Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 44

November 13, 2006

Volume 45, Issue 44

Pages 7305–7473

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
    8. Communications
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    1. Cover Picture: “Sulflower”: A New Form of Carbon Sulfide (Angew. Chem. Int. Ed. 44/2006) (page 7305)

      Konstantin Yu. Chernichenko, Viktor V. Sumerin, Roman V. Shpanchenko, Elizabeth S. Balenkova and Valentine G. Nenajdenko

      Article first published online: 6 NOV 2006 | DOI: 10.1002/anie.200690151

      The bloom of a sunflower is used to describe the highly symmetric planar structure of octathio[8]circulene, whose trivial name “sulflower” derives from sulfur and flower (see cover picture). In their Communication on page 7367 ff., V. G. Nenajdenko and co-workers describe the synthesis and characterization of sulflower, a molecule that can be considered as a new form of carbon sulfide and as an oligothiophene, that is, as both inorganic and organic. (Background picture: “Sunflowers” by Vincent van Gogh. Copyright: Neue Pinakothek, Munich.)

  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. Self-Assembly of Fibers and Fibrils (pages 7324–7328)

      Wolfgang H. Binder and Oskar W. Smrzka

      Article first published online: 20 OCT 2006 | DOI: 10.1002/anie.200602001

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      Too much fiber? Protein fibers play an important role in cellular processes, but are also involved in protein-folding diseases, such as Alzheimer's disease. Modern screening and validation models allow the investigation of the aggregation and deaggregation kinetics of protein fibers (see scheme). These studies can serve as a starting point for the development of new therapeutic strategies.

    2. Tamiflu: The Supply Problem (pages 7330–7334)

      Vittorio Farina and Jack D. Brown

      Article first published online: 19 OCT 2006 | DOI: 10.1002/anie.200602623

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      Taming of the flu: Shikimic and quinic acids are the established starting materials for Tamiflu, a viral neuraminidase inhibitor that is considered by many as the first-line treatment against a possible H5N1 (bird flu) pandemic. Several syntheses have been described recently that circumvent the use of these natural products. These, or related approaches, may provide an alternative practical approach to this important drug.

  6. Review

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    1. Reactions in Droplets in Microfluidic Channels (pages 7336–7356)

      Helen Song, Delai L. Chen and Rustem F. Ismagilov

      Article first published online: 6 NOV 2006 | DOI: 10.1002/anie.200601554

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      Reactions that go with the flow: Many applications in chemical research require multiple reactions to be performed in parallel and in series. Microfluidic droplets can be used as chemical microreactors for performing many reactions on small scale (see picture). New techniques in droplet-based microfluidics and their applications (e.g., for analysis of complex biological processes or optimization of reaction conditions) are discussed.

  7. Communications

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    1. High H2 Adsorption by Coordination-Framework Materials (pages 7358–7364)

      Xiang Lin, Junhua Jia, Xuebo Zhao, K. Mark Thomas, Alexander J. Blake, Gavin S. Walker, Neil R. Champness, Peter Hubberstey and Martin Schröder

      Article first published online: 23 AUG 2006 | DOI: 10.1002/anie.200601991

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      First-class accommodation: A series of coordination frameworks with different pore sizes (see structure of one; Cu blue, C gray, H white, O red) are prepared from CuII ions and carboxylate ligands of various lengths. Comparison of their sorption properties reveals that smaller pores allow higher densities of adsorbed H2, whereas larger pores allow higher maximum H2 storage capacities.

    2. Fluorescence Visualization of Newly Synthesized Proteins in Mammalian Cells (pages 7364–7367)

      Kimberly E. Beatty, Julie C. Liu, Fang Xie, Daniela C. Dieterich, Erin M. Schuman, Qian Wang and David A. Tirrell

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200602114

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      Playing tag: Noncanonical amino acid tagging enables the selective fluorescent visualization of newly synthesized proteins in mammalian cells (see the picture). Susceptibility to tagging is determined by the spatial and temporal character of the protein synthesis, thus providing a complement to methods which identify relevant members of the proteome.

    3. “Sulflower”: A New Form of Carbon Sulfide (pages 7367–7370)

      Konstantin Yu. Chernichenko, Viktor V. Sumerin, Roman V. Shpanchenko, Elizabeth S. Balenkova and Valentine G. Nenajdenko

      Article first published online: 26 SEP 2006 | DOI: 10.1002/anie.200602190

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      A sunny outlook: As the first fully heterocyclic circulene, sulflower opens the way to an unprecedented class of compounds that are both organic and inorganic. Sulflower is an oligothiophene as well as a new form of carbon sulfide that resembles a flower (see picture) and was synthesized in a short and effective approach.

    4. Highly Luminescent ZnO Nanocrystals Stabilized by Ionic-Liquid Components (pages 7370–7373)

      Da-Peng Liu, Guo-Dong Li, Yan Su and Jie-Sheng Chen

      Article first published online: 9 OCT 2006 | DOI: 10.1002/anie.200602429

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      A new approach to stabilization of ZnO nanocrystals by ionic-liquid components, which endow the nanocrystals with high thermal stability and good fluidity, is demonstrated. The ionic-liquid/ZnO composites exhibit tunable photoluminescence (see picture) with a high quantum yield.

    5. Tailor-Made Onionlike Stereocomplex Crystals in Incompatible, Enantiomeric, Polylactide-Containing Block Copolymer Blends (pages 7373–7376)

      Lu Sun, Lei Zhu, Lixia Rong and Benjamin S. Hsiao

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200602541

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      Unbalanced surface stresses, induced in stereocomplex crystals formed by blends of two enantiomeric polylactide diblock copolymers by the presence of immiscible blocks of different lengths, result in lamella curving and formation of onionlike multilamellar structures (see picture for schematic structure and a TEM image).

    6. Electrochemical Switching of the Cubic Nonlinear Optical Properties of an Aryldiethynyl-Linked Heterobimetallic Complex between Three Distinct States (pages 7376–7379)

      Marek Samoc, Nicolas Gauthier, Marie P. Cifuentes, Frédéric Paul, Claude Lapinte and Mark G. Humphrey

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200602684

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      Successive oxidation processes in a heterobimetallic iron–ruthenium complex (see picture) “switch” the optical transitions at long wavelengths, and these linear electrochromic effects are accompanied by changes in the nonlinear optical properties of the complex.

    7. Reversible Size Modification of Iron and Gallium Molecular Wheels: A Ga10 “Gallic Wheel” and Large Ga18 and Fe18 Wheels (pages 7379–7383)

      Philippa King, Theocharis C. Stamatatos, Khalil A. Abboud and George Christou

      Article first published online: 18 OCT 2006 | DOI: 10.1002/anie.200602743

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      Wheelin' and dealin': The M10 molecular wheels [M10(OMe)20(O2CR)10] (M=Ga, R=Me; M=Fe, R=Ph) were modified to M18 wheels in a nontemplate synthesis upon incorporation of a diolate ligand (see space-filling model of [Ga18(pd)12(pdH)12(O2CMe)6(NO3)6]6+; Ga yellow, O red, N blue, C gray; pdH2=1,3-propanediol). Remarkably, dissolution in MeOH converts both M18 wheels back into the M10 wheels.

    8. A Virus Spotlighted by an Autonomous DNA Machine (pages 7384–7388)

      Yossi Weizmann, Moritz K. Beissenhirtz, Zoya Cheglakov, Roni Nowarski, Moshe Kotler and Itamar Willner

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200602754

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      Highly sensitive: Analysis of viral DNA (M13 phage) is possible by using a DNA-based machine that is fueled by dNTPs and synthesizes DNAzyme reporter units. The DNAzymes mimic peroxidase and lead to a colorimetric or chemiluminescent readout of the analyzed DNA.

    9. The Tubulin-Bound Conformation of Discodermolide Derived by NMR Studies in Solution Supports a Common Pharmacophore Model for Epothilone and Discodermolide (pages 7388–7394)

      Víctor M. Sánchez-Pedregal, Karel Kubicek, Jens Meiler, Isabelle Lyothier, Ian Paterson and Teresa Carlomagno

      Article first published online: 12 OCT 2006 | DOI: 10.1002/anie.200602793

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      Bound to have similarities: Although the overall shape of discodermolide bound to tubulin resembles the structure of the free ligand, the precise conformation and orientation of the lactone ring are different. A partially overlapping pharmacophore model supported by protein-mediated interligand NOE signals (see picture) is proposed to explain the similar (but not fully equivalent) biological activity of discodermolide and epothilone A.

    10. A Tosylimido Analogue of a Nonheme Oxoiron(IV) Complex (pages 7394–7397)

      Eric J. Klinker, Timothy A. Jackson, Michael P. Jensen, Audria Stubna, Gergely Juhász, Emile L. Bominaar, Eckard Münck and Lawrence Que Jr.

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200602799

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      High-valent versatility: N4Py is a versatile pentadentate ligand demonstrated to stabilize both high-valent oxo and imido compounds. The [FeIV(NTs)(N4Py)]2+ complex (see DFT-optimized structure) has been characterized spectroscopically and formulated as having an S=1 iron(IV) center with an Fe[DOUBLE BOND]N bond (1.73 Å) that is longer than the Fe[DOUBLE BOND]O bond of its oxo analogue (1.65 Å).

    11. Catalytic, Asymmetric Synthesis of 1,4-Benzoxazinones: A Remarkably Enantioselective Route to α-Amino Acid Derivatives from o-Benzoquinone Imides (pages 7398–7400)

      Jamison Wolfer, Tefsit Bekele, Ciby J. Abraham, Cajetan Dogo-Isonagie and Thomas Lectka

      Article first published online: 12 OCT 2006 | DOI: 10.1002/anie.200602801

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      Cycloaddition of o-benzoquinone imides with chiral ketene enolates derived from cinchona alkaloid catalysts is the basis of a catalytic asymmetric synthesis of 1,4-benzoxazinones and 1,4-benzoxazines. The resulting cycloadducts can be derivatized in situ to provide α-amino acid products in good-to-excellent yields with very high enantioselectivities (see scheme; CAN=ceric ammonium nitrate, Nu=nucleophile).

    12. Dynamically Self-Assembling Metalloenzyme Models Based on Calixarenes (pages 7400–7404)

      Hüseyin Bakirci, Apurba L. Koner, Michael H. Dickman, Ulrich Kortz and Werner M. Nau

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200602999

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      Giving it a tri: Ternary complexes formed from a macrocyclic host (p-sulfonatocalix[4]arene), an organic guest (2,3-diazabicyclo[2.2.2]oct-2-ene), and transition-metal ions (see picture) result in a host-assisted formation of a metal–ligand bond. The system displays a very high selectivity as a result of triple supramolecular recognition involving Coulombic interactions, hydrophobic guest binding, and weak metal–ligand interactions.

    13. Chemisorption-Induced Double Hydrogen Bonding, Self-Assembly, and Stereoselection (pages 7404–7407)

      Stéphane Lavoie, Gautier Mahieu and Peter H. McBreen

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200603103

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      Surface value: Scanning tunneling microscopy reveals that aryl–carbonyl assemblies form through C[BOND]H⋅⋅⋅O interactions on a Pt(111) surface (see picture). The strong hydrogen bonding is activated by the chemisorption-induced polarization of the arene and is tunable by substitution on the aromatic ring. These findings are relevant to stereoselective heterogeneous and homogeneous catalysis.

    14. Substrate Mimicry in an Activity-Based Probe That Targets the Nitrilase Family of Enzymes (pages 7408–7411)

      Katherine T. Barglow and Benjamin F. Cravatt

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200603187

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      Up and at it: A set of activity-based proteomics probes containing a dipeptide α-chloroacetamide scaffold that targets the nitrilase family of enzymes is described. One member of the nitrilase class, ureidopropionase-β, was found to react selectively with a single probe that mimics the enzyme's endogenous substrate N-carbamoyl β-alanine.

    15. Self-Assembly of Nanometer-Scale [Cu24I10L12]14+ Cages and Ball-Shaped Keggin Clusters into a (4,12)-Connected 3D Framework with Photoluminescent and Electrochemical Properties (pages 7411–7414)

      Xin-Long Wang, Chao Qin, En-Bo Wang, Zhong-Min Su, Yang-Guang Li and Lin Xu

      Article first published online: 6 NOV 2006 | DOI: 10.1002/anie.200603250

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      Bridging two traditional but distinct research areas—polyoxometalate chemistry and cuprous halide clusters—the (4,12)-connected 3D framework (NH4)[Cu24I10L12][PMoV2MoVI10O40]3 has been built by covalent linkage of nanoscale Keggin anions and [Cu24I10L12]14+ clusters (see picture; L is a multidentate N-heterocyclic ligand); it exhibits remarkable photoluminescent and electrochemical properties.

    16. Single-Molecule Protein Encapsulation in a Rigid DNA Cage (pages 7414–7417)

      Christoph M. Erben, Russell P. Goodman and Andrew J. Turberfield

      Article first published online: 6 NOV 2006 | DOI: 10.1002/anie.200603392

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      Behind bars: A single molecule of the protein cytochrome c has been incarcerated within a rigid tetrahedral DNA cage (see picture). The central cavity is estimated to be large enough to accommodate a sphere of approximately 2.6 nm in radius, such as a 60-kDa globular protein (Mr of cytochrome c: 12.4 kDa). The finding demonstrates the potential of DNA containers as a new kind of drug-delivery system.

    17. Three-Step Synthesis of Sialic Acids and Derivatives (pages 7417–7421)

      Zhangyong Hong, Lei Liu, Che-Chang Hsu and Chi-Huey Wong

      Article first published online: 10 OCT 2006 | DOI: 10.1002/anie.200601555

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      Flexible yet efficient: Sialic acids such as L-N-acetylneuraminic acid (see picture) can be synthesized in only three steps by 1) vinylation of an aldose through a modified Petasis coupling reaction, 2) 1,3-dipolar cycloaddition with a nitrone to construct an isoxazolidine ring, and 3) base-catalyzed β elimination/ring opening of the isoxazolidine to generate a γ-hydroxy-α-keto acid.

    18. Carbon–Carbon Bond Formation at a Neutral Terminal Carbido Ligand: Generation of Cyclopropenylidene and Vinylidene Complexes (pages 7422–7424)

      Stephen R. Caskey, Michael H. Stewart, Marc J. A. Johnson and Jeff W. Kampf

      Article first published online: 17 OCT 2006 | DOI: 10.1002/anie.200601652

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      A C1source, the carbido complex [Ru(C)(PCy3)2Cl2] (1) adds cleanly to dimethylacetylene dicarboxylate (DMAD), affording the cyclopropenylidene complex 2 (red O, green Cl, yellow P, gray C). This product is surprising given the instability of its trans-cyclopropylidene analogue. HX reagents effect 1,1-addition and ring opening, forming vinylidene complexes such as 3 which catalyze the ring-opening metathesis polymerization of norbornene.

    19. Surface Modification of a Six-Capped Body-Centered Cube Ni9W6 Cluster: Structure and Single-Molecule Magnetism (pages 7424–7426)

      Jeong Hak Lim, Jung Hee Yoon, Hyoung Chan Kim and Chang Seop Hong

      Article first published online: 16 OCT 2006 | DOI: 10.1002/anie.200601759

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      To cap it off: A high-spin cyanide-bridged Ni9W6 cluster (S=12) shows ferromagnetic coupling between NiII (green) and WV (purple) ions within the molecule. The surface was modified by substituting the solvent molecules on the surface of the cluster with 2,2′-bipyridine to afford an air-stable Ni9W6 cluster with single-molecule magnetism.

    20. Room-Temperature AuI-Catalyzed C[BOND]C Bond Formation through a Tandem Friedel–Crafts-Type Addition/Carbocyclization Reaction (pages 7427–7430)

      Patrick Yves Toullec, Emilie Genin, Lucie Leseurre, Jean-Pierre Genêt and Véronique Michelet

      Article first published online: 11 OCT 2006 | DOI: 10.1002/anie.200601980

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      A golden tandem reaction: The [PPh3AuCl]/AgSbF6 catalytic system promotes a tandem reaction composed of a Friedel–Crafts-type addition of electron-rich aromatic and heteroaromatic derivatives to unactivated alkenes and a carbocyclization (see scheme; Z=C(CO2Me)2, C(SO2Ph)2, O, NTs). The reaction is compatible with various functional groups on the enynes and nucleophiles, and proceeds rapidly at room temperature.

    21. Selective Electrochemical Retro-Cycloaddition Reaction of Pyrrolidinofullerenes (pages 7430–7433)

      Olena Lukoyanova, Claudia M. Cardona, Margarita Altable, Salvatore Filippone, Ángel Martín Domenech, Nazario Martín and Luis Echegoyen

      Article first published online: 16 OCT 2006 | DOI: 10.1002/anie.200602431

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      Going retro: Controlled-potential electrolysis (CPE) is employed as a synthetic tool in the selective removal of addends from fullerene adducts. Reductive CPE has been extensively used in the retro-cyclopropanation of fullerenes without affecting pyrrolidine addends also present. Now oxidative CPE for the selective removal of pyrrolidine addends in the presence of methano adducts is reported (see scheme).

    22. Methane Oxidation by Aqueous Osmium Tetroxide and Sodium Periodate: Inhibition of Methanol Oxidation by Methane (pages 7433–7436)

      Takao Osako, Eric J. Watson, Ahmad Dehestani, Brian C. Bales and James M. Mayer

      Article first published online: 6 NOV 2006 | DOI: 10.1002/anie.200602560

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      Cast in a new role: Aqueous solutions of OsO4 and NaIO4 oxidize methane to methanol under very mild conditions (see scheme). The generated methanol is preserved over 5 days at 50 °C, although it is more readily oxidized than methane in separate experiments. Remarkably, methanol oxidation by aqueous OsO4/NaIO4 is inhibited by the presence of methane.

    23. A Highly Reactive and Stereoselective β-Mannopyranosylation System: Mannosyl 4-Pentenoate/PhSeOTf (pages 7436–7440)

      Ju Yuel Baek, Tae Jin Choi, Heung Bae Jeon and Kwan Soo Kim

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200602642

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      Controlled linkage: PhSeOTf-promoted glycosylations of a variety of acceptor alcohols with 4,6-O-benzylidene-2,3-di-O-benzylmannopyranosyl pentenoate afford β-mannopyranosides in high yields and with excellent stereoselectivity (see scheme). This method is even better than other known methods for the mannosylation of simple reactive primary alcohols. Tf=trifluoromethanesulfonyl, TTBP=2,4,6-tri-tert-butylpyrimidine.

    24. Mechanically Induced Generation of Counterions Inside Surface-Grafted Charged Macromolecular Films: Towards Enhanced Mechanotransduction in Artificial Systems (pages 7440–7443)

      Omar Azzaroni, Britta Trappmann, Patrick van Rijn, Feng Zhou, Bokyung Kong and Wilhelm T. S. Huck

      Article first published online: 10 OCT 2006 | DOI: 10.1002/anie.200602666

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      Brushing up on films: A simple model, based on strong ion-pairing interactions of a dye probe (bromothymol blue, BTB) within surface-grafted charged polyelectrolyte brushes, provides evidence that physical forces can be easily mechanotransducted into chemical signals (see picture, PDMS=poly(dimethylsiloxane)). The application of a mechanical force results in a shift of the equilibrium for BTB, which can be monitored by UV/Vis spectroscopy.

    25. Control of Vesicular Morphologies through Hydrophobic Block Length (pages 7443–7447)

      Tony Azzam and Adi Eisenberg

      Article first published online: 10 OCT 2006 | DOI: 10.1002/anie.200602897

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      About the size of it: A series of polystyrene-block-poly(acrylic acid) (PS-b-PAA) block copolymers were developed in which the length of the PAA block was kept constant and the length of the PS block was varied. This allowed a study of the effect of the PAA/PS block ratio on the vesicle sizes as well as on the wall thicknesses.

    26. Cyclic Carbodiphosphorane–Diphosphinocarbene Thermal Interconversion (pages 7447–7450)

      Sebastien Marrot, Tsuyoshi Kato, Fernando P. Cossío, Heinz Gornitzka and Antoine Baceiredo

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200603151

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      Unusual thermal ring contraction of five-membered cyclic azacarbodiphosphorane into a four-membered 1,2λ5-azaphosphete was observed (see scheme). Experimental and computational results indicate that the ring contraction results from a remarkable interconversion between two different types of divalent carbon species (dianionic and carbene): carbodiphosphorane and diphosphinocarbene.

    27. Detection of Nitric Oxide Release from Single Cells by Using Constant-Distance-Mode Scanning Electrochemical Microscopy (pages 7451–7454)

      Sonnur Isik and Wolfgang Schuhmann

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200601708

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      Pin point: Accurate positioning of highly sensitive and selective NO microsensors by using a shear-force-dependent constant-distance mode of SECM allows reproducible detection of stimulated NO release from adherently growing endothelial cells. The picture shows the diffusion profile of NO after stimulation of a cell (right) and the amperometric current trace of a microsensor positioned over a cell (left).

    28. Aryl Indanyl Ketones: Efficient Inhibitors of the Human Peptidyl Prolyl cis/trans Isomerase Pin1 (pages 7454–7458)

      Sebastian Daum, Frank Erdmann, Gunter Fischer, Boris Féaux de Lacroix, Anahita Hessamian-Alinejad, Sabine Houben, Walter Frank and Manfred Braun

      Article first published online: 18 OCT 2006 | DOI: 10.1002/anie.200601569

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      A good imitation: Aryl-1-indanyl ketones are found to be highly efficient, reversible, cell-penetrating inhibitors of the human peptidyl prolyl cis/trans isomerase Pin1. Owing to their structure 1, they are assumed to mimic the transition state 2 of the enzymatically catalyzed rotation about the imidic peptide bond preceding a proline residue.

    29. Polymer Brushes as Ionotropic Matrices for the Directed Fabrication of Microstructured Calcite Thin Films (pages 7458–7461)

      Stefano Tugulu, Marc Harms, Marc Fricke, Dirk Volkmer and Harm-Anton Klok

      Article first published online: 13 OCT 2006 | DOI: 10.1002/anie.200602382

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      How to get into films: Micropatterned poly(methacrylic acid) (PMAA) brushes are used as an ionotropic matrix for the fabrication of microstructured calcite thin films. The calcite films are an exact 3D replica of the PMAA brush matrix (see Scheme; ACC=amorphous CaCO3 phase).

    30. Reversible Red Fluorescent Molecular Switches (pages 7462–7465)

      Mariano Bossi, Vladimir Belov, Svetlana Polyakova and Stefan W. Hell

      Article first published online: 16 OCT 2006 | DOI: 10.1002/anie.200602591

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      I see red, I see red, I see red: Optically switchable compounds were synthesized whose visible fluorescence can be quenched down to 6 % with light at 360–400 nm and then restored with red light from a diode laser. The molecular switch offers potential applications in data storage and far-field microscopy with spatial resolution far below the diffraction limit.

    31. Transition-Metal Anions in Solids and Their Implications on Bonding (pages 7465–7469)

      Myung-Hwan Whangbo, Changhoon Lee and Jürgen Köhler

      Article first published online: 6 OCT 2006 | DOI: 10.1002/anie.200602712

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      A negative disposition: Electronic-band-structure calculations reveal that in La2M2In (M=Pt, Cu) the transition-metal atoms can be regarded as anions with fully occupied nd orbitals and bonding characters similar to that of the Ge3− ions in La2Ge2In. The orbital sequence in La2M2In is (n+1)s<nd<(n+1)p, as a result of the low oxidation states of the transition metals (see graph).

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