Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

April 10, 2012

Volume 51, Issue 15

Pages 3493–3722

  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. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Cover Picture: Plasmon Shaping by using Protein Nanoarrays and Molecular Lithography to Engineer Structural Color (Angew. Chem. Int. Ed. 15/2012) (page 3493)

      Alasdair W. Clark and Jonathan M. Cooper

      Version of Record online: 2 MAR 2012 | DOI: 10.1002/anie.201201326

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      Molecular binding events can be used to construct complex arrays and systems of plasmonic nanoparticles, as well as to influence the brilliant colors exhibited by these structures. In their Communication on page 3562 ff., J. M. Cooper and A. W. Clark demonstrate an engineered approach to a molecularly mediated plasmonic sensor in which direct-write nanolithography is combined with nanoscale protein patterning and an antibody binding assay to enable naked-eye detection of single protein binding at extreme sensitivities.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    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. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Inside Cover: Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-type Disialyloligosaccharide (Angew. Chem. Int. Ed. 15/2012) (page 3494)

      Masumi Murakami, Dr. Ryo Okamoto, Dr. Masayuki Izumi and Prof. Dr. Yasuhiro Kajihara

      Version of Record online: 14 FEB 2012 | DOI: 10.1002/anie.201200881

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      A homogeneous glycoprotein was prepared by the improved tert-Boc solid-phase peptide synthesis of acid-labile sialylglycopeptide α-thioesters, sophisticated peptide-coupling reactions, and native chemical ligation. In their Communication on page 3567 ff., Y. Kajihara and co-workers report the chemical synthesis of a homogeneous erythropoietin glycoform bearing a complex-type biantennary disialyloligosaccharide. This approach will open a new avenue for the investigation of oligosaccharide function.

  3. Inside Back Cover

    1. Top of page
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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. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Inside Back Cover: Enhancement of Proton Mobility in Extended-Nanospace Channels (Angew. Chem. Int. Ed. 15/2012) (page 3723)

      Hiroyuki Chinen, Dr. Kazuma Mawatari, Dr. Yuriy Pihosh, Kyojiro Morikawa, Dr. Yutaka Kazoe, Dr. Takehiko Tsukahara and Prof. Takehiko Kitamori

      Version of Record online: 6 FEB 2012 | DOI: 10.1002/anie.201200576

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      The enhancement of proton mobility in two-dimensional nanochannels fabricated on fused silica substrates has been verified for the first time by fluorescence microscopy using a pH-sensitive fluorescent probe. In their Communication on page 3573 ff., T. Kitamori and co-workers present the maximum value of the proton diffusion coefficient when the size of the extended nanochannels decreased to 180 nm, and they discuss the possible mechanism of proton transfer based on proton hopping.

  4. Back Cover

    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. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Back Cover: Enzymatically Incorporated Genomic Tags for Optical Mapping of DNA-Binding Proteins (Angew. Chem. Int. Ed. 15/2012) (page 3724)

      Soohong Kim, Anna Gottfried, Ron R. Lin, Dr. Thomas Dertinger, Andrew S. Kim, Sangyoon Chung, Dr. Ryan A. Colyer, Prof. Dr. Elmar Weinhold, Prof. Shimon Weiss and Dr. Yuval Ebenstein

      Version of Record online: 13 FEB 2012 | DOI: 10.1002/anie.201200628

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      The genome of the T7 bacteriophage can be mapped by using sequence-specific methyltransferase-induced labeling of DNA. In their Communication on page 3578 ff., E. Weinhold, S. Weiss, Y. Ebenstein, and co-workers show that the location of RNA polymerases that are bound to DNA can be visualized as a linear optical barcode, which allows structural variations in genomic DNA to be analyzed and provides an extra layer of contextual information about the genome at the single-molecule level.

  5. Graphical Abstract

    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. Minireview
    13. Review
    14. Communications
    15. Preview
  6. News

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
  7. Author Profile

    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. Minireview
    13. Review
    14. Communications
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    1. Warren E. Piers (page 3514)

      Version of Record online: 9 FEB 2012 | DOI: 10.1002/anie.201200052

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      “If I were not a scientist, I would be a chef or sommelier. My favorite place on earth is the summit of any mountain …” This and more about Warren E. Piers can be found on page 3514.

  8. News

    1. Top of page
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    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
    15. Preview
  9. Book Review

    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. Minireview
    13. Review
    14. Communications
    15. Preview
    1. Crystal Engineering. A Textbook. By Gautam R. Desiraju, Jagadese J. Vittal and Arunachalam Ramanan. (page 3516)

      Dario Braga

      Version of Record online: 14 MAR 2012 | DOI: 10.1002/anie.201200277

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      World Scientific Publishing, Singapore, 2011. 232 pp., softcover, € 99.00.—ISBN 978-9814338752

  10. Highlights

    1. Top of page
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    6. Graphical Abstract
    7. News
    8. Author Profile
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    10. Book Review
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    12. Minireview
    13. Review
    14. Communications
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    1. Mesoporous Materials

      Mesoporous Materials in Peptidome Analysis (pages 3518–3519)

      Feng Li, Brittany Dever, Dr. Hongquan Zhang, Prof. Xing-Fang Li and Prof. X. Chris Le

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201107849

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      Peptide profiles: The use of mesoporous materials, such as ordered mesoporous carbon, improves the efficiency and selectivity of peptide extraction for profiling complicated samples. Controling the pore size of such mesoporous materials during synthesis allows specific molecular weight cut-offs to be introduced, which can eliminate a large number of interfering entities, such as serum proteins.

    2. π-Conjugated Polymers

      Semiconducting Polymers Prepared by Direct Arylation Polycondensation (pages 3520–3523)

      Prof. Dr. Antonio Facchetti, Prof. Dr. Luigi Vaccaro and Prof. Dr. Assunta Marrocchi

      Version of Record online: 22 MAR 2012 | DOI: 10.1002/anie.201200199

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      Two flavors of π: Semiconducting π-conjugated polymers may open new opportunities for the fabrication of ecofriendly, inexpensive optoelectronic devices. These materials can be prepared by direct arylation polycondensation, a straightforward approach that generates little waste and no toxic by-products.

  11. Minireview

    1. Top of page
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    6. Graphical Abstract
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    8. Author Profile
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    10. Book Review
    11. Highlights
    12. Minireview
    13. Review
    14. Communications
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    1. Fingerprinting

      Advances in Fingerprint Analysis (pages 3524–3531)

      Dr. Pompi Hazarika and Prof. David A. Russell

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/anie.201104313

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      Reading the small print: The detection of analytes of forensic importance such as drugs of abuse and explosives from a person's fingerprint together with the ability to identify that person is an important development in forensic science. This Minireview highlights the advances in this area of research, such as the use of nanoparticles, magnetic particles, quantum dots, as well as mass spectrometry, and spectroscopy.

  12. Review

    1. Top of page
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    14. Communications
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    1. Chemical Sensors

      The Art of Fluorescence Imaging with Chemical Sensors (pages 3532–3554)

      Priv.-Doz. Dr. Michael Schäferling

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/anie.201105459

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      The art of sensorship: Fluorescence imaging methods in combination with optical chemical sensors enable the visualization of flows on surfaces (see picture), temperature gradients, and the two-dimensional distribution of certain chemical species (O2, H+, metal ions, H2O2) at an interface. This Review highlights the design of sensor materials, including nanoprobes, and the development of multiple sensors and their signal readout.

  13. Communications

    1. Top of page
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    10. Book Review
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    12. Minireview
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    14. Communications
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    1. Nanostructures

      Reversibly Shape-Shifting Organic Optical Waveguides: Formation of Organic Nanorings, Nanotubes, and Nanosheets (pages 3556–3561)

      Naisa Chandrasekhar and Prof. Dr. Rajadurai Chandrasekar

      Version of Record online: 17 JAN 2012 | DOI: 10.1002/anie.201106652

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      Shape-shifting: A method for reversibly transforming the shape of organic waveguides to form 2D nanosheets, 1D nanotubes, and 0D nanorings has been developed. The nanosheets can be turned into nanotubes and subsequently into nanorings by adding water to the solvent, whereas ultrasonication changes the nanotubes back into nanosheets. Both nanotubes and nanosheets act as waveguides and change the direction of incident laser light in a shape-dependent manner.

    2. Biosensors

      Plasmon Shaping by using Protein Nanoarrays and Molecular Lithography to Engineer Structural Color (pages 3562–3566)

      Alasdair W. Clark and Jonathan M. Cooper

      Version of Record online: 24 JAN 2012 | DOI: 10.1002/anie.201108007

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      Naked-eye detection: The versatility of direct-write nanolithography was combined with the unrivaled resolution and selectivity of molecular self-assembly to show, for the first time, the molecularly mediated placement, with nanometer accuracy, of single Au nanoparticles within a plasmonic array. In doing so, a coupled plasmonic systems was created which allowed colorimetric, naked-eye detection of protein–protein binding at extreme sensitivities.

    3. Glycoprotein Synthesis

      Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-type Disialyloligosaccharide (pages 3567–3572)

      Masumi Murakami, Dr. Ryo Okamoto, Dr. Masayuki Izumi and Prof. Dr. Yasuhiro Kajihara

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/anie.201109034

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      New and improved: New reaction conditions for tert-Boc-based solid-phase peptide synthesis make acid-labile sialyloligosaccharyl peptide α-thioesters accessible. To demonstrate this, a sialyloligosaccharyl-erythropoietin glycoform (see picture) with 166 amino acid residues was synthesized.

    4. Proton Mobility

      Enhancement of Proton Mobility in Extended-Nanospace Channels (pages 3573–3577)

      Hiroyuki Chinen, Dr. Kazuma Mawatari, Dr. Yuriy Pihosh, Kyojiro Morikawa, Dr. Yutaka Kazoe, Dr. Takehiko Tsukahara and Prof. Takehiko Kitamori

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/anie.201104883

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      Channeling of mobility: A new method for the direct measurement of proton mobilities based on a pH-sensitive fluorescence probe is described. The results verify the enhancement of proton mobility in two-dimensional extended nanospace channels and contribute to a deeper understanding of ion-transport processes inside nanochannels.

    5. Genomic Imaging

      Enzymatically Incorporated Genomic Tags for Optical Mapping of DNA-Binding Proteins (pages 3578–3581)

      Soohong Kim, Anna Gottfried, Ron R. Lin, Dr. Thomas Dertinger, Andrew S. Kim, Sangyoon Chung, Dr. Ryan A. Colyer, Prof. Dr. Elmar Weinhold, Prof. Shimon Weiss and Dr. Yuval Ebenstein

      Version of Record online: 16 FEB 2012 | DOI: 10.1002/anie.201107714

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      All smiles: Sequence-specific methyltransferase-induced labeling of DNA (SMILing DNA) creates a fluorescence pattern of the T7 bacteriophage genome (see picture). The pattern is visualized as a linear optical barcode showing the genomic location of individual RNA polymerases bound to the DNA. The precision of the measurement presents new opportunities for contextual genomic research on the single-molecule level.

    6. Unstable Borohydrides

      Screening of Metal Borohydrides by Mechanochemistry and Diffraction (pages 3582–3586)

      Dr. Dorthe B. Ravnsbæk, Lise H. Sørensen, Prof. Yaroslav Filinchuk, Prof. Flemming Besenbacher and Prof. Torben R. Jensen

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201106661

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      Ay, there's the rub: The formation of cadmium-based borohydrides is screened by mechanochemical synthesis using various reactants in different ratios. Sequential in situ variable-temperature diffraction studies provide simultaneous information about composition, structure, decomposition pathways, and properties of the compounds.

    7. Cage Compounds

      Chemistry at the Nanoscale: Synthesis of an N@C60–N@C60 Endohedral Fullerene Dimer (pages 3587–3590)

      B. J. Farrington, Dr. M. Jevric, Dr. G. A. Rance, Dr. A. Ardavan, Prof. A. N. Khlobystov, Prof. G. A. D. Briggs and Dr. K. Porfyrakis

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201107490

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      Rattling the cage: The rapid one-pot double 1,3-dipolar cycloaddition reaction of the rare endohedral fullerene N@C60 to an oligo(p-phenylene polyethylene) bis(aldehyde) using a novel amino acid derivative as an anchoring group is reported. The method provides the first example of a chemically linked, two-spin-center N@C60–N@C60 molecule (see picture). Assessment of this platform as an element of a quantum computing register is attractive.

    8. Lithium–Sulfur Battery

      Spherical Ordered Mesoporous Carbon Nanoparticles with High Porosity for Lithium–Sulfur Batteries (pages 3591–3595)

      Jörg Schuster, Guang He, Benjamin Mandlmeier, Taeeun Yim, Kyu Tae Lee, Prof. Dr. Thomas Bein and Prof. Dr. Linda F. Nazar

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201107817

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      Superior cathode material: Spherical ordered mesoporous carbon nanoparticles featuring very high inner porosity (pore volume of 2.32 cm3 g−1 and surface area of 2445 m2 g−1) were synthesized in a two-step casting process. They were successfully applied as cathode material in Li-S batteries, where they showed high reversible capacity up to 1200 mA h g−1 and excellent cycling efficiency.

    9. Mechanochemistry

      Mechanoradicals Created in “Polymeric Sponges” Drive Reactions in Aqueous Media (pages 3596–3600)

      Dr. H. Tarik Baytekin, Dr. Bilge Baytekin and Prof. Bartosz A. Grzybowski

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108110

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      Squeezing out the energy: Macroscopically reversible deformation of polymers in contact with water produces H2O2 in quantities that are sufficient to drive small-scale chemical syntheses. The amount of mechanosynthesized H2O2 scales with the polymer–water interfacial area, and the efficiency of the mechanical-to-chemical energy transduction can be as high as 30 % for soft, porous polymer “sponges”.

    10. Photonic Crystals

      Fabrication of Robust Optical Fibers by Controlling Film Drainage of Colloids in Capillaries (pages 3601–3605)

      Dr. Shin-Hyun Kim, Hyerim Hwang and Prof. Seung-Man Yang

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108324

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      Photonic crystal fibers have been created using the spontaneous crystallization of colloidal particles in a photocurable resin coated on the inner wall of microcapillaries. The controlled deposition of films on the microcapillaries allows the thickness and number of layers in the photonic crystal fibers to be controlled. A stop band in a colloidal photonic crystal fiber can enhance the efficiency of light guidance (see picture).

    11. Peptide Ligations

      Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins (pages 3606–3610)

      Dr. Brendan L. Wilkinson, Robin S. Stone, Chantelle J. Capicciotti, Dr. Morten Thaysen-Andersen, Prof. Jacqueline M. Matthews, Prof. Nicolle H. Packer, Prof. Robert N. Ben and Dr. Richard J. Payne

      Version of Record online: 2 MAR 2012 | DOI: 10.1002/anie.201108682

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      Don't freeze! A native chemical ligation–desulfurization strategy has been employed for the convergent synthesis of a library of defined antifreeze glycopeptides and glycoproteins (AFGPs) ranging in size from 1.2 to 19.5 kDa (see picture). These AFGPs possessed the secondary structure of a polyproline type II helix and exhibited significant ice recrystallization inhibition and thermal hysteresis activity.

    12. Ceria Foams

      Ceria Foam with Atomically Thin Single-Crystal Walls (pages 3611–3615)

      Jun Xing, Dr. Hai Feng Wang, Dr. Chen Yang, Dong Wang, Prof. Hui Jun Zhao, Prof. Guan Zhong Lu, Prof. Dr. P. Hu and Prof. Dr. Hua Gui Yang

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201108708

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      All in a lather: A three-dimensional CeO2 foam with long-range ultrathin (4–8 Å) single-crystalline walls was synthesized successfully by thermal decomposing CeGeO4 crystals under an NH3 atmosphere. First-principles calculations were also performed to understand the feasibility and reaction pathways of thermal decomposition of CeGeO4. Scale bar: 200 nm.

    13. Zeolite Catalysis

      X-ray Imaging of Zeolite Particles at the Nanoscale: Influence of Steaming on the State of Aluminum and the Methanol-To-Olefin Reaction (pages 3616–3619)

      Luis R. Aramburo, Dr. Emiel de Smit, Dr. Bjørnar Arstad, Matti M. van Schooneveld, Dr. Linn Sommer, Dr. Amélie Juhin, Dr. Tadahiro Yokosawa, Prof. Dr. Henny W. Zandbergen, Prof. Dr. Unni Olsbye, Prof. Dr. Frank M. F. de Groot and Prof. Dr. Bert M. Weckhuysen

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201109026

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      Zeolites in the spotlight: A combination of scanning transmission X-ray microscopy (see picture) and bulk methods give nanoscale chemical insight in the distribution of Al and C within ZSM-5 zeolites during methanol-to-olefin reactions. The distinct catalyst performances could be related to differences in the spatial distribution of the hydrocarbons.

    14. Riboswitches

      Orthogonal Riboswitches for Tuneable Coexpression in Bacteria (pages 3620–3624)

      Dr. Neil Dixon, Dr. Christopher J. Robinson, Dr. Torsten Geerlings, Dr. John N. Duncan, Dr. Sheona P. Drummond and Prof. Jason Micklefield

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201109106

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      Orthogonal gene control: Orthogonal riboswitches can be deployed in the same bacterial cell to independently control the coexpression of multiple genes in a dose-dependent response to distinct synthetic small molecules. This technique allows convenient access to highly dynamic expression landscapes and desirable protein stoichiometries.

    15. Linkage Isomerism

      Distal Pocket Control of Nitrite Binding in Myoglobin (pages 3625–3627)

      Dr. Jun Yi, Dr. Leonard M. Thomas and Dr. George B. Richter-Addo

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201200010

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      Who is in charge? Nitrite linkage isomerism in the same heme protein occurs as a function of the compound preparation method. An N-bound nitrite conformation is achieved when a pre-formed iron chlorin–nitrite model compound is inserted into apoMb. In contrast, an O-bound nitrite conformation is evident when nitrite is added to the chlorin-substituted Mb. The results suggest that the Mb distal pocket is in charge of directing the ligand binding mode.

    16. Colloidal Particles

      Wet-Chemical Synthesis of Amphiphilic Rodlike Silica Particles and their Molecular Mimetic Assembly in Selective Solvents (pages 3628–3633)

      Dr. Jie He, Binyu Yu, Matt J. Hourwitz, Yijing Liu, Maria Teresa Perez, Prof. Jun Yang and Prof. Zhihong Nie

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201105821

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      Flowers and stars: A wet-chemical method was developed to synthesize amphiphilic rodlike silica particles with hydrophilic (green in picture) and hydrophobic (red) blocks. The self-assembly of the amphiphilic rodlike particles leads to various structures including planar monolayers, bundle micelles, flower micelles, star micelles (right in picture), and reverse micelles (left) depending on the properties of the rods and the nature of the solvent.

    17. Metallacyclobutanes

      Preparation of 2-Azarhodacyclobutanes by Rhodium(I)–Olefin Oxidation (pages 3634–3637)

      Alexander Dauth and Prof. Jennifer A. Love

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201107669

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      AmAZAing metallacycles: Azarhodacyclobutane was prepared by oxidation of RhI–olefin complex 1 (see Scheme; Ts=p-toluenesulfonyl). Both isomers 2 a and 2 b were isolated and characterized by NMR spectroscopy and mass spectrometry; their configurations were unambiguously established by NOE experiments.

    18. Cross-Coupling

      Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary α-Carbonyl Alkyl Bromides (pages 3638–3641)

      Chao Liu, Shan Tang, Dong Liu, Jiwen Yuan, Liwei Zheng, Lingkui Meng and Prof. Aiwen Lei

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108350

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      Ni made it! A novel Heck-type reaction of secondary and tertiary α-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct α-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving NiI/NiII is proposed based on our experimental results. EWG=electron-withdrawing group.

    19. Synthetic Methods

      Copper-Catalyzed Amination of Arylboronates with N,N-Dialkylhydroxylamines (pages 3642–3645)

      Naoki Matsuda, Dr. Koji Hirano, Prof. Dr. Tetsuya Satoh and Prof. Dr. Masahiro Miura

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108773

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      A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan–Lam-type coupling.

    20. Homogeneous Catalysis

      Dehydrogenation of Diamine–Monoboranes to Cyclic Diaminoboranes: Efficient Ruthenium-Catalyzed Dehydrogenative Cyclization (pages 3646–3648)

      Dr. Christopher J. Wallis, Dr. Hellen Dyer, Dr. Laure Vendier, Dr. Gilles Alcaraz and Dr. Sylviane Sabo-Etienne

      Version of Record online: 15 FEB 2012 | DOI: 10.1002/anie.201108874

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      Remote control: The title reaction is the first example of a catalyzed dehydrogenative cyclization (CDC) of diamine–monoboranes to give cyclic diaminoboranes. The cyclization reaction is strongly dependent on the nature of the substitution pattern at the remote amino group.

    21. Synthetic Methods

      Enantioselective Oxidative Cross-Dehydrogenative Coupling of Tertiary Amines to Aldehydes (pages 3649–3652)

      Dr. Junmin Zhang, Dr. Bhoopendra Tiwari, Chong Xing, Xingkuan Chen and Prof. Dr. Yonggui Robin Chi

      Version of Record online: 2 MAR 2012 | DOI: 10.1002/anie.201109054

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      Cooperative catalysts: An enantioselective and direct oxidative coupling of aldehydes to tertiary amines to give β-amino alcohols is described. Catalyzed by copper(II), the reaction proceeds to give a racemic mixture of products; however, by using a combination of copper(II) and a chiral amine catalyst, the reaction gives the desired products with high enantioselectivity (see scheme).

    22. Asymmetric Catalysis

      Dihydropyridones: Catalytic Asymmetric Synthesis, N- to C-Sulfonyl Transfer, and Derivatizations (pages 3653–3657)

      Dr. Carmen Simal, Dr. Tomas Lebl, Prof. Alexandra M. Z. Slawin and Dr. Andrew D. Smith

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201109061

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      Benzotetramisole (1) promotes the reaction of ammonium enolates derived from arylacetic acids with N-tosyl-α,β-unsaturated ketimines, thus giving dihydropyridones with high diastereo- and enantiocontrol (see scheme). These products readily undergo N- to C-sulfonyl photoisomerization and are derivatized to afford stereodefined piperidines and tetrahydropyrans.

    23. Hydrides in Biology

      Characterization of the Fe[BOND]H Bond in a Three-Coordinate Terminal Hydride Complex of Iron(I) (pages 3658–3662)

      Karen P. Chiang, Dr. Christopher C. Scarborough, Dr. Masaki Horitani, Dr. Nicholas S. Lees, Dr. Keying Ding, Thomas R. Dugan, Dr. William W. Brennessel, Eckhard Bill, Prof. Brian M. Hoffman and Prof. Patrick L. Holland

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201109204

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      Three's company: Iron(I) hydride complexes are presented (see picture; N blue, O red) that are the first monomeric open-shell hydride complexes to be crystallographically verified as being three-coordinate at the metal. Backbonding into diketiminate π* orbitals stabilizes the low oxidation state. The Fe[BOND]H bonding has been analyzed using electron-nuclear double resonance (ENDOR).

    24. Synthetic Methods

      Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction (pages 3663–3667)

      Jesse R. McAtee, Sara E. S. Martin, Derek T. Ahneman, Keywan A. Johnson and Prof. Donald A. Watson

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201200060

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      Installing silicon is easy! A high-yielding protocol for the palladium-catalyzed silylation of terminal alkenes is reported. This method allows facile conversion of styrenes to E-β-silyl styrenes by using iodotrimethylsilane (TMSI) or chlorotrimethylsilane/lithium iodide (see scheme). Terminal allyl silanes with good E/Z ratios are also readily accessed from α-olefins.

    25. Azidocarbonylation

      Palladium-Catalyzed Aromatic Azidocarbonylation (pages 3668–3672)

      Fedor M. Miloserdov and Prof. Vladimir V. Grushin

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201200078

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      Aryl iodides smoothly react with NaN3 and CO in the presence of a Pd/Xantphos catalyst to give aroyl azides (ArCON3) in 75–92 % yield. The reaction occurs under mild reaction conditions (1 atm, 20–50 °C) and exhibits high functional-group tolerance. (Xantphos=9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)

    26. Reduction of Benzenes

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      Electron Transfer to Benzenes by Photoactivated Neutral Organic Electron Donor Molecules (pages 3673–3676)

      Elise Cahard, Prof. Dr. Franziska Schoenebeck, Jean Garnier, Sylvain P. Y. Cutulic, Dr. Shengze Zhou and Prof. Dr. John A. Murphy

      Version of Record online: 2 MAR 2012 | DOI: 10.1002/anie.201200084

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      Powerful reduction reactions: Simple organic electron donors, composed solely of the elements carbon, hydrogen, and nitrogen, reduce ground-state benzene rings to their radical anions by electron transfer upon photoactivation (DMF=dimethylformamide).

    27. Hydroheteroarylation

      A Versatile Rhodium(I) Catalyst System for the Addition of Heteroarenes to both Alkenes and Alkynes by a C[BOND]H Bond Activation (pages 3677–3681)

      Jaeyune Ryu, Dr. Seung Hwan Cho and Prof. Dr. Sukbok Chang

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201200120

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      Rhod to Addition: A highly efficient and convenient rhodium catalyst system was developed for the title transformation. A base co-catalyst was found to facilitate the key arene C[BOND]H bond-activation step and substrate scope was very broad, including both electron-deficient pyridine N-oxides, and electron-rich azoles. The catalytic system was effective for the hydroheteroarylation of both alkenes and alkynes and gave excellent regio- and stereoselectivity.

    28. Polymerization

      Palladium(0)-Catalyzed Synthesis of Cross-Conjugated Polymers: Transformation into Linear-Conjugated Polymers through the Diels–Alder Reaction (pages 3682–3685)

      Noriyuki Nishioka, Dr. Shotaro Hayashi and Prof. Toshio Koizumi

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201200303

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      Making the shift: The title reaction of a propargylic bis(carbonate) with diboron compounds leads to new cross-conjugated polymers 1 having 2,3-butadienylene moieties. 1 is then converted into the linear-conjugated polymers 2 through a Diels–Alder reaction. The fluorescent spectra of the cis-linked polymers 2 show large Stokes shifts compared to those of the cross-conjugated polymer precursors 1.

    29. Polyoxometalates

      Cyanosilylation of Carbonyl Compounds with Trimethylsilyl Cyanide Catalyzed by an Yttrium-Pillared Silicotungstate Dimer (pages 3686–3690)

      Dr. Yuji Kikukawa, Dr. Kosuke Suzuki, Midori Sugawa, Tomohisa Hirano, Dr. Keigo Kamata, Dr. Kazuya Yamaguchi and Prof. Dr. Noritaka Mizuno

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/anie.201200486

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      An yttrium-pillared silicotungstate dimer (see picture) catalyzes the cyanosilylation of structurally diverse ketones and aldehydes with trimethylsilyl cyanide (TMSCN). The reactions proceed selectively and afford the corresponding cyanohydrin trimethylsilyl ethers. The catalytic performance is significant, in particular for aldehydes, with a turnover number of 18 000 and a turnover frequency of 540 000 h−1 for n-hexanal.

    30. Coordination Chemistry

      Synthesis and Unexpected Coordination of a Silicon(II)-Based SiCSi Pincerlike Arene to Palladium (pages 3691–3694)

      Dipl.-Chem. Wenyuan Wang, Prof. Dr. Shigeyoshi Inoue, Dr. Elisabeth Irran and Prof. Dr. Matthias Driess

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201200632

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      SiCSi to pick up a metal: A bis(silylene) SiCSi pincerlike arene 1 (see scheme) has been synthesized through salt metathesis reaction of the dilithium salt of 2,4-di-tert-butyl-resorcinolate with the respective chloro silylene precursor [LSiCl]. Remarkably, 1 reacts with Pd(PPh3)4 in a molar ratio of 2:1 under loss of all phosphine ligands to give the pincer complex 2.

    31. Small-Ring Systems

      Cyclic SiS2: A New Perspective on the Walsh Rules (pages 3695–3698)

      Leonie Anna Mück, Dr. Valerio Lattanzi, Dr. Sven Thorwirth, Dr. Michael C. McCarthy and Prof. Dr. Jürgen Gauss

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201108982

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      A joint effort: By means of high-resolution rotational spectroscopy and highly accurate quantum-chemical calculations, the first observation and characterization of cyclic SiS2 was achieved. This provides a new perspective on the Walsh rules: Although the cyclic form of SiS2 is a local and not the global minimum, cyclic isomers of sixteen-electron triatomics containing second or even higher row elements are experimentally accessible.

    32. Oxidative Olefin Arylation

      Oxidative Heck Arylation for the Stereoselective Synthesis of Tetrasubstituted Olefins Using Nitroxides as Oxidants (pages 3699–3702)

      Zhiheng He, Dr. Sylvia Kirchberg, Dr. Roland Fröhlich and Prof. Dr. Armido Studer

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201108211

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      One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd-catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl-substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z-Tamoxifen.

    33. Methane Activation

      Direct Conversion of Methane into Formaldehyde Mediated by [Al2O3].+ at Room Temperature (pages 3703–3707)

      Dr. Zhe-Chen Wang, Dipl.-Chem. Nicolas Dietl, Dipl.-Chem. Robert Kretschmer, Jia-Bi Ma, Dr. Thomas Weiske, Dr. Maria Schlangen and Prof. Dr. Helmut Schwarz

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201200015

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      Just one step: Reactivity studies demonstrate that in the gas phase [Al2O3].+ clusters can efficiently conduct the direct conversion of CH4 into CH2O at room temperature (see scheme). The reaction mechanism is highly complex involving oxygen-atom transfer and a double hydrogen-atom transfer.

    34. Amide Mimics

      Braces for the Peptide Backbone: Insights into Structure–Activity Relationships of Protease Inhibitor Mimics with Locked Amide Conformations (pages 3708–3712)

      Marco Tischler, Daichi Nasu, Martin Empting, Dr. Stefan Schmelz, Prof. Dr. Dirk W. Heinz, Philipp Rottmann, Prof. Dr. Harald Kolmar, Prof. Dr. Gerd Buntkowsky, Dr. Daniel Tietze and Dr. Olga Avrutina

      Version of Record online: 28 FEB 2012 | DOI: 10.1002/anie.201108983

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      Flower power: Potent protease inhibitors containing triazolyl mimics of cis and trans backbone amides were engineered based on the structure of the sunflower trypsin inhibitor 1. The biologically relevant cis-Pro motif was successfully replaced with a non-prolyl unit. High-resolution crystal structures of 1,4- and 1,5-disubstituted 1,2,3-triazolyl peptidomimetics can serve in the design of tailor-made Bowman–Birk inhibitors.

    35. Trifluoromethylation

      Ortho-Trifluoromethylation of Functionalized Aromatic Triazenes (pages 3713–3715)

      Dipl.-Chem. Andreas Hafner and Prof. Dr. Stefan Bräse

      Version of Record online: 8 FEB 2012 | DOI: 10.1002/anie.201107414

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      A silver key to add CF3: In presence of in situ generated AgCF3, it is possible to trifluoromethylate aromatic triazenes in high ortho selectivity and good yields by means of a C[BOND]H substitution (see scheme). Owing to the further transformation possibilities offered by triazenes, a variety of CF3-substituted building blocks are then accessible.

    36. Selective Cell Adhesion

      Cell Adhesion Behavior on Enantiomerically Functionalized Zeolite L Monolayers (pages 3716–3720)

      Dr. Jehad El-Gindi, Kathrin Benson, Prof. Luisa De Cola, Prof. Hans-Joachim Galla and Dr. Nermin Seda Kehr

      Version of Record online: 1 MAR 2012 | DOI: 10.1002/anie.201109144

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      Zeolite L nanocrystals can be enantioselectively functionalized and their enantiomorphous SAMs prepared. The adhesion behavior of different cells with these new biomaterials was studied according to the respective surface chirality. This concept was demonstrated for cell separation of primary cells and cell lines (see picture).

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