc. Heinz Bülter, M. Sc. Fabian Peters, Dr. Julian Schwenzel and Prof. Dr. Gunther Wittstock

      Article first published online: 30 JUL 2014 | DOI: 10.1002/anie.201403935

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      Actively passivating: Lithium-ion batteries only operate safely if a passivating solid electrolyte interphase (SEI) prevents chemical reactions between strongly reducing lithiated graphite and electrolyte components. Spontaneous local fluctuations of the passivating properties of the SEI are detected by scanning electrochemical microscopy. The direct monitoring of the spatiotemporal dynamics of this critical SEI property offers potential for their optimization.

    44. Bioorthogonal Catalysis

      Progress towards Bioorthogonal Catalysis with Organometallic Compounds (pages 10536–10540)

      Timo Völker, Dr. Felix Dempwolff, Prof. Dr. Peter L. Graumann and Prof. Dr. Eric Meggers

      Article first published online: 19 AUG 2014 | DOI: 10.1002/anie.201404547

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      Organometallic ruthenium complexes have been developed for bioorthogonal catalysis under biologically relevant conditions as well as inside living mammalian cells. The catalysts activate allyl carbamate protected amines with unprecedented high catalytic activity. A fluorescence probe and a caged anticancer drug were efficiently activated within the cellular cytoplasm.

    45. Drug Delivery

      An Aptamer Intrinsically Comprising 5-Fluoro-2′-deoxyuridine for Targeted Chemotherapy (pages 10541–10544)

      Dipl.-Chem. Sven Kruspe and Prof. Dr. Ulrich Hahn

      Article first published online: 21 AUG 2014 | DOI: 10.1002/anie.201405778

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      A trojan chemotherapeutic: An aptamer intrinsically comprising multiple units of the nucleoside analogue 5-fluoro-2′-deoxyuridine can exert a direct cytostatic effect on certain cells. The aptamer, which can be synthesized in a single enzymatic step, binds to a cell surface receptor that is conveyed into the lysosome. Upon lysosomal degradation of the aptamer by intracellular nucleases, the active drug is released within the targeted cells exclusively.

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