Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 43

November 5, 2007

Volume 46, Issue 43

Pages 8091–8303

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Crystal Structure and Guest Uptake of a Mesoporous Metal–Organic Framework Containing Cages of 3.9 and 4.7 nm in Diameter (Angew. Chem. Int. Ed. 43/2007) (page 8091)

      Young Kwan Park, Sang Beom Choi, Hyunuk Kim, Kimoon Kim, Byoung-Ho Won, Kihang Choi, Jung-Sik Choi, Wha-Seung Ahn, Nayoun Won, Sungjee Kim, Dong Hyun Jung, Seung-Hoon Choi, Ghyung-Hwa Kim, Sun-Shin Cha, Young Ho Jhon, Jin Kuk Yang and Jaheon Kim

      Version of Record online: 26 OCT 2007 | DOI: 10.1002/anie.200790215

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      A metal-organic framework (MOF) with a hierarchical structure has been synthesized by the assembly of super tetrahedron units of Tb ions and organic tripodal linkers. The zeolite-like network (shown as stick models in the background) contains mesocages in which the smaller mesocages with diameters of 3.9 nm are fused to larger ones of diameter 4.7 nm (represented by space-filling models). The evacuated framework is robust and can accommodate gases or ferrocene molecules For more details see the Communication by J. Kim et al. on page 8230 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. Inside Cover: Homoleptic Silver(I) Acetylene Complexes (Angew. Chem. Int. Ed. 43/2007) (page 8092)

      Andreas Reisinger, Nils Trapp, Ingo Krossing, Sandra Altmannshofer, Verena Herz, Manuel Presnitz and Wolfgang Scherer

      Version of Record online: 26 OCT 2007 | DOI: 10.1002/anie.200790216

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      High up in permanent ice is where the homoleptic silver(I) acetylene complexes described by I. Krossing, W. Scherer, and co-workers in their Communication on page 8295 ff. would feel comfortable. Permanent cooling was required for synthesis, handling, and characterization. Nevertheless, even experimental charge-density studies could be carried out, which indicate a bonding situation that is intermediate between purely electrostatic and weakly covalent.

  3. Graphical Abstract

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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
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    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
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    9. Minireview
    10. Review
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      Massadine Chloride: A Biosynthetic Precursor of Massadine and Stylissadine (page 8107)

      Achim Grube, Stefan Immel, Phil S. Baran and Matthias Köck

      Version of Record online: 26 OCT 2007 | DOI: 10.1002/anie.200790221

      This article corrects:

      Massadine Chloride: A Biosynthetic Precursor of Massadine and Stylissadine1

      Vol. 46, Issue 35, 6721–6724, Version of Record online: 8 AUG 2007

  5. News

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
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    9. Minireview
    10. Review
    11. Communications
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  6. Book Reviews

    1. Top of page
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    1. The Pauling Catalogue. By Chris Petersen and Cliff Mead. (pages 8112–8113)

      George B. Kauffman

      Version of Record online: 26 OCT 2007 | DOI: 10.1002/anie.200685543

  7. Highlight

    1. Top of page
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    1. Will We Soon Be Fueling our Automobiles with Ammonia–Borane? (pages 8116–8118)

      Todd B. Marder

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200703150

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      The B all and N all? Ammonia–borane (AB, H3NBH3) contains 19.6 weight % H, and is one of the materials currently being examined as a possible H2 source for use in fuel cells to power automobiles. Challenges for this technology are noted, and recent advances, especially in the development of both transition-metal and acid catalysts which promote H2 release from AB under mild conditions, are highlighted.

  8. Minireview

    1. Top of page
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    5. Corrigenda
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    1. Fullerenes: Multitask Components in Molecular Machinery (pages 8120–8126)

      Aurelio Mateo-Alonso, Dirk M. Guldi, Francesco Paolucci and Maurizio Prato

      Version of Record online: 9 OCT 2007 | DOI: 10.1002/anie.200702725

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      A multipurpose component: Owing to their size and unique properties, fullerenes, and especially C60, have found applications in molecular machines, for example, as stoppers in rotaxanes. C60 has been introduced in molecular shuttles as an electro- and photoactive stopper that is able to induce and modulate shuttling through π–π interactions.

  9. Review

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    1. Peptide Fibrillization (pages 8128–8147)

      Ian W. Hamley

      Version of Record online: 12 OCT 2007 | DOI: 10.1002/anie.200700861

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      An important factor in many diseases based on the deposition of amyloids is the fibrillization of peptides. Furthermore, fibril formation also promises applications in bionanotechnology: fibrillar peptide hydrogels can be made for cell scaffolds and as substrates for functional and responsive biomaterials, biosensors, and nanowires. The mechanisms and kinetics of fibril formation are discussed.

  10. Communications

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. The Structure of Silicate Anions in Aqueous Alkaline Solutions (pages 8148–8152)

      Christopher T. G. Knight, Raymond J. Balec and Stephen D. Kinrade

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200702986

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      Molecular hieroglyphics: 29Si COSY NMR spectroscopy reveals the fascinating and beautiful array of aqueous silicate anions that exist in dynamic equilibrium under alkaline conditions. Six of the most abundant oligomers are shown above, with each line representing a Si-O-Si siloxane linkage.

    2. Catalyzed Dehydrogenation of Ammonia–Borane by Iridium Dihydrogen Pincer Complex Differs from Ethane Dehydrogenation (pages 8153–8156)

      Ankan Paul and Charles B. Musgrave

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702886

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      Not a bit like his brother: DFT studies show that ammonia–borane dehydrogenations by iridium pincer complexes occur by concerted hydride and proton transfer from ammonia–borane to the catalyst, not through B[BOND]H activation and subsequent β-hydride elimination from the nitrogen end, as had been suggested. Such a concerted dehydrogenation pathway does not exist for ethane, which is isoelectronic with ammonia–borane.

    3. The Enantioselective Synthesis of Phomopsin B (pages 8157–8159)

      Joshua S. Grimley, Andrew M. Sawayama, Hiroko Tanaka, Michelle M. Stohlmeyer, Thomas F. Woiwode and Thomas J. Wandless

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702537

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      Proven approach to a family of antimitotics: The total synthesis of phomopsin B, an antimitotic natural product, was achieved by assembling two fragments of equal complexity in a longest linear sequence of 26 steps. The approach features two catalytic transformations that set multiple stereocenters in single steps (red and blue boxes) and a general strategy for the preparation of dehydrated amino acids (green box).

    4. Mechanistic Studies of Proton-Donor Coordination to Samarium Diiodide (pages 8160–8163)

      Joseph A. Teprovich Jr., Marielle N. Balili, Tomislav Pintauer and Robert A. Flowers II

      Version of Record online: 7 SEP 2007 | DOI: 10.1002/anie.200702571

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      Three's a crowd: Initial coordination of diethylene glycol to SmI2 liberates THF or iodide, thus providing open coordination sites for substrates and enhancing reactivity. Concentrations of diethylene glycol that lead to coordinative saturation of SmI2 (see structure) reduce its reactivity. Replacement of a hydroxy proton with a methyl group decreases the affinity of the chelate for SmI2, resulting in a decrease in the reactivity of the complex.

    5. Cross-Linked Glycerol Dendrimers and Hyperbranched Polymers as Ionophoric, Organic Nanoparticles Soluble in Water and Organic Solvents (pages 8164–8167)

      Steven C. Zimmerman, Jordan R. Quinn, Ewelina Burakowska and Rainer Haag

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200702580

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      Like a big crown (ether): Cross-linked glycerol-based nanoparticles have been synthesized by ring-closing metathesis (RCM) of polyallyl glycerol dendrimers or hyperbranched polymers (see scheme). In organic solvents, the polyether nanoparticles show modest ionophoric abilities.

    6. Which Oxidant Is Really Responsible for Sulfur Oxidation by Cytochrome P450? (pages 8168–8170)

      Chunsen Li, Lixian Zhang, Chi Zhang, Hajime Hirao, Wei Wu and Sason Shaik

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702867

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      Clarifying a conundrum: The question of whether Compound I or Compound 0 (Cpd I or Cpd 0) is the reactive oxidant in the sulfoxidation of thiafatty acids by P450 is addressed by theory, which demonstrates that Cpd I leads to an extremely fast process, while Cpd 0 is at least six orders of magnitude slower. Most likely, thiafatty acids promote Cpd I formation even in the T[RIGHTWARDS ARROW]A mutant of P450BM3.

      Corrected by:

      Corrigendum: Which Oxidant is Really Responsible for Sulfur Oxidation by Cytochrome P450?

      Vol. 47, Issue 43, 8148, Version of Record online: 10 OCT 2008

    7. Collagen-Targeted MRI Contrast Agent for Molecular Imaging of Fibrosis (pages 8171–8173)

      Peter Caravan, Biplab Das, Stéphane Dumas, Frederick H. Epstein, Patrick A. Helm, Vincent Jacques, Steffi Koerner, Andrew Kolodziej, Luhua Shen, Wei-Chuan Sun and Zhaoda Zhang

      Version of Record online: 25 SEP 2007 | DOI: 10.1002/anie.200700700

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      A cyclic peptide specific for type I collagen is derivatized with three {Gd(dtpa)} moieties to create a molecular MRI contrast agent for fibrosis imaging. In a mouse model of myocardial infarction (heart attack), collagen levels are elevated in the infarct zone. MRI after injection of the contrast agent selectively enhances and delineates the infarct zone (see preinjection and postinjection images); dtpa=diethylenetriaminepentaacetate.

    8. Tetrahedral Colloidal Crystals of Ag2S Nanocrystals (pages 8174–8177)

      Zhongbin Zhuang, Qing Peng, Xun Wang and Yadong Li

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200701307

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      Perfectly faceted tetrahedral 3D superlattice crystals, which are built up of 3.5-nm Ag2S crystals, have been directly prepared through a simple one-step, two-phase reaction. The as-prepared nanocrystals assemble at the interface of water and dodecanethiol phases to form superlattice films, then break into triangular flakes, and finally stack to form tetrahedra; inset of TEM image: fast Fourier transform pattern of the superlattice (SL).

    9. One-Pot Enzymatic Resolution and Separation of sec-Alcohols Based on Ionic Acylating Agents (pages 8178–8181)

      Nuno M. T. Lourenço and Carlos A. M. Afonso

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200701774

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      Going their different ways: A simple, robust, efficient, and reusable system for the one-pot preparative resolution and separation of sec-alcohols is described. The system is based on the combination of sequential enzymatic kinetic resolution (lipase B from Candida Antarctica, CALB) and transesterification in ionic liquids (ILs) with an ionic acylating agent 1 and removal of each enantiomer by extraction with an organic solvent.

    10. Bimetallic Ru–Sn Nanoparticle Catalysts for the Solvent-Free Selective Hydrogenation of 1,5,9-Cyclododecatriene to Cyclododecene (pages 8182–8185)

      Richard D. Adams, Erin M. Boswell, Burjor Captain, Ana B. Hungria, Paul A. Midgley, Robert Raja and John Meurig Thomas

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702274

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      Tin(n)y catalysts: Bimetallic RuSn supported nanoparticle catalysts (see picture; Ru green, Sn blue, O red), prepared from the carbonyl-cluster precursors [Ru44-SnPh)2(μ-SnPh2)4−x(CO)12−x] (x=0, 2, 3, 4) are shown to be active catalysts for the highly selective hydrogenation of 1,5,9-cyclododecatriene to cyclododecene under mild conditions.

    11. Total Synthesis of Resveratrol-Based Natural Products: A Chemoselective Solution (pages 8186–8191)

      Scott A. Snyder, Alexandros L. Zografos and Yunqing Lin

      Version of Record online: 24 SEP 2007 | DOI: 10.1002/anie.200703333

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      Despite the attention paid to resveratrol (1) owing to its potent biological activity, little effort has been devoted to studying resveratrol-based oligomers (such as 24). The first general synthetic approach is outlined for accessing the carbogenic diversity possessed by this family of compounds.

    12. Synthesis and Structure of a Hydrido(hydrosilylene)ruthenium Complex and Its Reactions with Nitriles (pages 8192–8194)

      Mitsuyoshi Ochiai, Hisako Hashimoto and Hiromi Tobita

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200703154

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      Ring around the Ru[DOUBLE BOND]Si: Abstraction of a pyridine ligand with BPh3 was used to synthesize the silylene complex 1 (see scheme), which reacts with nitriles at room temperature to give silylisocyanide complex 3 by C[BOND]C bond activation. The structure of key intermediate 2 with an η2-Si[BOND]H agostic interaction is given along with mechanisms for the formation of 2 and 3.

    13. Biosynthesis of the Antibiotic Bacillaene, the Product of a Giant Polyketide Synthase Complex of the trans-AT Family (pages 8195–8197)

      Jana Moldenhauer, Xiao-Hua Chen, Rainer Borriss and Jörn Piel

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200703386

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      Molecular traffic jam: The engineering of a bacillaene polyketide synthase deficient in thioesterase (TE) has led to the production of 13 hydrolyzed biosynthetic intermediates (see picture). This unexpected effect provides detailed insights into almost the entire bacillaene pathway and related poorly characterized polyketide routes.

    14. Spectroscopic Visualization of Vortex Flows Using Dye-Containing Nanofibers (pages 8198–8202)

      Akihiko Tsuda, Md. Akhtarul Alam, Takayuki Harada, Tatsuya Yamaguchi, Noriyuki Ishii and Takuzo Aida

      Version of Record online: 4 SEP 2007 | DOI: 10.1002/anie.200703083

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      Which way around? A J-aggregated zinc porphyrin dendrimer can be used to detect the macroscopic chirality of a vortex. The sign of the circular dichroism response changes quickly upon switching from clockwise (CW) to counterclockwise (CCW) stirring (see picture). The observed chiroptical activity most likely arises from a macroscopic helical alignment of nanofibers formed from the polymeric J-aggregate.

    15. Macroscopic Origin of Circular Dichroism Effects by Alignment of Self-Assembled Fibers in Solution (pages 8203–8205)

      Martin Wolffs, Subi J. George, Željko Tomović, Stefan C. J. Meskers, Albertus P. H. J. Schenning and E. W. Meijer

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200703075

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      All lined up: Supramolecular assemblies are aligned by a convective flow in clear, nonviscous dilute solutions (see picture). The linear dichroism created by the alignment results in artifacts in circular dichroism measurements, the origins of which are explained.

    16. Helicity Induction and Amplification in an Oligo(p-phenylenevinylene) Assembly through Hydrogen-Bonded Chiral Acids (pages 8206–8211)

      Subi J. George, Željko Tomović, Maarten M. J. Smulders, Tom F. A. de Greef, Philippe E. L. G. Leclère, E. W. Meijer and Albertus P. H. J. Schenning

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702730

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      Regulating the twist: Tunable supramolecular chirality is induced in an achiral helical self-assembly (P, M; see picture) by hydrogen-bonded chiral guest molecules (yellow and purple rods). Chiroptical probing of the π-conjugated chromophore reveals the mechanistic pathways of chiral induction. “Majority rules” and “sergeant and soldiers” experiments give insight into the chiral amplification in the stacks.

    17. The Discriminatory Power of Differential Receptor Arrays Is Improved by Prescreening—A Demonstration in the Analysis of Tachykinins and Similar Peptides (pages 8212–8215)

      Aaron T. Wright, Nicola Y. Edwards, Eric V. Anslyn and John T. McDevitt

      Version of Record online: 26 SEP 2007 | DOI: 10.1002/anie.200701236

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      Patterning pain: Six strong-binding receptors for the decapeptide tachykinin neurotransmitter α-neurokinin were identified by screening a solid-supported library. Solution-phase studies with these six receptors metalated with three different metal salts in a 96-well plate array followed by principal component analysis showed the array's ability to recognize and discriminate substance P and α-neurokinin, as well as three similar peptides.

    18. Intracellular Hydrogelation of Small Molecules Inhibits Bacterial Growth (pages 8216–8219)

      Zhimou Yang, Gaolin Liang, Zufeng Guo, Zhihong Guo and Bing Xu

      Version of Record online: 20 AUG 2007 | DOI: 10.1002/anie.200701697

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      Control from within: Supramolecular hydrogelation to form nanostructures intracellularly (see picture) has been developed as a new methodology to control the fate of cells. Enzyme-regulated self-assembly of small molecules inside cells could lead to a new paradigm for managing cellular processes, understanding cellular functions, and developing new therapeutics through supramolecular chemistry.

    19. Single Crystals of Naturally Occurring Gas Hydrates: The Structures of Methane and Mixed Hydrocarbon Hydrates (pages 8220–8222)

      Konstantin A. Udachin, Hailong Lu, Gary D. Enright, Christopher I. Ratcliffe, John A. Ripmeester, N. Ross Chapman, Michael Riedel and George Spence

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200701821

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      Samples from the bottom of the sea were used in the exact determination of the crystals structures of naturally occurring hydrocarbon hydrates. The hydrates of methane, ethane, and propane had a cubic structure II with hexakaidecahedral and pentagonal dodecahedral cages occupied by the guest molecules (see picture; C blue, H gray, O white).

    20. Live-Cell-Permeable Poly(p-phenylene ethynylene) (pages 8223–8225)

      Joong Ho Moon, William McDaniel, Paul MacLean and Lawrence F. Hancock

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200701991

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      Light up my life: Stable, bright, conjugated-polymer nanoparticles (CPNs) show promise for fluorescence imaging of live cells. The cell-permeable CPNs are synthesized by a simple solvent exchange, and accumulate exclusively in the cytosol (see picture) without any noticeable inhibition of cell viability.

    21. Dextran-Based Polymeric Chemiluminescent Compounds for the Sensitive Optical Imaging of a Cytochrome P450 Protein on a Solid-Phase Membrane (pages 8226–8229)

      Huan Zhang, Chaivat Smanmoo, Tsutomu Kabashima, Jianzhong Lu and Masaaki Kai

      Version of Record online: 8 OCT 2007 | DOI: 10.1002/anie.200702290

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      Creating a good image: Macromolecular compounds comprising dextran, luminol, and biotin were used as nonenzymatic probes for the sensitive chemiluminescence imaging of a cytochrome P450 (CYP) protein on a poly(vinylidene difluoride) (PVDF) membrane (see picture). The polymeric framework is simply formed by mixing the probe with avidin in a ratio of 1:1. The target CYP3A4 protein can be detected rapidly at the femtomole level.

    22. Crystal Structure and Guest Uptake of a Mesoporous Metal–Organic Framework Containing Cages of 3.9 and 4.7 nm in Diameter (pages 8230–8233)

      Young Kwan Park, Sang Beom Choi, Hyunuk Kim, Kimoon Kim, Byoung-Ho Won, Kihang Choi, Jung-Sik Choi, Wha-Seung Ahn, Nayoun Won, Sungjee Kim, Dong Hyun Jung, Seung-Hoon Choi, Ghyung-Hwa Kim, Sun-Shin Cha, Young Ho Jhon, Jin Kuk Yang and Jaheon Kim

      Version of Record online: 7 AUG 2007 | DOI: 10.1002/anie.200702324

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      Supersized pores: A new mesoporous metal–organic framework that is mainly composed of Tb3+ ions and tripodal carboxylate ligands has cages of 3.9 and 4.7 nm in diameter (see picture). The evacuated framework is robust and can accommodate gases or ferrocene molecules, as verified by gas-sorption measurements and luminescence studies.

    23. Free Energy Profile of H-ras Membrane Anchor upon Membrane Insertion (pages 8234–8237)

      Alemayehu A. Gorfe, Arneh Babakhani and J. Andrew McCammon

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702379

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      Pushing the envelope: The calculated free energy profile for the insertion of H-ras anchor into a dimyristoyl-sn-glycero-3-phosphocholine bilayer shows a steeply downhill profile. The insertion into the hydrocarbon core of the ras lipids and the interfacial localization of the backbone together account for a binding free energy of about −30 kcal mol−1.

    24. Neurite Imaging of Living PC12 Cells with Scanning Electrochemical/Near-Field Optical/Atomic Force Microscopy (pages 8238–8241)

      Akio Ueda, Osamu Niwa, Kenichi Maruyama, Yutaka Shindo, Kotaro Oka and Koji Suzuki

      Version of Record online: 26 SEP 2007 | DOI: 10.1002/anie.200702617

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      Protection is the key: Improved resolution imaging is demonstrated with the title technique, in which a bent probe is surrounded by a 100-nm protective layer to prevent direct contact between the electrode and the sample. Submicrometer structures and characteristic chemical sites can be imaged in three different modes, as demonstrated for neurites of PC12 cells (see picture).

    25. Coordination Polymers with π-Stacked Metalloparacyclophane Motifs: F-Shaped Mixed-Coordination Dinuclear Connectors (pages 8242–8245)

      Brigitte Nohra, Yishan Yao, Christophe Lescop and Régis Réau

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200702756

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      Stringing letters together: Coordination polymers (CPs) featuring unprecedented F-shaped dinuclear CuI connectors and π-stacked metallocyclophane moieties are obtained in a one-pot synthesis from their molecular components (see picture; dppm=bis(diphenylphosphino)methane; Cu pink, C gray, H white, N blue, P red). The characterization of a potential intermediate suggests that these CPs are formed through a multilevel self-assembly process.

    26. An Alkylidyne Analogue of Tebbe's Reagent: Trapping Reactions of a Titanium Neopentylidyne by Incomplete and Complete 1,2-Additions (pages 8246–8249)

      Brad C. Bailey, Alison R. Fout, Hongjun Fan, John Tomaszewski, John C. Huffman and Daniel J. Mindiola

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200703079

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      Who is the man behind the aluminum mask? The first Group 4 Lewis acid stabilized alkylidyne (2; see picture) is generated by incomplete addition of trimethylaluminum across a {Ti[TRIPLE BOND]CtBu} moiety (1; PNP=[2-{P(CHMe2)2}-4-MeC6H3]2N). In contrast, B(OCH3)3 completely adds to 1 by B[BOND]O bond cleavage to afford an unusual alkylidene. Complex 2, a masked alkylidyne titanium compound, also ring-opens pyridine.

    27. Complex α-Pyrones Synthesized by a Gold-Catalyzed Coupling Reaction (pages 8250–8253)

      Tuoping Luo and Stuart L. Schreiber

      Version of Record online: 24 SEP 2007 | DOI: 10.1002/anie.200703276

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      Sequential alkyne activation of readily available propargyl propiolates by a gold(I) catalyst yields compounds with α-pyrone skeletons (see scheme). An intermediate oxocarbenium ion converts into distinct products by two pathways: H elimination or Friedel–Crafts-type addition of electron-rich aromatic and heteroaromatic derivatives.

    28. Molecular Structure and Theoretical Studies of (PPh4)2[Bi10Cu10(SPh)24] (pages 8254–8257)

      Reinhart Ahlrichs, Andreas Eichhöfer, Dieter Fenske, Klaus May and Heino Sommer

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200703325

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      Shielded bismuth chains: The reaction of Bi(SPh)3 with CuSPh in the presence of PPh4Cl and PhSSiMe3 produced the title cluster (see picture of the cluster core; Bi red, Cu blue, S yellow). A surprising structural feature is the branched Bi10 chain, which exhibits a structure expected for a neutral and yet unknown klado-Bi10 cluster.

    29. Buckybowls on Metal Surfaces: Symmetry Mismatch and Enantiomorphism of Corannulene on Cu(110) (pages 8258–8261)

      Manfred Parschau, Roman Fasel, Karl-Heinz Ernst, Oliver Gröning, Louis Brandenberger, Richard Schillinger, Thomas Greber, Ari P. Seitsonen, Yao-Ting Wu and Jay S. Siegel

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200700610

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      Fivefold versus twofold: Symmetry-breaking interactions in the monolayer of the buckybowl corannulene on Cu(110) lead to the formation of extended mirror domains (see picture). The molecules are adsorbed in a tilted geometry with the bowl opening pointing away from the surface.

    30. Electrocatalysis of Hydrogen Oxidation—Theoretical Foundations (pages 8262–8265)

      Elizabeth Santos and Wolfgang Schmickler

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200702338

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      Understanding fuel cell catalysis: The electrochemical oxidation of hydrogen to two protons involves a major reorganization of the solvent. The reaction can be catalyzed by electrodes that have a d band near the Fermi level interacting strongly with hydrogen (see the potential surface for the oxidation of H2 on platinum).

    31. Potent Inhibitors of tRNA-Guanine Transglycosylase, an Enzyme Linked to the Pathogenicity of the Shigella Bacterium: Charge-Assisted Hydrogen Bonding (pages 8266–8269)

      Simone R. Hörtner, Tina Ritschel, Bernhard Stengl, Christian Kramer, W. Bernd Schweizer, Björn Wagner, Manfred Kansy, Gerhard Klebe and François Diederich

      Version of Record online: 27 SEP 2007 | DOI: 10.1002/anie.200702961

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      Improving inhibition: tRNA-Guanine transglycosylase (TGT) is a newly recognized target to reduce the pathogenicity of disease-causing Shigella bacteria. A potent family of inhibitors of this enzyme has been developed by structure-based design. Crystallographic data and pKa analysis suggest that the aminoimidazole moiety of the central lin-benzoguanine scaffold is protonated and stabilization of the complexes results from charge-assisted hydrogen bonding.

    32. Molecular Torsion Balances: Evidence for Favorable Orthogonal Dipolar Interactions Between Organic Fluorine and Amide Groups (pages 8270–8273)

      Felix R. Fischer, W. Bernd Schweizer and François Diederich

      Version of Record online: 26 SEP 2007 | DOI: 10.1002/anie.200702497

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      Finding the right balance: An indole-extended molecular torsion balance has the geometry for measuring a truly orthogonal noncovalent interaction between a C[BOND]F bond dipole and an amide carbonyl group (see picture, green F, red O, blue N). Employing a double-mutant cycle approach, negative interaction free enthalpies were determined. Thus orthogonal dipolar interactions can be a new tool for stabilizing protein–ligand complexes and assembling supramolecular architectures.

    33. Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Olefins (pages 8274–8276)

      Marcus G. Schrems, Eva Neumann and Andreas Pfaltz

      Version of Record online: 21 SEP 2007 | DOI: 10.1002/anie.200702555

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      Even notoriously unreactive substrates such as tetrasubstituted unfunctionalized olefins can be hydrogenated with high efficiency and excellent enantioselectivity using readily accessible chiral Ir catalysts. In this way, two adjacent stereogenic centers can be introduced in a single step (see scheme for an example; BArF=tetrakis(3,5-di(trifluoromethyl)phenyl)borate, o-Tol=ortho-tolyl).

    34. Formation of Mixed-Valent Aryltellurenyl Halides RX2TeTeR (pages 8277–8280)

      Jens Beckmann, Malte Hesse, Helmut Poleschner and Konrad Seppelt

      Version of Record online: 18 SEP 2007 | DOI: 10.1002/anie.200702341

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      Mixed doubles: The mixed-valent dinuclear aryltellurenyl halides PhBr2TeTePh (see picture), and RX2TeTeR (X=ClBr, R=2,6-Mes2C6H3), the monomeric 2,6-Mes2C6H3TeI, and the charge-transfer complex 2,6-Mes2C6H3TeI⋅⋅⋅I2 are presented. The stability of H3CEX (E=S, Se, Te; X=F, Cl, Br, I) as determined by ab initio methods are also discussed.

    35. From Monomeric tBuLi⋅(R,R)-TMCDA to α-Lithiated (R,R)-TMCDA (pages 8281–8283)

      Carsten Strohmann and Viktoria H. Gessner

      Version of Record online: 26 SEP 2007 | DOI: 10.1002/anie.200702116

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      The α-lithiation of amines by direct deprotonation has to date only been possible in a few systems. The enantiomerically pure amine (R,R)-TMCDA coordinates to tBuLi to form a monomeric molecular structure. Starting from tBuLi⋅(R,R)-TMCDA, lithiation of the ligand occurs, which results in a trimeric α-lithiated amine (see picture).

    36. Action of atrop-Abyssomicin C as an Inhibitor of 4-Amino-4-deoxychorismate Synthase PabB (pages 8284–8286)

      Simone Keller, Heiko S. Schadt, Ingo Ortel and Roderich D. Süssmuth

      Version of Record online: 20 SEP 2007 | DOI: 10.1002/anie.200701836

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      Subtle restraint: Abyssomicin C and atrop-abyssomicin C are polyketide-type antibiotics produced by the marine actinomycete of the genus Verrucosispora. Investigations of the functional pathway show that a subunit of 4-amino-4-deoxychorismate synthase from Bacillus subtilis is irreversibly inhibited through covalent binding to the side chain of Cys 263, undergoing a rearrangement to a structure of the abyssomicin D type (see scheme).

    37. Biosynthesis of the Off-Flavor 2-Methylisoborneol by the Myxobacterium Nannocystis exedens (pages 8287–8290)

      Jeroen S. Dickschat, Thorben Nawrath, Verena Thiel, Brigitte Kunze, Rolf Müller and Stefan Schulz

      Version of Record online: 26 SEP 2007 | DOI: 10.1002/anie.200702496

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      A bouquet of bacteria: Methylisoborneol (1) is a widely occurring volatile from bacteria and an undesirable flavor (off-flavor) in the food industry. The analysis of isotopomers obtained by feeding isotopically labeled precursors to myxobacteria revealed the biosynthetic pathway to 1. Geranylpyrophosphate (GPP) is alkylated by S-adenosylmethionine (SAM) and the product is cyclized to 1. The methylation of GPP is unprecedented in nature.

    38. A General Ruthenium-Catalyzed Synthesis of Aromatic Amines (pages 8291–8294)

      Dirk Hollmann, Sebastian Bähn, Annegret Tillack and Matthias Beller

      Version of Record online: 24 SEP 2007 | DOI: 10.1002/anie.200703119

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      Simple as that: The synthesis of aromatic amines from aliphatic amines proceeds under transfer hydrogenation conditions (see scheme). By applying the Shvo catalyst, general applicability is shown in the conversion of a variety of functionalized anilines and aliphatic amines. This base- and salt-free method can be an excellent alternative to the known synthesis of anilines.

    39. Homoleptic Silver(I) Acetylene Complexes (pages 8295–8298)

      Andreas Reisinger, Nils Trapp, Ingo Krossing, Sandra Altmannshofer, Verena Herz, Manuel Presnitz and Wolfgang Scherer

      Version of Record online: 17 OCT 2007 | DOI: 10.1002/anie.200702688

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      Hanging on to acetylene: The solid-state structures of the first homoleptic metal HC[TRIPLE BOND]CH complexes [M(C2H2)x]n (M=any metal; n, x=any number), salts of [Ag(η2-C2H2)n]+ (n=3,4), are described (see picture). The electronic structure of a [Ag(η2-C2H2)] model complex has been investigated by experimental charge-density studies.

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