Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 44

October 19, 2009

Volume 48, Issue 44

Pages 8151–8379

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
    1. Cover Picture: Tumor-Associated MUC1 Tandem-Repeat Glycopeptide Microarrays to Evaluate Serum– and Monoclonal–Antibody Specificity (Angew. Chem. Int. Ed. 44/2009) (page 8151)

      Ulrika Westerlind, Hendrik Schröder, Alexandra Hobel, Nikola Gaidzik, Anton Kaiser, Christof M. Niemeyer, Edgar Schmitt, Herbert Waldmann and Horst Kunz

      Version of Record online: 30 SEP 2009 | DOI: 10.1002/anie.200904924

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      A synthetic vaccine consisting of a MUC1 tandem-repeat glycopeptide conjugated to the tetanus toxoid protein was prepared and immunized in mice. A very strong immune response with antibodies specific to the MUC1 glycopeptide was obtained, as described in the Communication by H. Kunz and co-workers in issue 41 on page 7551 ff. To further evaluate the specificity of the antibodies from this and other synthetic vaccines, a MUC1 tandem-repeat glycopeptide microarray platform (see cover picture) was developed by H. Kunz, H. Waldmann, and co-workers, as reported in their Communication on page 8263 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. Inside Cover: Controlled Stability of Molecular Junctions (Angew. Chem. Int. Ed. 44/2009) (page 8152)

      Diana Dulić, Florian Pump, Stephane Campidelli, Pascal Lavie, Gianaurelio Cuniberti and Arianna Filoramo

      Version of Record online: 30 SEP 2009 | DOI: 10.1002/anie.200905076

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      The key role of the interfaces in the electrode–molecule contact can be probed by studying the time evolution of molecular junctions. In their Communication on page 8273 ff., A. Filoramo and co-workers show that the “blinking” of the thiol–gold bond can be suppressed by an appropriate choice of molecule: devices that contain the terphenylene molecule exhibit a stochastic variation in the conductance, while devices that contain the terthiophene molecule are extremely stable over a period of several weeks (Illustration: D. Nozaki).

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
  4. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
    14. Preview
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  5. Apology

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
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    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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      Dynamic Motion in Crown Ether Dendrimer Complexes: A “Spacewalk” on the Molecular Scale (page 8167)

      Henrik D. F. Winkler, Dominik P. Weimann, Andreas Springer and Christoph A. Schalley

      Version of Record online: 13 OCT 2009 | DOI: 10.1002/anie.200990229

      This article corrects:

      Dynamic Motion in Crown Ether Dendrimer Complexes: A “Spacewalk” on the Molecular Scale1

      Vol. 48, Issue 39, 7246–7250, Version of Record online: 24 AUG 2009

  6. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
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    1. Matthias Westerhausen (page 8174)

      Version of Record online: 22 SEP 2009 | DOI: 10.1002/anie.200904772

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      “When I was eighteen I wanted to be an architect or a chemist—in both professions creativity is necessary in order to create new structures. The most significant scientific advance of the last 100 years has been the understanding of chemical bonding and the development of quantum mechanics‥ …” This and more about Matthias Westerhausen can be found on page 8174.

  8. Book Reviews

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
    6. Apology
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    9. Book Reviews
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    11. Minireview
    12. Review
    13. Communications
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    1. Chemical Biology. Learning through Case Studies. Edited by Herbert Waldmann and Petra Janning. (page 8175)

      Michaela Mühlberg, Verena Böhrsch and Christian P. R. Hackenberger

      Version of Record online: 13 OCT 2009 | DOI: 10.1002/anie.200904323

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      Wiley-VCH, Weinheim 2009. 271 pp., softcover € 39.90.—ISBN 978-3527323302

    2. Practical Biotransformations. A Beginner's Guide. Postgraduate Chemistry Series. By Gideon Grogan. (pages 8175–8176)

      Michael Müller

      Version of Record online: 13 OCT 2009 | DOI: 10.1002/anie.200904318

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      John Wiley & Sons, Hoboken 2009. 344 pp., softcover € 44.90.—ISBN 978-1405171250

  9. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. Water Splitting

      Water Splitting by Cooperative Catalysis (pages 8178–8181)

      Dennis G. H. Hetterscheid, Jarl Ivar van der Vlugt, Bas de Bruin and Joost N. H. Reek

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200902455

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      Pinching water: A mononuclear Ru complex is shown to efficiently split water into H2 and O2 in consecutive steps through a heat- and light-driven process (see picture). Thermally driven H2 formation involves the aid of a non-innocent ligand scaffold, while dioxygen is generated by initial photochemically induced reductive elimination of hydrogen peroxide. These features might be the onset for new designs of catalytic water-splitting systems.

    2. Complex Zeolites

      Flipping Marvelous: New Zeolites by New Methods (pages 8182–8184)

      Michael O'Keeffe

      Version of Record online: 11 SEP 2009 | DOI: 10.1002/anie.200903573

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      Complexity conquered: Zeolite structures of unprecedented complexity have been determined using the new methods of charge flipping and histogram matching applied to X-ray powder diffraction data combined with data from electron microscopy. ITQ-37 (see picture) has a chiral structure of exceptionally low density and large ring size.

  10. Minireview

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

      New Syntheses of Diazo Compounds (pages 8186–8195)

      Gerhard Maas

      Version of Record online: 29 SEP 2009 | DOI: 10.1002/anie.200902785

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      More and more synthetic chemists worldwide have started to appreciate aliphatic diazo compounds as versatile synthetic building blocks (see scheme). This versatility continuously provides incentives for the development of novel methods and improved procedures for the synthesis of diazo compounds. These new methods and recent developments are outlined.

  11. Review

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. Apology
    7. News
    8. Author Profile
    9. Book Reviews
    10. Highlights
    11. Minireview
    12. Review
    13. Communications
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    1. 200 Years Since Davy

      A Molecular Perspective on Lithium–Ammonia Solutions (pages 8198–8232)

      Eva Zurek, Peter P. Edwards and Roald Hoffmann

      Version of Record online: 9 OCT 2009 | DOI: 10.1002/anie.200900373

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      If, to ammonia one adds a metal, The solution grows real unsettled. A fine blue color is seen throughout First by Humphry Davy, no doubt. From lithium, electrons are released The density of the solution decreased! Soaked electrons are born, spins pair Until a real band forms, debonaire! Lowering the T of this ebullition Impels a liquid–liquid partition, Superconductivity? Why not? Molecular orbitals hit the spot. From blue to gold, the story unfolds.

  12. Communications

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
    6. Apology
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    8. Author Profile
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    11. Minireview
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    1. Chemoselective Reactions

      Chemoselective Staudinger-Phosphite Reaction of Azides for the Phosphorylation of Proteins (pages 8234–8239)

      Remigiusz Serwa, Ina Wilkening, Giuseppe Del Signore, Michaela Mühlberg, Iris Claußnitzer, Christoph Weise, Michael Gerrits and Christian P. R. Hackenberger

      Version of Record online: 27 JUL 2009 | DOI: 10.1002/anie.200902118

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      Extending the toolbox: The title reaction was identified as a chemoselective means to modify azides in peptides and proteins in high yields at room temperature in various solvents including aqueous buffers at physiological pH. In combination with nonnatural protein translation the Staudinger-phosphite reaction allows the site-specific incorporation of phosphorylated Tyr analogues in proteins.

    2. Mass Spectrometry

      In Vivo, In Situ Tissue Analysis Using Rapid Evaporative Ionization Mass Spectrometry (pages 8240–8242)

      Karl-Christian Schäfer, Júlia Dénes, Katalin Albrecht, Tamás Szaniszló, Júlia Balog, Réka Skoumal, Mária Katona, Miklós Tóth, Lajos Balogh and Zoltán Takáts

      Version of Record online: 10 SEP 2009 | DOI: 10.1002/anie.200902546

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      Beam me up: A novel mass spectrometric ionization technique based on rapid evaporation of biological tissues (see picture) can be used to analyze vital tissues during surgical intervention as well as for processed tissue specimens. A tissue identification system based on principal-component analysis was developed. The method differentiates malignant tumor cells from the surrounding healthy tissue.

    3. Cross-Coupling

      Gold and Palladium Combined for Cross-Coupling (pages 8243–8246)

      A. Stephen K. Hashmi, Christian Lothschütz, René Döpp, Matthias Rudolph, Tanuja D. Ramamurthi and Frank Rominger

      Version of Record online: 29 SEP 2009 | DOI: 10.1002/anie.200902942

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      Gold and palladium—a unique liason: A study of the transmetalation abilities of organogold compounds builds the basis for a new class of cross-coupling reactions. Stable intermediates of gold catalysis deliver new complex products by a palladium-catalyzed coupling reaction. (see Scheme)

    4. Gold Catlysis

      Gold Catalysis: Isolation of Vinylgold Complexes Derived from Alkynes (pages 8247–8249)

      A. Stephen K. Hashmi, Andreas M. Schuster and Frank Rominger

      Version of Record online: 19 SEP 2009 | DOI: 10.1002/anie.200903134

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      Gold plated rings: N-Propargylcarboxamides (1) when reacted with a gold complex containing the IPr N-heterocyclic carbene ligand, delivers the first isolable vinylgold intermediates obtained from alkynes. [see Scheme; IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylide]

    5. DNA Structures

      Binaphthyl-DNA: Stacking and Fluorescence of a Nonplanar Aromatic Base Surrogate in DNA (pages 8250–8253)

      Sven Hainke and Oliver Seitz

      Version of Record online: 29 SEP 2009 | DOI: 10.1002/anie.200903194

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      A flexible hinge allows multiple binaphthyl-modified bases to stabilize DNA duplexes through both intrahelical and extrahelical stacking interactions. Two successive binaphthyl pairs stabilize the duplex structure as efficiently as two successive AT pairs. The stacking of these binaphthyl bases in DNA does not lead to self-quenching of fluorescence.

    6. Polymer Nanostructures

      Nanocomposites with Structure Domains of 0.5 to 3 nm by Polymerization of Silicon Spiro Compounds (pages 8254–8258)

      Stefan Spange, Patrick Kempe, Andreas Seifert, Alexander A. Auer, Petra Ecorchard, Heinrich Lang, Meiken Falke, Michael Hietschold, Andreas Pohlers, Walter Hoyer, Gerhard Cox, Emanuel Kockrick and Stefan Kaskel

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200901113

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      Two from one: It is possible to form two different, interpenetrating polymer structures—silicon dioxide and a phenolic resin—simultaneously in a single step without the formation of by-products by using a readily polymerizable, organic silicon spiro compound. This new polymerization process enables the fabrication of materials with domain sizes of 0.5 to 3 nm.

    7. Protein Structures

      Use of Relaxation Enhancements in a Paramagnetic Environment for the Structure Determination of Proteins Using NMR Spectroscopy (pages 8259–8262)

      Tobias Madl, Wolfgang Bermel and Klaus Zangger

      Version of Record online: 22 SEP 2009 | DOI: 10.1002/anie.200902561

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      More information: Relaxation enhancements induced by an inert paramagnetic environment (PREs) are used together with a limited NOE data set in a model-free alternative protein structure refinement procedure. Structures of two model systems (8 kDa ubiquitin and the 42 kDa maltodextrin-binding protein in complex with β-cyclodextrin) were obtained employing PREs and NOEs of exchangeable protons.

    8. Microarrays

      Tumor-Associated MUC1 Tandem-Repeat Glycopeptide Microarrays to Evaluate Serum– and Monoclonal–Antibody Specificity (pages 8263–8267)

      Ulrika Westerlind, Hendrik Schröder, Alexandra Hobel, Nikola Gaidzik, Anton Kaiser, Christof M. Niemeyer, Edgar Schmitt, Herbert Waldmann and Horst Kunz

      Version of Record online: 28 AUG 2009 | DOI: 10.1002/anie.200902963

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      Sugar coated diagnosis: A microarray of mucin sialyl-TN and TN-tandem-repeat glycopeptides was developed (see picture) and used to study the specificity of serum antibodies raised by immunization of mice with synthetic cancer vaccines.

    9. Directed Evolution

      Creation of an Amino Acid Network of Structurally Coupled Residues in the Directed Evolution of a Thermostable Enzyme (pages 8268–8272)

      Manfred T. Reetz, Pankaj Soni, Juan Pablo Acevedo and Joaquin Sanchis

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200904209

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      Molecular orchestration: In the directed evolution of a hyperthermally stabilized enzyme, remote residues have been structurally coupled as a result of the creation of an extensive communicating amino acid network on the surface of the protein.

    10. Molecular Electronics

      Controlled Stability of Molecular Junctions (pages 8273–8276)

      Diana Dulić, Florian Pump, Stephane Campidelli, Pascal Lavie, Gianaurelio Cuniberti and Arianna Filoramo

      Version of Record online: 2 SEP 2009 | DOI: 10.1002/anie.200902168

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      Influence of interfaces on thiol-terminated molecular wires consisting of three phenyl (P3) or three thiophene (T3) rings was monitored by a new statistical approach based on mechanical controllable break junction technique (see SEM image of the junction and schematic of molecular arrangement). The P3 molecule exhibits stochastic variations in conductance G, in contrast to the T3 molecule.

    11. Mass Spectrometry

      Rapid Characterization of Complex Viscous Liquids at the Molecular Level (pages 8277–8280)

      Wai Siang Law, Huanwen Chen, Jianhua Ding, Shuiping Yang, Liang Zhu, Gerardo Gamez, Konstantin Chingin, Yulin Ren and Renato Zenobi

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200902360

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      Sticky subject: An N2 stream forms bubbles inside bulk viscous liquids, which create an aerosol sample through a microjetting mechanism (see picture). This aerosol is then analyzed by extractive electrospray ionization (EESI) mass spectrometry (MS). EESI-MS reveals the molecular composition of complex liquids and the kinetics of ongoing processes occurring in the highly viscous liquids without any sample pretreatment.

    12. Morphology Control

      Micelles and Vesicles Formed by Polyoxometalate–Block Copolymer Composites (pages 8281–8284)

      Weifeng Bu, Sayaka Uchida and Noritaka Mizuno

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/anie.200904116

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      Core–corona composites were prepared by incorporating a hydrophilic polyoxometalate (POM) into poly(styrene-b-4-vinyl-N-methylpyridinium iodide) matrices in acidic aqueous solution (see scheme). On dispersal in toluene they self-assemble into micellar and vesicular morphologies (see TEM images), which can be controlled by means of the weight fraction of POM.

    13. Magnetic Materials

      Calix[4]arene-Based Single-Molecule Magnets (pages 8285–8288)

      Georgios Karotsis, Simon J. Teat, Wolfgang Wernsdorfer, Stergios Piligkos, Scott J. Dalgarno and Euan K. Brechin

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200904094

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      Protective skin: Single-molecule magnets (SMMs) that are protected by two calix[4]arenes have been synthesized (see picture: Mn purple, O red, N blue, C gray). The calixarene allows supramolecular isolation of the SMM, and alteration of its upper rim provides control over the orientation in the solid state by altering the distances between layers.

    14. Heterogeneous Catalysis

      Maximizing the Localized Relaxation: The Origin of the Outstanding Oxygen Storage Capacity of κ-Ce2Zr2O8 (pages 8289–8292)

      Hai-Feng Wang, Yang-Long Guo, Guan-Zhong Lu and P. Hu

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200903907

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      Pretty vacant: The excellent oxygen storage capacity (OSC) of κ-Ce2Zr2O8 (see picture; Ce gray, Zr green, O red) is shown to be a result of its unique structural features; after removing oxygen atoms, the structural relaxation is local (vacancy shown in brown), and both the localized structural relaxation and the number of localized structural relaxations are maximized.

    15. Malaria

      Functional Profiling, Identification, and Inhibition of Plasmepsins in Intraerythrocytic Malaria Parasites (pages 8293–8297)

      Kai Liu, Haibin Shi, Huogen Xiao, Alvin G. L. Chong, Xuezhi Bi, Young-Tae Chang, Kevin S. W. Tan, Rickey Y. Yada and Shao Q. Yao

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200903747

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      Profile and eliminate! Plasmepsins (PMs), aspartic proteases required for malaria-parasite growth, are promising antimalarial targets. The in situ screening of PMs with probes formed from β-hydroxyazides 1 and alkynes with a photo-cross-linking unit and a tetraethylrhodamine reporter led to the identification of the small-molecule inhibitor 2, which inhibits all four food-vacuole PMs and showed potent antimalarial activity in red-blood-cell cultures.

    16. Carbon Nanotubes

      High-Yield Synthesis of Ultrathin Metal Nanowires in Carbon Nanotubes (pages 8298–8302)

      R. Kitaura, R. Nakanishi, T. Saito, H. Yoshikawa, K. Awaga and H. Shinohara

      Version of Record online: 22 SEP 2009 | DOI: 10.1002/anie.200902615

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      Filling the tube: Ultrathin metal nanowires with diameters of single atoms (ca. 1.7 nm) were synthesized in high yield by using a nanofilling reaction using the nanospace of carbon nanotubes (CNTs). As the nanowires are protected by the wall of the CNTs, they resist oxidation and structural disintegration even under ambient conditions.

    17. Cell Patterning

      Patterning Mammalian Cells for Modeling Three Types of Naturally Occurring Cell–Cell Interactions (pages 8303–8305)

      Zhenling Chen, Yong Li, Wenwen Liu, Dongzhou Zhang, Yuyun Zhao, Bo Yuan and Xingyu Jiang

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200902708

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      Types of stripes: Microfluidic techniques are combined with surface chemistry to pattern multiple types of cells on the same substrate to simulate three types of naturally occurring cell–cell interactions. PDMS=poly(dimethylsiloxane) stamp, FN=fibronectin to promote cell adhesion, SAM=self-assembled monolayer of an applied alkanethiol that resists cell adhesion.

    18. Membrane Proteins

      One β Hairpin after the Other: Exploring Mechanical Unfolding Pathways of the Transmembrane β-Barrel Protein OmpG (pages 8306–8308)

      K. Tanuj Sapra, Mehdi Damaghi, Stefan Köster, Özkan Yildiz, Werner Kühlbrandt and Daniel J. Muller

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200904361

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      Roll out the barrel: By using single-molecule force spectroscopy, a β-barrel-forming outer-membrane protein is unfolded for the first time. OmpG from E. coli shows a surprising unfolding behavior: Single β strands do not unfold individually but as β hairpins. These β hairpins unfold one after another until the entire β-barrel membrane protein is unfolded (see structural representation).

    19. Polyoxometalates

      Synthesis of Modular “Inorganic–Organic–Inorganic” Polyoxometalates and Their Assembly into Vesicles (pages 8309–8313)

      Chullikkattil P. Pradeep, Mauricio F. Misdrahi, Feng-Yan Li, Jie Zhang, Lin Xu, De-Liang Long, Tianbo Liu and Leroy Cronin

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200903070

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      Connecting clusters: A new class of approximately 3.4 nm sized inorganic–organic–inorganic hybrids was synthesized by covalent functionalization of V3-capped Wells–Dawson-type clusters with linear bis(Tris) ligands (see scheme; TBA=nBu4N+). These hybrids were characterized using single-crystal XRD and ESI-MS techniques. Dynamic light scattering studies revealed the surfactant properties of these compounds, which lead to the formation of supramolecular vesicles in solutions.

    20. Metal–Organic Frameworks

      Breathing Transitions in MIL-53(Al) Metal–Organic Framework Upon Xenon Adsorption (pages 8314–8317)

      Anne Boutin, Marie-Anne Springuel-Huet, Andrei Nossov, Antoine Gédéon, Thierry Loiseau, Christophe Volkringer, Gérard Férey, François-Xavier Coudert and Alain H. Fuchs

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/anie.200903153

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      MOFs come alive: The combination of gas-adsorption experiments at various temperatures with an osmotic thermodynamic model produced a generic temperature–loading phase diagram that displays unexpected re-entrant behavior. The breathing effect in the metal–organic framework MIL-53(Al) is predicted to be general and should be observed over a limited temperature range regardless of the guest adsorbate.

    21. Cycloaddition Reactions

      Rhodium(I)-Catalyzed [4+1] Cycloaddition Reactions of α,β-Unsaturated Imines with Terminal Alkynes for the Preparation of Pyrrole Derivatives (pages 8318–8320)

      Akio Mizuno, Hiroyuki Kusama and Nobuharu Iwasawa

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200904402

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      Rhodium vinylidene intermediates are characteristic for the title reaction (see scheme; coe=cyclooctene, cy=cyclohexyl). This reaction proceeds by the nucleophilic addition of the nitrogen atom of the imine to the rhodium vinylidene complex to give a zwitterionic intermediate, which undergoes intramolecular cyclization to afford the corresponding pyrrole.

    22. Microwave Effects

      Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects (pages 8321–8324)

      David Obermayer, Bernhard Gutmann and C. Oliver Kappe

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200904185

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      Running oil-bath chemistry in a microwave! Using reaction vials made out of strongly microwave-absorbing silicon carbide (SiC) in a microwave reactor simulates experiments conducted in an autoclave with conductive heating because of the efficient shielding of the electromagnetic field by the SiC vial. This technology makes it possible to study the significance of microwave effects.

    23. Hydroamination

      Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination-Based Reaction Sequence (pages 8325–8327)

      Toni Rizk, Eric J.-F. Bilodeau and André M. Beauchemin

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200903922

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      A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p-Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redox-neutral aromatization step to occur.

    24. Ring-Opening Polymerization

      Tunable, Temperature-Responsive Polynorbornenes with Side Chains Based on an Elastin Peptide Sequence (pages 8328–8330)

      Rosemary M. Conrad and Robert H. Grubbs

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200903888

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      Live on: Random copolymers made by living ring-opening metathesis polymerization of norbornene monomers containing either the elastin peptide sequence -(VPGVG)- or pentaethylene glycol (see scheme; Mes=mesityl, pyr=pyridine) exhibit a lower critical solution temperature (LCST). The LCST can be easily modified by varying the ratio of the co-monomers in the polymer feed.

    25. Conducting Polymers

      Cathodic Deposition of Polypyrrole Enabling the One-Step Assembly of Metal–Polymer Hybrid Electrodes (pages 8331–8334)

      Yongju Jung, Nikhilendra Singh and Kyoung-Shin Choi

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200903596

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      Deposit account: The generation of oxidizing agents in situ allows the cathodic deposition of polypyrrole (ppy) by oxidative polymerization. Conducting polymers are synthesized with new nanoscale morphologies (e.g., nanospheres creating a three-dimensional porous network, see picture). Metal–conducting polymer hybrid electrodes are assembled by a one-step synthesis.

    26. Gas Diffusion

      Transport Diffusivity of CO2 in the Highly Flexible Metal–Organic Framework MIL-53(Cr) (pages 8335–8339)

      Fabrice Salles, Hervé Jobic, Aziz Ghoufi, Philip L. Llewellyn, Christian Serre, Sandrine Bourrelly, Gérard Férey and Guillaume Maurin

      Version of Record online: 23 SEP 2009 | DOI: 10.1002/anie.200902998

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      The diffusion mechanism of CO2 in the highly flexible metal–organic framework MIL-53(Cr) (see picture), which undergoes a structural transition between large- and narrow-pore forms, was explored by a combination of quasi-elastic neutron scattering measurements and molecular dynamics simulations. Normal one-dimensional diffusion in the large-pore form and single-file one-dimensional diffusion in the narrow-pore form were evidenced.

    27. IR Spectroscopy

      Room-Temperature Infrared Spectroscopy Combined with Mass Spectrometry Distinguishes Gas-Phase Protein Isomers (pages 8340–8342)

      Y. M. Eva Fung, Thierry Besson, Joël Lemaire, Philippe Maitre and Roman A. Zubarev

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/anie.200901516

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      Differential IR spectra of gas-phase proteins at room temperature can be obtained by a combination of IR multiphoton dissociation (IRMPD) and FT ion cyclotron resonance mass spectrometry. This new approach yields unique spectra for all-L and singly D-substituted isomers of the protein Trp-cage (see depicted differential spectrum) and thus avoids possible unfolding of proteins during IR irradiation that can affect conventional IRMPD measurements.

    28. Kinetic Resolution

      Kinetic Resolution of Quaternary and Tertiary β-Hydroxy Esters (pages 8343–8347)

      Derek J. Schipper, Sophie Rousseaux and Keith Fagnou

      Version of Record online: 29 SEP 2009 | DOI: 10.1002/anie.200902373

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      Selectivity factors: The resolution of tertiary and secondary alcohols, which arise from ketone and aldehyde aldol additions, proceeds in the presence of (1S,2R)-N-methylephedrine (see example). The method is technically simple, easily scalable, and provides tertiary and secondary alcohols in high enantiomeric ratios.

    29. Radical Reactions

      Unexpected Acid Catalysis in Reactions of Peroxyl Radicals with Phenols (pages 8348–8351)

      Luca Valgimigli, Riccardo Amorati, Silvia Petrucci, Gian Franco Pedulli, Di Hu, Jason J. Hanthorn and Derek A. Pratt

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200903360

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      Weak organic acids in millimolar concentrations increase the reactivity of peroxyl radicals with common phenolic antioxidants dramatically. This counterintuitive phenomenon relies on a substantially different reaction mechanism from that in the absence of an acid: rate-determining electron transfer occurs from the hydrogen-bonded phenol to the hydroperoxide cation radical present in equilibrium with the peroxyl radical under these conditions (see scheme).

    30. Heterocyclic-Ring Opening

      Beyond C[BOND]H Activation with Uranium: A Cascade of Reactions Mediated by a Uranium Dialkyl Complex (pages 8352–8355)

      Marisa J. Monreal, Saeed Khan and Paula L. Diaconescu

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200903270

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      A neutral uranium dibenzyl complex mediated the C[BOND]H activation of two aromatic N heterocycles, followed by a cascade of reactions which led to the opening and functionalization of imidazole rings (see scheme). This double C[BOND]H activation and the sequence of transformations succeeding it are unique to uranium and point to the use of this element for the cleavage of other strong carbon–heteroatom bonds.

    31. Hierarchically Ordered Structures

      Evolution of Ordered Block Copolymer Serpentines into a Macroscopic, Hierarchically Ordered Web (pages 8356–8360)

      Suck Won Hong, Jun Wang and Zhiqun Lin

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/anie.200903552

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      Polymer coffee rings: Evaporation of diblock copolymer solutions confined in a sphere-on-flat geometry yields concentric serpentine microstructures over large areas (see picture, left). Selective solvent vapor annealing then transforms these microstructures into a macroscopic pattern of regularly arranged microporous mesh arrays (see picture, right) while at the same time forming domains of nanoscopic cylinders of diblock copolymer.

    32. Amine Synthesis

      Tantalum–Amidate Complexes for the Hydroaminoalkylation of Secondary Amines: Enhanced Substrate Scope and Enantioselective Chiral Amine Synthesis (pages 8361–8365)

      Patrick Eisenberger, Rashidat O. Ayinla, Jean Michel P. Lauzon and Laurel L. Schafer

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200903656

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      Tantalizing reactivity: New mono- and bis(amidate)–tantalum complexes have been prepared, characterized, and used for the catalytic α-alkylation of secondary amines (see scheme). Spontaneous β-hydrogen abstraction is observed to give a fully characterized example of the first catalytically active tantallaaziridine complex.

    33. Exhaust Control

      Enhanced NH3 Selective Catalytic Reduction for NOx Abatement (pages 8366–8368)

      Pio Forzatti, Isabella Nova and Enrico Tronconi

      Version of Record online: 28 SEP 2009 | DOI: 10.1002/anie.200903857

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      Enhanced NO reduction efficiencies, close to those obtained under the conditions of fast selective catalytic reduction (SCR; see diagram), were achieved over commercial vanadium and iron-exchanged zeolite SCR catalysts at low temperatures (200–300 °C) in the absence of NO2 by reaction of NO with ammonia and an aqueous solution of ammonium nitrate.

    34. Conjugated Ligands

      Naphthalene-Mediated Electronic Communication in Tetrakis(imino)pyracene Complexes (pages 8369–8371)

      Kalyan V. Vasudevan, Ignacio Vargas-Baca and Alan H. Cowley

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/anie.200904122

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      A hot tip: Bifunctional tetrakis(imino)pyracene (tip) ligands undergo one-electron reduction at both diimine functionalities when treated with potassium metal, germanium dichloride, or decamethyleuropocene (see scheme, Cp*=C5Me5). The transferred electrons pair up in an orbital that is delocalized over both diazabutadiene moieties and the naphthalene bridge.

    35. Synthetic Methods

      Gold- or Platinum-Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality (pages 8372–8375)

      Paul W. Davies and Sébastien J.-C. Albrecht

      Version of Record online: 25 SEP 2009 | DOI: 10.1002/anie.200904309

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      It′s no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π-acid catalysis in an atom-economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit generates a sulfur ylide, which undergoes 2,3-sigmatropic rearrangement. Acyclic substrates are cycloisomerized to afford functionalized dihydrothiophenones (see scheme) and dihydrothiopyranones.

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