Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 23

May 26, 2008

Volume 47, Issue 23

Pages 4239–4447

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. Cover Picture: A Highly Selective DNAzyme Sensor for Mercuric Ions (Angew. Chem. Int. Ed. 23/2008) (page 4239)

      Marcel Hollenstein, Christopher Hipolito, Curtis Lam, David Dietrich and David M. Perrin

      Article first published online: 16 MAY 2008 | DOI: 10.1002/anie.200890106

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      On quicksilver, or mercury, a self-cleaving DNA discovered in vivo and containing imidazole and amine groups responds selectively and with high sensitivity, as D. M. Perrin et al. reveal in their Communication on page 4346 ff. The cover picture shows the formula of the DNAzyme along with the periodic table, indicating elements that have been tested (red bars) and the Hg cleaving efficiency (green).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. Inside Cover: Supramolecular Metal Oxides: Programmed Hierarchical Assembly of a Protein-Sized 21 kDa [(C16H36N)19{H2NC(CH2O)3P2V3W15O59}4]5− Polyoxometalate Assembly (Angew. Chem. Int. Ed. 23/2008) (page 4240)

      Chullikkattil P. Pradeep, De-Liang Long, Graham N. Newton, Yu-Fei Song and Leroy Cronin

      Article first published online: 16 MAY 2008 | DOI: 10.1002/anie.200890107

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      The direct correlation between gas-phase and solid-state supramolecular structures of massive protein-sized polyoxometalate clusters (ca. 21 kDa) has been probed using cryospray mass spectrometry. In their Communication on page 4388 ff., L. Cronin et al. show that such clusters can be crystallized into the solid state, and their macromolecular structure controlled, thus allowing the stability of many different building blocks to be investigated.

  3. Graphical Abstract

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    5. News
    6. Book Review
    7. Highlights
    8. Review
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 23/2008 (pages 4243–4253)

      Article first published online: 16 MAY 2008 | DOI: 10.1002/anie.200890108

  4. News

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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  5. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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  6. Highlights

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Book Review
    7. Highlights
    8. Review
    9. Communications
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    1. Pores by Pillaring: Not Always a Maze (pages 4262–4263)

      Michael Tsapatsis and Sudeep Maheshwari

      Article first published online: 25 APR 2008 | DOI: 10.1002/anie.200705755

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      Pillaring with perfection: The construction of molecular pillars in layered materials (see scheme) while preserving the three-dimensional crystallinity enables the creation of porous structures with a narrow pore-size distribution. This method opens up a route to prepare composite materials with unusual combinations of properties.

    2. Asymmetric Catalysis Using Air: Clean Kinetic Resolution of Secondary Alcohols (pages 4264–4267)

      Martin Wills

      Article first published online: 6 MAY 2008 | DOI: 10.1002/anie.200801152

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      An air of excitement: Enantioselective catalysts have been developed for the kinetic resolution of racemic alcohols using aerobic oxidation. The iridium(III) complex shown (Ms=methanesulfonyl), which was developed by Ikariya et al., proved to be particularly efficient. Besides several other examples, the aspects of the mechanism are discussed.

  7. Review

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    1. Cycloisomerization of 1,n-Enynes: Challenging Metal-Catalyzed Rearrangements and Mechanistic Insights (pages 4268–4315)

      Véronique Michelet, Patrick Y. Toullec and Jean-Pierre Genêt

      Article first published online: 1 APR 2008 | DOI: 10.1002/anie.200701589

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      Rounding it up: Metal-catalyzed cycloisomerization reactions of 1,n-enynes are highly attractive processes as they contribute to the highly demanded search for atom economy. Besides palladium catalysts, several other metals have been identified as excellent catalysts. The molecular complexity of the synthesized products, such as 14, can be greatly enhanced through metal-catalyzed tandem reactions.

  8. Communications

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    1. Temperature-Controlled Molecular Depolarization Gates in Nuclear Magnetic Resonance (pages 4316–4320)

      Leif Schröder, Lana Chavez, Tyler Meldrum, Monica Smith, Thomas J. Lowery, David E. Wemmer and Alexander Pines

      Article first published online: 6 MAY 2008 | DOI: 10.1002/anie.200800382

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      Down the drain: Cryptophane cages in combination with selective radiofrequency spin labeling can be used as molecular “transpletor” units for transferring depletion of spin polarization from a hyperpolarized source spin ensemble to a drain ensemble. The flow of nuclei through the gate is adjustable by the ambient temperature, thereby enabling controlled consumption of hyperpolarization (see scheme).

    2. Electron-Density Investigation of Metal–Metal Bonding in the Dinuclear “Borylene” Complex [{Cp(CO)2Mn}2(μ-BtBu)] (pages 4321–4325)

      Ulrike Flierler, Michael Burzler, Dirk Leusser, Julian Henn, Holger Ott, Holger Braunschweig and Dietmar Stalke

      Article first published online: 2 MAY 2008 | DOI: 10.1002/anie.200705257

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      Close but not bonded are the two manganese atoms in the title borylene complex. The charge-density study demonstrates that the μ-bridging BR ligand forms valence shell charge concentrations to each metal center rather than a single one to the metal–metal midpoint as found for the isolobal C[DOUBLE BOND]O ligand in analogous dinuclear species.

    3. Sculpting an RNA Conformational Energy Landscape by a Methyl Group Modification—A Single-Molecule FRET Study (pages 4326–4330)

      Andrei Yu. Kobitski, Martin Hengesbach, Mark Helm and G. Ulrich Nienhaus

      Article first published online: 30 APR 2008 | DOI: 10.1002/anie.200705675

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      With or without Me: The effect of a single methyl group on the free energies of functional and nonfunctional conformations of human mitochondrial lysine transfer RNA (tRNALys) has been studied. The stabilization of the three distinct conformations by Mg2+ ion binding and free energy changes resulting from methylation were characterized and revealed a preference for the functionally relevant cloverleaf-shaped tRNA form (see picture).

    4. Azadipeptide Nitriles: Highly Potent and Proteolytically Stable Inhibitors of Papain-Like Cysteine Proteases (pages 4331–4334)

      Reik Löser, Maxim Frizler, Klaus Schilling and Michael Gütschow

      Article first published online: 11 APR 2008 | DOI: 10.1002/anie.200705858

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      Nitrogen instead of carbon: Azadipeptide nitriles resulting from CH/N exchange in the P1 position (see picture) are hitherto unknown. To access these compounds by conversion of amino acid-derived hydrazides with cyanogen bromide both nitrogen atoms of the hydrazide must be substituted. Despite a methylated P2-P1 peptide bond, the azadipeptide nitriles show a strong inhibitory activity against cysteine proteases, and a high stability towards chymotryptic hydrolysis.

    5. Synthesis of 35-Deoxy Amphotericin B Methyl Ester: A Strategy for Molecular Editing (pages 4335–4338)

      Alex M. Szpilman, Damiano M. Cereghetti, Nicholas R. Wurtz, Jeffrey M. Manthorpe and Erick M. Carreira

      Article first published online: 2 MAY 2008 | DOI: 10.1002/anie.200800589

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      A modular strategy for the assembly of amphotericin B analogues with modifications in the macrolactone ring relies on the efficient gram-scale synthesis of all major and minor motifs of amphotericin B. Proof of concept has been achieved by the preparation of the 35-deoxy aglycone en route to the long-sought-after 35-deoxy analogue of amphotericin B.

    6. Synthesis and Biological Studies of 35-Deoxy Amphotericin B Methyl Ester (pages 4339–4342)

      Alex M. Szpilman, Jeffrey M. Manthorpe and Erick M. Carreira

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800590

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      An indispensable OH group: The synthesis of 35-deoxy amphotericin B methyl ester was completed by using a novel method for the coupling of the mycosamine to the aglycone. The investigation of the antifungal activity and efflux-inducing ability of this compound provided data that underscore the relevance of the hydroxy group at C35 and supports the involvement of double-barrel ion channels.

    7. The Synthesis and Isolation of a Metal-Substituted Bis-silene (pages 4343–4345)

      Dmitry Bravo-Zhivotovskii, Roman Dobrovetsky, Dmitry Nemirovsky, Victoria Molev, Michael Bendikov, Gregory Molev, Mark Botoshansky and Yitzhak Apeloig

      Article first published online: 30 APR 2008 | DOI: 10.1002/anie.200800973

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      Si, Si: The reaction of bis(lithiosilyl)mercury with R3Si=iPr3Si with two equivalents of 1-adamantoyl chloride gave, by thermal Brook rearrangement, the first metal-substituted bis-silene. The reaction of bis(lithiosilyl)mercury having smaller tBuMe2Si substituents led to a bis(acylsilyl)mercury, which did not rearrange to the bis-silene. The effect of steric congestion on Brook rearrangement was studied computationally.

    8. A Highly Selective DNAzyme Sensor for Mercuric Ions (pages 4346–4350)

      Marcel Hollenstein, Christopher Hipolito, Curtis Lam, David Dietrich and David M. Perrin

      Article first published online: 25 APR 2008 | DOI: 10.1002/anie.200800960

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      The mercury project: A self-cleaving DNAzyme that “switches on” in the presence of Hg2+ has been revealed by in vitro selection. The enzyme 10-13 (see picture) utilizes two modified nucleobases to confer an RNaseA-like catalytic activity that requires only Hg2+ and no other divalent metal cofactor. This DNAzyme is highly selective for mercuric cations.

    9. Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to α-Ketoesters (pages 4351–4353)

      Hai-Feng Duan, Jian-Hua Xie, Xiang-Chen Qiao, Li-Xin Wang and Qi-Lin Zhou

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800423

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      Rhodium catalysis: The first example of a catalytic asymmetric addition of arylboronic acids to α-ketoesters was realized by using a chiral RhI–spirophosphite ligand complex in aqueous solvent to provide tertiary α-hydroxyesters in good yields with high enantioselectivities (see scheme; DCE=1,2-dichloroethane).

    10. Strained Metallocenophanes with Late Transition Metals in the Bridge: Syntheses and Structures of Nickel- and Platinum-Bridged [1]Ferrocenophanes (pages 4354–4357)

      George R. Whittell, Benjamin M. Partridge, Oliver C. Presly, Christopher J. Adams and Ian Manners

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200705672

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      Late and unexpected: The first strained metallocenophanes with a single late transition-metal atom in the bridge have been prepared (see scheme). The nickel- and platinum-bridged complexes are the first [1]ferrocenophanes where the bridging atom has a distorted square-planar geometry, and the compounds are substantially more tilted and electron-rich than early transition-metal analogues.

    11. Supported Gold(III) Catalysts for Highly Efficient Three-Component Coupling Reactions (pages 4358–4361)

      Xin Zhang and Avelino Corma

      Article first published online: 25 APR 2008 | DOI: 10.1002/anie.200800098

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      Charged gold species stabilized on nanocrystalline CeO2 or ZrO2 are highly active catalysts for the one-pot, three-component coupling of aldehydes, amines, and alkynes/N-protected ethynylaniline, which yields multifunctionalized propargylamines and indoles in good to excellent yields (see picture; Ts=toluene-4-sulfonyl).

    12. Osmium(II) CNN Pincer Complexes as Efficient Catalysts for Both Asymmetric Transfer and H2 Hydrogenation of Ketones (pages 4362–4365)

      Walter Baratta, Maurizio Ballico, Giorgio Chelucci, Katia Siega and Pierluigi Rigo

      Article first published online: 28 APR 2008 | DOI: 10.1002/anie.200800339

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      Catalysis at a pinch: Osmium CNN pincer complexes [OsCl(CNN)P2] (see graphic) are extremely active and productive catalysts for both the transfer and asymmetric hydrogenation of ketones (TOF≈106 h−1 and TON≈105). High enantioselectivity is achieved in the presence of only 0.005–0.002 mol % of the chiral osmium derivatives. [OsX(CNN)(dppb)] species with X=H and OR are involved in these catalytic TH and HY reactions.

    13. Carbocycle Synthesis through Facile and Efficient Palladium-Catalyzed Allylative De-aromatization of Naphthalene and Phenanthrene Allyl Chlorides (pages 4366–4369)

      Shirong Lu, Zhanwei Xu, Ming Bao and Yoshinori Yamamoto

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800529

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      Ring of truth: The palladium-catalyzed reaction of allyltributylstannane with naphthalene or phenanthrene derivatives bearing an allyl chloride group proceeds smoothly to provide de-aromatized products with unique structures (see scheme). These products are very stable and can be used as intermediates to give fused-ring systems.

    14. Detection of Enzymatic Activity by PARACEST MRI: A General Approach to Target a Large Variety of Enzymes (pages 4370–4372)

      Thomas Chauvin, Philippe Durand, Michèle Bernier, Hervé Meudal, Bich-Thuy Doan, Fanny Noury, Bernard Badet, Jean-Claude Beloeil and Éva Tóth

      Article first published online: 2 MAY 2008 | DOI: 10.1002/anie.200800809

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      Perfect timing: A “smart” pro-PARACEST agent has been designed to detect β-galactosidase activity. Upon enzymatic attack, the self-immolative benzyloxycarbamate linker bearing the enzyme-specific substrate is cleaved and yields [Yb(dota-NH2)], which is endowed with a PARACEST effect. This pro-PARACEST agent is the first representative of a family of molecular imaging probes for the specific detection of a large variety of enzymatic activities using PARACEST.

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      Total Synthesis of (±)-Platencin (pages 4373–4376)

      Joji Hayashida and Viresh H. Rawal

      Article first published online: 2 MAY 2008 | DOI: 10.1002/anie.200800756

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      Resistant bacteria—beware! Platencin, a structurally novel broad-spectrum antibacterial agent, was the target of a total synthesis from o-anisic acid (see scheme). A Diels–Alder reaction with an α-substituted cyclohexenone as well as a [Ni(cod)2]-promoted 1,4-addition enables the concise and stereocontrolled formation of the core. A protecting group free coupling with an aniline unit completed the synthesis. cod=1,5-cyclooctadiene.

    16. Mimicking Biosynthesis: Total Synthesis of the Triterpene Natural Product Abudinol B from a Squalene-like Precursor (pages 4377–4379)

      Rongbiao Tong and Frank E. McDonald

      Article first published online: 5 MAY 2008 | DOI: 10.1002/anie.200800749

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      A short synthesis of the enantiomer of the title compound relies on Lewis acid promoted tandem oxa- and carbacyclizations (see scheme). This demonstration of tandem cyclizations provides experimental support for the chemical viability of a proposed biogenetic pathway.

    17. Monodentate, N-Heterocyclic Carbene-Type Coordination of 2,2′-Bipyridine and 1,10-Phenanthroline to Iridium (pages 4380–4383)

      Salvador Conejero, Patricia Lara, Margarita Paneque, Ana Petronilho, Manuel L. Poveda, Oracio Serrano, Florencia Vattier, Eleuterio Álvarez, Celia Maya, Verónica Salazar and Ernesto Carmona

      Article first published online: 30 APR 2008 | DOI: 10.1002/anie.200800705

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      Unusual Carbenes: 2,2′-Bipyridine and 1,10-phenanthroline are capable of coordinating to iridium as monodentate N-heterocyclic carbene ligands stabilized by N[BOND]H⋅⋅⋅N bonding. This reactivity leads to complexes like 1 and their analogues with 2 as the carbene ligand. [Ir]: [hydrotris(3,5-dimethylpyrazolyl)borate]iridium.

    18. Capture of Periodate in a {W18O54} Cluster Cage Yielding a Catalytically Active Polyoxometalate [H3W18O56(IO6)]6− Embedded with High-Valent Iodine (pages 4384–4387)

      De-Liang Long, Yu-Fei Song, Elizabeth F. Wilson, Paul Kögerler, Si-Xuan Guo, Alan M. Bond, Justin S. J. Hargreaves and Leroy Cronin

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800041

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      Periodate in the mix: The first crystallographically characterized tungstatoperiodate cluster of the form β*-[H3W18O56(IO6)]6−, with periodate embedded inside a {W18O54} cluster cage, remains intact in solution, and is the first in a new class of [HnW18O56(XO6)]m heteropolyoxotungstates. Mass spectrometry, and electrochemical and catalytic studies, verified by DFT calculations, reveal its unusual physical properties.

    19. Supramolecular Metal Oxides: Programmed Hierarchical Assembly of a Protein-Sized 21 kDa [(C16H36N)19{H2NC(CH2O)3P2V3W15O59}4]5− Polyoxometalate Assembly (pages 4388–4391)

      Chullikkattil P. Pradeep, De-Liang Long, Graham N. Newton, Yu-Fei Song and Leroy Cronin

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800431

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      Covalent grafting of “organic caps” onto Dawson metal oxide clusters controls their supramolecular self-assembly in the solid and solution phase. Formation can be controlled by changing the solvent and the hydrogen-bonding groups on the cap. A gigantic nanoassembly with a mass of ca. 21 kDa is characterized unambiguously in the solid state using single-crystal XRD, and detected in solution/gas phase by cryospray mass spectrometry as the 5 ion.

    20. Cadiot–Chodkiewicz Active Template Synthesis of Rotaxanes and Switchable Molecular Shuttles with Weak Intercomponent Interactions (pages 4392–4396)

      José Berná, Stephen M. Goldup, Ai-Lan Lee, David A. Leigh, Mark D. Symes, Gilberto Teobaldi and Francesco Zerbetto

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800891

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      Shuttling fast and loose: Weak interaction, switchable, rotaxane-based molecular shuttles, in which the positional fidelity of the macrocycle is conferred by a single hydrogen bond in each state, are constructed through the high-yielding and selective active template heterocoupling of different functionalized alkynes using the Cadiot–Chodkiewicz reaction.

    21. Mechanical-Force-Induced Nucleation and Growth of Peptide Nanofibers at Liquid/Solid Interfaces (pages 4397–4400)

      Hong Yang, Shan-Yu Fung, Mark Pritzker and P. Chen

      Article first published online: 30 APR 2008 | DOI: 10.1002/anie.200705404

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      Tap to induce nanofiber growth: Mechanical force applied by a tapping AFM tip can break peptide nanofibers into active “seeds” for local growth of new nanofibers at liquid/solid interfaces (see AFM images). The combination of such an approach with certain solution conditions allows one to fabricate peptide-nanostructure-patterned surfaces.

    22. Combining Structure Modeling and Electron Microscopy to Determine Complex Zeolite Framework Structures (pages 4401–4405)

      Yi Li, Jihong Yu, Ruren Xu, Christian Baerlocher and Lynne B. McCusker

      Article first published online: 24 APR 2008 | DOI: 10.1002/anie.200705175

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      A single HRTEM image is used to build up a potential map as starting point of a computer simulation method to solve complex zeolite structures. During the simulation, atoms are generated randomly and “pushed” into regions of high potential to fit the HRTEM image (see scheme). At the end of the simulation, models with reasonable bonding geometry and good agreement with the HRTEM image are chosen as candidates for the final structure solution.

    23. Surface Synthesis of 2D Branched Polymer Nanostructures (pages 4406–4410)

      Sigrid Weigelt, Carsten Busse, Christian Bombis, Martin M. Knudsen, Kurt V. Gothelf, Erik Lægsgaard, Flemming Besenbacher and Trolle R. Linderoth

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200705079

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      Root and branch: A two-dimensional polyimine network (see picture) is formed by condensation polymerization of trialdehydes and diamines co-adsorbed on an Au(111) surface under ultrahigh-vacuum conditions. The local bonding pattern is characterized by STM, which shows that the connectivity of the network is influenced by the kinetic parameters of the preparation procedure.

    24. Cysteine-Free Peptide and Glycopeptide Ligation by Direct Aminolysis (pages 4411–4415)

      Richard J. Payne, Simon Ficht, William A. Greenberg and Chi-Huey Wong

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200705298

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      Left to their own devices in a mixed-solvent system, peptides undergo efficient aminolysis with peptide thioesters (see scheme). This ligation method, which does not require coupling reagents, auxiliaries, or an N-terminal cysteine residue, is suitable for a variety of amino acids at the ligation junction. Its effectiveness was demonstrated by the synthesis of a 6.9-kDa section of the cancer-associated MUC1 tandem repeat.

    25. Photochemical and Electrochemical Encoding of Erasable Magnetic Patterns (pages 4416–4420)

      Michael Riskin, Vitaly Gutkin, Israel Felner and Itamar Willner

      Article first published online: 24 APR 2008 | DOI: 10.1002/anie.200705793

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      General patterns: A photoisomerizable nitrospiropyran monolayer associated with a gold surface enables the photolithographic patterning of the surface with nitromerocyanine domains. The selective association of Co2+ ions on the nitromerocyanine domains (red) allows the electrochemical generation of magnetic Co0 nanoparticles (NPs) on these domains. The magnetic information can be electrochemically erased and restored.

    26. Photochemical Surface Patterning by the Thiol-Ene Reaction (pages 4421–4424)

      Pascal Jonkheijm, Dirk Weinrich, Maja Köhn, Hans Engelkamp, Peter C. M. Christianen, Jürgen Kuhlmann, Jan C. Maan, Dirk Nüsse, Hendrik Schroeder, Ron Wacker, Rolf Breinbauer, Christof M. Niemeyer and Herbert Waldmann

      Article first published online: 21 APR 2008 | DOI: 10.1002/anie.200800101

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      The photochemical coupling of olefin-capped (bio)molecules to surface-bound thiols can be used to control protein immobilization on length scales of centimeters to sub-micrometers (see the fluorescence microscopy image of a nanopattern after treatment with labeled streptavidin). Two enzymes immobilized on the resulting patterns retained their enzymatic activity and underwent protein–protein interactions similar to those in the solution phase.

    27. Controlling the Activation of White Phosphorus: Formation of Phosphorous Acid and Ruthenium-Coordinated 1-Hydroxytriphosphane by Hydrolysis of Doubly Metalated P4 (pages 4425–4427)

      Pierluigi Barbaro, Massimo Di Vaira, Maurizio Peruzzini, Stefano Seniori Costantini and Piero Stoppioni

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800723

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      Successfully tamed: When coordinated to two {CpRu(PPh3)2} moieties, white phosphorus (P4) reacts selectively with a large excess of water to yield phosphorous acid (H3PO3) and the previously unknown 1-hydroxytriphosphane (PH(OH)PHPH2), which is stabilized as a bridging ligand by coordination to the ruthenium moieties (see scheme).

    28. Experimental Substantiation of the “Energy Landscape Concept” for Solids: Synthesis of a New Modification of LiBr (pages 4428–4431)

      Yvonne Liebold-Ribeiro, Dieter Fischer and Martin Jansen

      Article first published online: 5 MAY 2008 | DOI: 10.1002/anie.200800333

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      Global exploration of the energy landscape of lithium bromide led to the prediction of a new, metastable polymorph, β-LiBr (wurtzite structure type), which has now been synthesized (see E/V plot for comparison of polymorphs). Single-phase thick films of β-LiBr were obtained at −50 °C and 2.3×10−4 mbar using the low-temperature-deposition technique.

    29. Divergent Synthesis of a Pochonin Library Targeting HSP90 and In Vivo Efficacy of an Identified Inhibitor (pages 4432–4435)

      Sofia Barluenga, Cuihua Wang, Jean-Gonzague Fontaine, Kaïss Aouadi, Kristin Beebe, Shinji Tsutsumi, Len Neckers and Nicolas Winssinger

      Article first published online: 25 APR 2008 | DOI: 10.1002/anie.200800233

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      Make a clean breast of it: The generation of a library of pochonin D derivatives by a solid-phase approach has led to the discovery of pochoxime (see scheme), a potent inhibitor of the heat-shock protein 90, with over 100-fold improved incellular activity. Pochoxime was found to be effective in breast tumor xenografts, leading to a reduction in the tumor size.

    30. Efficient Solvent-Free Syntheses of [2]- and [4]Rotaxanes (pages 4436–4439)

      Sheng-Yao Hsueh, Kuang-Wei Cheng, Chien-Chen Lai and Sheng-Hsien Chiu

      Article first published online: 29 APR 2008 | DOI: 10.1002/anie.200800530

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      Waste not want not: A [2]rotaxane has been generated in 49 % yield through the direct grinding of solid macrocyclic, threadlike, and stoppering components. The same solid-state ball-milling reactions of solids of pseudorotaxanes and stoppers produced both [2]- and [4]rotaxanes in high yield (see picture). The approach relies on solid-state condensations and is convenient and waste-free (water is the only by-product).

    31. Phosphine Oxide Monolayers on SiO2 Surfaces (pages 4440–4442)

      Roie Yerushalmi, Johnny C. Ho, Zhiyong Fan and Ali Javey

      Article first published online: 6 MAY 2008 | DOI: 10.1002/anie.200800737

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      Getting a grip: H-bond formation is shown to be the main mode of interaction for monolayer formation of phosphine oxides on SiO2 substrates (see images), with covalent reaction involved to a lesser extent. In contrast to the situation with the more widely studied polar phosphonic acids, formation of these monolayers is self-limiting. The results may have important implications for many applications based on phosphine oxide monolayers.

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      Preview: Angew. Chem. Int. Ed. 24/2008 (page 4447)

      Article first published online: 16 MAY 2008 | DOI: 10.1002/anie.200890110

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