Angewandte Chemie International Edition

Cover image for Vol. 47 Issue 50

December 1, 2008

Volume 47, Issue 50

Pages 9575–9781

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Cover Picture: Chemical Strategies for Generating Protein Biochips (Angew. Chem. Int. Ed. 50/2008) (page 9575)

      Pascal Jonkheijm, Dirk Weinrich, Hendrik Schröder, Christof M. Niemeyer and Herbert Waldmann

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200890256

      Thumbnail image of graphical abstract

      Chemistry has become a powerful tool in protein biochip generation by providing methods to specifically functionalize proteins and immobilize them on surfaces. C. M. Niemeyer, H. Waldmann, and co-workers outline the range of available chemical methods for preparation of high-quality protein biochips in the Review on page 9618 ff. The cover picture shows the sequence of events in a protein microarray protein–protein interaction assay: two different proteins are immobilized through specific interactions with the surface; a third, fluorescently labeled protein is used for read-out.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Inside Cover: Highly Selective Metal Catalysts for Intermolecular Carbenoid Insertion into Primary C[BOND]H Bonds and Enantioselective C[BOND]C Bond Formation (Angew. Chem. Int. Ed. 50/2008) (page 9576)

      Hung-Yat Thu, Glenna So-Ming Tong, Jie-Sheng Huang, Sharon Lai-Fung Chan, Qing-Hai Deng and Chi-Ming Che

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200890257

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      Analogous to a microreactor that has twelve inlets, but with only one large enough for secondary C[BOND]H bonds to approach reactive metal–carbene groups, a rhodium catalyst bearing a bis-pocket porphyrin that imposes a high steric hindrance to secondary C[BOND]H bonds is described by C.-M. Che et al. in their Communication on page 9747 ff. The porphyrin directs reactions to occur at the less reactive primary C[BOND]H bonds of n-alkanes, with an approximate primary/secondary selectivity of 11:1.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. You have free access to this content
      Covalently Linked Dimers of Clusters: Loop- and Dumbbell-Shaped Mn24 and Mn26 Single-Molecule Magnets (page 9590)

      Theocharis C. Stamatatos, Khalil A. Abboud, Wolfgang Wernsdorfer and George Christou

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200890259

      This article corrects:

      Covalently Linked Dimers of Clusters: Loop- and Dumbbell-Shaped Mn24 and Mn26 Single-Molecule Magnets1

      Vol. 47, Issue 35, 6694–6698, Version of Record online: 18 JUL 2008

    2. You have free access to this content
      An Epilogue on the C78-Fullerene Family: The Discovery and Characterization of an Elusive Isomer (page 9590)

      Kalin S. Simeonov, Konstantin Yu. Amsharov, Evangelos Krokos and Martin Jansen

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200890262

      This article corrects:

      An Epilogue on the C78-Fullerene Family: The Discovery and Characterization of an Elusive Isomer1

      Vol. 47, Issue 33, 6283–6285, Version of Record online: 10 JUL 2008

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
  6. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
  7. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
  8. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
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    1. Soluble B[BOND]N Polymers

      Soluble Boron–Nitrogen High Polymers from Metal-Complex-Catalyzed Amine Borane Dehydrogenation (pages 9600–9602)

      Vincent Pons and R. Tom Baker

      Version of Record online: 12 NOV 2008 | DOI: 10.1002/anie.200803089

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      Taking the high road is what reactions of primary amine boranes do, according to results recently obtained by Manners and co-workers, when a homogeneous catalyst is used to prepare soluble aminoborane polymers and copolymers (see scheme; pocop=ϰ3-1,3-(OPtBu2)2C6H3). Such metal-catalyzed dehydrocoupling reactions for the synthesis of new B[BOND]N analogues of α-olefins are of fundamental interest for materials science.

    2. Supramolecular Chemistry

      Metal–Organic Scaffolds: Heavy-Metal Approaches to Synthetic Ion Channels and Pores (pages 9603–9607)

      Naomi Sakai and Stefan Matile

      Version of Record online: 31 OCT 2008 | DOI: 10.1002/anie.200803300

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      Space—the final frontier: Recent progress with metal–organic scaffolds (see picture for an example) to create synthetic ion channels and pores is summarized in this Highlight. The great advantage of this approach is access to a stable and large confined space from small structural units. Current breakthroughs promise future progress toward the synthesis of tubular structures and their multiple functionalization.

  9. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
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    1. Amber

      Chemical Signatures of Fossilized Resins and Recent Plant Exudates (pages 9608–9616)

      Joseph B. Lambert, Jorge A. Santiago-Blay and Ken B. Anderson

      Version of Record online: 16 OCT 2008 | DOI: 10.1002/anie.200705973

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      The chemical fingerprint of amber may be detected in terms of molecular components by pyrolysis GC–MS or in terms of 13C NMR resonances. Understanding the components of amber can permit association with geographical and botanical sources. The picture shows an exudate with entrapped ants from a pine tree in the U.S. National Arboretum, Washington, DC. (Photograph by Chip Clark, National Museum of Natural History, Washington, DC).

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Protein Biochips

      Chemical Strategies for Generating Protein Biochips (pages 9618–9647)

      Pascal Jonkheijm, Dirk Weinrich, Hendrik Schröder, Christof M. Niemeyer and Herbert Waldmann

      Version of Record online: 21 NOV 2008 | DOI: 10.1002/anie.200801711

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      Putting the protein on the chip: This Review discusses chemical strategies, both covalent and noncovalent, for attaching proteins to surfaces to make protein biochips. Particular emphasis is put on the chemical specificity of protein attachment and on retention of protein function. Strategies for creating protein patterns (as opposed to protein arrays) are also presented.

  11. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Review
    8. News
    9. Highlights
    10. Minireview
    11. Review
    12. Communications
    13. Preview
    1. Polymeric Extractants

      Poly(methyl methacrylate)s with Pendant Calixpyrroles and Crown Ethers: Polymeric Extractants for Potassium Halides (pages 9648–9652)

      Abdullah Aydogan, Daniel J. Coady, Sung Kuk Kim, Ahmet Akar, Christopher W. Bielawski, Manuel Marquez and Jonathan L. Sessler

      Version of Record online: 16 OCT 2008 | DOI: 10.1002/anie.200803970

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      Fishing for KF: Potassium fluoride and chloride salts can be extracted from aqueous media using poly(methyl methacrylate)s containing pendant calix[4]pyrrole and crown ether groups (see picture). These polymers are able to extract these salts much more efficiently than calixpyrrole, crown ether, linked crown ether calixpyrrole monomers, polymers containing either recognition unit, or poly(methyl methacrylate) controls.

    2. Gold Nanostructures

      Facile Synthesis of Branched Au Nanostructures by Templating Against a Self-Destructive Lattice of Magnetic Fe Nanoparticles (pages 9653–9656)

      Zhengquan Li, Weiyang Li, Pedro H. C. Camargo and Younan Xia

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200804634

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      Self-destruct mechanism: Gold multipods are formed by a galvanic replacement reaction of AuCl with a self-destructive template consisting of a three-dimensional aggregate of magnetic iron nanoparticles. As a unique feature of this system, the template spontaneously falls apart during the reaction to automatically release the resultant gold multipods.

    3. Aromaticity

      Protonation-Triggered Conformational Changes to Möbius Aromatic [32]Heptaphyrins(1.1.1.1.1.1.1) (pages 9657–9660)

      Shohei Saito, Jae-Yoon Shin, Jong Min Lim, Kil Suk Kim, Dongho Kim and Atsuhiro Osuka

      Version of Record online: 19 NOV 2008 | DOI: 10.1002/anie.200804457

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      Switching Aromaticity: Conformations of [32]heptaphyrins(1.1.1.1.1.1.1) are dependent upon meso-aryl substituents, solvents, temperature, and protonation. Particularly, protonation of meso-pentafluorophenyl-substituted [32]heptaphyrin triggers conformational changes to form twisted aromatic Möbius structures (see picture), even at room temperature.

    4. Porphyrinoids

      A Stable Radical Species from Facile Oxygenation of meso-Free 5,10,20,25-Tetrakis(pentafluorophenyl)-Substituted [26]Hexaphyrin(1.1.1.1.1.1) (pages 9661–9665)

      Taro Koide, Gengo Kashiwazaki, Masaaki Suzuki, Ko Furukawa, Min-Chul Yoon, Sung Cho, Dongho Kim and Atsuhiro Osuka

      Version of Record online: 10 NOV 2008 | DOI: 10.1002/anie.200804570

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      A stable radical: The title compound 1 has been synthesized as the first example of a meso-free variant and characterized as a strongly aromatic macrocycle with a spectacles-like planar conformation. The incorporation of free meso positions is promising for the exploration of novel structural and electronic properties.

    5. Radical Cations

      Structure of the Observable Histidine Radical Cation in the Gas Phase: A Captodative α-Radical Ion (pages 9666–9668)

      Jeffrey Steill, Junfang Zhao, Chi-Kit Siu, Yuyong Ke, Udo H. Verkerk, Jos Oomens, Robert C. Dunbar, Alan C. Hopkinson and K. W. Michael Siu

      Version of Record online: 10 NOV 2008 | DOI: 10.1002/anie.200804101

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      The observable histidine radical cation generated by collision-induced dissociation of the [CuII(2,2′:6′,2′′-terpyridine)(His)].2+ complex carries the positive charge on the protonated imidazole ring and the radical formally on the α carbon. This structure has been confirmed by infrared multiple photon dissociation (IRMPD) spectroscopy and density functional calculations.

    6. Metal–Coenzyme Complexes

      Proton Shift upon One-Electron Reduction in Ruthenium(II)-Coordinated Pterins (pages 9669–9672)

      Soushi Miyazaki, Kei Ohkubo, Takahiko Kojima and Shunichi Fukuzumi

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200802835

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      A shift in focus: Fully oxidized pterins coordinated to ruthenium(II) undergo a first protonation at the nitrogen atom at the 1-position of the pyrimidinone moiety. Subsequent one-electron reduction induces an unprecedented proton shift from the nitrogen atom at the 1-position to that at the 8-position of the pyrazine moiety (see picture; C white, H yellow, N blue, O red).

    7. Surface Nucleobase Pairing

      Specificity of Watson–Crick Base Pairing on a Solid Surface Studied at the Atomic Scale (pages 9673–9676)

      Roberto Otero, Wei Xu, Maya Lukas, Ross E. A. Kelly, Erik Lægsgaard, Ivan Stensgaard, Jørgen Kjems, Lev N. Kantorovich and Flemming Besenbacher

      Version of Record online: 10 NOV 2008 | DOI: 10.1002/anie.200803333

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      Surface Watson–Crick base pairing makes binary mixtures of the complementary nucleobases guanine (G) and cytosine (C) on Au(111) thermally stable up to the desorption temperature of the bases, whereas binary mixtures of the noncomplementary adenine (A) and cytosine segregate on heating (see STM images with DFT structures).

    8. Protein Dynamics

      Isotope-Coded Affinity Tags with Tunable Reactivities for Protein Footprinting (pages 9677–9680)

      Eric S. Underbakke, Yimin Zhu and Laura L. Kiessling

      Version of Record online: 31 OCT 2008 | DOI: 10.1002/anie.200803378

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      Another foot forward: Isotope-coded affinity tag (ICAT) reagents are versatile probes for footprinting dynamic protein structure. To render ICAT footprinting effective, a series of ICAT reagents with alkylation rates that span five orders of magnitude was designed. With this toolkit, an unprecedented range of Cys residues can be footprinted, including those deeply buried in the protein core and those involved in protein–protein interactions of modest affinity.

    9. Metallocycles

      Heterometallic Rings Made From Chromium Stick Together Easily (pages 9681–9684)

      Grigore A. Timco, Eric J. L. McInnes, Robin G. Pritchard, Floriana Tuna and Richard E. P. Winpenny

      Version of Record online: 6 NOV 2008 | DOI: 10.1002/anie.200803637

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      Sugared donuts: Reactions of hydrated chromium fluoride with N-ethyl-D-glucamine (H5Etglu) in pivalic acid, in the presence of nickel carbonate, leads to heterometallic “glu-ed” rings. These rings allow for construction of polyring arrays, for example an assembly where four glu-ed rings are attached to tetrapyridylporphyrin (see structure; F yellow, O red, N blue, Cr purple, Ni green, C black).

    10. Ordered Assemblies

      Ordered Gold Nanostructure Assemblies Formed By Droplet Evaporation (pages 9685–9690)

      Tian Ming, Xiaoshan Kou, Huanjun Chen, Tao Wang, Hoi-Lam Tam, Kok-Wai Cheah, Ji-Yao Chen and Jianfang Wang

      Version of Record online: 10 NOV 2008 | DOI: 10.1002/anie.200803642

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      The order of gold: Ordered assemblies of gold nanostructures are produced by droplet evaporation from single- and two-component systems. The ordering of the assemblies is highly dependent on the shape and size of gold nanostructures and includes nanorods, nanocubes, polyhedra, and bipyramids. The two-photon-excited luminescence of ordered gold nanorod assemblies is larger than that of disordered nanorod assemblies.

    11. α-Helix Mimetics

      Controlling Curvature in a Family of Oligoamide α-Helix Mimetics (pages 9691–9694)

      Ishu Saraogi, Christopher D. Incarvito and Andrew D. Hamilton

      Version of Record online: 6 NOV 2008 | DOI: 10.1002/anie.200803778

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      Catching up with the curve! The natural curvature found in a majority of α helices has been mimicked in small synthetic oligoamide scaffolds. Differences in hydrogen-bonding patterns in these scaffolds lead to mimetics with varying degrees of curvature in the backbone. This adds another parameter to the structural and functional mimicry of α helices.

    12. Cluster Compounds

      Supertetrahedral and Bi-supertetrahedral Cages: Synthesis, Structures, and Magnetic Properties of Deca- and Enneadecametallic Cobalt(II) Clusters (pages 9695–9699)

      Laurent Lisnard, Floriana Tuna, Andrea Candini, Marco Affronte, Richard E. P. Winpenny and Eric J. L. McInnes

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200804147

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      Magnetic cage: Simple cobalt(II) diketonates react with triols under solvothermal conditions to give a family of compounds based on supertetrahedral cage structures: a regular and a distorted {CoII10} species, and a bi-supertetrahedral {CoII19} species. Magnetic studies show unusual properties, such as nonvanishing magnetization below 12 K, which until now have only been detected in a family of {Ni10} clusters.

    13. Homogeneous Catalysis

      Synthesis of (Z)-1-Aza-1,3-enynes by the Cross-Coupling of Terminal Alkynes with Isocyanides Catalyzed by Rare-Earth Metal Complexes (pages 9700–9703)

      Wen-Xiong Zhang, Masayoshi Nishiura and Zhaomin Hou

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200804306

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      Rare reactivity: A binuclear catalyst intermediate leads to the Z-selective cross-coupling of terminal alkynes with isocyanides to exclusively yield the (Z)-1-aza-1,3-enyne products for the first time (see scheme).

    14. Clathrate Structures

      Transformation of the Hexagonal-Structure Clathrate Hydrate of Cyclooctane to a Low-Symmetry Form Below 167 K (pages 9704–9707)

      Konstantin A. Udachin, Christopher I. Ratcliffe, Gary D. Enright and John A. Ripmeester

      Version of Record online: 31 OCT 2008 | DOI: 10.1002/anie.200801694

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      Cold guests lower the tone: The thermally induced phase transition in the hexagonal clathrate hydrate containing cyclooctane is reversible. This transition is most likely related to the freezing-in of the motion of the low-symmetry cyclooctane guest (see picture: colors indicate different orientations of the guest and associated distortions of the host).

    15. Asymmetric Catalysis

      Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts (pages 9708–9710)

      Norito Takenaka, Robindro Singh Sarangthem and Burjor Captain

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200803338

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      Helical Chiral Catalysts: The gram-scale synthesis of 1-azahelicenes, structural characterization of the corresponding N-oxides, and the application of this new family of catalysts to the catalytic, enantioselective ring-opening of meso epoxides is described (see scheme). Included is the first demonstration that the appropriate structural modifications beneath the plane of the pyridine N-oxide can serve as a powerful means for tuning the catalyst enantioselectivity.

    16. Mesoporous Cathodes

      Synthesis of Ordered Mesoporous Li–Mn–O Spinel as a Positive Electrode for Rechargeable Lithium Batteries (pages 9711–9716)

      Feng Jiao, Jianli Bao, Adrian H. Hill and Peter G. Bruce

      Version of Record online: 6 NOV 2008 | DOI: 10.1002/anie.200803431

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      Sturdy spinel: A mesoporous Li–Mn–O spinel (Li1.12Mn1.88O4) with superior rate capability at ambient temperature is synthesized. Comparable stability to the bulk material at elevated temperatures is also observed, despite a surface area of 90 m2 g−1 for the mesopore, suggesting that the internal mesopore surfaces are more stable than the external surface.

    17. Catalyst Design

      Isolation of Single-Component Trimerization and Polymerization Chromium Catalysts: The Role of the Metal Oxidation State (pages 9717–9721)

      Amir Jabri, Chris B. Mason, Yan Sim, Sandro Gambarotta, Tara J. Burchell and Robbert Duchateau

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200803434

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      One more trimer: A series of chromium complexes of different oxidation states are employed as catalysts for the polymerization/oligomerization of ethylene. The results suggest a link between chromium oxidation state and catalytic performance, with CrIII leading to oligomerization, CrII to polymerization, and CrI to selective trimerization.

    18. Enzyme Catalysis

      IspH Protein of the Deoxyxylulose Phosphate Pathway: Mechanistic Studies with C1-Deuterium-Labeled Substrate and Fluorinated Analogue (pages 9722–9725)

      Youli Xiao and Pinghua Liu

      Version of Record online: 3 NOV 2008 | DOI: 10.1002/anie.200803452

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      The last step of the deoxylxylulose phosphate pathway is catalyzed by IspH to synthesize two precursors for isoprenoid biosynthesis. The lack of a primary kinetic isotope effect at C1and enzymatic evaluation with a fluorinated analogue (see scheme) suggest that the C1-position is not involved in the IspH-catalyzed reaction. FldA=flavodoxin, Fpr=flavodoxin reductase, NADPH=nicotinamide adenine dinucleotide phosphate, PPi=P2O63−.

    19. Mucus-Penetrating Particles

      Addressing the PEG Mucoadhesivity Paradox to Engineer Nanoparticles that “Slip” through the Human Mucus Barrier (pages 9726–9729)

      Ying-Ying Wang, Samuel K. Lai, Jung Soo Suk, Amanda Pace, Richard Cone and Justin Hanes

      Version of Record online: 31 OCT 2008 | DOI: 10.1002/anie.200803526

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      Outsmarting the barrier: Conventional poly(ethylene glycol) (PEG) coated particles (green with light purple border) are immobilized in human mucus networks by adhesive interactions (red) with the mucus mesh (black lines). A dense, low molecular weight PEG coating (blue) uniquely endows nanoparticles with a mucoinert surface that enables their rapid mucus penetration (trajectory indicated by grey line).

    20. Photocatalysis

      Visible-Light-Induced Aerobic Oxidation of Alcohols in a Coupled Photocatalytic System of Dye-Sensitized TiO2 and TEMPO (pages 9730–9733)

      Miao Zhang, Chuncheng Chen, Wanhong Ma and Jincai Zhao

      Version of Record online: 4 NOV 2008 | DOI: 10.1002/anie.200803630

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      Like a differential gear: Upon irradiation with visible light, excited dye molecules inject electrons into TiO2 and form dye radicals, which can oxidize TEMPO to TEMPO+, which in turn oxidizes alcohols in the presence of O2 selectively to corresponding aldehydes. One reason for the selectivity is that the irradiation is downshifted to visible light.

    21. Vaccines

      Synthesis of Diacylated Trehalose Sulfates: Candidates for a Tuberculosis Vaccine (pages 9734–9738)

      Julie Guiard, Anthony Collmann, Martine Gilleron, Lucia Mori, Gennaro De Libero, Jacques Prandi and Germain Puzo

      Version of Record online: 3 NOV 2008 | DOI: 10.1002/anie.200803835

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      Able antigen analogues: Analogues of the mycobacterial sulfoglycolipid antigen 1 isolated from Mycobacterium tuberculosis have been prepared by a short and general route. Some derivatives showed interesting immunogenic properties and activated cytotoxic T cells. Immunogenic analogues contained a chiral saturated or α,β-unsaturated polymethylated fatty acid with S configured stereogenic centers at the 3-position of the trehalose core.

    22. Electrophilic Reaction Media

      Lewis Acid Catalyst Free Electrophilic Alkylation of Silicon-Capped π Donors in 1,1,1,3,3,3-Hexafluoro-2-propanol (pages 9739–9742)

      Maxim O. Ratnikov, Vasily V. Tumanov and William A. Smit

      Version of Record online: 3 NOV 2008 | DOI: 10.1002/anie.200803927

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      A credit to donation: A diverse range of electrophilic addition reactions, conventionally carried out using Lewis acid catalysts, have been performed in electrophilic media without acidic reagents. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) acts as an efficient hydrogen-bond donor and highly polar solvent for a wide range of substrates in reactions with Si-capped π donors.

    23. Synthetic Methods

      Dual Macrolactonization/Pyran–Hemiketal Formation via Acylketenes: Applications to the Synthesis of (−)-Callipeltoside A and a Lyngbyaloside B Model System (pages 9743–9746)

      Thomas R. Hoye, Michael E. Danielson, Aaron E. May and Hongyu Zhao

      Version of Record online: 31 OCT 2008 | DOI: 10.1002/anie.200804049

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      Two for one: Thermal generation of acylketenes in diol-containing substrates results in the title transformation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and tetraol substrates have also been cyclized in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved.

    24. C[BOND]H Activation

      Highly Selective Metal Catalysts for Intermolecular Carbenoid Insertion into Primary C[BOND]H Bonds and Enantioselective C[BOND]C Bond Formation (pages 9747–9751)

      Hung-Yat Thu, Glenna So-Ming Tong, Jie-Sheng Huang, Sharon Lai-Fung Chan, Qing-Hai Deng and Chi-Ming Che

      Version of Record online: 15 OCT 2008 | DOI: 10.1002/anie.200803157

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      Primary C[BOND]H bond activation! A Rh complex of bis-pocket porphyrin I catalyzes carbenoid insertion into the C[BOND]H bonds of n-alkanes with a primary/secondary selectivity (per C[BOND]H bond) of up to 11.4:1 (see picture). Enantioselective secondary C[BOND]H bond functionalization catalyzed by a Rh complex of Halterman's chiral porphyrin features up to 93 % ee. These reactions exhibit up to 6477 turnovers after the catalyst was recycled five times.

    25. Bionanotechnology

      Label-Free Pathogen Detection with Sensor Chips Assembled from Peptide Nanotubes (pages 9752–9755)

      Roberto de la Rica, Ernest Mendoza, Laura M. Lechuga and Hiroshi Matsui

      Version of Record online: 6 NOV 2008 | DOI: 10.1002/anie.200804299

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      A robust viral sensor was developed by bridging a pair of gold electrodes with antibody-coated peptide nanotubes. The nanotubes concentrated the target virus on their surface by molecular recognition between the antibody and the virus (see picture). The nanotubes fit perfectly within the electric field line distribution to enable the extremely sensitive impedimetric detection of viral particles.

    26. Hydrogenase Models

      [FeFe]-Hydrogenase Models and Hydrogen: Oxidative Addition of Dihydrogen and Silanes (pages 9756–9759)

      Zachariah M. Heiden, Giuseppe Zampella, Luca De Gioia and Thomas B. Rauchfuss

      Version of Record online: 10 NOV 2008 | DOI: 10.1002/anie.200804400

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      Super model: Diiron dithiolates exist in nature in [FeFe]-hydrogenase, for the purpose of making or oxidizing molecular hydrogen. Evidence for how H2 interacts with diiron complexes has been realized using model diiron dithiolato carbonyl complexes. The pathway for this interaction has been elucidated computationally as well as synthetically, by using silanes in place of H2.

    27. Synthetic Methods

      Modular Approach to Silicon-Bridged Biaryls: Palladium-Catalyzed Intramolecular Coupling of 2-(Arylsilyl)aryl Triflates (pages 9760–9764)

      Masaki Shimizu, Kenji Mochida and Tamejiro Hiyama

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200804146

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      Bridge of Si: Intramolecular direct arylation of 2-(arylsilyl)aryl triflates is catalyzed smoothly by Pd(OAc)2/PCy3 in the presence of Et2NH in dimethylacetamide (DMA), giving rise to the corresponding silicon-bridged biaryls in good to excellent yields. The new approach has led to the synthesis of a silicon-bridged 2-phenylindole (see scheme) that exhibits blue photoluminescence in the solid state with extremely high quantum yields.

    28. Carbene Complexes

      “Pincer” Pyridine–Dicarbene–Iridium Complexes: Facile C[BOND]H Activation and Unexpected η2-Imidazol-2-ylidene Coordination (pages 9765–9767)

      Andreas A. Danopoulos, David Pugh and Joseph A. Wright

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200804573

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      A bridge to somewhere: A series of pyridine dicarbene iridium “pincer” complexes is easily accessible when pyridine ring metalation is suppressed by methyl substitution (see structure; NHC=N-heterocyclic carbene). A new bridging binding mode of the imidazol-2-ylidene heterocycle, involving η2-alkene-like coordination, has been observed crystallographically.

    29. Electrochemical Reduction

      Synthesis and Electrochemical Reduction of a Ruthenium Complex Bearing an N,N-Bis[(benzo[g][1,5]naphthyridin-2-yl)methyl]propane-2-amine Ligand as an NAD+/NADH-Type Redox Site (pages 9768–9771)

      Masahiro Kimura and Koji Tanaka

      Version of Record online: 4 NOV 2008 | DOI: 10.1002/anie.200804404

      Thumbnail image of graphical abstract

      Going slightly NADH: The electrochemical reduction of [Ru(bbnma)(bpy)(CO)](PF6)2 (bbnma=N,N-bis[(benzo[g][1,5]naphthyridin-2-yl)methyl]propane-2-amine, bpy=2,2′-bipyridine) in the presence of pivalic acid gave [Ru(bbnmaH4)(bpy)(CO)](PF6)2, the NADH-type product of a four-electron reduction.

    30. Relative Reactivity

      Probing the Reactivity of a Stable Silene Using Muonium (pages 9772–9774)

      Brett M. McCollum, Takashi Abe, Jean-Claude Brodovitch, Jason A. C. Clyburne, Takeaki Iwamoto, Mitsuo Kira, Paul W. Percival and Robert West

      Version of Record online: 5 NOV 2008 | DOI: 10.1002/anie.200804458

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      Taking the silenic route: Addition of a hydrogen atom analogue, muonium (Mu), to stable silene 1 gives rise to two distinct radical species, 1-CMu and 1-SiMu, allowing the relative reactivity of silenic carbon and silicon atoms to be probed. The former is the first reported example of a muoniated silyl radical. The radical species are detected by muon spin rotation and resonance spectroscopy (μSR).

    31. Cellular Adhesion

      A Bond for a Lifetime: Employing Membrane Nanotubes from Living Cells to Determine Receptor–Ligand Kinetics (pages 9775–9777)

      Michael Krieg, Jonne Helenius, Carl-Philipp Heisenberg and Daniel J. Muller

      Version of Record online: 26 NOV 2008 | DOI: 10.1002/anie.200803552

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      The name's Bond: Separated cells form membranous nanotubes whose tips are tethered by adhesive bonds (see picture). The lifetime of receptor–ligand interactions can be measured by using membrane nanotubes of living cells as constant force actuators. Because the nanotubes are extruded from living cells at conditions approaching the physiological, cellular processes can be both studied and utilized.

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