Angewandte Chemie International Edition

Cover image for Vol. 52 Issue 46

November 11, 2013

Volume 52, Issue 46

Pages 11943–12191

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. You have free access to this content
      Cover Picture: Lipid-Bilayer-Spanning DNA Nanopores with a Bifunctional Porphyrin Anchor (Angew. Chem. Int. Ed. 46/2013) (page 11943)

      Dr. Jonathan R. Burns, Kerstin Göpfrich, James W. Wood, Vivek V. Thacker, Dr. Eugen Stulz, Dr. Ulrich F. Keyser and Dr. Stefan Howorka

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/anie.201308381

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      Membrane nanopores self-assembled from DNA are the most recent type of synthetic channels. Inserting negatively charged DNA origami structures into a hydrophobic membrane can be achieved with just two porphyrin-based lipid anchors, as shown by S. Howorka and co-workers in their Communication on page 12069 ff. Minimal chemical intervention paves the way to new DNA pores for label-free biosensing and research into single molecules and biomimetic nanoarchitectures. (Simplified illustration of origami pores by Silvio Bianco, Hugh Martin, Jonathan R. Burns.)

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      Inside Cover: Fluorescent-Ligand-Mediated Screening of G-Quadruplex Structures Using a DNA Microarray (Angew. Chem. Int. Ed. 46/2013) (page 11944)

      Keisuke Iida, Takahiro Nakamura, Dr. Wataru Yoshida, Dr. Masayuki Tera, Dr. Kazuhiko Nakabayashi, Dr. Kenichiro Hata, Prof. Dr. Kazunori Ikebukuro and Prof. Dr. Kazuo Nagasawa

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201308949

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      G-Quadruplexes in the genomic DNA have become new key structures for understanding life phenomena; however, only a limited number of G-quadruplexes are known. In their Communication on page 12052 ff., K. Nagasawa, K. Ikebukuro, and co-workers describe a high-throughput screening method for the discovery of novel G-quadruplexes by using fluorescent probe molecules and a DNA microarray.

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      Inside Back Cover: Development of an Activity-Based Probe and In Silico Design Reveal Highly Selective Inhibitors for Diacylglycerol Lipase-α in Brain (Angew. Chem. Int. Ed. 46/2013) (page 12193)

      M. Sc. Marc P. Baggelaar, M. Sc. Freek J. Janssen, Annelot C. M. van Esbroeck, Ing. Hans den Dulk, M. Sc. Marco Allarà, M. Sc. Sascha Hoogendoorn, Dr. Ross McGuire, Dr. Bogdan I. Florea, Ing. Nico Meeuwenoord, Ing. Hans van den Elst, Prof. Dr. Gijsbert A. van der Marel, Prof. Dr. Jaap Brouwer, Prof. Dr. Vincenzo Di Marzo, Prof. Dr. Herman S. Overkleeft and Dr. Mario van der Stelt

      Version of Record online: 7 NOV 2013 | DOI: 10.1002/anie.201308975

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      In silico screening in combination with activity-based protein profiling as a strategy for discovering selective hits in complex brain proteome is presented by M. van der Stelt et al. in their Communication on page 12081 ff. A common starting point was used for the generation of both the pharmacophore model and the activity-based probe. This resulted in the identification of a novel class of diacylglycerol lipase-α inhibitors with high selectivity in the brain proteome.

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      Back Cover: Lyotropic Lamellar Phase Formed from Monolayered θ-Shaped Carborane-Cage Amphiphiles (Angew. Chem. Int. Ed. 46/2013) (page 12194)

      Damien Brusselle, Dr. Pierre Bauduin, Dr. Luc Girard, Adnana Zaulet, Prof. Clara Viñas, Prof. Francesc Teixidor, Isabelle Ly and Dr. Olivier Diat

      Version of Record online: 5 NOV 2013 | DOI: 10.1002/anie.201308830

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      Unlike the self-assembly of other surfactants, that of metallacarborane clusters, described as θ-shaped amphiphiles, does not originate from the hydrophobic effect. In their Communication on page 12114 ff., P. Bauduin et al. show that specific interactions involving many intermolecular dihydrogen bonds, such as C[BOND]Hδ+⋅⋅⋅δH[BOND]B, are the key to understanding the aggregation process in water. This peculiarity results in the formation of lyotropic lamellar phases with a unique monomolecular structure.

  2. Editorial

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
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      Editorial: Scientists (of the World) Behave! (pages 11946–11947)

      Prof. Katharina Al-Shamery

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/anie.201306690

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      “… Scientists need to be able to trust and rely on each other as a matter of care and responsibility towards our society.My further personal plea is that we have to give our students an awareness of good scientific practice and help them to find self-confidence …” Read more in the Editorial by Katharina Al-Shamery.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. You have free access to this content
      Corrigendum: Se-Phenyl Prop-2-eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions (page 11963)

      Prof. Michael E. Jung, Felix Perez, Dr. Collin F. Regan, Dr. Sung Wook Yi and Dr. Quentin Perron

      Version of Record online: 8 NOV 2013 | DOI: 10.1002/anie.201308557

      This article corrects:

      Se-Phenyl Prop-2-eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions1

      Vol. 52, Issue 7, 2060–2062, Version of Record online: 11 JAN 2013

  5. News

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Chi-Ming Che (pages 11970–11971)

      Version of Record online: 31 MAY 2013 | DOI: 10.1002/anie.201303445

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      “My favorite place on earth is Hong Kong. I lose track of time when I chat with my friends and students. …” This and more about Chi-Ming Che can be found on page 11970–11971.

  7. News

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Symmetry Relationships between Crystal Structures. Applications of Crystallographic Group Theory in Crystal Chemistry. By Ulrich Müller. (page 11973)

      Ulli Englert

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201306902

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      Oxford University Press, Oxford, 2013. 352 pp., hardcover, £ 49.95.—ISBN 978-0199669950

  9. Highlight

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

      Metal/N-Heterocyclic Carbene Complexes: Opportunities for the Development of Anticancer Metallodrugs (pages 11976–11978)

      Dr. Federico Cisnetti and Dr. Arnaud Gautier

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/anie.201306682

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      Death trap: The rational design of metal/N-heterocyclic carbene complexes allows mitochondria to be targeted. Activation of several apoptotic processes (which do not include direct DNA damage) induces cell death and significant tumor suppression.

      Corrected by:

      Corrigendum: Corrigendum: Metal/N-Heterocyclic Carbene Complexes: Opportunities for the Development of Anticancer Metallodrugs

      Vol. 53, Issue 9, 2269, Version of Record online: 20 FEB 2014

  10. Essay

    1. Top of page
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    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
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    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Sustainable Chemistry

      Shale Gas Revolution: An Opportunity for the Production of Biobased Chemicals? (pages 11980–11987)

      Dr. Pieter C. A. Bruijnincx and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 18 OCT 2013 | DOI: 10.1002/anie.201305058

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      Saying a (bio)mass for the future: The shale gas revolution will strongly impact the availability of a number of key building blocks of the chemical industry, in particular butadiene and aromatics. These developments provide an opportunity for the on-purpose production of these bulk chemicals from renewable resources, such as biomass. Current efforts and developments from industry and academia in this direction are highlighted.

  11. Minireview

    1. Top of page
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    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Synthetic Erythropoiesis Protein

      Bringing the Science of Proteins into the Realm of Organic Chemistry: Total Chemical Synthesis of SEP (Synthetic Erythropoiesis Protein) (pages 11988–11996)

      Prof. Dr. Stephen B. H. Kent

      Version of Record online: 11 OCT 2013 | DOI: 10.1002/anie.201304116

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      The glycoprotein mimetic SEP (synthetic erythropoiesis protein) was prepared in homogenous form by total chemical synthesis. SEP had full biological activities and improved pharmacokinetic properties compared with first-generation recombinant human EPO. This work demonstrated that synthetic chemistry can be employed to systematically improve the properties of a protein biotherapeutic by the use of designed chemical moieties not found in nature.

  12. Review

    1. Top of page
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    5. Corrigendum
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    7. Author Profile
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    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Job Plots

      Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry (pages 11998–12013)

      Dr. Joseph S. Renny, Laura L. Tomasevich, Evan H. Tallmadge and Prof. David B. Collum

      Version of Record online: 24 OCT 2013 | DOI: 10.1002/anie.201304157

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      Lending a hand: Job plots, also known as the method of continuous variations (MCV), are used extensively throughout chemistry and biochemistry to study molecular associations. This review serves as a tutorial on using Job plots and a survey of the surprisingly few applications in organometallic chemistry.

  13. Communications

    1. Top of page
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    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. News
    9. Book Review
    10. Highlight
    11. Essay
    12. Minireview
    13. Review
    14. Communications
    1. Single-Molecule Magnets

      A {CrIII2DyIII2} Single-Molecule Magnet: Enhancing the Blocking Temperature through 3d Magnetic Exchange (pages 12014–12019)

      Dr. Stuart K. Langley, Daniel P. Wielechowski, Veacheslav Vieru, Nicholas F. Chilton, Dr. Boujemaa Moubaraki, Prof. Brendan F. Abrahams, Prof. Liviu F. Chibotaru and Prof. Keith S. Murray

      Version of Record online: 17 SEP 2013 | DOI: 10.1002/anie.201306329

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      Butterfly magnet: The replacement of diamagnetic CoIII for CrIII in a 3d-4f butterfly complex results in vastly improved single-molecule magnet properties. Longer relaxation times are found, with magnetic hysteresis observed. This is due to exchange interactions between the DyIII and CrIII ions, resulting in a multilevel exchange barrier with significantly reduced quantum tunneling of the magnetization.

    2. Cyclic Peptides

      Vicinal Disulfide Constrained Cyclic Peptidomimetics: a Turn Mimetic Scaffold Targeting the Norepinephrine Transporter (pages 12020–12023)

      Dr. Andreas Brust, Dr. Ching-I. A. Wang, Prof. Norelle L. Daly, Joe Kennerly, Mahsa Sadeghi, Prof. Macdonald J. Christie, Prof. Richard J. Lewis, Dr. Mehdi Mobli and Prof. Paul F. Alewood

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201304660

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      Loopy peptides: Peptide turn mimetics of a clinically relevant norepinephrine reuptake inhibitor were developed employing a high-throughput synthesis approach to generate peptide thioesters, with subsequent cyclization through native chemical ligation. The vicinal disulfide constrained cyclic peptidomimetics (see scheme) show high structural and functional similarity to the parent peptide, though with superior metabolic stability.

    3. Surface Chemistry

      Light-Activated Electroactive Molecule-Based Memory Microcells Confined on a Silicon Surface (pages 12024–12027)

      Prof. Dr. Bruno Fabre, Dr. Yan Li, Dr. Luc Scheres, Dr. Sidharam P. Pujari and Prof. Dr. Han Zuilhof

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201304688

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      Ultrahigh-capacity molecular AND gates provide the potential for the next-generation dynamic random access memory. The ferrocene-terminated monolayer on oxide-free silicon system allows a highly stable and independent switching with both light and potential, yielding precisely such an AND gate (see picture).

    4. Pre-MicroRNA Labeling

      Chemical Synthesis of Mono- and Bis-Labeled Pre-MicroRNAs (pages 12028–12032)

      Dr. Ugo Pradère, Dr. Andreas Brunschweiger, Dr. Luca F. R. Gebert, Matije Lucic, Martina Roos and Prof. Dr. Jonathan Hall

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201304986

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      A chemical method for the post-synthetic labeling of pre-miRNAs on solid support using easily accessible reagents was developed. The procedure was employed to generate a library of 31 pre-microRNAs carrying labels commonly used in chemical biology, including Cy3, trioxalen, biotin, and BHQ-1.

    5. Drug Delivery

      Cucurbit[7]uril Containers for Targeted Delivery of Oxaliplatin to Cancer Cells (pages 12033–12037)

      Dr. Liping Cao, Gaya Hettiarachchi, Prof. Dr. Volker Briken and Prof. Dr. Lyle Isaacs

      Version of Record online: 13 SEP 2013 | DOI: 10.1002/anie.201305061

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      Stay on target: The cucurbit[7]uril derivative 1, which bears a covalently attached biotin targeting ligand allows for the efficient delivery of oxaliplatin as its 1⋅oxaliplatin complex to cancer cells resulting in enhanced cytotoxicity relative to oxaliplatin alone.

    6. Functional Aerogels

      Nanocellulose Aerogels Functionalized by Rapid Layer-by-Layer Assembly for High Charge Storage and Beyond (pages 12038–12042)

      Dr. Mahiar Hamedi, Erdem Karabulut, Andrew Marais, Dr. Anna Herland, Dr. Gustav Nyström and Prof. Lars Wågberg

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201305137

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      Step by step: A robust and rapid method for the layer-by-layer assembly of polymers and nanoparticles on strong and elastic aerogels has been developed. Thin films of biomolecules, conducting polymers, and carbon nanotubes were assembled, which resulted in aerogels with a number of functions, including a high charge-storage capacity.

    7. NMR Porosity Screening

      Ex Situ NMR Relaxometry of Metal–Organic Frameworks for Rapid Surface-Area Screening (pages 12043–12046)

      Joseph J. Chen, Dr. Xueqian Kong, Dr. Kenji Sumida, Mary Anne Manumpil, Dr. Jeffrey R. Long and Dr. Jeffrey A. Reimer

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201305247

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      Taking a relaxed approach: The NMR relaxation behavior of imbibed solvent has been used to estimate the surface area of a variety of microporous metal–organic frameworks and zeolites. This NMR technique is amenable to automation and can expedite the characterization of microporous materials by identifying any nonporous or low-surface-area structures.

    8. Hybrid Photovoltaics

      You have full text access to this OnlineOpen article
      Low-Temperature Solution Processing of Mesoporous Metal–Sulfide Semiconductors as Light-Harvesting Photoanodes (pages 12047–12051)

      Flannan T. F. O'Mahony, Dr. Ute B. Cappel, Dr. Nurlan Tokmoldin, Dr. Thierry Lutz, Rebecka Lindblad, Prof. Håkan Rensmo and Dr. Saif A. Haque

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201305276

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      Structured absorbers: Mesoporous films of highly crystalline Sb2S3 are prepared from a doctor-bladed precursor paste that is thermally annealed. This facile and versatile processing route allows for control of the pore size through variation of the annealing temperature. The resulting high surface area allows for efficient charge transfer to a polymeric hole acceptor; hence, such films could form the basis of a novel hybrid organic–inorganic photovoltaic device.

    9. G-Quadruplexes

      Fluorescent-Ligand-Mediated Screening of G-Quadruplex Structures Using a DNA Microarray (pages 12052–12055)

      Keisuke Iida, Takahiro Nakamura, Dr. Wataru Yoshida, Dr. Masayuki Tera, Dr. Kazuhiko Nakabayashi, Dr. Kenichiro Hata, Prof. Dr. Kazunori Ikebukuro and Prof. Dr. Kazuo Nagasawa

      Version of Record online: 21 OCT 2013 | DOI: 10.1002/anie.201305366

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      Light up, G-quadruplexes! A fast high-throughput screening for the discovery of novel G-quadruplex-forming oligonucleotides (GFOs) has been developed. By using a fluorescent G-quadruplex ligand and a DNA microarray, 1998 novel GFO candidates in CpG islands were disclosed. (CpG=cytosine-phosphate-guanosine).

    10. Click Chemistry

      Discovery of Chemoselective and Biocompatible Reactions Using a High-Throughput Immunoassay Screening (pages 12056–12060)

      Sergii Kolodych, Dr. Evelia Rasolofonjatovo, Dr. Manon Chaumontet, Marie-Claire Nevers, Dr. Christophe Créminon and Dr. Frédéric Taran

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/anie.201305645

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      An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents.

    11. Nitrite Reduction

      Generation of HNO and HSNO from Nitrite by Heme-Iron-Catalyzed Metabolism with H2S (pages 12061–12064)

      Jan Lj. Miljkovic, Isabell Kenkel, Prof. Dr. Ivana Ivanović-Burmazović and Dr. Milos R. Filipovic

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201305669

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      Taking NO for an answer: A mechanistic study has shown that a heme-iron-catalyzed pathway (see scheme) could lead to the nitrite-/sulfide-induced formation of NO and HNO within mitochondria, and suggests that H2S may be the elusive thiol responsible for the reduction of nitrite. This study offers an answer to the decades-old question on the role of nitrite in the treatment of H2S poisoning.

    12. Nonconventional Hydrogen Bonding

      Backbone FC[BOND]H⋅⋅⋅O Hydrogen Bonds in 2′F-Substituted Nucleic Acids (pages 12065–12068)

      Dr. Nerea Martin-Pintado, Dr. Glen F. Deleavey, Dr. Guillem Portella, Dr. Ramón Campos-Olivas, Prof. Modesto Orozco, Prof. Masad J. Damha and Prof. Carlos González

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201305710

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      Polarizing C[BOND]H⋅⋅⋅O hydrogen bonds: The structure of oligonucleotides containing alternating and contiguous tracts of 2′F-RNA and 2′F-ANA nucleotides reveals that nonconventional FC[BOND]H⋅⋅⋅O hydrogen bonds have a strong stabilizing effect on 2′-fluorinated duplexes.

    13. DNA Nanotechnology

      You have full text access to this OnlineOpen article
      Lipid-Bilayer-Spanning DNA Nanopores with a Bifunctional Porphyrin Anchor (pages 12069–12072)

      Dr. Jonathan R. Burns, Kerstin Göpfrich, James W. Wood, Vivek V. Thacker, Dr. Eugen Stulz, Dr. Ulrich F. Keyser and Dr. Stefan Howorka

      Version of Record online: 6 SEP 2013 | DOI: 10.1002/anie.201305765

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      Holding tight: An artificial membrane nanopore assembled from DNA oligonucleotides carries porphyrin tags (red), which anchor the nanostructure into the lipid bilayer. The porphyrin moieties also act as fluorescent dyes to aid the microscopic visualization of the DNA nanopore.

    14. Synthetic Methods

      Selective C[BOND]F Bond Activation: Substitution of Unactivated Alkyl Fluorides using YbI3 (pages 12073–12076)

      Dr. Annika M. Träff, Mario Janjetovic, Linda Ta and Prof. Dr. Göran Hilmersson

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201306104

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      F makes the break: The carbon–fluorine single bond is quite strong, thus making aliphatic C[BOND]F bond scission unusually challenging. A new methodology utilizing YbI3 leads to the conversion of a C[BOND]F bond into a C[BOND]I bond, and is compatible with various functional groups. The reaction is exceptionally selective towards alkyl fluorides and proceeds under mild conditions.

    15. Biological Signaling

      Dynamic Display of Bioactivity through Host–Guest Chemistry (pages 12077–12080)

      Dr. Job Boekhoven, Dr. Charles M. Rubert Pérez, Dr. Shantanu Sur, Dr. Amanda Worthy and Prof. Samuel I. Stupp

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201306278

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      A molecular host, β-cyclodextrin (CD), covalently attached to an alginate matrix enables dynamic control of cue display through exchange of guest molecules. Addition of soluble RGDS-containing guest molecules to culture medium induced focal adhesion formation and spreading of 3T3 fibroblasts on the otherwise non-spreading alginate surface. The spreading could be reversed by adding competitive guest molecules bearing the mutated non-bioactive sequence RGES.

    16. Enzyme Inhibition

      Development of an Activity-Based Probe and In Silico Design Reveal Highly Selective Inhibitors for Diacylglycerol Lipase-α in Brain (pages 12081–12085)

      M. Sc. Marc P. Baggelaar, M. Sc. Freek J. Janssen, Annelot C. M. van Esbroeck, Ing. Hans den Dulk, M. Sc. Marco Allarà, M. Sc. Sascha Hoogendoorn, Dr. Ross McGuire, Dr. Bogdan I. Florea, Ing. Nico Meeuwenoord, Ing. Hans van den Elst, Prof. Dr. Gijsbert A. van der Marel, Prof. Dr. Jaap Brouwer, Prof. Dr. Vincenzo Di Marzo, Prof. Dr. Herman S. Overkleeft and Dr. Mario van der Stelt

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/anie.201306295

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      A model method: A strategy that combines a knowledge-based in silico design approach and the development of novel activity-based probes (ABPs) for the detection of endogenous diacylglycerol lipase-α (DAGL-α) is presented. This approach resulted in the rapid identification of new DAGL-α inhibitors with high selectivity in the brain proteome. ABPP=activity-based protein profiling.

    17. Strained Aromatic Compounds

      Highly Strained Phenylene Bicyclophanes (pages 12086–12090)

      Gabi Ohlendorf, Dr. Christian W. Mahler, Dr. Stefan-S. Jester, Dr. Gregor Schnakenburg, Prof. Dr. Stefan Grimme and Prof. Dr. Sigurd Höger

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201306299

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      Bending the rules: Strained bicyclophanes (see structure) with highly bent biphenylene units and a central aromatic moiety (yellow) forced into a perpendicular position were accessible in high yields by cyclization of the appropriate bromides by Yamamoto condensation. They were able to bind to graphite cutouts in solution and were adsorbed at the liquid/highly oriented pyrolytic graphite (HOPG) interface to form extended 2D structures.

    18. π-Electron Systems

      Diarylated Bi(thieno[2,3-c]thiophene)s: A Ring-Fusing Strategy for Controlling the Molecular Alignment of Oligoarenes (pages 12091–12095)

      Dr. Aiko Fukazawa, Daisuke Kishi, Yuki Tanaka, Prof. Dr. Shu Seki and Prof. Dr. Shigehiro Yamaguchi

      Version of Record online: 20 SEP 2013 | DOI: 10.1002/anie.201306323

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      Red means go: The dense π stacking of thiophene-fused bithiophene derivatives in the crystalline state led to significantly red-shifted absorption and fluorescence bands (see the photograph of one compound in solution and in the solid state under UV irradiation). The π-stacking structure could be altered by changing the orientation of one of the fused thiophene rings.

    19. Supramolecular Chemistry

      Silver-Mediated Formation of a Cofacial Porphyrin Dimer with the Ability to Intercalate Aromatic Molecules (pages 12096–12100)

      Dr. Takashi Nakamura, Dr. Hitoshi Ube and Prof. Dr. Mitsuhiko Shionoya

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201306510

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      Guests welcome: Complex formation between AgI ions and a Zn-porphyrin ligand (L) possessing four 2,2′-bipyridyl groups produced a dimeric complex [Ag4L2]4+, wherein the interplane distance between the Zn-porphyrin groups was ideal for intercalation of aromatic molecules through π–π interactions. The cofacial dimer [Ag4L2]4+ serves as an excellent receptor for π-electron-deficient guests.

    20. Cancer Immunotherapy

      Recruiting Cytotoxic T Cells to Folate-Receptor-Positive Cancer Cells (pages 12101–12104)

      Dr. Sumith A. Kularatne, Vishal Deshmukh, Dr. Marco Gymnopoulos, Dr. Sandra L. Biroc, Dr. Jinming Xia, Shailaja Srinagesh, Dr. Ying Sun, Dr. Ning Zou, Dr. Mark Shimazu, Dr. Jason Pinkstaff, Dr. Semsi Ensari, Nick Knudsen, Anthony Manibusan, Dr. Jun Y. Axup, Dr. Chan Hyuk Kim, Prof. Vaughn V. Smider, Dr. Tsotne Javahishvili and Prof.Dr. Peter G. Schultz

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201306866

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      A Fab-ulous killer: An anti-CD3 Fab-folate conjugate that targets cytotoxic T cells to folate-receptor-positive (FR+) tumors results in efficient killing of tumor cells by activated T cells. This chemical approach to the synthesis of bispecific antibodies using unnatural amino acids with orthogonal chemical reactivity affords homogenous conjugates with precise control over the relative geometry of the antibody binding sites in excellent yields.

    21. Multifunctional 2D Nanohybrids

      Polyaniline-Coupled Multifunctional 2D Metal Oxide/Hydroxide Graphene Nanohybrids (pages 12105–12109)

      Shuang Li, Dr. Dongqing Wu, Chong Cheng, Jinzuan Wang, Dr. Fan Zhang, Dr. Yuezeng Su and Prof. Xinliang Feng

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201306871

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      Particles and sheets: Polyaniline is used as a linker to couple metal oxides and hydroxides to graphene sheets. Hydrothermal treatment converts these coupled hybrids into nitrogen-doped 2D carbon nanosheets integrated with size-controlled metal nanoparticles. This structure gives these 2D nanohybrids promising electrochemical behavior in supercapacitors and oxygen-reduction reactions.

    22. Reaction Mechanisms

      Direct Evidence for the Attack of a Free N-Heterocyclic Carbene at a Carbonyl Ligand: A Zwitterionic Osmium Carbonyl Cluster (pages 12110–12113)

      Yu Liu, Dr. Rakesh Ganguly, Prof. Han Vinh Huynh and Prof. Weng Kee Leong

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201307102

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      A key suspect arrested: The initial site of attack of a free N-heterocyclic carbene (NHC) on the triosmium carbonyl cluster [Os3(CO)12] was found to be a carbonyl ligand. The stable zwitterionic species thus formed (blue background in the scheme) was characterized crystallographically. CO substitution proceeds from this intermediate by the loss of a CO group and migratory deinsertion.

    23. Boron Cluster Lamellar Phases

      Lyotropic Lamellar Phase Formed from Monolayered θ-Shaped Carborane-Cage Amphiphiles (pages 12114–12118)

      Damien Brusselle, Dr. Pierre Bauduin, Dr. Luc Girard, Adnana Zaulet, Prof. Clara Viñas, Prof. Francesc Teixidor, Isabelle Ly and Dr. Olivier Diat

      Version of Record online: 4 NOV 2013 | DOI: 10.1002/anie.201307357

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      B in phase: Lyotropic lamellar phases can not only be formed from alkyl-chain-based surfactants with a well-defined amphiphilic structure, now they can be obtained from metallacarborane clusters, described as θ-shaped amphiphiles. The lamellae formed are unique as they have a monomolecular thickness.

    24. CO2 Utilization

      Carbon Dioxide as a C1 Building Block for the Formation of Carboxylic Acids by Formal Catalytic Hydrocarboxylation (pages 12119–12123)

      Dr. Thomas G. Ostapowicz, Marc Schmitz, Monika Krystof, Prof. Dr. Jürgen Klankermayer and Prof. Dr. Walter Leitner

      Version of Record online: 3 SEP 2013 | DOI: 10.1002/anie.201304529

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      A happy marriage of two processes: An effective catalytic system was identified for the direct synthesis of carboxylic acids from non-activated olefins or alcohols, CO2, and H2. Detailed analysis together with labeling studies indicated that the overall hydrocarboxylation of simple olefins results from a combination of the reverse water–gas shift (rWGS) reaction and a hydroxycarbonylation step, each promoted by a rhodium catalyst (see scheme).

    25. Analytical Methods

      Solid-Phase Microextraction: A Complementary In Vivo Sampling Method to Microdialysis (pages 12124–12126)

      Erasmus Cudjoe, Dr. Barbara Bojko, Dr. Inés de Lannoy, Victor Saldivia and Prof. Janusz Pawliszyn

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201304538

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      Two's compliment: Solid-phase microextraction (SPME) was validated against microdialysis (MD) in simultaneous targeted analysis of selected neurotransmitters in brain tissue. Complementary data was obtained from global brain profiling with both methods. MD extracts primarily polar species, and SPME detects semi hydrophobic and hydrophobic compounds, including lipids related to neurodegenerative diseases. RT=retention time.

    26. Supramolecular Chemistry

      Discrete Double-to-Quadruple Aromatic Stacks: Stepwise Integration of Face-to-Face Geometries in Cocrystals Based on Indolocarbazole (pages 12127–12130)

      Jelena Stojaković, Avery M. Whitis and Prof. Dr. Leonard R. MacGillivray

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201304615

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      One, two, three, four: An indolocarbazole organizes double, triple, and quadruple stacks of aromatic molecules within multicomponent solids. The aromatic units are sequentially integrated into discrete assemblies and undergo [2+2] photodimerization.

    27. Carbohydrates

      Chiral Brønsted Acid Mediated Glycosylation with Recognition of Alcohol Chirality (pages 12131–12134)

      Tomoya Kimura, Maiko Sekine, Dr. Daisuke Takahashi and Prof. Dr. Kazunobu Toshima

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201304830

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      Sugar sugar: In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β-stereo- and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.

    28. Polyamorphism

      Low-Density Macroporous Foams Obtained from a Molecular Sieve by Temperature-Induced Amorphization (pages 12135–12138)

      Dr. Stanislav Ferdov

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201305335

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      Featherweight foams: Uncommon polyamorphism in silicate molecular sieves is described. This finding is used for the synthesis of hierarchical macroporous foams with controllable density.

    29. Lithium Ion Batteries

      Experimental Confirmation of Low Surface Energy in LiCoO2 and Implications for Lithium Battery Electrodes (pages 12139–12142)

      Pardha S. Maram, Gustavo C. C. Costa and Alexandra Navrotsky

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201305375

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      Water adsorption on the surface of LiCoO2 nanoparticles was investigated. As the water coverage increases the adsorption enthalpy decreases reaching the enthalpy of water condensation (−44 kJ mol−1). The experimentally observed average surface energy corresponding to all facets agree well with those reported from DFT calculations. The observed low surface energy is attributed to the surface Co3+ spin transition in nanophase LiCoO2.

    30. Organocatalysis

      Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes (pages 12143–12147)

      Han Yong Bae, Jae Hun Sim, Ji-Woong Lee, Prof. Dr. Benjamin List and Prof. Dr. Choong Eui Song

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201306297

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      Copycat: A highly enantioselective biomimetic aldol reaction of malonic acid half thioesters with a variety of aldehydes affords optically active β-hydroxy thioesters by employing the cinchona-derived sulfonamide organocatalyst 1. The synthetic utility of this protocol was demonstrated by performing formal syntheses of the antidepressants (R)-fluoxetine, (R)-tomoxetine, (−)-paroxetine, and (R)-duloxetine.

    31. Polymerization

      Bioinspired Iron-Based Catalyst for Atom Transfer Radical Polymerization (pages 12148–12151)

      Antonina Simakova, Matthew Mackenzie, Saadyah E. Averick, Sangwoo Park and Krzysztof Matyjaszewski

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201306337

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      Naturally occurring hemin, an iron-containing porphyrin, and its synthetic derivatives were used as atom transfer radical polymerization (ATRP; see picture) catalysts. The effects of the halide salt concentration, attachment of poly(ethylene glycol) moieties, and hydrogenation of the hemin vinyl groups on the catalyst performance were studied.

    32. C[BOND]H Activation

      Palladium-Catalyzed Direct Functionalization of 2-Aminobutanoic Acid Derivatives: Application of a Convenient and Versatile Auxiliary (pages 12152–12155)

      Mengyang Fan and Prof. Dr. Dawei Ma

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201306583

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      New group on the block: 2-Methoxyiminoacetyl is a readily available auxiliary for promoting palladium-catalyzed γ arylation of C(sp3)[BOND]H bonds. This auxiliary can be easily removed by either treatment with 1 n KOH at room temperature, or converted into a glycine moiety for peptide synthesis.

    33. Homogeneous Catalysis

      Selective Methylation of Amines with Carbon Dioxide and H2 (pages 12156–12160)

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

      Version of Record online: 25 SEP 2013 | DOI: 10.1002/anie.201306850

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      Put a label on it: Carbon dioxide with H2 is shown to be an efficient and selective methylation reagent for aromatic and aliphatic amines (see scheme; acac=acetylacetonate, triphos = 1,1,1-tris(diphenylphosphanylmethyl)ethane). A variety of functionalized amines including 13C-labelled drugs were obtained with good yields and functional-group tolerance.

    34. Heterocycles

      Nickel-Catalyzed Cycloaddition of 1,3-Dienes with 3-Azetidinones and 3-Oxetanones (pages 12161–12165)

      Ashish Thakur, Megan E. Facer and Prof. Dr. Janis Louie

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201306869

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      A growth and expansion strategy: A Ni/P(p-tol)3-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones produced eight-membered heterocycles with a variety of substituents (see scheme; Boc=tert-butoxycarbonyl). The synthesis of the reduced azocine and oxocine derivatives involved the challenging steps of C(sp2)[BOND]C(sp3) bond activation and C(sp3)[BOND]C(sp3) reductive elimination.

    35. Natural Product Synthesis

      Total Synthesis of (+)-Asperolide C by Iridium-Catalyzed Enantioselective Polyene Cyclization (pages 12166–12169)

      Oliver F. Jeker, Alberto G. Kravina and Prof. Dr. Erick M. Carreira

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/anie.201307187

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      Domino rings: A general synthetic entry into labdane-type diterpenoids has been developed based on an iridium-catalyzed enantioselective polyene cyclization cascade. The potential of this process is demonstrated in the first total synthesis of the tetranorlabdane diterpene asperolide C (PMB=p-methoxybenzyl, TMS= trimethylsilyl).

    36. Biomimetic Synthesis

      Biomimetic Total Synthesis of (±)-Merochlorin A (pages 12170–12173)

      Henry P. Pepper and Dr. Jonathan H. George

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201307200

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      Inspired: The proposed biosynthetic pathway toward the potent antibiotic meroterpenoid (±)-merochlorin A inspired its concise total synthesis. The key steps in the synthesis are a one-pot aromatization–alkylation reaction, followed by a biomimetic oxidative dearomatization of a highly functionalized naphthalene derivative, which forms two rings and four contiguous stereocenters in a single step.

    37. Microporous Polymers

      An Anionic Microporous Polymer Network Prepared by the Polymerization of Weakly Coordinating Anions (pages 12174–12178)

      Sabrina Fischer, Dr. Johannes Schmidt, Prof. Dr. Peter Strauch and Prof. Arne Thomas

      Version of Record online: 22 OCT 2013 | DOI: 10.1002/anie.201303045

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      Organic zeolite: A microporous, covalent organic network with high surface area was synthesized by polymerization of [B(C6F4Br)4]. The countercations, located within the pore channels, are highly accessible and can be easily exchanged, comparable to the extra-framework cations in zeolites. In this way a [MnII(bpy)]2+ complex can be synthesized and immobilized in the network.

    38. Main-Group Chemistry

      NHC-Stabilized Silagermenylidene: A Heavier Analogue of Vinylidene (pages 12179–12182)

      Dr. Anukul Jana, Dr. Volker Huch and Prof. Dr. David Scheschkewitz

      Version of Record online: 20 SEP 2013 | DOI: 10.1002/anie.201306780

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      Stable vinylidene analogue: The synthesis of the first representative of a new compound class of low-valent Group 14 elements, namely silagermenylidene A, is achieved by reduction of Tip2SiCl2 and NHC⋅GeCl2 (Tip=2,4,6-iPr3C6H2; NHC=1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene). The potential of A as a synthon is demonstrated by the formal [2+2] cycloaddition with phenylacetylene to afford NHC-stabilized cyclic germylene B.

    39. Natural Product Synthesis

      The Bidirectional Total Synthesis of Sampsonione P and Hyperibone I (pages 12183–12186)

      Dipl.-Chem. Katharina Lindermayr and Prof. Dr. Bernd Plietker

      Version of Record online: 20 SEP 2013 | DOI: 10.1002/anie.201306256

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      Make it simple: The separation of framework-decorating from framework-constructing steps facilitated the selective introduction of one prenyl group next to allyl groups. The selective epoxidation of the more electron-rich prenyl group led to the efficient formation of the tetrahydrofuran moiety in the title compounds. Spectroscopic analysis of hyperibone I and comparison with literature data led to a revision of the original structure.

    40. Helix Mimetics

      You have full text access to this OnlineOpen article
      Highly Functionalized Terpyridines as Competitive Inhibitors of AKAP–PKA Interactions (pages 12187–12191)

      Dr. Gesa Schäfer, Dr. Jelena Milić, Dr. Adeeb Eldahshan, Dr. Frank Götz, Dr. Kerstin Zühlke, Christian Schillinger, Annika Kreuchwig, Dr. Jonathan M. Elkins, Kamal R. Abdul Azeez, Andreas Oder, Dr. Marie C. Moutty, Nanako Masada, Monika Beerbaum, Brigitte Schlegel, Sylvia Niquet, Dr. Peter Schmieder, Dr. Gerd Krause, Dr. Jens Peter von Kries, Prof. Dermot M. F. Cooper, Prof. Dr. Stefan Knapp, Prof. Jörg Rademann, Prof. Dr. Walter Rosenthal and Priv.-Doz. Dr. Enno Klussmann

      Version of Record online: 23 SEP 2013 | DOI: 10.1002/anie.201304686

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      A good fit: Interactions between A-kinase anchoring proteins (AKAPs) and protein kinase A (PKA) play key roles in a plethora of physiologically relevant processes whose dysregulation causes or is associated with diseases such as heart failure. Terpyridines have been developed as α-helix mimetics for the inhibition of such interactions and are the first biologically active, nonpeptidic compounds that block the AKAP binding site of PKA.

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