Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 44

October 29, 2012

Volume 51, Issue 44

Pages 10905–11169

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Cover Picture: Enhancing the Light Harvesting Capability of a Photosynthetic Reaction Center by a Tailored Molecular Fluorophore (Angew. Chem. Int. Ed. 44/2012) (page 10905)

      Dr. Francesco Milano, Dr. Rocco Roberto Tangorra, Dr. Omar Hassan Omar, Dr. Roberta Ragni, Dr. Alessandra Operamolla, Prof. Angela Agostiano, Prof. Gianluca M. Farinola and Dr. Massimo Trotta

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/anie.201207837

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      A hybrid photosynthetic machine capable of exploiting solar energy for photoconversion is described by G. M. Farinola, M. Trotta, and co-workers in their Communication on page 11019 ff. The simplest photosynthetic protein able to convert sunlight into other energy forms is covalently functionalized with a tailored organic dye to obtain a fully functional hybrid complex that outperforms the natural system in conversion and light-harvesting ability. Photograph by Francesca Suaria.

    2. You have free access to this content
      Inside Cover: Selective RNA Versus DNA G-Quadruplex Targeting by In Situ Click Chemistry (Angew. Chem. Int. Ed. 44/2012) (page 10906)

      Dr. Marco Di Antonio, Giulia Biffi, Angelica Mariani, Dr. Eun-Ang Raiber, Dr. Raphaël Rodriguez and Prof. Shankar Balasubramanian

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/anie.201207794

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      The rational design of small molecules to selectively target a defined RNA is highly challenging. Such probes ultimately provide the means to interrogate RNA functions within a cellular context with high temporal resolution. In their Communication on page 11073 ff., R. Rodriguez, S. Balasubramanian, and co-workers report the use of in situ click chemistry to identify a small molecule that selectively interacts with the telomeric repeat-containing RNA (TERRA) through recognition of the G-quadruplex structure. The same approach was used to identify a related analogue that targets its DNA counterpart with high efficiency.

    3. You have free access to this content
      Inside Back Cover: The Reaction Coordinate of a Bacterial GH47 α-Mannosidase: A Combined Quantum Mechanical and Structural Approach (Angew. Chem. Int. Ed. 44/2012) (page 11171)

      Andrew J. Thompson, Dr. Jerome Dabin, Javier Iglesias-Fernández, Dr. Albert Ardèvol, Dr. Zoran Dinev, Assoc. Prof. Spencer J. Williams, Dr. Omprakash Bande, Dr. Aloysius Siriwardena, Carl Moreland, Dr. Ting-Chou Hu, David K. Smith, Prof. Harry J. Gilbert, Prof. Carme Rovira and Prof. Gideon J. Davies

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/anie.201207917

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      Mannosidases are glycoside hydrolases that face special stereoelectronic challenges in effecting the hydrolysis of the glycosidic bond. In their Communication on page 10997 ff., C. Rovira, G. J. Davies, and co-workers use QM/MM calculations, supported by X-ray structures of the enzyme with ligands mimicking the substrate, transition state, and product, to show that the free-energy landscape of an isolated alpha-mannoside is shaped on-enzyme into a single conformational itinerary along the reaction coordinate.

    4. You have free access to this content
      Back Cover: Ceria Nanoparticles that can Protect against Ischemic Stroke (Angew. Chem. Int. Ed. 44/2012) (page 11172)

      Dr. Chi Kyung Kim, Taeho Kim, In-Young Choi, Min Soh, Dr. Dohoung Kim, Young-Ju Kim, Dr. Hyunduk Jang, Hye-Sung Yang, Dr. Jun Yup Kim, Dr. Hong-Kyun Park, Dr. Seung Pyo Park, Sangseung Park, Dr. Taekyung Yu, Prof. Byung-Woo Yoon, Prof. Seung-Hoon Lee and Prof. Taeghwan Hyeon

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/anie.201207798

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      Ceria nanoparticles are known to exhibit free-radical scavenging activity by reversibly binding oxygen. In their Communication on page 11039 ff., S.-H. Lee, T. Hyeon, et al. show that discrete, uniform 3 nm PEGylated ceria nanoparticles can protect against ischemic stroke by scavenging reactive oxygen species and reducing apoptosis. Optimal doses of ceria nanoparticles reduce infarct volumes and the rate of ischemic cell death, and target the infarct site in vivo.

  2. Graphical Abstract

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Corrigendum: A Multicolor Nanoprobe for Detection and Imaging of Tumor-Related mRNAs in Living Cells (page 10922)

      Dr. Na Li, Chenyang Chang, Wei Pan and Prof. Bo Tang

      Version of Record online: 24 OCT 2012 | DOI: 10.1002/anie.201206766

      This article corrects:

      A Multicolor Nanoprobe for Detection and Imaging of Tumor-Related mRNAs in Living Cells1

      Vol. 51, Issue 30, 7426–7430, Version of Record online: 2 JUL 2012

  4. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    1. Gerard Meijer (page 10930)

      Version of Record online: 21 JUN 2012 | DOI: 10.1002/anie.201203997

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      “The best advice I have ever been given is to follow my heart. I like refereeing because it is an excellent way to stay up-to-date in the research field. …” This and more about Gerard Meijer can be found on page 10930.

  6. News

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    1. Supramolecular Polymer Chemistry. Edited by Akira Harada. (page 10933)

      Hans-Werner Schmidt

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201206234

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      Wiley-VCH, Weinheim, 2011. 372 pp., hardcover, € 139.00.—ISBN 978-3527323210

  8. Highlights

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

      Chiral Aryl–Copper(III) Electrophiles: New Opportunities in Catalytic Enantioselective Arylations and Domino Processes (pages 10934–10935)

      Dr. Sophie Rousseaux, Dr. Emmanuel Vrancken and Prof. Dr. Jean-Marc Campagne

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201205805

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      “Chiral aryl cation” equivalents: The combination of diaryliodonium salts and catalytic amounts of chiral copper complexes provides facile access to “chiral aryl cation” synthons. These reagents offer new possibilities for asymmetric arylation reactions that initiate further domino processes.

    2. Graphene

      Graphene from Molecules (pages 10936–10937)

      Prof. Armin Gölzhäuser

      Version of Record online: 23 SEP 2012 | DOI: 10.1002/anie.201205955

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      Step by step: According to the molecular approach to the production of graphene, precursor molecules are cross-linked to form two-dimensional intermediates, and pyrolysis transforms the intermediates into graphene. This type of highly efficient synthesis of high-quality graphene is crucial to the development of innovative applications.

  9. Minireview

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

      Catalytic, Asymmetric Halofunctionalization of Alkenes—A Critical Perspective (pages 10938–10953)

      Prof. Dr. Scott E. Denmark, William E. Kuester and Dr. Matthew T. Burk

      Version of Record online: 25 SEP 2012 | DOI: 10.1002/anie.201204347

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      The return of the salt makers: Catalytic enantioselective versions of halofunctionalizations have recently appeared and although important breakthroughs, they represent just the very beginnings of a nascent field. Herein is a critical analysis of the challenges that accompany the development of general and highly enantioselective halofunctionalizations. Various modes of catalysis and the different strategies implemented for asymmetric induction are identified.

  10. Review

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

      Catalytic Selective Synthesis (pages 10954–10990)

      Jessada Mahatthananchai, Dr. Aaron M. Dumas and Prof. Dr. Jeffrey W. Bode

      Version of Record online: 25 SEP 2012 | DOI: 10.1002/anie.201201787

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      A tale of two catalysts: Catalyst-controlled selectivity is well established for enantioselective catalysis but less formulated for catalytic regio-, chemo,- or product-selective reactions. This Review describes selective transformations of the same starting materials into two or more different products simply by the choice of catalyst even when the reaction conditions are nearly identical.

  11. Communications

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

      Single Nanoscale Cluster Species Revealed by 1H NMR Diffusion-Ordered Spectroscopy and Small-Angle X-ray Scattering (pages 10992–10996)

      Anna F. Oliveri, Matthew E. Carnes, Matthew M. Baseman, Erik K. Richman, Prof. Dr. James E. Hutchison and Prof. Dr. Darren W. Johnson

      Version of Record online: 10 OCT 2012 | DOI: 10.1002/anie.201206386

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      A solved structure: The hydrated Ga13 cluster, [Ga133-OH)6(μ-OH)18(H2O)24](NO3)15], persists as a discrete nanoscale structure in an aqueous polar solvent at millimolar concentration. SAXS data confirm the presence of Ga13 in dimethyl sulfoxide (DMSO). In aqueous [D6]DMSO 1H NMR signals for the hydroxo and aquo ligands of Ga13 were detected, thus showing a cluster with a hydrodynamic radius of (11.2±0.8) Å (see picture).

    2. Computational Chemistry

      The Reaction Coordinate of a Bacterial GH47 α-Mannosidase: A Combined Quantum Mechanical and Structural Approach (pages 10997–11001)

      Andrew J. Thompson, Dr. Jerome Dabin, Javier Iglesias-Fernández, Dr. Albert Ardèvol, Dr. Zoran Dinev, Assoc. Prof. Spencer J. Williams, Dr. Omprakash Bande, Dr. Aloysius Siriwardena, Carl Moreland, Dr. Ting-Chou Hu, David K. Smith, Prof. Harry J. Gilbert, Prof. Carme Rovira and Prof. Gideon J. Davies

      Version of Record online: 26 SEP 2012 | DOI: 10.1002/anie.201205338

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      Mannosides in the southern hemisphere: Conformational analysis of enzymatic mannoside hydrolysis informs strategies for enzyme inhibition and inspires solutions to mannoside synthesis. Atomic resolution structures along the reaction coordinate of an inverting α-mannosidase show how the enzyme distorts the substrate and transition state. QM/MM calculations reveal how the free energy landscape of isolated α-D-mannose is molded on enzyme to only allow one conformationally accessible reaction coordinate.

    3. DNA Structures

      Tri-G-Quadruplex: Controlled Assembly of a G-Quadruplex Structure from Three G-Rich Strands (pages 11002–11005)

      Dr. Jun Zhou, Dr. Anne Bourdoncle, Dr. Frédéric Rosu, Dr. Valérie Gabelica and Dr. Jean-Louis Mergny

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205390

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      In my (DNA) dreams: A tri-G-quadruplex was constructed from three strands (T1–T3) of DNA using duplex formation to guide the G-rich tracts into close proximity with the addition of Li+ ions (see scheme). The defined G-quadruplex structure was formed upon addition of Na+ ions and characterized by gel electrophoresis and spectroscopy.

    4. Fluorescent Probes

      DNA Detection Based on Fluorogenic Nanospheres (pages 11006–11009)

      Xin Shu, Yonghui Liu and Prof. Dr. Jin Zhu

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205628

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      High and dry fluorescence: Fluorogenic nanospheres (green, see scheme) are conjugated to DNA (pink) and used to detect target DNA (aqua). Upon addition of N-butylmorpholine (droplet), the nanospheres dissolve, releasing fluorophores, and intense blue fluorescence is emitted at the site of DNA hybridization. The separation of DNA hybridization and signal amplification gives high sensitivity (100 zmol) and selectivity.

    5. Nitrogen-Oxide Adsorption

      Entropy-Driven Chemisorption of NOx on Phosphotungstic Acid (pages 11010–11013)

      Steven Heylen, Lennart Joos, Prof. Tatjana N. Parac-Vogt, Prof. Veronique Van Speybroeck, Prof. Christine E. A. Kirschhock and Prof. Johan A. Martens

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205636

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      Free-energy calculations indicated that the NOx adsorption process on heteropolyacids is entropy-driven, as more gas molecules are released than adsorbed by substitution of H5O2+ with NO+ species. P yellow, W light blue, O red, H pink, N small dark blue spheres.

    6. Cell Targeting

      Click and Pick: Identification of Sialoside Analogues for Siglec-Based Cell Targeting (pages 11014–11018)

      Cory D. Rillahan, Dr. Erik Schwartz, Ryan McBride, Prof. Valery V. Fokin and Prof. James C. Paulson

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205831

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      Click ‘n’ chips: Azide and alkyne-bearing sialic acids (purple diamond; see picture) were subjected to high-throughput click chemistry to generate a library of sialic acid analogues. Microarray printing of the library and screening with the siglec family of sialic-acid-binding proteins, led to the identification of high-affinity ligands for siglec-9 and siglec-10.

    7. Hybrid photosynthetic complexes

      Enhancing the Light Harvesting Capability of a Photosynthetic Reaction Center by a Tailored Molecular Fluorophore (pages 11019–11023)

      Dr. Francesco Milano, Dr. Rocco Roberto Tangorra, Dr. Omar Hassan Omar, Dr. Roberta Ragni, Dr. Alessandra Operamolla, Prof. Angela Agostiano, Prof. Gianluca M. Farinola and Dr. Massimo Trotta

      Version of Record online: 26 SEP 2012 | DOI: 10.1002/anie.201203404

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      Light machine: The simplest photosynthetic protein able to convert sunlight into other energy forms is covalently functionalized with a tailored organic dye to obtain a fully functional hybrid complex that outperforms the natural system in light harvesting and conversion ability.

    8. Supramolecular Chemistry

      Induced Self-Assembly of a Tetrathiafulvalene-Based Open-Shell Dyad through Intramolecular Electron Transfer (pages 11024–11028)

      Dr. Judith Guasch, Dr. Luca Grisanti, Dr. Vega Lloveras, Dr. José Vidal-Gancedo, Manuel Souto, Dayana C. Morales, Dr. Marta Vilaseca, Dr. Cristina Sissa, Prof. Anna Painelli, Dr. Imma Ratera, Prof. Concepció Rovira and Prof. Jaume Veciana

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203448

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      An organic switch: An open-shell dyad, consisting of an electron acceptor perchlorotriphenylmethyl radical unit linked to an electron π-donor tetrathiafulvalene unit through a vinylene π-bridge, was synthesized (see picture). The self-assembly of the dyad in solution induced by its intramolecular electron transfer was studied.

    9. Bulk Water Modeling

      Proton Defect Solvation and Dynamics in Aqueous Acid and Base (pages 11029–11032)

      Dr. Seyit Kale and Prof.Dr. Judith Herzfeld

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203568

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      Easy come, easy go: LEWIS, a new model of reactive and polarizable water that enables the simulation of a statistically reliable number of proton hopping events in aqueous acid and base at concentrations of practical interest, is used to evaluate proton transfer intermediates in aqueous acid and base (picture, left and right, respectively).

    10. Supramolecular Catalysis

      Mechanistic Insights into a Supramolecular Self-Assembling Catalyst System: Evidence for Hydrogen Bonding during Rhodium-Catalyzed Hydroformylation (pages 11033–11038)

      Urs Gellrich, Dr. Wolfgang Seiche, Dr. Manfred Keller and Prof. Dr. Bernhard Breit

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201203768

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      The structural integrity and flexibility provided by intermolecular hydrogen bonds leads to the outstanding properties of the 6-diphenylphosphinopyridin-(2H)-1-one ligand (see scheme) in the rhodium-catalyzed hydroformylation of terminal alkenes, as demonstrated by the combination of spectroscopic methods and DFT computations. Hydrogen bonds were also detected in a competent intermediate of the catalytic cycle.

    11. Therapeutic Nanoparticles

      Ceria Nanoparticles that can Protect against Ischemic Stroke (pages 11039–11043)

      Dr. Chi Kyung Kim, Taeho Kim, In-Young Choi, Min Soh, Dr. Dohoung Kim, Young-Ju Kim, Dr. Hyunduk Jang, Hye-Sung Yang, Dr. Jun Yup Kim, Dr. Hong-Kyun Park, Dr. Seung Pyo Park, Sangseung Park, Dr. Taekyung Yu, Prof. Byung-Woo Yoon, Prof. Seung-Hoon Lee and Prof. Taeghwan Hyeon

      Version of Record online: 11 SEP 2012 | DOI: 10.1002/anie.201203780

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      Uniform 3 nm-sized ceria nanoparticles can protect against ischemic stroke by scavenging reactive oxygen species (ROS) and reducing apoptosis. PEGylated ceria nanoparticles showed protective effects against ROS-induced cell death in vitro. Optimal doses of ceria nanoparticles reduced infarct volumes and the rate of ischemic cell death in vivo.

    12. Metal–Organic Frameworks

      Enhanced Stability in Rigid Peptide-Based Porous Materials (pages 11044–11048)

      Dr. Carlos Martí-Gastaldo, Dr. John E. Warren, Dr. Kyriakos C. Stylianou, Natasha L. O. Flack and Prof. Matthew J. Rosseinsky

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203929

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      Pepped up: Notwithstanding the intrinsic conformational flexibility of peptides, [Zn(Gly–Thr)2] behaves as a robust porous metal–organic framework thanks to the rigidity introduced by the use of Gly–Thr (see scheme). This rigidity arises from the sequence of amino acids in the dipeptide that locks its conformational flexibility in the framework.

    13. Spin Crossover

      Four-Site Cooperative Spin Crossover in a Mononuclear FeII Complex (pages 11049–11052)

      Dr. Anders Lennartson, Prof. Andrew D. Bond, Dr. Stergios Piligkos and Prof. Christine J. McKenzie

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204207

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      Round and round: A mononuclear FeII complex (see picture) with an N4S2 coordination set has been characterized in four polymorphic forms. Two of the polymorphs display four-site cooperative spin crossover (SCO), shown conclusively by the crystal structure of a fully ordered 1:3 high-spin/low-spin state. The presence of S donor atoms in SCO-active compounds is unusual, and further investigation of FeII complexes for SCO activity is warranted.

    14. Sensors

      Room-Temperature Hydrogen Sensing with Heteronanostructures Based on Reduced Graphene Oxide and Tin Oxide (pages 11053–11057)

      Dr. Patrícia A. Russo, Dr. Nicola Donato, Dr. Salvatore Gianluca Leonardi, Seunghwan Baek, Dr. Donato E. Conte, Prof. Giovanni Neri and Prof. Nicola Pinna

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204373

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      There's something in the air … A nanocomposite consisting of well-dispersed SnO2 and Pt nanoparticles on reduced graphene oxide (see the high-resolution TEM image) exhibited very high responses to hydrogen at concentrations between 0.5 and 3 % in air, with response times of 3–7 s and recovery times of 2–6 s. The sensor was prepared by a straightforward microwave-assisted non-aqueous sol–gel approach.

    15. Molecular Chirality

      Detection of Molecular Chirality by Induced Resonance Raman Optical Activity in Europium Complexes (pages 11058–11061)

      Dr. Shigeki Yamamoto and Dr. Petr Bouř

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204765

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      Beef up the signal: Induced resonance Raman optical activity (IRROA) in the presence of a europium complex enabled the detection of molecular chirality (see picture) with a 104-fold increase in sensitivity relative to that observed with conventional nonresonant vibrational ROA. The method can thus be used as a sensitive tool for the determination of the absolute configuration and enantiomeric excess of organic and biologically relevant compounds.

    16. Gel–Air Electrodes

      From Li–O2 to Li–Air Batteries: Carbon Nanotubes/Ionic Liquid Gels with a Tricontinuous Passage of Electrons, Ions, and Oxygen (pages 11062–11067)

      Dr. Tao Zhang and Prof. Haoshen Zhou

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204983

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      A salt and battery: The combination of single-walled carbon nanotubes (SWNTs) and an ionic liquid (IL) cross-linked network gel (CNG) allows the conventional three-phase reactive interface to be expanded to the whole cross-linked network (see picture). Thus, it integrates high specific energy and specific power with the feasibility of operating in ambient air.

    17. π-Conjugated Polymers

      A Strategy for Revealing the Packing in Semicrystalline π-Conjugated Polymers: Crystal Structure of Bulk Poly-3-hexyl-thiophene (P3HT) (pages 11068–11072)

      Dr. Dmytro Dudenko, Dr. Adam Kiersnowski, Dr. Jie Shu, Dr. Wojciech Pisula, Prof. Dr. Daniel Sebastiani, Prof. Dr. Hans Wolfgang Spiess and Dr. Michael Ryan Hansen

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205075

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      To tilt or not to tilt: The crystal structure for bulk P3HT (phase I) was determined by “multi-technique crystallography”, which combines X-ray diffraction, solid-state NMR spectroscopy, and DFT calculations. The results showed that this semiconducting polymer crystallizes in the monoclinic space group P21/c with nontilted π-stacks at a distance of 3.9 Å (see picture).

    18. Bioorganic Chemistry

      You have full text access to this OnlineOpen article
      Selective RNA Versus DNA G-Quadruplex Targeting by In Situ Click Chemistry (pages 11073–11078)

      Dr. Marco Di Antonio, Giulia Biffi, Angelica Mariani, Dr. Eun-Ang Raiber, Dr. Raphaël Rodriguez and Prof. Shankar Balasubramanian

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201206281

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      It all clicks into place: A potent telomere-targeting small molecule has been identified by using the copper-free 1,3-dipolar cycloaddition of a series of alkyne and azide building blocks catalyzed by a non-Watson–Crick DNA secondary structure (see picture). This method rapidly identifies, otherwise unanticipated, potent small-molecule probes to selectively target a given RNA or DNA.

    19. Photoelectrochemistry

      Self-Enhanced Electrochemiluminescence of an Iridium(III) Complex: Mechanistic Insight (pages 11079–11082)

      Kalen N. Swanick, Sébastien Ladouceur, Prof. Dr. Eli Zysman-Colman and Prof. Dr. Zhifeng Ding

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201206074

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      Improved luminophore: The electrochemiluminescence (ECL) of an iridium complex self-enhanced up to 16 times is reported. Three excited states were observed in the emission spectra (see picture). The ECL efficiency of this complex is the highest reported for an iridium complex.

    20. Photochemistry

      Photonic Engineering of Hybrid Metal–Organic Chromophores (pages 11083–11087)

      Mickaël P. Busson, Brice Rolly, Dr. Brian Stout, Dr. Nicolas Bonod, Dr. Jérôme Wenger and Dr. Sébastien Bidault

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205995

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      An aureate dye: Confined electromagnetic fields in DNA-templated gold nanoparticle dimers were tuned to engineer the fluorescence properties of organic dyes in water (see picture). Purified suspensions of hybrid metal–organic chromophores featured unprecedented photophysical properties, such as a short lifetime and low quantum yield but high brightness.

    21. Pyrrole Synthesis

      Multicomponent Synthesis of Pyrroles from Cyclopropanes: A One-Pot Palladium(0)-Catalyzed Dehydrocarbonylation/Dehydration (pages 11088–11091)

      William J. Humenny, Polydoros Kyriacou, Katarina Sapeta, Avedis Karadeolian and Dr. Michael A. Kerr

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201206177

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      Ring the changes: The cycloaddition of nitrones with 1-carboallyloxy-1-carbomethoxycyclopropanes yields tetrahydro-1,2-oxazines, which in turn undergo a Tsuji dehydrocarbonylation to give dihydro-1,2-oxazines (see scheme; dba=dibenzylideneacetone). Addition of base to this reaction mixture results in clean conversion to pyrroles. The result is a flexible three-component strategy for the synthesis of tetrasubstituted pyrroles.

    22. Synthetic Methods

      Oxidative Geminal Functionalization of Organoboron Compounds (pages 11092–11096)

      Zhi He, Piera Trinchera, Dr. Shinya Adachi, Jeffrey D. St. Denis and Prof. Dr. Andrei K. Yudin

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201206501

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      Excellent tolerance: Stable acylboronates equipped with N-methyliminodiacetyl (MIDA) boryl groups ([B]) were prepared by using a sequence of oxidative manipulations at the boron-bound carbon center (green in scheme). Chemoselective transformations of these acylated organoboron building blocks yielded a range of multifunctionalized boron derivatives and supplied access to valuable borylated heterocycles (see scheme).

    23. Heterogeneous Catalysis

      Production of p-Xylene from Biomass by Catalytic Fast Pyrolysis Using ZSM-5 Catalysts with Reduced Pore Openings (pages 11097–11100)

      Dr. Yu-Ting Cheng, Dr. Zhuopeng Wang, Christopher J. Gilbert, Prof. Wei Fan and Prof. George W. Huber

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205230

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      Pores for thought: Chemical liquid deposition of silica onto ZSM-5 catalysts led to smaller pore openings that resulted in >90 % selectivity for p-xylene over the other xylenes in the catalytic fast pyrolysis of furan and 2-methylfuran (see scheme). The p-xylene selectivity increased from 51 % with gallium spray-dried ZSM-5 to 72 % with a pore-mouth-modified catalyst in the pyrolysis of pine wood.

    24. Synthetic Methods

      Diastereoselective Metal-Catalyzed Synthesis of C-Aryl and C-Vinyl Glycosides (pages 11101–11104)

      Dr. Lionel Nicolas, Dr. Patrick Angibaud, Dr. Ian Stansfield, Dr. Pascal Bonnet, Dr. Lieven Meerpoel, Dr. Sébastien Reymond and Prof. Dr. Janine Cossy

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204786

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      Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N′-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1–3:1.

    25. Glycosides

      Dissecting the Influence of Oxazolidinones and Cyclic Carbonates in Sialic Acid Chemistry (pages 11105–11109)

      Dr. Pavan K. Kancharla, Chandrasekhar Navuluri and Prof. Dr. David Crich

      Version of Record online: 13 SEP 2012 | DOI: 10.1002/anie.201204400

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      At a moment′s notice: Thermal equilibration of 1 and mass spectral analysis of sialyl phosphates suggest that the 4O,5N-oxazolidinone and the 4,5-O-carbonate systems influence the anomeric effect and the mechanisms of sialidation by virtue of their dipole moment in the mean plane of the pyranose ring. The electron-withdrawing effect destabilizes 2 and promotes associative glycosylation mechanisms. TEMPO=2,2,6,6-tetramethylpiperidine N-oxide.

    26. Expanded Phthalocyanines

      Superazaporphyrins: Meso-Pentaazapentaphyrins and One of Their Low-Symmetry Derivatives (pages 11110–11114)

      Dr. Taniyuki Furuyama, Yosuke Ogura, Dr. Kenji Yoza and Prof. Dr. Nagao Kobayashi

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203191

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      Supersized: Three pentaazapentaphyrin derivatives, that is, the superazaporphyrins (SAzPs), as well as a superphthalocyanine (SPc) and a mixed low-symmetry derivative have been prepared and characterized. Decaaryl SAzPs have a distorted (4n+2) π structure and show the Q bands at about λ=840–880 nm. These compounds are relatively air stable.

    27. Hydridosilicate σ-Complexes

      Stabilization of ArSiH4 and SiH62− Anions in Diruthenium Si[BOND]H σ-Complexes (pages 11115–11121)

      Mark C. Lipke and Prof. T. Don Tilley

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201202328

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      Hydridosilicate anions ([ArSiH4] and [SiH6]2−) were stabilized as ligands in diruthenium Si[BOND]H σ-complexes [{(PhBPPh3)Ru}2(μ-Cl)(μ-η33-H4SiAr)] (Ar=2-MeOC6H4, Mes, Ph) and [{(PhBPPh3)Ru}2(μ-η44-H6Si)] (see picture). These complexes were formed under mild conditions and characterized by single-crystal X-ray diffraction (see picture), NMR and IR spectroscopy, and computational techniques.

    28. Polymersomes

      Encapsulation of Biomacromolecules within Polymersomes by Electroporation (pages 11122–11125)

      Dr. Linge Wang, Luca Chierico, Daniel Little, Nisa Patikarnmonthon, Zhou Yang, Prof. Dr. Mimoun Azzouz, Dr. Jeppe Madsen, Prof. Dr. Steven P. Armes and Prof. Dr. Giuseppe Battaglia

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201204169

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      Biological macromolecules can be encapsulated into preformed polymersomes by controlled temporary destabilization of the vesicle membrane. The morphology and the size of the polymersome are unchanged after electroporation, suggesting that the polymersome membrane is reformed. The surface charge of the biomacromolecules plays a key role for the electroporation process.

    29. Biosensors

      Back-Scattering Interferometry: An Ultrasensitive Method for the Unperturbed Detection of Acetylcholinesterase–Inhibitor Interactions (pages 11126–11130)

      Gabrielle L. Haddad, Sherri C. Young, Ned D. Heindel, Prof. Darryl J. Bornhop and Prof. Robert A. Flowers II

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203640

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      A series of inhibitors of acetylcholinesterase (AChE) have been screened by back-scattering interferometry (BSI). Enzyme levels as low as 100 pM (22 000 molecules of AChE) can be detected. This method can be used to screen for mixed AChE inhibitors, agents that have shown high efficacy against Alzheimer's disease, by detecting dual-binding interactions. E=enzyme, I=inhibitor, S=substrate.

    30. Conjugated Polymers

      Controllable Processes for Generating Large Single Crystals of Poly(3-hexylthiophene) (pages 11131–11135)

      Khosrow Rahimi, Dr. Ioan Botiz, Dr. Natalie Stingelin, Navaphun Kayunkid, Dr. Michael Sommer, Felix Peter Vinzenz Koch, Ha Nguyen, Dr. Olivier Coulembier, Prof. Philippe Dubois, Prof. Martin Brinkmann and Prof. Günter Reiter

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205653

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      Sowing the seeds: A simple strategy based on self-seeding allows large single crystals of long regioregular poly(3-hexylthiophene) chains to be grown from solution. When appropriately crystallized, materials differing in their degrees of regioregularity and molecular weights formed monoclinic form II crystals with interdigitated hexyl side groups (see picture).

    31. Engineered Biosynthesis

      Heterologous Expression and Manipulation of Three Tetracycline Biosynthetic Pathways (pages 11136–11140)

      Peng Wang, Dr. Woncheol Kim, Dr. Lauren B. Pickens, Xue Gao and Prof. Yi Tang

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205426

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      A very accommodating host: Three tetracycline biosynthetic pathways were overexpressed and manipulated in the heterologous host Streptomyces lividans K4-114. Through the inactivation of various genes and characterization of the resulting biosynthetic intermediates, new tetracycline-modifying enzymes were identified (see scheme).

    32. Rare-Earth Catalysis

      [(NHC)Yb{N(SiMe3)2}2]-Catalyzed Cross-Dehydrogenative Coupling of Silanes with Amines (pages 11141–11144)

      Weilong Xie, Hongfan Hu and Prof. Dr. Chunming Cui

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205317

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      Top cat: [(NHC)Yb{N(SiMe3)2}2] adducts (NHC=N-heterocyclic carbene) are efficient catalysts for catalytic cross-dehydrogenative coupling of silanes with a range of primary and secondary amines to yield silylamines in high yields (82–100 %) under mild reaction conditions. The catalytic activity and selectivity of the rare-earth-metal silylamides are modulated by altering the steric bulk of the NHC.

    33. Assay Development

      Using Smell To Triage Samples in Point-of-Care Assays (pages 11145–11148)

      Hemakesh Mohapatra and Prof. Scott T. Phillips

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201207008

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      Smell of success: Reagent 1 provides the dual readouts of odor (ethanethiol) and fluorescence (derivative of 7-hydroxycoumarin) and can be used in down-selection assays based on smell and quantitative fluorescence assays of the samples that give a positive result. An important feature of 1 is the matched sensitivity of the two outputs. This reagent is designed for use in resource-limited settings and is demonstrated in assays that detect enzymes.

    34. Gold Catalysis

      Anion-Induced Enantioselective Cyclization of Diynamides to Pyrrolidines Catalyzed by Cationic Gold Complexes (pages 11149–11152)

      Asmaa Kamal Mourad, Juliane Leutzow and Dr. Constantin Czekelius

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205416

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      Only chiral anions do the job! Optically active gold complexes derived from substituted binol hydrogen phosphate catalyze the desymmetrizing cyclization of 1,4-diynamides. This reaction provides access to synthetically useful, chiral methylene pyrrolidines with an all-carbon-substituted quaternary stereocenter.

    35. Synthetic Methods

      Domino Reactions of Donor–Acceptor-Substituted Cyclopropanes for the Synthesis of 3,3′-Linked Oligopyrroles and Pyrrolo[3,2-e]indoles (pages 11153–11156)

      Dipl.-Chem. Johannes Kaschel, Dipl.-Chem. Tobias F. Schneider, Dipl.-Chem. Daniel Kratzert, Prof. Dr. Dietmar Stalke and Priv.-Doz. Dr. Daniel B. Werz

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/anie.201205880

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      Multiple displacement of oxygen: Electron-rich oligopyrroles and pyrrolo[3,2-e]indoles are generated by a domino process induced by donor–acceptor-substituted cyclopropanes. Up to seven molecules of water are eliminated, thus allowing the introduction of nitrogen and aromaticity.

    36. Organoaluminum Reagents

      Direct Pd-Catalyzed Cross-Coupling of Functionalized Organoaluminum Reagents (pages 11157–11161)

      Klaus Groll, Tobias D. Blümke, Andreas Unsinn, Diana Haas and Prof. Dr. Paul Knochel

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201205987

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      A handsome couple: Through the use of the simple Pd catalyst [Pd(tmpp)2Cl2] (tmpp=tris(2,4,6-trimethoxyphenyl)phosphine) and THF/DMF as solvent, various aryl-, heteroaryl-, benzyl- and alkylaluminum reagents can be readily cross-coupled with aryl or heteroaryl iodides, bromides, and nonaflates, and in special cases even with chlorides and triflates. This cross-coupling tolerates free NH2 groups, aldehydes, ketones, esters, and nitro functions.

    37. Modified RNA nucleosides

      You have full text access to this OnlineOpen article
      Isotope-Based Analysis of Modified tRNA Nucleosides Correlates Modification Density with Translational Efficiency (pages 11162–11165)

      M. Chem. Caterina Brandmayr, Dipl.-Chem. Mirko Wagner, Dr. Tobias Brückl, Dr. Daniel Globisch, Dr. David Pearson, M. Sc. Andrea Christa Kneuttinger, Dipl.-Chem. Veronika Reiter, Dr. Antje Hienzsch, Dipl.-Biol. Susanne Koch, M. Sc. Ines Thoma, Dipl.-Chem. Peter Thumbs, Dr. Stylianos Michalakis, Dr. Markus Müller, Prof. Dr. Martin Biel and Prof. Dr. Thomas Carell

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201203769

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      Useful diversity: Quantification of modified tRNA nucleobases in different murine and porcine tissues reveals a tissue-specific overall modification content. The modification content correlates with rates of protein synthesis in vitro, suggesting a direct link between tRNA modification levels and tissue-specific translational efficiency.

    38. RNA Repair

      An RNA–Deaminase Conjugate Selectively Repairs Point Mutations (pages 11166–11169)

      Dr. Thorsten Stafforst and Marius F. Schneider

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/anie.201206489

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      Checking for mistakes: By conjugating a catalytic domain with a guide RNA, deamination activity can be harnessed to repair a specific codon on mRNA. This method can be used for the highly selective repair of point mutations in mRNA by site-selective editing.

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