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Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 1

January 3, 2014

Volume 53, Issue 1

Pages 1–328

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorials
    4. Graphical Abstract
    5. Flashback
    6. News
    7. Author Profile
    8. News
    9. Miscellaneous
    10. Highlights
    11. Essay
    12. Minireview
    13. Reviews
    14. Communications
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      Cover Picture: Recoding the Genetic Code with Selenocysteine (Angew. Chem. Int. Ed. 1/2014) (page 1)

      Dr. Markus J. Bröcker, Joanne M. L. Ho, Prof. George M. Church, Prof. Dieter Söll and Prof. Patrick O'Donoghue

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201310509

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      Named after Selene, goddess of the moon selenocysteine (Sec) is unique in its unrivaled catalytic power and its insertion into proteins by redefinition of specific UGA stop codons to Sec. In their Communication on page 319 ff., D. Söll, P. O'Donoghue et al. describe the engineering of the Sec-insertion machinery to redefine nearly all 64 codons. Here, the ring-shaped decameric selenocysteine synthase SeIA is essential in providing tRNA-bound Sec as the central building block for selenoprotein translation.

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      Inside Cover: Graphene-Supported Ultrafine Metal Nanoparticles Encapsulated by Mesoporous Silica: Robust Catalysts for Oxidation and Reduction Reactions (Angew. Chem. Int. Ed. 1/2014) (page 2)

      Dr. Lu Shang, Tong Bian, Baihui Zhang, Dr. Donghui Zhang, Prof. Li-Zhu Wu, Prof. Chen-Ho Tung, Prof. Yadong Yin and Prof. Tierui Zhang

      Article first published online: 18 DEC 2013 | DOI: 10.1002/anie.201310508

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      Ultrafine metal nanoparticles can be supported on graphene nanosheets and encapsulated by a thin mesoporous silica layer to produce a robust catalyst, as demonstrated by Y. Yin, T. R. Zhang et al. in their Communication on page 250 ff. The catalyst exhibits high activity, good stability against sintering under high temperature conditions, and excellent recycling and reusability in both gas- and solution-phase reactions.

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      Inside Back Cover: Constructing Hybrid Protein Zymogens through Protective Dendritic Assembly (Angew. Chem. Int. Ed. 1/2014) (page 329)

      David Y. W. Ng, Matthias Arzt, Yuzhou Wu, Dr. Seah Ling Kuan, Markus Lamla and Prof. Dr. Tanja Weil

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201310545

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      Dynamic supramolecular assembly was used to construct synthetic hybrid enzymes with a protective dendritic shell. In their Communication on page 324 ff., T. Weil and co-workers employ boronic acid/salicyl hydroxamate complexation to endow enzymes with pH-responsive modulated activity and the capability for efficient membrane translocation and localization. The biomimetic strategy explores a unique class of structurally defined biohybrids as enzyme therapeutics.

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      Back Cover: Accelerated Self-Replication under Non-Equilibrium, Periodic Energy Delivery (Angew. Chem. Int. Ed. 1/2014) (page 330)

      Dr. Rui Zhang, David A. Walker, Prof. Bartosz A. Grzybowski and Prof. Monica Olvera de la Cruz

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201310558

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      The self-replication of light-sensitive nanoparticle dimers has an optimal rate of replication under pulsed, noncontinuous energy inputs, as shown by B. A. Grzybowski, M. O. de la Cruz, et al. in their Communication on page 173 ff. The optimization of self-replication does not necessarily require constant energetic expenditure; instead what matters is the proper timing with which the energy is delivered to the system.

  2. Editorials

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    3. Editorials
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    9. Miscellaneous
    10. Highlights
    11. Essay
    12. Minireview
    13. Reviews
    14. Communications
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      Editorial: Angewandte Chemie Always New (pages 4–7)

      Dr. Peter Gölitz

      Article first published online: 17 DEC 2013 | DOI: 10.1002/anie.201309909

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      Editorial: What Matters? (pages 8–9)

      Prof. Alois Fürstner

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201309315

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  3. Graphical Abstract

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    14. Communications
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      Graphical Abstract: Angew. Chem. Int. Ed. 1/2014 (pages 14–29)

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201390055

  4. Flashback

    1. Top of page
    2. Cover Pictures
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    4. Graphical Abstract
    5. Flashback
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    9. Miscellaneous
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    11. Essay
    12. Minireview
    13. Reviews
    14. Communications
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      50 Years Ago ... (page 27)

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201309444

  5. News

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    9. Miscellaneous
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    11. Essay
    12. Minireview
    13. Reviews
    14. Communications
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  6. Author Profile

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    14. Communications
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      Steven H. Strauss (pages 36–37)

      Article first published online: 31 OCT 2013 | DOI: 10.1002/anie.201307440

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      “I would have liked to have discovered a new element. The most exciting thing about my research is working closely with young co-workers and watching their transition from science students into scientists. …” This and more about Steven H. Strauss can be found on page 34.

  7. News

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    11. Essay
    12. Minireview
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  8. Miscellaneous

    1. Top of page
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    9. Miscellaneous
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    11. Essay
    12. Minireview
    13. Reviews
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      Angewandte Chemie—many faces … one quality journal! (pages 43–45)

      Article first published online: 23 DEC 2013 | DOI: 10.1002/anie.201390056

  9. Highlights

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    2. Cover Pictures
    3. Editorials
    4. Graphical Abstract
    5. Flashback
    6. News
    7. Author Profile
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    9. Miscellaneous
    10. Highlights
    11. Essay
    12. Minireview
    13. Reviews
    14. Communications
    1. Multicomponent Reactions

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      Multicomponent Reactions in Polymer Synthesis (pages 46–48)

      Dr. Ryohei Kakuchi

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201305538

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      More participants, yet efficient reactions: Multicomponent reactions (MCRs) have found application in polymer chemistry both in the synthesis of multifunctional monomers and in post-polymerization modification. Examples include the Passerini three-component reaction, the Ugi four-component reaction, and the copper-catalyzed MCR (see scheme).

    2. Drug Delivery

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      pH-Responsive Micro- and Nanocarrier Systems (pages 49–51)

      M. Sc. Sabrina Nowag and Prof. Dr. Rainer Haag

      Article first published online: 4 DEC 2013 | DOI: 10.1002/anie.201308619

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      Release on demand: The pH gradients between extra- and intracellular regions can be utilized for the controlled release of drugs and biological cargos from delivery systems. Biocompatible carrier systems with pH-cleavable units must fulfill many other criteria as well, for example, a long blood circulation time. This can be achieved by tailored micro- and nanocarriers based on macromolecular architectures or stable self-assembled systems.

  10. Essay

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    11. Essay
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    13. Reviews
    14. Communications
    1. Gold Nanoparticle Catalysts

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      Chance and Necessity: My Encounter with Gold Catalysts (pages 52–56)

      Prof. Masatake Haruta

      Article first published online: 27 NOV 2013 | DOI: 10.1002/anie.201305987

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      “Have you tried gold?” This question after a presentation on hydrogen oxidation steered Masatake Haruta's research on heterogeneous catalysis. He found that gold combined with 3d transition metal oxides could exhibit surprisingly high catalytic activity for carbon monoxide oxidation at temperatures as low as 203 K.

  11. Minireview

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    13. Reviews
    14. Communications
    1. Magnetogenic Probes

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      Magnetogenesis in Water Induced by a Chemical Analyte (pages 60–73)

      Prof.Dr. Jens Hasserodt, Dr. Jacek Lukasz Kolanowski and Dr. Faycal Touti

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201305662

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      No way back: Molecules that change the magnetic properties of a solution-phase sample in response to a chemical stimulus all operate through a reversible mechanism. The lessons learned can be used in the design of high-performance probes that, similar to optically responsive agents, react irreversibly. A discussion of the capabilities of two recently reported irreversible probes allow the readers to form their own views on this field.

  12. Reviews

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    13. Reviews
    14. Communications
    1. Cross-Coupling

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      The Cross-Dehydrogenative Coupling of C sp 3[BOND]H Bonds: A Versatile Strategy for C[BOND]C Bond Formations (pages 74–100)

      Simon A. Girard, Dr. Thomas Knauber and Prof. Dr. Chao-Jun Li

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201304268

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      Waste not, want not: The title CDC reactions have emerged as versatile tools for selective and waste-minimized C[BOND]C bond formations. They rely on the direct coupling of two different C[BOND]H bonds under oxidative conditions. This Review focuses on the recent progress in cross-dehydrogenative Cinline image[BOND]C formation and provides a comprehensive overview on existing procedures and employed methodologies.

    2. Nanostructured Electrocatalysts

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      Oxygen Electrochemistry as a Cornerstone for Sustainable Energy Conversion (pages 102–121)

      Dr. Ioannis Katsounaros, Dr. Serhiy Cherevko, Dr. Aleksandar R. Zeradjanin and Dr. Karl J. J. Mayrhofer

      Article first published online: 11 DEC 2013 | DOI: 10.1002/anie.201306588

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      The deployment of sustainable energy technologies is limited by severe challenges in the design of nanostructured electrocatalysts. Efficient catalysts must meet the criteria of high activity, long-term stability, and abundance of the materials used. Integrated solutions will be provided only by multidisciplinary approaches that include fundamental electrochemistry, materials science, and chemical engineering. ORR/OER=O2 reduction/evolution reaction.

  13. Communications

    1. Top of page
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    7. Author Profile
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    9. Miscellaneous
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    11. Essay
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    13. Reviews
    14. Communications
    1. Electrocatalysis

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      An Effective Pd–Ni2P/C Anode Catalyst for Direct Formic Acid Fuel Cells (pages 122–126)

      Jinfa Chang, Dr. Ligang Feng, Prof. Dr. Changpeng Liu, Prof. Dr. Wei Xing and Prof. Dr. Xile Hu

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201308620

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      Giving Pd a boost: A novel Pd–Ni2P/C electrocatalyst has been developed for formic acid oxidation. A direct formic acid fuel cell integrating this catalyst showed superior power density and discharge stability than a state-of-the-art commercial Pd/C catalyst.

    2. Nanocatalyst

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      A Palladium-Nanoparticle and Silicon-Nanowire-Array Hybrid: A Platform for Catalytic Heterogeneous Reactions (pages 127–131)

      Dr. Yoichi M. A. Yamada, Yoshinari Yuyama, Dr. Takuma Sato, Dr. Shigenori Fujikawa and Dr. Yasuhiro Uozumi

      Article first published online: 15 NOV 2013 | DOI: 10.1002/anie.201308541

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      An array of reactions: A silicon-nanowire-array-stabilized palladium-nanoparticle catalyst, SiNA-Pd, was designed and used in the palladium-catalyzed Mizoroki–Heck reaction. It can catalyze a variety of other reactions and has a high reusability.

    3. Protein Engineering

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      An Antibody with a Variable-Region Coiled-Coil “Knob” Domain (pages 132–135)

      Dr. Yong Zhang, Dr. Devrishi Goswami, Dr. Danling Wang, Dr. Tsung-Shing Andrew Wang, Shiladitya Sen, Dr. Thomas J. Magliery, Dr. Patrick R. Griffin, Dr. Feng Wang and Dr. Peter G. Schultz

      Article first published online: 19 NOV 2013 | DOI: 10.1002/anie.201307939

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      With knob and stalk: A bovine antibody is featured with a unique solvent exposed, antiparallel β-strand “stalk” fused to a disulfide cross-linked “knob” domain in its complementarity determining region 3 (CDR3). Substitution of the stalk with an antiparallel heterodimeric coiled-coil generates a novel coiled-coil CDR3 motif that provides a new strategy for generating stable, potent antibody chimeras.

    4. Drug Biosynthesis

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      Unusual Acetylation-Dependent Reaction Cascade in the Biosynthesis of the Pyrroloindole Drug Physostigmine (pages 136–139)

      Joyce Liu, Tailun Ng, Dr. Zhe Rui, Omer Ad and Prof. Dr. Wenjun Zhang

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201308069

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      A tightly choreographed act: A biosynthetic gene cluster for physostigmine was identified by genome mining. In vitro reconstitution showed that seven enzymes, PsmA–F and PsmH, are required for the synthesis of physostigmine from 5-hydroxytryptophan (see scheme; ATP=adenosine 5′-triphosphate, CoA=coenzyme A, SAM=S-adenosylmethionine) through a series of highly coordinated methylation and acetylation/deacetylation reactions.

    5. Mixed-Metal Aggregates

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      Clamshell Opening in the Mixed-Metal Supramolecular Aggregates Formed by Fourfold Reduced Corannulene for Maximizing Intercalated Metal Content (pages 140–145)

      Dr. Alexander S. Filatov, Dr. Alexander V. Zabula, Dr. Sarah N. Spisak, Prof. Dr. Andrey Yu. Rogachev and Prof. Dr. Marina A. Petrukhina

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201308090

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      Pearls in a clamshell: A new class of supramolecular organometallic compounds with mixed-alkali-metal clusters, LiK5 and Li3K3, sandwiched between two highly reduced corannulene decks have been prepared and characterized. They show a coordination record for corannulene tetraanions able to bind six alkali-metal ions. Previously unseen engagement of the hub-site of C20H104− in lithium binding is accompanied by unprecedented shifts up to −24 ppm in 7Li NMR spectra.

    6. Multicompartment Cascade Reactions

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      Cascade Reactions in Multicompartmentalized Polymersomes (pages 146–150)

      Ruud J. R. W. Peters, Maïté Marguet, Sébastien Marais, Prof. Marco W. Fraaije, Prof. Jan C. M. van Hest and Prof. Sébastien Lecommandoux

      Article first published online: 19 NOV 2013 | DOI: 10.1002/anie.201308141

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      Mimicking cells: Enzyme-filled polystyrene-b-poly(3-(isocyano-L-alanylaminoethyl)thiophene) (PS-b-PIAT) nanoreactors have been encapsulated together with free enzymes and substrates in a larger polymersome to form a multicompartmentalized structure, which shows structural resemblance to a cell and its organelles (see picture). An original cofactor-dependent three-enzyme cascade reaction, with either compatible or incompatible enzymes, takes place across multiple compartments.

    7. Remote Stereocontrol

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      Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction (pages 151–155)

      Dr. Liam Byrne, Dr. Jordi Solà, Dr. Thomas Boddaert, Dr. Tommaso Marcelli, Dr. Ralph W. Adams, Prof. Gareth A. Morris and Prof. Jonathan Clayden

      Article first published online: 8 NOV 2013 | DOI: 10.1002/anie.201308264

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      Reaction at a distance: By inducing a quantitative, persistent preference for right-handed helicity, chirality at one end of an otherwise achiral helical molecule is able to control the stereoselectivity of reactions at sites located up to 60 bonds away, shattering previous records for remote stereochemical control.

    8. Imaging

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      Copper-64-Alloyed Gold Nanoparticles for Cancer Imaging: Improved Radiolabel Stability and Diagnostic Accuracy (pages 156–159)

      Dr. Yongfeng Zhao, Deborah Sultan, Lisa Detering, Sangho Cho, Dr. Guorong Sun, Prof. Richard Pierce, Prof. Karen L. Wooley and Prof. Yongjian Liu

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201308494

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      Copper goes for gold: Alloyed copper–gold nanoparticles with controlled integration of 64Cu (64CuAuNPs) are ideal for positron emission tomography imaging. The direct incorporation of 64Cu into the lattice of gold nanoparticles ensured greatly improved radiolabel stability and detection sensitivity. The superior biodistribution profile and imaging capability demonstrated the potential of these alloyed nanoparticles for further investigation.

    9. Supramolecular Chemistry

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      Design, Synthesis, and X-Ray Crystal Structure of a Fullerene-Linked Metal–Organic Framework (pages 160–163)

      Dr. Ping Peng, Dr. Fang-Fang Li, Venkata S. Pavan K. Neti, Dr. Alejandro J. Metta-Magana and Prof. Dr. Luis Echegoyen

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201306761

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      Linked in: A new hexakisfullerene derivative, possessing two pairs of phenyl pyridine groups attached to two methano-carbon atoms located at trans-1 positions, was designed, synthesized, and used to assemble the first fullerene-linked metal–organic framework.

    10. Mass Spectrometry

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      Proteins with Highly Similar Native Folds Can Show Vastly Dissimilar Folding Behavior When Desolvated (pages 164–168)

      Mag. Moritz Schennach and Priv.-Doz. Dr. Kathrin Breuker

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201306838

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      Electron capture dissociation has been used to study horse (example at the top) and tuna (example at the bottom) heart cytochromes c in the complete absence of solvent. It was shown that in the absence of hydrophobic bonding, folding is slow, complex, and driven by electrostatic interactions. Y=Yield.

    11. DNA Damage

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      Molecular Characterization of DNA Double Strand Breaks with Tip-Enhanced Raman Scattering (pages 169–172)

      Ewelina Lipiec, Dr. Ryo Sekine, Dr. Jakub Bielecki, Prof. Dr. Wojciech M. Kwiatek and Assoc. Prof. Bayden R. Wood

      Article first published online: 15 NOV 2013 | DOI: 10.1002/anie.201307271

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      Individual DNA double strand breaks (DSBs) were first detected and located by atomic force microscopy, and the molecular structure of this damage was characterized with tip-enhanced Raman scattering (see picture) using a top-down configuration and a reflective substrate. The first experimental evidence is reported confirming that individual DSBs result from cleavage at the 3′- and 5′-bonds of deoxyribose upon exposure to ultraviolet C radiation.

    12. Self-Replication

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      Accelerated Self-Replication under Non-Equilibrium, Periodic Energy Delivery (pages 173–177)

      Dr. Rui Zhang, David A. Walker, Prof. Bartosz A. Grzybowski and Prof. Monica Olvera de la Cruz

      Article first published online: 15 NOV 2013 | DOI: 10.1002/anie.201307339

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      A finger on the pulse: The rate of self-replication can be significantly enhanced by delivering energy to the system in pulses rather than continuously. In other words, optimal self-replication does not necessarily require constant energetic expenditure; instead what matters is the timing with which energy is delivered to the system.

    13. Panchromatic Sensitizers

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      Highly Efficient Dye-Sensitized Solar Cells Based on Panchromatic Ruthenium Sensitizers with Quinolinylbipyridine Anchors (pages 178–183)

      Chun-Cheng Chou, Fa-Chun Hu, Hsiu-Hsuan Yeh, Hsin-Pei Wu, Yun Chi, John N. Clifford, Emilio Palomares, Shih-Hung Liu, Pi-Tai Chou and Gene-Hsiang Lee

      Article first published online: 11 NOV 2013 | DOI: 10.1002/anie.201305975

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      Go with the flow: The increased π conjugation of panchromatic RuII sensitizers of type 1 containing a 6-quinolin-8-yl-2,2′-bipyridine rather than a traditional 2,2′:6′,2′′-terpyridine anchor (structure 2) led to a remarkable improvement in absorptivity across the whole UV/Vis/NIR spectral regime. A bulky tert-butyl substituent on the quinolinyl fragment caused an increase in the short-circuit current by suppressing dye aggregation.

    14. Photoacoustic Imaging

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      Non-Invasive and In Situ Characterization of the Degradation of Biomaterial Scaffolds by Volumetric Photoacoustic Microscopy (pages 184–188)

      Dr. Yu Shrike Zhang, Xin Cai, Dr. Junjie Yao, Wenxin Xing, Prof. Lihong V. Wang and Prof. Younan Xia

      Article first published online: 15 OCT 2013 | DOI: 10.1002/anie.201306282

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      Seeing is believing: By doping a polymer scaffold with an absorption contrast agent, the degradation of this scaffold could be non-invasively monitored and quantified using volumetric photoacoustic microscopy (see pictures). Dual-wavelength imaging further provided the capability to record the vascular remodeling and scaffold degradation simultaneously and in vivo.

    15. Immunology

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      Covalently Coupled Immunostimulant Heterodimers (pages 189–192)

      Dr. Rock J. Mancini, Janine K. Tom and Prof. Aaron P. Esser-Kahn

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201306551

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      Big PAMPin': Many vaccines present spatially organized agonists known as pathogen-associated molecular patterns (PAMPs) to immune-cell receptors (see picture, left). In a study to probe the spatial aspects of immune-cell activation involving multiple, unique receptors, greater stimulation of dendritic cells was observed with heterodimers of covalently linked immunostimulants than with a mixture of the two unconjugated immunostimulants.

    16. Metal–Organic Frameworks

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      Guest-Adaptable and Water-Stable Peptide-Based Porous Materials by Imidazolate Side Chain Control (pages 193–198)

      Dr. Alexandros P. Katsoulidis, Dr. Kyo Sung Park, Dr. Dmytro Antypov, Dr. Carlos Martí-Gastaldo, Dr. Gary J. Miller, Dr. John E. Warren, Dr. Craig M. Robertson, Dr. Frédéric Blanc, Dr. George R. Darling, Dr. Neil G. Berry, Dr. John A. Purton, Dr. Dave J. Adams and Prof. Matthew J. Rosseinsky

      Article first published online: 2 DEC 2013 | DOI: 10.1002/anie.201307074

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      A peptide-based porous framework (ZnCar⋅DMF), which is formed by the assembly of Zn with carnosine, exhibits permanent microporosity and has pores of chiral shape. Zn–imidazolate bonding to the histidine side chain affords the chemical stability of the framework in water, and the His-β-Ala main chain provides flexibility while conferring structural adaptability on the framework in the presence of different guest molecules.

    17. Drug Design

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      Therapeutic Targeting of Oncogenic K-Ras by a Covalent Catalytic Site Inhibitor (pages 199–204)

      Dr. Sang Min Lim, Dr. Kenneth D. Westover, Dr. Scott B. Ficarro, Rane A. Harrison, Dr. Hwan Geun Choi, Dr. Michael E. Pacold, Dr. Martin Carrasco, Dr. John Hunter, Dr. Nam Doo Kim, Ting Xie, Dr. Taebo Sim, Dr. Pasi A. Jänne, Dr. Matthew Meyerson, Dr. Jarrod A. Marto, Dr. John R. Engen and Dr. Nathanael S. Gray

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201307387

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      Putting a stop to Ras: Two new selective, direct-acting covalent inhibitors of the K-Ras G12C mutant are reported. Studies suggest that the modification of K-Ras with SML-8-73-1 renders the protein inactive. These novel covalent inhibitors demonstrate that irreversible targeting of the K-Ras guanine-nucleotide binding site is potentially a viable therapeutic strategy for inhibition of Ras signaling.

    18. Water Oxidation

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      A Self-Improved Water-Oxidation Catalyst: Is One Site Really Enough? (pages 205–209)

      Isidoro López, Dr. Mehmed Z. Ertem, Dr. Somnath Maji, Dr. Jordi Benet-Buchholz, Anke Keidel, Dr. Uwe Kuhlmann, Prof. Peter Hildebrandt, Prof. Christopher J. Cramer, Prof. Victor S. Batista and Prof. Antoni Llobet

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201307509

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      In for the long haul: The transformation of a highly active mononuclear ruthenium–aqua water-oxidation catalyst into a dinuclear complex during oxygen-evolution catalysis led to the coexistence of two different catalytic cycles in solution (see picture; Ru pink, N blue, O red). The dinuclear species was much more robust than its mononuclear counterpart and remained an active catalyst for water oxidation for extended periods of time.

    19. Photochemistry

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      Photonenergy-Controlled Symmetry Breaking with Circularly Polarized Light (pages 210–214)

      Dr. Cornelia Meinert, Dr. Søren V. Hoffmann, Dr. Patrick Cassam-Chenaï, Dr. Amanda C. Evans, Chaitanya Giri, Dr. Laurent Nahon and Prof. Dr. Uwe J. Meierhenrich

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201307855

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      Light-induced chirality: Exposure of rac-alanine to tunable circularly polarized light (CPL) has led to the highest optical purities ever generated for this family of compounds by asymmetric photolysis. These enantiomeric enrichments are dependent upon the helicity and energy of the CPL used.

    20. High-Pressure Chemistry

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      Observing High-Pressure Chemistry in Graphene Bubbles (pages 215–219)

      Candy Haley Yi Xuan Lim, Milos Nesladek and Prof. Kian Ping Loh

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201308682

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      Graphene anvil: Graphene bubbles can be used as a bench-top anvil cell for studying high-pressure chemistry. Pressure-sensitive molecules that undergo conformational changes were used to probe the internal pressures inside the bubbles, which are 0.5–1 GPa over a temperature window of up to 673 K. The pressure-induced oligomerization of C60 molecules occurring at distinct PT windows could be followed using FTIR spectroscopy.

    21. Molecular Diversity

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      Synthesis of Complex and Diverse Compounds through Ring Distortion of Abietic Acid (pages 220–224)

      Dr. Ryan J. Rafferty, Robert W. Hicklin, Katherine A. Maloof and Prof. Paul J. Hergenrother

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201308743

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      Abietic acid was used as the starting point for the synthesis of 84 complex and diverse small molecules. Their complexity was assessed by the fraction of sp3-hybridized carbon atoms and the number of stereogenic centers, and their diversity was evaluated by Tanimoto analysis. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens.

    22. Synthetic Methods

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      Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones (pages 225–229)

      Prof. Dr. Qing Xu, Jianhui Chen, Haiwen Tian, Xueqin Yuan, Shuangyan Li, Chongkuan Zhou and Dr. Jianping Liu

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201308642

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      Plain and simple: The title reaction has been realized under simple and practical conditions without using external catalysts, and can afford alkylated ketone or alcohol products in a one-pot manner and on a large scale. The reaction proceeds by C[DOUBLE BOND]C bond formation of the in situ generated intermediates with subsequent controllable and selective Meerwein–Pondorf–Verley–Oppenauer-type redox processes.

    23. Isotopic Exchange

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      Regioselective and Stereospecific Deuteration of Bioactive Aza Compounds by the Use of Ruthenium Nanoparticles (pages 230–234)

      Dr. Grégory Pieters, Céline Taglang, Dr. Eric Bonnefille, Dr. Torsten Gutmann, Céline Puente, Dr. Jean-Claude Berthet, Dr. Christophe Dugave, Dr. Bruno Chaudret and Dr. Bernard Rousseau

      Article first published online: 19 NOV 2013 | DOI: 10.1002/anie.201307930

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      Don't just slap a label on it! A regioselective and stereospecific method for the deuteration of nitrogen-containing compounds has been developed on the basis of a C[BOND]H activation process triggered by Ru nanoparticles (RuNps). This general and efficient approach to deuterium labeling was applied to 22 compounds, including 8 biologically active substances (see scheme; PVP=polyvinylpyrrolidone).

    24. Asymmetric Catalysis

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      Chiral Silver Phosphate Catalyzed Transformation of ortho-Alkynylaryl Ketones into 1H-Isochromene Derivatives through an Intramolecular-Cyclization/Enantioselective-Reduction Sequence (pages 235–239)

      Prof. Dr. Masahiro Terada, Feng Li and Dr. Yasunori Toda

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201307371

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      Dependent on its other half: The title reaction of ortho-alkynylaryl ketones in the presence of a silver catalyst with a chiral counteranion afforded 1H-isochromene derivatives in high yield with good to high enantioselectivity (see scheme; R1=alkyl, aryl; R2=aryl; R3=H, F). An asymmetric synthesis of the 9-oxabicyclo[3.3.1]nona-2,6-diene framework found in biologically active molecules highlights the synthetic utility of this method.

    25. Electrocatalysis

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      Pulsed-EPR Evidence of a Manganese(II) Hydroxycarbonyl Intermediate in the Electrocatalytic Reduction of Carbon Dioxide by a Manganese Bipyridyl Derivative (pages 240–243)

      Dr. Marc Bourrez, Dr. Maylis Orio, Florian Molton, Dr. Hervé Vezin, Dr. Carole Duboc, Dr. Alain Deronzier and Dr. Sylvie Chardon-Noblat

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201306750

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      New insights into the catalytic mechanism pathway for selective electrocatalytic reduction of carbon dioxide to carbon monoxide by a manganese(I) carbonyl catalyst are given by using pulsed-EPR spectroscopy combined with DFT calculations. The results directly show the formation of a metal(II)–carboxylic acid–CO2 adduct (see picture) after oxidative addition of CO2 and H+ to a Mn0 carbonyl dimer.

    26. Photoresponsive Materials

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      Enhancement of the Photoresponse in Organic Field-Effect Transistors by Incorporating Thin DNA Layers (pages 244–249)

      Dr. Yuan Zhang, Prof. Mingfeng Wang, Samuel D. Collins, Dr. Huiqiong Zhou, Hung Phan, Christopher Proctor, Dr. Alexander Mikhailovsky, Prof. Fred Wudl and Prof. Thuc-Quyen Nguyen

      Article first published online: 18 NOV 2013 | DOI: 10.1002/anie.201306763

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      With a thin DNA layer inserted beneath the top source and drain electrodes, the photoresponse of n-type field-effect transistors based on PCBDR (chemical structure shown in the picture) increases remarkably at low gate bias. This result is primarily attributable to the improved exciton dissociation assisted by the interfacial dipole created at the DNA/PCBDR interface.

    27. Hetergeneous Catalysts

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      Graphene-Supported Ultrafine Metal Nanoparticles Encapsulated by Mesoporous Silica: Robust Catalysts for Oxidation and Reduction Reactions (pages 250–254)

      Dr. Lu Shang, Tong Bian, Baihui Zhang, Dr. Donghui Zhang, Prof. Li-Zhu Wu, Prof. Chen-Ho Tung, Prof. Yadong Yin and Prof. Tierui Zhang

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201306863

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      Layer cake: The synthesis of graphene-nanosheet-supported ultrafine metal nanoparticles encapsulated by thin mesoporous silica layers is reported. The resulting class of robust catalysts was shown to possess high activity, good stability under high temperature conditions, and excellent recyclability and reusability in both gas- and solution-phase reactions.

    28. Asymmetric Catalysis

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      Dynamic Kinetic Asymmetric Transformations of β-Stereogenic α-Ketoesters by Direct Aldolization (pages 255–259)

      Michael T. Corbett and Prof. Dr. Jeffrey S. Johnson

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201306873

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      Dynamic and efficient: Dynamic kinetic asymmetric transformations of racemic β-bromo-α-ketoesters through the direct aldolization of nitromethane and acetone provided access to fully substituted α-glycolic acid derivatives bearing a β-stereocenter (see scheme; PNBA=p-nitrobenzoic acid). The aldol adducts were obtained in excellent yield with high relative and absolute stereocontrol under mild reaction conditions.

    29. Homogeneous Catalysis

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      Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single Palladium-Catalyzed Triple Relay Process (pages 260–264)

      Tiezheng Jia, Dr. Ana Bellomo, Dr. Sonia Montel, Mengnan Zhang, Kawtar EL Baina, Bing Zheng and Prof. Patrick J. Walsh

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201307172

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      Three for one: The [Pd(dba)2]/NiXantPhos (dba=dibenzylideneacetone) catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, C[BOND]S bond cleavage, and C[BOND]S bond formation to give diaryl sulfoxides (see picture). Aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides reacted with various (hetero)aryl bromides.

    30. Molecular Dynamics Simulations

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      Isomerization and Decomposition of a Criegee Intermediate in the Ozonolysis of Alkenes: Dynamics Using a Multireference Potential (pages 265–268)

      Jaroslaw Kalinowski, Prof. Markku Räsänen, Dr. Petri Heinonen, Prof. Ilkka Kilpeläinen and Prof. R. Benny Gerber

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201307286

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      Reading the wave function: The isomerization and decomposition dynamics of the simplest Criegee intermediate CH2OO were studied by classical trajectory simulations using the multireference ab initio MR-T2 potential on the fly (see picture, numbers are bond lengths (Å) and partial charges). The contributions of different configurations to the multiconfigurational total electronic wave function vary dramatically along the trajectories.

    31. Photochemistry

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      Acylsilanes in Rhodium(III)-Catalyzed Directed Aromatic C–H Alkenylations and Siloxycarbene Reactions with C[BOND]C Double Bonds (pages 269–271)

      Peter Becker, Dr. Daniel L. Priebbenow, Ramona Pirwerdjan and Prof. Dr. Carsten Bolm

      Article first published online: 19 NOV 2013 | DOI: 10.1002/anie.201307446

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      Circle of light: A rhodium(III)-catalyzed olefination process allows access to ortho-olefinated aroylsilanes through C–H functionalization in high yields. A light-induced cyclization leads to silyl ethers of indanones in excellent yields as determined by NMR spectroscopy. Mechanistically, the latter transformation proceeds via siloxycarbene intermediates.

    32. Natural Product Synthesis

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      Asymmetric Total Synthesis of (+)-Bermudenynol, a C15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation (pages 272–276)

      Gyudong Kim, Dr. Te-ik Sohn, Prof. Dr. Deukjoon Kim and Dr. Robert S. Paton

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201308077

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      Bermuda octagon: A substrate-controlled asymmetric total synthesis of the title compound was developed. The oxocene core (shown in red), which contains a vinyl chloride unit, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This work demonstrates the utility of the IAEA method, which provides a useful alternative for cases in which ring-closing metathesis (RCM) is inefficient.

    33. Asymmetric Catalysis

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      Enantioselective Double Manipulation of Tetrahydroisoquinolines with Terminal Alkynes and Aldehydes under Copper(I) Catalysis (pages 277–281)

      Weilong Lin, Tao Cao, Wu Fan, Yulin Han, Jinqiang Kuang, Hongwen Luo, Bukeyan Miao, Xinjun Tang, Qiong Yu, Weiming Yuan, Jiasheng Zhang, Can Zhu and Prof. Dr. Shengming Ma

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201308699

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      Two groups for the price of one: A mild copper-catalyzed α-alkynylation of unsubstituted tetrahydroisoquinolines with aldehydes and terminal alkynes proceeded with high chemo- and enantioselectivity at a low catalyst loading to provide the core structure of a large class of alkaloids (see scheme). This reaction offers access to a broad range of alkaloid precursors with an N-benzyl group and a C[BOND]C triple bond for further manipulation.

    34. Aminocatalysis

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      The Catalytic Asymmetric α-Benzylation of Aldehydes (pages 282–285)

      Prof. Dr. Benjamin List, Dr. Ilija Čorić, Dr. Oleksandr O. Grygorenko, Philip S. J. Kaib, Prof. Dr. Igor Komarov, Dr. Anna Lee, Markus Leutzsch, Dr. Subhas Chandra Pan, Andrey V. Tymtsunik and Manuel van Gemmeren

      Article first published online: 24 NOV 2013 | DOI: 10.1002/anie.201306037

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      A sterically demanding proline derivative promotes the first aminocatalyzed α-alkylation of α-branched aldehydes with benzyl bromides as alkylating agents. Racemic α-branched aldehydes react with alkylating agents in a DYKAT process to give the corresponding α-alkylated aldehydes with quaternary stereogenic centers in good yields and high enantioselectivities.

    35. Iterative Synthesis

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      Iterative Synthesis of Nucleoside Oligophosphates with Phosphoramidites (pages 286–289)

      Gregor S. Cremosnik, Alexandre Hofer and Dr. Henning J. Jessen

      Article first published online: 12 NOV 2013 | DOI: 10.1002/anie.201306265

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      Omne trium perfectum: Nucleoside triphosphates can be synthesized by an iterative approach based on P-amidite chemistry (coupling, oxidation, deprotection). The reactions occur under ambient conditions without drying of any solvent or reagent. The process is very convenient, fast, and works with all canonical nucleosides. An extension of this approach is the iterative coupling applied to a controlled pore glass bound nucleoside.

    36. Mixed-Element Ligands

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      An Approach to Mixed PnAsm Ligand Complexes (pages 290–293)

      Dr. Christoph Schwarzmaier, Dr. Michael Bodensteiner, Dr. Alexey Y. Timoshkin and Prof. Dr. Manfred Scheer

      Article first published online: 13 NOV 2013 | DOI: 10.1002/anie.201308239

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      A P4 butterfly complex reacts with yellow arsenic to yield the largest mixed PnAsm ligand complexes synthesized to date. Mass spectrometry together with NMR spectroscopy and X-ray crystallography give clear evidence about the arrangement of the E positions within the cyclo-E5 and E4 moieties of the products. Moreover, the results of DFT calculations agree well with the experimental determined outcomes.

    37. Nanoparticle Detection

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      Nanoparticle-Imprinted Polymers for Size-Selective Recognition of Nanoparticles (pages 294–298)

      Shlomit Kraus-Ophir, Julia Witt, Prof. Gunther Wittstock and Prof. Daniel Mandler

      Article first published online: 4 NOV 2013 | DOI: 10.1002/anie.201305962

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      Suitable refills: Gold nanoparticles transferred together with monolayers of polyaniline onto a conducting substrate can be electro-oxidized leaving behind cavities of uniform size in the polymer films. The cavities show size-exclusion properties and the films can be used as an analytical tool for the recognition of nanoparticles.

    38. Electron Transfer

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      Catching an Entatic State—A Pair of Copper Complexes (pages 299–304)

      Dr. Alexander Hoffmann, Dr. Stephan Binder, Anton Jesser, Dr. Roxana Haase, Dr. Ulrich Flörke, Dr. Manuel Gnida, Dr. Marco Salomone Stagni, Dr. Wolfram Meyer-Klaucke, Benjamin Lebsanft, Lara Elena Grünig, Simon Schneider, Maryam Hashemi, Arne Goos, Alina Wetzel, Prof. Dr. Michael Rübhausen and Prof. Dr. Sonja Herres-Pawlis

      Article first published online: 7 NOV 2013 | DOI: 10.1002/anie.201306061

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      Independent of the oxidation state, two guanidine–quinoline copper complexes have structures that are virtually identical in both the solid state and in solution. They can be interconverted by a reversible electron transfer at 0.33 V. By resonant excitation of the two copper complexes, the transition state of the electron transfer is accessible through vibrational modes.

    39. Metal-Containing Inhibitors

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      An Organometallic Inhibitor for the Human Repair Enzyme 7,8-Dihydro-8-oxoguanosine Triphosphatase (pages 305–309)

      Manuel Streib, Katja Kräling, Kristin Richter, Dr. Xiulan Xie, Dr. Holger Steuber and Prof. Dr. Eric Meggers

      Article first published online: 20 NOV 2013 | DOI: 10.1002/anie.201307849

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      Not a canonical inhibitor: A ruthenium complex has been shown to be a low-nanomolar and selective inhibitor of an enzyme that hydrolyzes oxidized purine nucleoside triphosphates. This work provides a blueprint for the discovery and development of organometallic inhibitors of other purine nucleotide binding proteins which rely on ruthenium-coordinated adenine and quinazoline derivatives with tailored coordination spheres.

    40. Oligodiacetylenes

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      Optically Pure, Monodisperse cis-Oligodiacetylenes: Aggregation-Induced Chirality Enhancement (pages 310–314)

      Dr. Erin T. Chernick, Dr. Gabor Börzsönyi, Christian Steiner, Maximilian Ammon, David Gessner, Sabine Frühbeißer, Prof. Dr. Franziska Gröhn, Prof. Dr. Sabine Maier and Prof. Dr. Rik R. Tykwinski

      Article first published online: 29 NOV 2013 | DOI: 10.1002/anie.201307904

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      Conformation, conjugation: A series of optically pure, monodisperse cis-oligodiacetylenes (cis-ODAs) based on D-camphor building blocks has been synthesized up to the tridecamer length, which represents the longest cis-ODA reported to date. Optical spectroscopy and STM/AFM measurements indicate that the oligomers assume a linear, planar conformation in THF. Conversely, in iPrOH solution ODAs with n≥9 form chiral aggregates.

    41. Epigenetics

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      Synthesis of a DNA Promoter Segment Containing All Four Epigenetic Nucleosides: 5-Methyl-, 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxy-2′-Deoxycytidine (pages 315–318)

      Arne S. Schröder, Jessica Steinbacher, Barbara Steigenberger, Felix A. Gnerlich, Stefan Schiesser, Toni Pfaffeneder and Prof. Dr. Thomas Carell

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201308469

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      Biologically relevant promoter segments with all four epigenetic nucleosides are finally accessible by solid-phase synthesis. With the fdC-phosphoramidite building block introduced herein, no side reactions of 5-formylcytosine were observed. Furthermore, mild deprotection conditions prevented oxidative or reductive lesions, which was proven by detailed mass spectrometric analysis.

    42. RNA Engineering

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      Recoding the Genetic Code with Selenocysteine (pages 319–323)

      Dr. Markus J. Bröcker, Joanne M. L. Ho, Prof. George M. Church, Prof. Dieter Söll and Prof. Patrick O'Donoghue

      Article first published online: 25 NOV 2013 | DOI: 10.1002/anie.201308584

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      The selenocysteine insertion machinery was engineered to recode multiple sense codons. This was demonstrated for Escherichia coli formate dehydrogenase and recombinant human thioredoxin reductase. In the picture the canonical genetic code table is overlaid with a single assay in which purple-colored cells express active Sec-containing enzymes.

    43. Supramolecular Enzyme Hybrids

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      Constructing Hybrid Protein Zymogens through Protective Dendritic Assembly (pages 324–328)

      David Y. W. Ng, Matthias Arzt, Yuzhou Wu, Dr. Seah Ling Kuan, Markus Lamla and Prof. Dr. Tanja Weil

      Article first published online: 20 DEC 2013 | DOI: 10.1002/anie.201308533

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      The programmed self-assembly of a dendritic shell onto enzymes was used to modulate enzyme activity as well as induce cellular entry and release of the active proteins. The defined dendritic construct represents a contemporary avenue for smart protein therapeutics.

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