Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 32

August 11, 2006

Volume 45, Issue 32

Pages 5227–5395

  1. Cover Picture

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
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    1. Cover Picture: Crystalline Nanoflowers with Different Chemical Compositions and Physical Properties Grown by Limited Ligand Protection (Angew. Chem. Int. Ed. 32/2006) (page 5227)

      Arun Narayanaswamy, Huifang Xu, Narayan Pradhan and Xiaogang Peng

      Article first published online: 7 AUG 2006 | DOI: 10.1002/anie.200690109

      Single-crystal nanoflowers …… (shown in the cover picture) are grown by a general approach called limited ligand protection (LLP). LLP destabilizes the primary nanoparticles and promotes their three-dimensionally oriented attachment into complex nanostructures. LLP offers a low degree of ligand protection and can be used to yield both nanodots and nanoflowers. For more information see the Communication by X. Peng and co-workers on page 5361 ff.

  2. Graphical Abstract

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  3. News

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    4. News
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  4. Book Reviews

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  5. Highlights

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    1. Enantioselective Palladium-Catalyzed Decarboxylative Allylic Alkylations (pages 5246–5248)

      Shu-Li You and Li-Xin Dai

      Article first published online: 21 JUL 2006 | DOI: 10.1002/anie.200601889

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      Triple A: Recent developments in palladium-catalyzed decarboxylative asymmetric allylic alkylation (AAA) reactions provide easy access to highly enantioenriched ketones with α-positioned quaternary or tertiary carbon stereocenters under mild conditions.

    2. Intermolecular Coupling of Motion under Photochemical Control (pages 5249–5251)

      Françisco M. Raymo

      Article first published online: 26 JUL 2006 | DOI: 10.1002/anie.200602516

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      An interesting twist: A system in which controlled motion in one part of the molecule is transmitted as rotary motion in a bound guest molecule represents a significant advance toward artificial molecular machines. Light initiates a scissoring motion in the host molecule, a ferrocene unit attached to an azobenzene handle (red) and to two Zn porphyrin units (red squares), which twists the bidentate guest compound (blue part).

  6. Review

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    1. Transition-Metal Complexes of Boron—New Insights and Novel Coordination Modes (pages 5254–5274)

      Holger Braunschweig, Carsten Kollann and Daniela Rais

      Article first published online: 7 JUL 2006 | DOI: 10.1002/anie.200600506

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      Glory B! The number and variety of compounds that feature a transition-metal–boron bond have grown significantly in the past fifteen years, and a range of hitherto unknown coordination modes of boron-based ligands have been realized (see scheme). This review article highlights the most useful synthetic strategies for the generation of transition-metal–boron bonds and discusses the most recent and intriguing compounds that have been reported.

  7. Communications

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    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
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    1. Integrated Microfluidics for Parallel Screening of an In Situ Click Chemistry Library (pages 5276–5281)

      Jinyi Wang, Guodong Sui, Vani P. Mocharla, Rachel J. Lin, Michael E. Phelps, Hartmuth C. Kolb and Hsian-Rong Tseng

      Article first published online: 6 JUL 2006 | DOI: 10.1002/anie.200601677

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      State-of-the-art: Automated chemical reaction circuits have been demonstrated to serve as a miniaturized operation platform for the parallel screening of 32 in situ click chemistry reactions with reduced consumption of reagents. A proof-of-concept study was performed with the bovine carbonic anhydrase II (bCAII) click chemistry system.

    2. Organizing Supramolecular Functional Dye–Zeolite Crystals (pages 5282–5287)

      Arantzazu Zabala Ruiz, Huanrong Li and Gion Calzaferri

      Article first published online: 11 JUL 2006 | DOI: 10.1002/anie.200504286

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      Unidirectional antennas: Dyes in the open channels of the robust monolayers of zeolite L crystals on a glass substrate create a hierarchical order (see picture). Coupling the dye-loaded monolayers to an external acceptor or donor stopcock dye at the channel ends enables electronic excitation energy to be trapped from donor molecules inside the crystal or to inject it to an acceptor inside the channels.

    3. Facile Monolayer Assembly of Fluorophore-Containing Zeolite Rods in Uniform Orientations for Anisotropic Photoluminescence (pages 5288–5292)

      Jin Seok Lee, Hyunjin Lim, Kwang Ha, Hyeonsik Cheong and Kyung Byung Yoon

      Article first published online: 11 JUL 2006 | DOI: 10.1002/anie.200600075

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      Which way to turn: The tendency of microcrystals to attach to surfaces through their largest faces has resulted in two orientations of zeolite L monolayers on glass. Fluorophore-containing cylindrical and hexagonal columnar zeolite L crystals assemble into vertically and horizontally oriented monolayers, respectively, on glass plates (see pictures). The photoluminescences of the monolayers are highly anisotropic.

    4. “Click” Chemistry by Microcontact Printing (pages 5292–5296)

      Dorota I. Rozkiewicz, Dominik Jańczewski, Willem Verboom, Bart Jan Ravoo and David N. Reinhoudt

      Article first published online: 12 JUL 2006 | DOI: 10.1002/anie.200601090

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      Print and click: “Click” chemistry can be efficiently combined with microcontact printing. Synthesis in the nanoscale confinement between an elastomeric stamp and a reactive substrate leads to the desired product within a short time, without a catalyst, and under ambient conditions. As a result, 1-octadecyne could be printed onto an azido-terminated, self-assembled monolayer on a silicon oxide substrate (see scheme).

    5. Self-Assembled Signaling Aptamer DNA Arrays for Protein Detection (pages 5296–5301)

      Chenxiang Lin, Evaldas Katilius, Yan Liu, Junping Zhang and Hao Yan

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600438

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      Sticking the tiles: A DNA-tile-directed self-assembly of signaling aptamers into high-density nanoarrays allows subnanomolar detection of protein molecules by using confocal fluorescence microscopy imaging. This water-soluble aptamer microarray provides a novel strategy for developing programmable sensor arrays.

    6. Complementary Sequence Preferences of Electron-Capture Dissociation and Vibrational Excitation in Fragmentation of Polypeptide Polycations (pages 5301–5303)

      Mikhail M. Savitski, Frank Kjeldsen, Michael L. Nielsen and Roman A. Zubarev

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601240

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      Complementary cleavage: A large-scale (ca. 15 000 spectra) comparison between the cleavage sites and the preferences of collision-activated dissociation (CAD) and electron-capture dissociation (ECD) in tandem mass spectrometry has proved beyond doubt their complementary nature (see picture, red: high, blue: low). The study has also suggested the presence of a preferred N-terminal structure in gas-phase tryptic peptide dications.

    7. Self-Assembling Molecular Dumbbells: From Nanohelices to Nanocapsules Triggered by Guest Intercalation (pages 5304–5307)

      Ja-Hyoung Ryu, Ho-Joong Kim, Zhegang Huang, Eunji Lee and Myongsoo Lee

      Article first published online: 12 JUL 2006 | DOI: 10.1002/anie.200600971

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      Dumbbells that are not dumb: Dumbbell-shaped molecules based on a hexa-p-phenylene derivative self-assemble into well-defined left-handed helical fibers in aqueous solution. These helical nanofibers convert reversibly into hollow nanocapsules by intercalation of aromatic guest molecules (red spheres).

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      N-Terminal Protein Modification through a Biomimetic Transamination Reaction (pages 5307–5311)

      Joshua M. Gilmore, Rebecca A. Scheck, Aaron P. Esser-Kahn, Neel S. Joshi and Matthew B. Francis

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600368

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      One hit wonder: A biomimetic transamination reaction has been developed that employs pyridoxal-5-phosphate to modify the N terminus of proteins and peptides under mild conditions. This technique introduces a uniquely reactive carbonyl group in a single location (see scheme), thus allowing further elaboration through oxime or hydrazone formation. This modification strategy is also compatible with proteins containing a free cysteine residue.

      Corrected by:

      Corrigendum: N-Terminal Protein Modification through a Biomimetic Transamination Reaction

      Vol. 47, Issue 41, 7788, Article first published online: 24 SEP 2008

    9. High Thermal Stability of 5′-5′-Linked Alternate Hoogsteen Triplexes at Physiological pH (pages 5311–5315)

      Vyacheslav V. Filichev, Mads C. Nielsen, Niels Bomholt, Carsten H. Jessen and Erik B. Pedersen

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601127

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      DNA glue: A new alternate-strand linker (shown in green) has been synthesized that can connect two short DNA sequences (5- and 9-mers, yellow) and bind to double-stranded DNA through major-groove interactions at pH 7.2 (see model). The resulting triple helices have high thermal stabilities as shown by melting temperatures exceeding 37 °C at physiological pH values.

    10. Novel Nanocomposite Pt/RuO2x H2O/Carbon Nanotube Catalysts for Direct Methanol Fuel Cells (pages 5315–5319)

      Lin Cao, Frieder Scheiba, Christina Roth, Franz Schweiger, Carsten Cremers, Ulrich Stimming, Hartmut Fuess, Liquan Chen, Wentao Zhu and Xinping Qiu

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601301

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      The perfect combination: RuO2x H2O for donating and accepting protons and electrons and carbon nanotubes (CNTs) for compensating the loss of electron conductivity caused by the RuO2 coating, improving the electrode microstructure, and lowering the electrode resistance. The result: superb performance of the title catalyst for direct electrooxidation of methanol.

    11. A Chemomechanical Polymer that Functions in Blood Plasma with High Glucose Selectivity (pages 5319–5322)

      George K. Samoei, Weihua Wang, Jorge O. Escobedo, Xiangyang Xu, Hans-Jörg Schneider, Robert L. Cook and Robert M. Strongin

      Article first published online: 6 JUL 2006 | DOI: 10.1002/anie.200601398

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      See the shrink: Systematic modification of poly(methyl methacrylate) leads to a chemomechanical polymer that selectively contracts in the presence of glucose at physiological levels in human blood plasma. The polymer also exhibits good reversibility allowing continuous expansion–contraction cycles.

    12. The Structure of Fractionally Charged Tetracyanobenzenen Present in [TCNB]32− (pages 5322–5326)

      Joshua D. Bagnato, William W. Shum, Mark Strohmeier, David M. Grant, Atta M. Arif and Joel S. Miller

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601070

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      On a reduced charge: The reduction of 1,2,4,5-tetracyanobenzene (TCNB) with tetrakis(dimethylamino)ethylene (TDAE) forms [TDAE][TCNB]3⋅MeCN. Characterization reveals that the [TDAE]2+ ion is present, and that TCNB is reduced forming diamagnetic [TCNB]32−. The reduced TCNB units (see picture) are best described as [TCNB]≈0.5−[TCNB]≈1−[TCNB]≈0.5− containing fractionally charged organic species.

    13. Room-Temperature Organic-Based Magnet (Tc≈50 °C) Containing Tetracyanobenzene and Hexacarbonylvanadate(−I) (pages 5326–5331)

      Michelle L. Taliaferro, Matthew S. Thorum and Joel S. Miller

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600988

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      A matter of attraction: A magnet of nominal VII(TCNB)1.5(TCNB0)x−1.5[V−I(CO)v]0.5z solvent composition (Tc=325 K) is synthesized and its magnetic properties examined. Its amorphous nature makes it difficult to determine its complex composition and structure. It is a soft ferrimagnet with a coercive field of 7 Oe. The picture shows a sample in a capillary tube being attracted to a magnet at room temperature.

    14. Fixation of CO2 by Magnesium Cations: A Reinterpretation (pages 5331–5334)

      Harminder Phull, Davide Alberti, Ilia Korobkov, Sandro Gambarotta and Peter H. M. Budzelaar

      Article first published online: 20 JUL 2006 | DOI: 10.1002/anie.200601834

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      OCO or NCO? The case of irreversible CO2 coordination to Mg cations has been revisited and reinterpreted as a more straightforward case of reaction of CO2 with silazanate ligands and formation of coordinated NCO ligands on the basis of DFT calculations, NMR, and chemical-degradation experiments.

    15. Formal Synthesis of (+)-Catharanthine (pages 5334–5336)

      Lionel Moisan, Pierre Thuéry, Marc Nicolas, Eric Doris and Bernard Rousseau

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601307

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      Madagascan periwinkle is the current source of (+)-catharanthine, the crucial building block of the major antitumor agent vinorelbine. In the formal synthesis of this natural product, the key intermediate 1 described by Büchi and co-workers was obtained in virtually optically pure form from L-serine. The strategy presented may be viewed as a general synthetic approach to optically active isoquinuclidines.

    16. Carbon Monoxide Inside an Open-Cage Fullerene (pages 5337–5340)

      Sho-ichi Iwamatsu, Christopher M. Stanisky, R. James Cross, Martin Saunders, Naomi Mizorogi, Shigeru Nagase and Shizuaki Murata

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601241

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      Inside the ball: An endohedral carbon monoxide complex of an open-cage derivative of a [60]fullerene is prepared by insertion of CO through the opening. The incorporation of CO within the C60 cage is confirmed by mass spectrometry as well as 13C NMR and IR spectroscopic studies. The product releases CO under ambient conditions to recover a mixture of the endohedral water complex and the empty cage.

    17. Cooperative Self-Assembly of Adenosine and Uridine Nucleotides on a 2D Synthetic Template (pages 5340–5344)

      Dmitry S. Turygin, Michael Subat, Oleg A. Raitman, Vladimir V. Arslanov, Burkhard König and Maria A. Kalinina

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600450

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      Double plane: Base pairing mediates sterically induced, cooperative self-assembly of complementary nucleotides on a template formed from amphiphilic bis(ZnII–cyclen) derivatives ordered on thiolated surface. Real-time monitoring of binding events proved precise harboring of equal amounts of A and U nucleotides from their arbitrary combinations in solution into planar bilayers (see picture).

    18. Selective Inhibition of Glycosidases by Feedback Prodrugs (pages 5345–5348)

      Jun Guo, Jinkeng Asong and Geert-Jan Boons

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600808

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      In the loop: A novel concept for the selective inhibition of glycosidases has been developed whereby a glycosidase inhibitor is released by glycosidase-mediated hydrolysis of a prodrug, which subsequently inhibits the glycosidase that initiated the release of the inhibitor.

    19. The Core and Most Useful Molecules in Organic Chemistry (pages 5348–5354)

      Kyle J. M. Bishop, Rafal Klajn and Bartosz A. Grzybowski

      Article first published online: 11 JUL 2006 | DOI: 10.1002/anie.200600881

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      The fruitful core: Organic syntheses reported in the literature from 1850 to 2004 are analyzed with mathematical tools from network theory and statistical physics. There is a set of substances (the core) from which the majority of other organic compounds can be made (see picture; red: core, blue: periphery, green: islands). Search algorithms are used to identify small optimal sets of maximally useful chemicals.

    20. Solid-State Self-Inclusion: The Missing Link (pages 5354–5358)

      Gareth O. Lloyd, Jo Alen, Martin W. Bredenkamp, Elise J. C. de Vries, Catharine Esterhuysen and Leonard J. Barbour

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601665

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      Molecular cannibalism: The concept of self-inclusion in the solid state can be subjective. A host–guest system is prepared in which the same compound (2,7-dimethyl-octa-3,5-diyne-2,7-diol) unequivocally plays both roles simultaneously.

    21. Supramolecular Assemblies of Chiral Propargylic Alcohols (pages 5358–5360)

      Marilise Hyacinth, Maksymilian Chruszcz, Ki Sung Lee, Michal Sabat, Ge Gao and Lin Pu

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200601594

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      Six pack: A hexameric supramolecular structure with alternating enantiomers is formed in the solid state from propargylic alcohols. These hexamers further assemble to form channels and cages that host solvent molecules. The synergistic cooperation of O[BOND]H⋅⋅⋅O, C[BOND]H⋅⋅⋅F[BOND]C, and π–π interactions is important in establishing the supramolecular assembly.

    22. Crystalline Nanoflowers with Different Chemical Compositions and Physical Properties Grown by Limited Ligand Protection (pages 5361–5364)

      Arun Narayanaswamy, Huifang Xu, Narayan Pradhan and Xiaogang Peng

      Article first published online: 6 JUL 2006 | DOI: 10.1002/anie.200601553

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      A varied bouquet: Crystalline nanoflowers (see picture) of compounds with different chemical and physical properties, for example, In2O3, ZnO, CoO, MnO, and ZnSe, are grown by a new approach, limited ligand protection (LLP). LLP destabilizes the primary nanoparticles and promotes their three-dimensionally oriented attachment into complex nanostructures.

    23. Synthesis of Highly Substituted N-Hydroxyindoles through 1,5-Addition of Carbon Nucleophiles to In Situ Generated Unsaturated Nitrones (pages 5364–5368)

      K. C. Nicolaou, Anthony A. Estrada, Sang Hyup Lee and Graeme C. Freestone

      Article first published online: 18 JUL 2006 | DOI: 10.1002/anie.200601808

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      As easy as 1[RIGHTWARDS ARROW]2[RIGHTWARDS ARROW]3: Generation (1[RIGHTWARDS ARROW]2) and subsequent capture (2[RIGHTWARDS ARROW]3) of the reactive α,β-unsaturated nitrone species 2 with silyl enol ethers, silanes, and stannanes leads to a facile and direct entry to a variety of highly substituted N-hydroxyindoles 3 through carbon–carbon bond formation.

    24. Reducing Product Inhibition in DNA-Template-Controlled Ligation Reactions (pages 5369–5373)

      Christian Dose, Simon Ficht and Oliver Seitz

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600464

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      Loosening the zipper: A ligation–rearrangement reaction sequence is the key to signal amplification in chemical DNA-templated ligation reactions. The rearrangement increases the flexibility of the ligation intermediate, thereby reducing the affinity of the rearranged product for the DNA template. A fluorescence-resonant-energy-transfer technique is used for convenient and product-specific real-time detection of product signals.

    25. Na6[Ge10{Fe(CO)4}8]⋅18 THF: A Centaur Polyhedron of Germanium Atoms (pages 5373–5376)

      Andreas Schnepf and Christian Schenk

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600928

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      Mythological figure: The reaction of GeBr with Na2[Fe(CO)4] yields the polyhedral Ge10 cluster compound Na6[Ge10{Fe(CO)4}8]⋅18 THF. The arrangement of the 10 germanium atoms (blue spheres in figure) in the cluster core can be described as a centaur polyhedron and therefore represents a new structural motif in germanium cluster chemistry.

    26. Thymine Oxetanes as Charge Traps for Chemical Monitoring of Nucleic Acid Mediated Transfer of Excess Electrons (pages 5376–5380)

      Thorsten Stafforst and Ulf Diederichsen

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600150

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      Detecting electrons migrating: When incorporated into nucleic acids, thymine oxetanes make it possible to monitor excess-electron transfer with remarkably high quantum yields owing to their favorable redox potentials and fast cycloreversion (see scheme; PNA=peptide nucleic acid). In a first experiment, the distance dependence of the charge transfer was investigated and found to be typical for a hopping mechanism.

    27. A Screening System for the Directed Evolution of Epoxygenases: Importance of Position 184 in P450 BM3 for Stereoselective Styrene Epoxidation (pages 5380–5383)

      Kang Lan Tee and Ulrich Schwaneberg

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200600255

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      Positively charged: A screening system for the directed evolution of epoxygenases has been developed. Validation reveals that introducing a positively charged amino acid at position 184 (see picture) results in inversion of enantioselectivity in the epoxidation of styrene. The synthetic potential of epoxygenases can now be tailored by methods of directed evolution.

    28. Topochemical Polymerization in Supramolecular Polymers of Oligopeptide-Functionalized Diacetylenes (pages 5383–5386)

      Eike Jahnke, Ingo Lieberwirth, Nikolai Severin, Jürgen P. Rabe and Holger Frauenrath

      Article first published online: 20 JUL 2006 | DOI: 10.1002/anie.200600610

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      Diacetylene macromonomers functionalized with a β-sheet-forming oligopeptide and a hydrogenated poly(isoprene) coil segment self-assembled into supramolecular polymers with a double-helical, tubular topology and a diameter of a few nanometers. Subsequent “1D topochemical polymerization” affords poly(diacetylene)s with a conjugated backbone and a high degree of biochemically relevant functionalization, as well as a defined hierarchical structure.

    29. Structural Model of the Membrane-Bound C Terminus of Lipid-Modified Human N-Ras Protein (pages 5387–5390)

      Guido Reuther, Kui-Thong Tan, Julia Köhler, Christine Nowak, André Pampel, Klaus Arnold, Jürgen Kuhlmann, Herbert Waldmann and Daniel Huster

      Article first published online: 17 JUL 2006 | DOI: 10.1002/anie.200504266

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      Solid-state NMR spectroscopy was used to determine a structural model of the backbone of the lipid anchor of membrane-bound N-Ras protein. The fully functional lipid-modified protein was obtained by ligating the expressed water-soluble N terminus with a chemically synthesized 13C-labeled lipidated peptide. After the NMR signals had been assigned by correlation experiments, a structural model was calculated from torsion angles derived from 1H and 13C chemical-shift data.

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    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
    8. Communications
    9. Preview
    1. You have free access to this content
      Preview: Angew. Chem. Int. Ed. 32/2006 (page 5395)

      Article first published online: 7 AUG 2006 | DOI: 10.1002/anie.200690111

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