Angewandte Chemie International Edition

Cover image for Vol. 51 Issue 3

January 16, 2012

Volume 51, Issue 3

Pages 559–822

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: Enantiopure Metal–Organic Framework Thin Films: Oriented SURMOF Growth and Enantioselective Adsorption (Angew. Chem. Int. Ed. 3/2012) (page 559)

      Dr. Bo Liu, Dr. Osama Shekhah, Hasan K. Arslan, Dr. Jinxuan Liu, Prof. Dr. Christof Wöll and Prof. Dr. Roland A. Fischer

      Version of Record online: 12 DEC 2011 | DOI: 10.1002/anie.201108286

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      The integration of metal–organic frameworks (MOFs) into devices, such as sensors, requires that the MOF is bound to a substrate to give a surface-attached metal–organic framework (SURMOF). In their Communication on page 807 ff. R. A. Fischer, C. Wöll, et al. describe the liquid-phase epitaxial growth of a MOF with camphorate as a chiral framework component. The different adsorption kinetics of pairs of enantiomeric molecules were monitored with a quartz crystal microbalance.

  2. Inside Cover

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    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
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    1. Inside Cover: A Touchscreen as a Biomolecule Detection Platform (Angew. Chem. Int. Ed. 3/2012) (page 560)

      Dr. Byoung Yeon Won and Prof. Hyun Gyu Park

      Version of Record online: 15 NOV 2011 | DOI: 10.1002/anie.201107486

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      Touchscreen technology could be used for biomolecule detection. In their Communication on page 748 ff., H. G. Park and B. Y. Won describe a detection platform that utilizes a capacitive touchscreen to measure DNA concentration, which could lead the way to personalized portable biosensors.

  3. Inside Back Cover

    1. Top of page
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    6. Graphical Abstract
    7. News
    8. Author Profile
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
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    1. Inside Back Cover: Characterization of the Reaction Path and Transition States for RNA Transphosphorylation Models from Theory and Experiment (Angew. Chem. Int. Ed. 3/2012) (page 823)

      Dr. Kin-Yiu Wong, Dr. Hong Gu, Dr. Shuming Zhang, Prof. Joseph A. Piccirilli, Prof. Michael E. Harris and Prof. Darrin M. York

      Version of Record online: 8 DEC 2011 | DOI: 10.1002/anie.201108319

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      The elucidation of RNA reaction mechanisms has a wide range of implications, from the origin of life to biotechnology. In their Communication on page 647 ff., K.-Y. Wong, J. A. Piccirilli, M. E. Harris, D. M. York, et al. report a joint theoretical and experimental study on kinetic isotope effects in models of RNA cleavage transesterification. The characteristics of the mechanism and the transition states are distinctly different in the reaction with the native compound relative to two thio-substituted analogues.

  4. Back Cover

    1. Top of page
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    6. Graphical Abstract
    7. News
    8. Author Profile
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Back Cover: Reinforced Multifunctionalized Nanofibrous Scaffolds Using Mussel Adhesive Proteins (Angew. Chem. Int. Ed. 3/2012) (page 824)

      Bum Jin Kim, Prof. Yoo Seong Choi and Prof. Hyung Joon Cha

      Version of Record online: 7 NOV 2011 | DOI: 10.1002/anie.201107545

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      Sticky nanofibrous scaffolds based on mussel adhesive proteins (MAPS) can be functionalized with diverse types of biomolecules. In their Communication on page 675 ff., H. J. Cha and co-workers report that the adhesive and chemical properties of MAPS are conducive to functionalization without surface modification. These nanofibers show promise for tissue engineering applications.

  5. Graphical Abstract

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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  6. News

    1. Top of page
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    9. News
    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  7. Author Profile

    1. Top of page
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    7. News
    8. Author Profile
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
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    15. Communications
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    1. Keiji Maruoka (pages 580–581)

      Version of Record online: 16 DEC 2011 | DOI: 10.1002/anie.201107615

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      “The most important thing I learned from my parents is ‘persistence is power’. My favorite place on earth is Hawaii …” This and more about Keiji Maruoka can be found on page 580.

  8. News

    1. Top of page
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  9. Book Review

    1. Top of page
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    10. Book Review
    11. Highlights
    12. Essay
    13. Minireview
    14. Review
    15. Communications
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    1. Biomimetic Organic Synthesis. Edited by Erwan Poupon and Bastien Nay. (page 583)

      Markus Kalesse

      Version of Record online: 13 DEC 2011 | DOI: 10.1002/anie.201107291

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      Wiley-VCH, Weinheim, 2011. 2 Volumes, 956 pp., hardcover, € 349.00.—ISBN 978-3527325801

  10. Highlights

    1. Top of page
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    7. News
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    12. Essay
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    15. Communications
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    1. Porous Organic Crystals

      Rational Design of Multifunctional Nanopores by Mixing Matching Molecules (pages 584–586)

      Dr. Michael Mastalerz

      Version of Record online: 21 DEC 2011 | DOI: 10.1002/anie.201107828

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      Alloying allowed: The self-assembling motifs of rigid steroid molecules (see scheme, left) into nanoporous crystals allows the combination of functional groups (shown in red and blue) inside the pores of binary, ternary, and quaternary co-crystals, resulting multifunctional porous materials.

    2. Endohedral Fullerene

      A Single Water Molecule Trapped Inside Hydrophobic C60 (pages 587–589)

      Prof. Carlo Thilgen

      Version of Record online: 23 DEC 2011 | DOI: 10.1002/anie.201107379

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      Dry water in a wet dungeon? An isolated H2O molecule has been trapped permanently inside hydrophobic C60 (see picture; green C, white H, red O). The endohedral fullerene H2O@C60 was synthesized by opening, filling, and reclosing the carbon cage. The incarcerated water does not alter the structure of the cage, but it confers an appreciable dipole moment to the new entity with its intrinsically apolar carbon sphere.

  11. Essay

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    13. Minireview
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    15. Communications
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    1. Symbolism of Arrows

      Chemistry: A Panoply of Arrows (pages 590–600)

      Prof. Santiago Alvarez

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201101767

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      Alchemists incorporated arrows in their symbolism (see picture) hundreds of years before modern chemists adopted arrows in chemical equations. The next time you insert an arrow in a chemical text consider why precisely that arrow is needed. What does it really mean? How did we learn to use arrows in chemistry? What do our arrows have in common with those of abstract artists?

  12. Minireview

    1. Top of page
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    1. Heterogeneous Catalysis

      Catalysis Based on Nanocrystals with Well-Defined Facets (pages 602–613)

      Prof. Kebin Zhou and Prof. Yadong Li

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201102619

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      Shape-controlled nanocrystals (NCs) are a new frontier in heterogeneous catalysis. Research into these NCs has shown that the catalytic properties of a material are sensitive not only to the size but also to the shape of the NCs owing to well-defined facets. Shape-controlled NCs may serve to bridge the gap between model surfaces and real catalysts.

  13. Review

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    1. Metal Catalysis

      Similarities and Differences between the “Relativistic” Triad Gold, Platinum, and Mercury in Catalysis (pages 614–635)

      Dr. Antonio Leyva-Pérez and Prof. Avelino Corma

      Version of Record online: 15 NOV 2011 | DOI: 10.1002/anie.201101726

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      Relatively related: Relativistic effects in the valence shell of the chemical elements reach a maximum in the triad Pt–Au–Hg and influence their catalytic activity in organic reactions. The catalytic activity for some representative reactions is examined together with other relevant properties, such as toxicity, price, and availability. For the reactions considered, gold is generally preferred to mercury or platinum catalysts.

  14. Communications

    1. Top of page
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    1. Gold Nanorods

      Quantitative Replacement of Cetyl Trimethylammonium Bromide by Cationic Thiol Ligands on the Surface of Gold Nanorods and Their Extremely Large Uptake by Cancer Cells (pages 636–641)

      Leonid Vigderman, Dr. Pramit Manna and Prof. Eugene R. Zubarev

      Version of Record online: 15 NOV 2011 | DOI: 10.1002/anie.201107304

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      Stable and biocompatible: The chemical composition of synthesized cationic thiolate-monolayer-protected gold nanorods was precisely determined. In vitro cell culture experiments showed no cytotoxicity of these nanorods, and the number of nanorods that were taken up by each cancer cell exceeded two million particles (see picture).

    2. Computational Chemistry

      Conformational Selection versus Induced Fit in Kinases: The Case of PI3K-γ (pages 642–646)

      Dr. Marco D'Abramo, Dr. Obdulia Rabal, Dr. Julen Oyarzabal and Dr. Francesco Luigi Gervasio

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201103264

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      Kinase binding: The mechanism of molecular recognition in the pharmacologically relevant phosphoinositide 3-kinase PI3K-γ has been investigated. The analysis of molecular dynamics simulations, free energy calculations, and docking interactions suggests that a combination of two proposed limiting mechanisms, conformational selection and induced fit, may best explain binding events between the ligand and its target.

    3. Reaction Mechanisms

      Characterization of the Reaction Path and Transition States for RNA Transphosphorylation Models from Theory and Experiment (pages 647–651)

      Dr. Kin-Yiu Wong, Dr. Hong Gu, Dr. Shuming Zhang, Prof. Joseph A. Piccirilli, Prof. Michael E. Harris and Prof. Darrin M. York

      Version of Record online: 11 NOV 2011 | DOI: 10.1002/anie.201104147

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      Model behavior: The primary and secondary kinetic isotope effects for a model compound which represents RNA cleavage transesterification were calculated and compared with experimental measurements. Based on the good agreement between theory and experiments, the energy profile, reaction pathway, and two distinct transition states for the reactions of the model compound and two thio-substituted analogues were characterized (see scheme).

    4. Zeolites

      Detailed Reaction Paths for Zeolite Dealumination and Desilication From Density Functional Calculations (pages 652–655)

      Dr. Sami Malola, Prof. Dr. Stian Svelle, Dr. Francesca Lønstad Bleken and Dr. Ole Swang

      Version of Record online: 6 DEC 2011 | DOI: 10.1002/anie.201104462

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      Birth of a silanol nest: Reaction paths for the extraction of Al and Si from zeolites by reaction with steam were investigated by first-principles DFT calculations. The results show that dealumination is energetically favored over desilication (see picture: O red, Si yellow, Al purple, H white).

    5. Supramolecular Chemistry

      Self-Assembly of Tubular Microstructures from Mixed-Valence Metal Complexes and Their Reversible Transformation by External Stimuli (pages 656–659)

      Dr. Keita Kuroiwa, Masaki Yoshida, Dr. Shigeyuki Masaoka, Prof. Dr. Kenji Kaneko, Prof. Dr. Ken Sakai and Prof. Dr. Nobuo Kimizuka

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201105080

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      Mix and shake: Lipid packaged dinuclear ruthenium(II,III) complexes of class III mixed-valence state produce a reversible hypochromic effect upon external physical stimuli, such as shaking, due to the arrangement of transition dipole moments. The effect is accompanied by tubular-to-ribbon structural changes (see scheme).

    6. Anisotropic Materials

      Chemically Controlled Bending of Compositionally Anisotropic Microcylinders (pages 660–665)

      Dr. Sampa Saha, Davor Copic, Dr. Srijanani Bhaskar, Nicholas Clay, Alessandro Donini, Prof. A. John Hart and Prof. Joerg Lahann

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201105387

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      The bends: Surface modification of multi-compartmental microcylinders by spatio-selective click chemistry and subsequent surface-initiated atom-transfer radical polymerization (ATRP) yield novel amphiphilic microcylinders (see scheme). Depending on the aspect ratio of the microcylinders, they can be bent or coiled.

    7. Hybrid Materials

      ECS-3: A Crystalline Hybrid Organic–Inorganic Aluminosilicate with Open Porosity (pages 666–669)

      Dr. Giuseppe Bellussi, Dr. Erica Montanari, Dr. Eleonora Di Paola, Dr. Roberto Millini, Dr. Angela Carati, Dr. Caterina Rizzo, Dr. Wallace O'Neil Parker Jr., Dr. Mauro Gemmi, Dr. Enrico Mugnaioli, Prof. Ute Kolb and Dr. Stefano Zanardi

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/anie.201105496

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      Automated diffraction tomography was used to collect electron-diffraction data for solving the crystal structure of ECS-3, which is the first example of a crystalline hybrid organic–inorganic aluminosilicate with open porosity, generated by a regular arrangement of phenylene rings interconnecting aluminosilicate layers (see picture; Al turquoise, C gray, O red, Si gold).

    8. Virus Labeling

      Multicolor Labeling of Living-Virus Particles in Live Cells (pages 670–674)

      Peng Zhou, Zhenhua Zheng, Wen Lu, Fuxian Zhang, Zhenfeng Zhang, Prof. Daiwen Pang, Prof. Bin Hu, Prof. Zhike He and Prof. Hanzhong Wang

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201105701

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      Dual-color virus particles were obtained by labeling a glycoprotein (GP64) on the surface of a baculovirus with a green fluorescent protein (GFP) and labeling the nucleic acid (dsDNA) at the same time with the red fluorescent [Ru(phen)2(dppz)]2+ complex during the viral replication in host cells, by using an in vivo virus self-assembly system. This labeling strategy does not affect the viral infectivity.

    9. Nanostructures

      Reinforced Multifunctionalized Nanofibrous Scaffolds Using Mussel Adhesive Proteins (pages 675–678)

      Bum Jin Kim, Prof. Yoo Seong Choi and Prof. Hyung Joon Cha

      Version of Record online: 19 OCT 2011 | DOI: 10.1002/anie.201105789

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      Sticky stuff: The novel composite nanofibrous scaffolds based on mussel adhesive proteins (MAPs) provide a mechanically durable structural backbone with the function of bioactive peptides. It can also be easily coated with a variety of biomolecules. This biofunctionalized nanofiber platform could be a promising tool for successful tissue-engineering applications.

    10. Amyloid–Peptide Interactions

      Cross-Amyloid Interaction of Aβ and IAPP at Lipid Membranes (pages 679–683)

      Janine Seeliger, Dr. Florian Evers, Christoph Jeworrek, Shobhna Kapoor, Dr. Katrin Weise, Erika Andreetto, Prof. Dr. Metin Tolan, Prof. Dr. Aphrodite Kapurniotu and Prof. Dr. Roland Winter

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201105877

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      Membrane controlled protein assembly: A study of the amyloid interaction of the islet amyloid polypeptide (IAPP), β-amyloid (Aβ), and a mixture of both with an anionic model raft membrane showed the dominant effect of IAPP on the aggregation process and on the hydrogen-bonding pattern of the assemblies present in the mixture (see picture). The analysis of the interaction of Aβ with IAPP-GI—a non-amyloidogenic IAPP mimic—confirmed these findings.

    11. Nanocrystals

      Exceptionally Mild Reactive Stripping of Native Ligands from Nanocrystal Surfaces by Using Meerwein’s Salt (pages 684–689)

      Dr. Evelyn L. Rosen, Dr. Raffaella Buonsanti, Dr. Anna Llordes, Dr. April M. Sawvel, Dr. Delia J. Milliron and Dr. Brett A. Helms

      Version of Record online: 6 DEC 2011 | DOI: 10.1002/anie.201105996

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      Ole-ain't: Trialkyl oxonium salts are universal reagents for native-ligand stripping of carboxylate- (e.g., oleate-), phosphonate-, and amine-passivated nanocrystal thin films and dispersions to give bare or BF4/DMF-passivated surfaces. Meerwein-activated PbSe nanocrystal thin films (see picture) show hole mobilities of about 2–4 cm2 V−1 s−1, which suggest applications of this process in fabricating high-performance devices.

    12. Oxide Ion Conductors

      Remarkably High Oxide Ion Conductivity at Low Temperature in an Ordered Fluorite-Type Superstructure (pages 690–694)

      Xiaojun Kuang, Julia L. Payne, Mark R. Johnson and Ivana Radosavljevic Evans

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201106111

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      Mobile oxide ions: A remarkably high oxide ion conductivity at low temperatures has been found in an ordered δ-Bi2O3 superstructure with the composition Bi1−xVxO1.5+x (x=0.087 and 0.095), and attributed to a combination of highly polarizable sublattice with vacancies, central atoms able to support variable coordination numbers and geometries, as well as rotational flexibility of these coordination polyhedra, co-existing in a pseudo-cubic structure (see picture).

    13. Heterocyclic Chemistry

      λ5-Phospha[7]helicenes: Synthesis, Properties, and Columnar Aggregation with One-Way Chirality (pages 695–699)

      Dr. Koji Nakano, Hiromi Oyama, Yoshio Nishimura, Satoshi Nakasako and Prof. Dr. Kyoko Nozaki

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201106157

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      One-way street: A new family of λ5-phospha[7]helicenes which form one-dimensional columnar stacks in the solid state were synthesized (see scheme). Neighboring stacks have opposite dipole directions and, in the case of the racemic phosphole sulfide based helicene, columns with a given dipole direction consist of one enantiomer, whereas columns with the opposite dipole direction consist of the other enantiomer.

    14. Historical Pigments

      Insights into the Maya Blue Technology: Greenish Pellets from the Ancient City of La Blanca (pages 700–703)

      Prof. Antonio Doménech, Prof. María Teresa Doménech-Carbó, Prof. Cristina Vidal-Lorenzo and Dr. María Luisa Vázquez de Agredos-Pascual

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201106562

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      Historic chemistry: The discovery of a set of greenish pellets from ancient plaster at the La Blanca archaeological site (Guatemala) provides evidence that the Maya people used a material akin to Maya Blue also outside of pottery, murals, sculptures or religious context. Obviously, the Maya people developed different preparative strategies to obtain inorganic–organic hybrid materials.

    15. Lanthanides

      Circularly Polarized Lanthanide Luminescence from Langmuir–Blodgett Films Formed from Optically Active and Amphiphilic EuIII-Based Self-Assembly Complexes (pages 704–708)

      Dr. Jonathan A. Kitchen, Dawn E. Barry, Dr. Laszlo Mercs, Prof. Martin Albrecht, Prof. Robert D. Peacock and Prof. Thorfinnur Gunnlaugsson

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201106863

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      Europium union: The development of chiral amphiphilic self-assembled complexes by europium(III)-directed synthesis is described. These systems form stable Langmuir–Blodgett (LB) films on quartz slides to give stable monolayers that exhibit the first example of time-delayed EuIII-centered emission and circularly polarized luminescence (CPL) from an LB film.

    16. Rotaxanes

      Switchable Intermolecular Communication in a Four-Fold Rotaxane (pages 709–713)

      Dr. Yasuyuki Yamada, Mitsuhiro Okamoto, Dr. Ko Furukawa, Prof. Dr. Tatsuhisa Kato and Prof. Dr. Kentaro Tanaka

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201107104

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      Firmly tied: A four-fold rotaxane was prepared from a porphyrin unit with four alkylammonium chains and a phthalocyanine unit with four peripheral crown ethers. In a dinuclear Cu2+ complex of the four-fold rotaxane, the Cu2+–porphyrin and the Cu2+–phthalocyanine moieties were stacked efficiently on one another to afford spin–spin communication. The spin states were switched reversibly (see picture).

    17. π-Aggregation Control

      Macrocyclic Restriction with Flexible Alkylene Linkers: A Simple Strategy to Control the Solid-State Properties of π-Conjugated Systems (pages 714–717)

      Dr. Shohei Saito, Ken Nakakura and Prof. Dr. Shigehiro Yamaguchi

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/anie.201107172

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      Cyclic and flexible: A simple molecular design for controlling the packing structure and solid-state properties of π-conjugated skeletons is proposed. A subtle difference of the flexible alkylene linker chain lengths of cyclic terthiophene dimers leads to distinct packing structures, and accordingly the solid-state properties, such as the gelation ability and photophysical properties.

    18. Protein Chemical Synthesis

      Synthesis of a Biologically Active Triazole-Containing Analogue of Cystatin A Through Successive Peptidomimetic Alkyne–Azide Ligations (pages 718–722)

      Dr. Ibai E. Valverde, Dr. Fabien Lecaille, Prof. Dr. Gilles Lalmanach, Dr. Vincent Aucagne and Dr. Agnès F. Delmas

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/anie.201107222

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      “Click” protein: CuI-catalyzed cycloaddition of azides and terminal alkynes has been applied to the successive ligations of three unprotected peptide fragments. Peptidomimetic triazole ligation (PTL, see scheme) as a new method for the chemical production of bioactive proteins is applied for the synthesis of a triazole-containing analogue of the 97 amino acid protein cystatin A.

    19. Homogeneous Catalysis

      Cyclization by Catalytic Ruthenium Carbene Insertion into Cmath image[BOND]H Bonds (pages 723–727)

      Fermín Cambeiro, Dr. Susana López, Dr. Jesús A. Varela and Prof. Carlos Saá

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/anie.201107344

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      A novel tandem Ru-catalyzed carbene addition to terminal alkynes/insertion into Cmath image[BOND]H bonds in alkynyl acetals, ethers, and amines has been accomplished under mild reaction conditions (see scheme; TMS=trimethylsilyl). This cascade provides an efficient approach to form complex spiro and fused bicyclic structures by 1,5- and 1,6-hydride shift/cyclization sequences from vinylcarbene Ru intermediates.

    20. Natural Product Synthesis

      A Practical Sulfenylation of 2,5-Diketopiperazines (pages 728–732)

      Prof. Dr. K. C. Nicolaou, Dr. Denis Giguère, Sotirios Totokotsopoulos and Dr. Ya-Ping Sun

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201107623

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      Sulfurs in action: A practical and simple method has been developed for the introduction of sulfur atoms into 2,5-diketopiperazines (I) under mild conditions. The reaction provides more or less complex epidithiodiketopiperazines (II) and bis-methylthiodiketopiperazines (III).

    21. Hybrid Materials

      Mesoscale Integration in Titania/J-Aggregate Hybrid Nanofibers (pages 733–737)

      Dr. Avinash J Patil, Young-Chul Lee, Prof. Ji-Won Yang and Prof. Stephen Mann

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201101383

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      Enveloping porphyrin arrays: Supramolecular arrays of self-assembled tetrakis(4-sulfonatophenyl)porphyrin (TPPS) molecules have been enveloped with an ultrathin layer of titanium dioxide (see picture; scale bar: 25 nm). Integration of the hybrid components at close-to-molecular dimensions preserves optical and chiral properties of J-aggregate superstructures but also enhances photocatalytic activity of TiO2.

    22. Quantum-Dot Synthesis

      Room-Temperature Synthesis of Air-Stable and Size-Tunable Luminescent ZnS-Coated Cd3P2 Nanocrystals with High Quantum Yields (pages 738–741)

      Wilfried-Solo Ojo, Shu Xu, Fabien Delpech, Céline Nayral and Bruno Chaudret

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201104864

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      By designing highly soluble precursors, Cd3P2/ZnS quantum dots (QDs) can be prepared at room temperature. They are shown to be air-stable, size-tunable, and of high optical quality (quantum yields over 50 %). A large photoluminescence range can be covered by simple modulation of the concentration of reactants (see picture) and of the temperature (30 °C, 90 °C).

    23. Solid-Sate Chemistry

      At the Border of Intermetallic Compounds and Transition-Metal Oxides: Crystal Intergrowth of the Zintl Phase Cs4Ge9 and Cs2WO4 or Cs3VO4 as well as Nine-Atom Cluster Relocation in the Solid State (pages 742–747)

      Dr. Viktor Hlukhyy and Prof. Dr. Thomas F. Fässler

      Version of Record online: 9 DEC 2011 | DOI: 10.1002/anie.201105033

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      Crystal engineering: The syntheses, crystal structures, Raman spectra, and thermal properties of Cs10[Ge9]2[WO4] and Cs11[Ge9]2[VO4] containing [Ge9]4− clusters and oxometallate anions [MO4]x (M=W und V) are reported. The picture shows a Raman spectrum obtained from single crystals of the double salt Cs10[Ge9]2[WO4] as well as the temperature-dependent Ge9 cluster relocation in Cs11[Ge9]2[VO4].

    24. Biosensors

      A Touchscreen as a Biomolecule Detection Platform (pages 748–751)

      Dr. Byoung Yeon Won and Prof. Hyun Gyu Park

      Version of Record online: 26 OCT 2011 | DOI: 10.1002/anie.201105986

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      Touchscreen testing: A biomolecular detection platform is presented that utilizes a capacitive touchscreen to measure DNA concentration. The technology is ready for integration into touchscreen-equipped smart phones or smart pads, and should truly accelerate the realization of personalized portable biosensors.

    25. Natural Products

      The Interplay between Mutasynthesis and Semisynthesis: Generation and Evaluation of an Ansamitocin Library (pages 752–757)

      Dr. Simone Eichner, Dr. Tobias Knobloch, Prof. Heinz G. Floss, Jörg Fohrer, Dr. Kirsten Harmrolfs, Jekaterina Hermane, Anne Schulz, Dr. Florenz Sasse, Prof. Dr. Peter Spiteller, Dr. Florian Taft and Prof. Dr. Andreas Kirschning

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201106249

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      Working hand in hand! The synthetic power of three mutant strains that produce ansamitocin and geldanamycin is combined with chemical synthesis, thus leading to 27 new ansamitocin derivatives. Structure–activity studies show that the N of the carbinolamide moiety is not important for cytotoxic activity but the α orientation of the OH group at C9 is key [see structures; chemical synthesis (red), mutasynthesis (blue), biosynthesis (black)].

    26. Ubiquitin Chains

      Chemical Synthesis of Ubiquitinated Peptides with Varying Lengths and Types of Ubiquitin Chains to Explore the Activity of Deubiquitinases (pages 758–763)

      Dr. Sudhir N. Bavikar, Liat Spasser, Mahmood Haj-Yahya, Dr. Subramanian Vedhanarayanan Karthikeyan, Tal Moyal, Dr. K. S. Ajish Kumar and Prof. Ashraf Brik

      Version of Record online: 30 NOV 2011 | DOI: 10.1002/anie.201106430

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      Adding one at a time: A general and effective synthesis yields a peptide attached to mono-, di-, tri-, and tetraubiquitin (Ub) chains (see picture for peptides with Ub and Ub4), linked through lysine residues K48 or K63. These sets of ubiquitinated peptides were prepared in good quantities, and the activity of the enzymes UCH-L3 and IsoT with these different substrates was studied.

    27. Host–Guest Chemistry

      Synthesis and Methane-Binding Properties of Disulfide-Linked Cryptophane-0.0.0 (pages 764–766)

      Marc A. Little, Jessica Donkin, Dr. Julie Fisher, Prof. Malcolm A. Halcrow, Jordan Loder and Dr. Michaele J. Hardie

      Version of Record online: 5 DEC 2011 | DOI: 10.1002/anie.201106512

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      Into the crypt: Direct coupling of cyclotrithiophenolene gives a new class of cryptophane with labile disulfide linkages, which is the smallest cryptophane yet reported. The new cryptophane (see structure, S yellow, C gray, H light gray) is shown to bind methane or nitrogen in solution.

    28. Organocatalysis

      Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines (pages 767–770)

      Xiaoyu Han, Fangrui Zhong, Prof. Dr. Youqing Wang and Prof. Dr. Yixin Lu

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201106672

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      A fast one: The title reaction proceeds in the presence of 5 mol % of the catalyst 1, and is complete within an hour. The 2-alkyl- and 2-aryl-substituted 3-pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of (+)-trachelanthamidine is also demonstrated. Boc=tert-butoxycarbonyl, M.S.=molecular sieves, TBDPS=tert-butyldiphenylsilyl.

    29. Asymmetric Relay Catalysis

      Step-Economical Synthesis of Tetrahydroquinolines by Asymmetric Relay Catalytic Friedländer Condensation/Transfer Hydrogenation (pages 771–774)

      Lei Ren, Tao Lei, Jia-Xi Ye and Prof. Liu-Zhu Gong

      Version of Record online: 14 DEC 2011 | DOI: 10.1002/anie.201106808

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      Two steps in one reaction: The title relay reaction relies on a combination of an achiral Lewis acid and a chiral Brønsted acid (B*-H in the scheme). This one-pot method provides access to tetrahydroquinoline derivatives with multiple continuous stereogenic centers in high stereoselectivity (>20:1 d.r., 98 % ee).

    30. C[BOND]H Functionalization

      Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups (pages 775–779)

      Tomoyuki Yao, Dr. Koji Hirano, Prof. Dr. Tetsuya Satoh and Prof. Dr. Masahiro Miura

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201106825

      Thumbnail image of graphical abstract

      A matter of catalyst: Azole compounds can be directly alkylated with N-tosylhydrazones that bear unactivated alkyl groups (see scheme; phen=1,10-phenanthroline, Ts=p-toluenesulfonyl). Nickel catalysis enables the introduction of simple secondary alkyl chains into benzoxazole compounds, whereas the alkylation of 5-aryloxazoles and benzothiazole is possible by using a cobalt catalyst.

    31. Asymmetric Catalysis

      Rhodium-Catalyzed, Highly Enantioselective 1,2-Addition of Aryl Boronic Acids to α-Ketoesters and α-Diketones Using Simple, Chiral Sulfur–Olefin Ligands (pages 780–783)

      Ting-Shun Zhu, Shen-Shuang Jin and Prof. Dr. Ming-Hua Xu

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201106972

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      Simply the best: The title reaction has been achieved by asymmetric rhodium catalysis employing an extremely simple, chiral N-(sulfinyl)cinnamylamine ligand. A variety of highly enantioenriched, tertiary α-hydroxy carbonyl derivatives were easily accessed at room temperature under mild conditions with enantioselectivities of up to 99 %.

    32. Photochemistry

      Highly Efficient Aerobic Oxidative Hydroxylation of Arylboronic Acids: Photoredox Catalysis Using Visible Light (pages 784–788)

      You-Quan Zou, Dr. Jia-Rong Chen, Xiao-Peng Liu, Dr. Liang-Qiu Lu, Dr. Rebecca L. Davis, Prof. Dr. Karl Anker Jørgensen and Prof. Dr. Wen-Jing Xiao

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201107028

      Thumbnail image of graphical abstract

      To shed light on: The title reaction allows the generation of a variety of functionalized phenols and analogues using [Ru(bpy)3Cl2]⋅6 H2O as the photocatalyst under very mild reaction conditions. This reaction not only incorporates an oxygen atom from molecular oxygen directly into the product, but also expands the application of visible-light photocatalysis. bpy=bipyridine.

    33. Germylidyne Complexes

      Open-Shell Complexes Containing Metal–Germanium Triple Bonds (pages 789–793)

      Prof. Dr. Alexander C. Filippou, Dr. Ali Barandov, Dr. Gregor Schnakenburg, Dr. Burhanshah Lewall, Dr. Maurice van Gastel and Dr. Aliaksandr Marchanka

      Version of Record online: 15 DEC 2011 | DOI: 10.1002/anie.201107120

      Thumbnail image of graphical abstract

      Ge force: One-electron oxidation of the 18 valence electron (VE) germylidyne complexes 1 provides access to the first open-shell germylidyne complexes 2 (see scheme; M=Mo, W; R=C6H3-2,6-Mes2) that are analogous to metal alkylidyne complexes. The geometric and electronic structures of the 17 VE complexes 2 were determined by a combination of experimental and theoretical methods.

    34. Asymmetric Catalysis

      Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoesters (pages 794–797)

      Ludovic Gremaud and Prof. Alexandre Alexakis

      Version of Record online: 1 DEC 2011 | DOI: 10.1002/anie.201107324

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      Not a cop out: The copper-catalyzed asymmetric conjugate addition of organometallic reagents to Michael acceptors is an important methodology for forming a C[BOND]C bond in an enantioselective manner. Such an addition of Me3Al to β,γ-unsaturated α-ketoesters is described to proceed in high yield and selectivity. CuTC=copper(I) thiophene-2-carboxylate.

    35. Palladium Catalysis

      Palladium-Catalyzed Carbonylative α-Arylation for Accessing 1,3-Diketones (pages 798–801)

      Thomas M. Gøgsig, Dr. Rolf H. Taaning, Dr. Anders T. Lindhardt and Prof. Dr. Troels Skrydstrup

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/anie.201107494

      Thumbnail image of graphical abstract

      With a hint of CO: The first Pd-catalyzed carbonylative α-arylations of simple ketones with carbon monoxide is presented for the direct synthesis of 1,3-diketones (see scheme). The method uses only stoichiometric amounts of CO, and hence allows for the simple installment of carbon isotopes into the core structures of heterocyclic compounds.

    36. Fullerenes

      Highly Efficient Cu(OAc)2-Catalyzed Dimerization of Monofunctionalized Hydrofullerenes Leading to Single-Bonded [60]Fullerene Dimers (pages 802–806)

      Shirong Lu, Prof. Dr. Tienan Jin, Dr. Eunsang Kwon, Prof. Dr. Ming Bao and Prof. Dr. Yoshinori Yamamoto

      Version of Record online: 2 DEC 2011 | DOI: 10.1002/anie.201107505

      Thumbnail image of graphical abstract

      Dimers are a girl's best friend: The title reaction allows the formation of single-bonded fullerene dimers with extremely high chemical yield and high compatibility with various functional groups, which are highly soluble in organic solvents. The use of Cu(OAc)2 catalyst with dimethylformamide or acetonitrile as additives under air is the critical factor in achieving the highly efficient catalytic dimerization.

    37. Metal–Organic Frameworks

      Enantiopure Metal–Organic Framework Thin Films: Oriented SURMOF Growth and Enantioselective Adsorption (pages 807–810)

      Dr. Bo Liu, Dr. Osama Shekhah, Hasan K. Arslan, Dr. Jinxuan Liu, Prof. Dr. Christof Wöll and Prof. Dr. Roland A. Fischer

      Version of Record online: 3 NOV 2011 | DOI: 10.1002/anie.201104240

      Thumbnail image of graphical abstract

      Stuck on you: Preferred (110) and (001) orientation of enantiopure [{Zn2((+)cam)2(dabco)}n] ((+)cam=(1R,3S)-(+)-camphoric acid, dabco=1,4-diazabicyclo(2.2.2)octane) thin films can be controlled by carboxylate and pyridyl groups on self-assembled monolayers (SAMs). With a quartz crystal microbalance, the enantioselective adsorption of enantiomeric hexanediol pairs by enantiopure surface-attached metal–organic frameworks (SURMOF) [Zn2((±)cam)2(dabco)] pairs can be demonstrated (see picture).

    38. Natural Products

      Myxoprincomide: A Natural Product from Myxococcus xanthus Discovered by Comprehensive Analysis of the Secondary Metabolome (pages 811–816)

      M. Sc. Niña Socorro Cortina, Dr. Daniel Krug, Dr. Alberto Plaza, Dipl.-Chem. Ole Revermann and Prof. Dr. Rolf Müller

      Version of Record online: 7 DEC 2011 | DOI: 10.1002/anie.201106305

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      Come to the fore: The novel myxobacterial metabolite myxoprincomide is easy to overlook in the complex LC-MS data recorded for the metabolome of Myxococcus xanthus DK1622, such that advanced analytical techniques were needed for its discovery. By enhancing genomics-based natural products research with powerful analytical tools for in-depth metabolome mining, two additional such “hidden” metabolites have been uncovered.

    39. Methane Activation

      Activated Methane on Small Cationic Platinum Clusters (pages 817–819)

      Dr. Dan J. Harding, Christian Kerpal, Prof. Dr. Gerard Meijer and Dr. André Fielicke

      Version of Record online: 6 DEC 2011 | DOI: 10.1002/anie.201107042

      Thumbnail image of graphical abstract

      Stretch Me[BOND]H: Methane activated by adsorption on small platinum clusters is characterized by the vibrational fingerprint of the cluster complex. The C[BOND]H bond activation is distributed over two bonds, which corresponds with a decreased activation of each of the bonds but should lead to improved control over the reactivity of methane.

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      Version of Record online: 12 JAN 2012 | DOI: 10.1002/anie.201290003

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