Angewandte Chemie International Edition

Cover image for Vol. 49 Issue 45

November 2, 2010

Volume 49, Issue 45

Pages 8277–8533

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
    13. Preview
    1. Cover Picture: Palladium-Catalyzed Coupling of Aldehyde-Derived Hydrazones: Practical Synthesis of Triazolopyridines and Related Heterocycles (Angew. Chem. Int. Ed. 45/2010) (page 8277)

      Dr. Oliver R. Thiel, Dr. Michal M. Achmatowicz, Dr. Andreas Reichelt and Dr. Robert D. Larsen

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201004361

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      Pharmaceutically active compounds … and their intermediates require selective, efficient, and robust syntheses that utilize green chemistry principles. In their Communication on page 8395 ff., O. R. Thiel, M. Achmatowicz, and co-workers describe a two-step procedure involving selective palladium-catalyzed carbon–nitrogen bond formation followed by a clean oxidative cyclization that affords access to a variety of bicyclic and tricyclic heteroaromatic scaffolds.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
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    1. Inside Cover: Solid-State 17O NMR Spectroscopy of Large Protein–Ligand Complexes (Angew. Chem. Int. Ed. 45/2010) (page 8278)

      Dr. Jianfeng Zhu, Dr. Eric Ye, Dr. Victor Terskikh and Prof. Dr. Gang Wu

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201004202

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      Large biomolecular systems have been probed for the first time by solid-state 17O NMR spectroscopy. In their Communication on page 8399 ff., G. Wu and co-workers show that high-quality solid-state 17O NMR spectra can be obtained for large protein–ligand complexes at an ultrahigh magnetic field of 21 T. The sensitivity of solid-state 17O NMR experiments at this field should allow biomolecular systems of up to 300 kDa in size to be tackled.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
    13. Preview
  4. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
    13. Preview
    1. You have free access to this content
      Corrigendum: Inversion of Particle-Stabilized Emulsions to Form High-Internal-Phase Emulsions (page 8295)

      Guanqing Sun, Zifu Li and Prof. To Ngai

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201090145

      This article corrects:

      Inversion of Particle-Stabilized Emulsions to Form High-Internal-Phase Emulsions1

      Vol. 49, Issue 12, 2163–2166, Version of Record online: 19 FEB 2010

  5. News

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
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  6. Author Profile

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    8. Highlights
    9. Essay
    10. Minireview
    11. Reviews
    12. Communications
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    1. Milko E. van der Boom (page 8301)

      Version of Record online: 27 SEP 2010 | DOI: 10.1002/anie.201005062

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      “The part of my job which I enjoy the most is working with motivated and talented students. I am waiting for the day when someone will discover a cure for major diseases such as Alzheimer's disease and cancer …” This and more about Milko E. van der Boom can be found on page 8301.

  7. Highlights

    1. Top of page
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    4. Graphical Abstract
    5. Corrigendum
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    8. Highlights
    9. Essay
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    1. Reactive Species

      Trapping Unstable Benzoquinone Analogues by Coordination to a [(η5-C5Me5)Ir] Fragment and the Anticancer Activity of the Resulting Complexes (pages 8304–8305)

      Dr. Christian G. Hartinger

      Version of Record online: 27 AUG 2010 | DOI: 10.1002/anie.201003565

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      Gotcha! Unstable dithio- and diselenobenzoquinones can be trapped by coordination to an [(η5-C5Me5)Ir] moiety (see structure; gray C, white H, pink Ir, yellow Se). In vitro investigations on the anticancer activity of the resulting complexes showed them to be comparable to cis-platin. These organometallic species could form the basis for new anticancer agents.

    2. Asymmetric Synthesis

      Enantioselective Halocyclization Reactions for the Synthesis of Chiral Cyclic Compounds (pages 8306–8308)

      Guofei Chen and Prof. Dr. Shengming Ma

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003114

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      Ground-breaking progress has been made in the synthesis of chiral cyclic compounds from nonchiral unsaturated substrates with a nucleophilic functionality. A number of highly enantioselective electrophilic halocyclizations based on either the interaction of a chiral Lewis acid with an unsaturated substrate or the generation of a chiral electrophilic intermediate in situ from an electrophile and a chiral reagent (see scheme) were developed.

  8. Essay

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    1. History in the Making

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      Zurich′s Contributions to 50 Years Development of Bruker (pages 8310–8315)

      Richard R. Ernst

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/anie.201005067

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      Humble beginnings: It is 50 years since the foundation of Bruker Physik AG in Karlsruhe. In this Essay, Prof. Richard R. Ernst looks at the early years of the company, and how researchers in Zurich contributed to its success in the field of NMR instrumentation.

  9. Minireview

    1. Top of page
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    1. Macrocyclization Strategies

      Prins-Type Macrocyclizations as an Efficient Ring-Closing Strategy in Natural Product Synthesis (pages 8316–8326)

      Erika A. Crane and Prof. Karl A. Scheidt

      Version of Record online: 7 OCT 2010 | DOI: 10.1002/anie.201002809

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      A “Prins” among reactions: The first report of a Prins macrocyclization appeared in 1979, but only since late 2008 has this strategy gained momentum in natural product synthesis. Convergent, selective, and high yielding, the Prins macrocyclization forms tetrahydropyran-containing macrocycles in a merged C[BOND]O and C[BOND]C bond-forming event (see scheme).

  10. Reviews

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    1. Porous Materials

      Functional Materials: From Hard to Soft Porous Frameworks (pages 8328–8344)

      Prof. Dr. Arne Thomas

      Version of Record online: 14 OCT 2010 | DOI: 10.1002/anie.201000167

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      Pores for thought: This Review describes porous functional materials in which the organic groups act as a part of the pore wall. The focus is on functional mesoporous organosilicas as well as meso- and microporous polymers. The large number of functional groups in such porous materials allows, for example, a new approach to bridging the gap between homogeneous and heterogeneous catalysis.

    2. Spectroscopic Methods

      Solid-State NMR Spectroscopy on Complex Biomolecules (pages 8346–8357)

      Dr. Marie Renault, Dr. Abhishek Cukkemane and Prof. Dr. Marc Baldus

      Version of Record online: 12 OCT 2010 | DOI: 10.1002/anie.201002823

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      The bigger they are, the harder they fall: Recent advancements in NMR spectroscopy, biophysics, and related research areas have resulted in solid-state NMR (ssNMR) spectroscopy having the potential to study complex biomolecular systems at atomic resolution in situ. Methodological challenges of ssNMR spectroscopy for studying complex biomolecules are described as well as recent and possible applications.

  11. Communications

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    1. NMR Signal Enhancement

      Continuous 1H and 13C Signal Enhancement in NMR Spectroscopy and MRI Using Parahydrogen and Hollow-Fiber Membranes (pages 8358–8362)

      Dipl.-Chem. Meike Roth, Petra Kindervater, Hans-Peter Raich, Prof. Joachim Bargon, Prof. Hans W. Spiess and Dr. Kerstin Münnemann

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201002725

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      Parahydrogen-induced polarization is used for the continuous generation of hyperpolarized molecules. Constant 1H and 13C NMR signal enhancement is demonstrated using a continuous delivery of parahydrogen by hollow fiber membranes (see picture, left), which allows the acquisition of two-dimensional NMR signals requiring multiple acquisitions with constant initial polarization.

    2. Imaging in Microfluidics

      Microfluidic Gas-Flow Imaging Utilizing Parahydrogen-Induced Polarization and Remote-Detection NMR (pages 8363–8366)

      Dr. Ville-Veikko Telkki, Dr. Vladimir V. Zhivonitko, Susanna Ahola, Dr. Kirill V. Kovtunov, Prof. Jukka Jokisaari and Prof. Igor V. Koptyug

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201002685

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      Sensitivity enhancement of several orders of magnitude provided by combining parahydrogen-induced polarization (PHIP) and remote-detection (RD) NMR techniques enables gas-flow visualization in microfluidic devices (see scheme). A 7700-fold reduction in the imaging time compared to the current state-of-the-art is achieved, and it can also be used to significantly improve the spatial resolution in such experiments.

    3. Stereoselective Protonation

      Intramolecular Stereoselective Protonation of Aldehyde-Derived Enolates (pages 8367–8369)

      Anastasie Kena Diba, Claudia Noll, Michael Richter, Marc Timo Gieseler and Prof. Dr. Markus Kalesse

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201004619

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      Picking sides: Asymmetric protonation of the titled compounds poses a most significant challenge and has been addressed by taking advantage of internal protonation and subsequent hemiacetal formation to avoid epimerization (see scheme). The substrates employed in these transformations can be easily accessed through a sequence of vinylogous aldol reactions with subsequent conjugate reductions.

    4. Enantioselective Catalysis

      Quaternary Carbon Stereogenic Centers through Copper-Catalyzed Enantioselective Allylic Substitutions with Readily Accessible Aryl- or Heteroaryllithium Reagents and Aluminum Chlorides (pages 8370–8374)

      Fang Gao, Yunmi Lee, Kyoko Mandai and Prof. Amir H. Hoveyda

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/anie.201005124

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      The case of the notorious aryls is solved: The first efficient catalytic and enantioselective method for allylic substitutions that furnish quaternary carbon stereogenic centers by additions of aryl- or heteroarylmetals is reported (see scheme). Highly site- and enantioselective processes begin with readily available organolithium reagents.

    5. Bionanotechnology

      Three-Dimensional Directed Self-Assembly of Peptide Nanowires into Micrometer-Sized Crystalline Cubes with Nanoparticle Joints (pages 8375–8378)

      Prerna Kaur, Dr. Yoshiaki Maeda, Andrew C. Mutter, Prof. Tadashi Matsunaga, Prof. Yujia Xu and Prof. Hiroshi Matsui

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201004716

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      Micro construction sites: Engineered peptides and ligand-functionalized gold nanoparticles have been assembled into micrometer-scale 3D cube-shaped crystals (see picture), creating a physical framework for a biomimetic assembly strategy. The NPs join the peptide nanowires through streptavidin–biotin interactions to create cubic unit cells.

    6. Asymmetric Synthesis

      Organocatalytic Asymmetric Sulfa-Michael/Michael Addition Reactions: A Strategy for the Synthesis of Highly Substituted Chromans with a Quaternary Stereocenter (pages 8379–8383)

      Xu-Fan Wang, Qiu-Lin Hua, Ying Cheng, Xiao-Lei An, Qing-Qing Yang, Dr. Jia-Rong Chen and Prof. Dr. Wen-Jing Xiao

      Version of Record online: 7 OCT 2010 | DOI: 10.1002/anie.201004534

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      Simply complex: Diverse and structurally complex chroman derivatives with a quaternary stereocenter have been obtained through the titled reaction of thiols with nitroolefin enoates using the bifunctional catalyst 1. The reaction features simple experimental procedures, high yield, enantiomeric excess, and excellent diastereoselectivity.

    7. Polyoxometalates

      Giant Crown-Shaped Polytungstate Formed by Self-Assembly of CeIII-Stabilized Dilacunary Keggin Fragments (pages 8384–8388)

      Dr. Santiago Reinoso, Mónica Giménez-Marqués, Dr. José Ramón Galán-Mascarós, Pablo Vitoria and Prof. Juan M. Gutiérrez-Zorrilla

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201004207

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      The largest tungstogermanate and third-largest polytungstate (see picture) was obtained by K+-directed self-assembly of three unprecedented types of [GeW10O38]12− fragments stabilized by coordination of Ce ions on the vacancies. In its Ce6O42 central ring, which displays antiferromagnetic interactions, a K+ cation is captured by internal water molecules. Gray octahedra WO6, green tetrahedra GeO4; Ce orange, K purple, O red.

    8. Organic Frustrated Lewis Pairs

      Heterolytic S[BOND]S Bond Cleavage by a Purely Carbogenic Frustrated Lewis Pair (pages 8389–8391)

      Dr. Blanca Inés, Sigrid Holle, Dr. Richard Goddard and Dr. Manuel Alcarazo

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/anie.201004149

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      Boranes were getting borin': Owing to the Lewis acidic character of the central carbon atom, a bisfluorenyl-substituted allene 1 could be used instead of B(C6F5)3 for the generation of frustrated Lewis pairs. Mixtures of the allene and the bulky N-heterocyclic carbene shown in red (Dipp=diisopropylphenyl) caused heterolytic cleavage of the S[BOND]S bond in disulfides.

    9. DNA-Damage Detection

      Selective Detection of 5-Formyl-2′-deoxyuridine, an Oxidative Lesion of Thymidine, in DNA by a Fluorogenic Reagent (pages 8392–8394)

      Wataru Hirose, Dr. Kousuke Sato and Prof. Dr. Akira Matsuda

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201004087

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      Chemoselectivity in DNA: The thymidine lesion 5-formyl-2′-deoxyuridine (1) induces the mutation of DNA. Its derivatization with the specific fluorogenic reagent 2-amino-4,5-dimethoxythiophenol (2) gives 3, which shows strong fluorescence. This fast method for the detection of 1 requires no enzymatic digestion, HPLC separation, or MS analysis. ROS=reactive oxygen species.

    10. Synthetic Methods

      Palladium-Catalyzed Coupling of Aldehyde-Derived Hydrazones: Practical Synthesis of Triazolopyridines and Related Heterocycles (pages 8395–8398)

      Dr. Oliver R. Thiel, Dr. Michal M. Achmatowicz, Dr. Andreas Reichelt and Dr. Robert D. Larsen

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201001999

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      The palladium-catalyzed intermolecular coupling of aldehyde-derived hydrazones with chloroazines, followed by oxidative cyclization under mild conditions afforded access to a broad variety of bicyclic heterocyclic scaffolds (see scheme) that have potential for use in drug discovery.

    11. NMR Spectroscopy

      Solid-State 17O NMR Spectroscopy of Large Protein–Ligand Complexes (pages 8399–8402)

      Dr. Jianfeng Zhu, Dr. Eric Ye, Dr. Victor Terskikh and Prof. Dr. Gang Wu

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201002041

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      Oxygen, oxygen, everywhere! Poor sensitivity has hindered the development of solid-state 17O NMR spectroscopy as a practical technique for the structural elucidation of protein complexes. However, this has now changed and it has been demonstrated that multinuclear 17O, 27Al, 13C NMR parameters can be used to aid structural refinement for a protein-bound ligand molecule (see picture).

    12. Catalytic Fenton Reaction

      Gold on Diamond Nanoparticles as a Highly Efficient Fenton Catalyst (pages 8403–8407)

      Dr. Sergio Navalon, Roberto Martin, Dr. Mercedes Alvaro and Prof. Dr. Hermenegildo Garcia

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201003216

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      Nanojewels as catalysts: Degradation of phenol with a small excess of H2O2 can be achieved by using gold nanoparticles supported on Fenton-treated diamond nanoparticles as a highly selective (at least 79 %) and efficient (turnover number: 321 000) catalyst for the Fenton reaction at room temperature. The proposed mechanism is shown schematically in the picture.

    13. Electrochemistry

      Fabrication of Graphene-Encapsulated Oxide Nanoparticles: Towards High-Performance Anode Materials for Lithium Storage (pages 8408–8411)

      Dr. Shubin Yang, Dr. Xinliang Feng, Dr. Sorin Ivanovici and Prof. Dr. Klaus Müllen

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201003485

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      Storage shells: The assembly of negatively charged graphene oxide and positively charged oxide nanoparticles by electrostatic interactions, and subsequent chemical reduction, leads to metal oxides encapsulated in flexible and ultrathin graphene shells (see picture). These electrochemically active nanoparticles show a remarkable lithium storage capacity, with an excellent cycle performance.

    14. Asymmetric Catalysis

      Formal [3+2] Cycloaddition of Ketenes and Oxaziridines Catalyzed by Chiral Lewis Bases: Enantioselective Synthesis of Oxazolin-4-ones (pages 8412–8416)

      Pan-Lin Shao, Xiang-Yu Chen and Prof. Dr. Song Ye

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201003532

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      Choose the right cat.: A highly enantioselective synthesis of oxazolin-4-ones by the formal [3+2] cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N-heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4-toluenesulfonyl).

    15. Oxidative Rearrangement

      Copper-Catalyzed Rearrangement of Tertiary Amines through Oxidation of Aliphatic C[BOND]H Bonds in Air or Oxygen: Direct Synthesis of α-Amino Acetals (pages 8417–8420)

      Jie-Sheng Tian and Prof. Dr. Teck-Peng Loh

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201003646

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      A surprising turn of events: Mechanistic studies, including trapping, control, and isotope-labeling experiments, led to the proposal of a rearrangement mechanism involving oxidation of aliphatic C[BOND]H bonds (see scheme; TMEDA=tetramethylethylenediamine).

    16. Isopeptide Bonds

      NMR Spectroscopic and Theoretical Analysis of a Spontaneously Formed Lys–Asp Isopeptide Bond (pages 8421–8425)

      Dr. Robert M. Hagan, Ragnar Björnsson, Dr. Stephen A. McMahon, Benjamin Schomburg, Vickie Braithwaite, Prof. Michael Bühl, Prof. James H. Naismith and Dr. Ulrich Schwarz-Linek

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201004340

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      One bond makes all the difference: Three suitably positioned amino acid side chains (see picture) and a hydrophobic environment are all that is required for an amidation reaction with remarkable consequences. An emerging central building block of bacterial surface proteins owes its stability to a spontaneously formed isopeptide bond. The impact of this bond on protein structure and dynamics and the mechanism of its formation are scrutinized in detail.

    17. Drug Delivery

      Probing the Kinetics of Short-Distance Drug Release from Nanocarriers to Nanoacceptors (pages 8426–8430)

      Hong Wang, Jun Xu, Jinghao Wang, Tao Chen, Yong Wang, Yan Wen Tan, Prof. Haibin Su, Dr. Khai Leok Chan and Prof. Hongyu Chen

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201001065

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      Quick release: Polymer-coated gold nanoparticles (AuNPs) are used as nanocarriers and nanoscale acceptors are used to represent proteins and lipid membranes in a model drug-delivery system. The fluorescence of a drug is quenched in the vicinity of the AuNPs but reemerges upon its release (see picture). The critical role of nanoacceptors in facilitating drug release is demonstrated.

    18. High-Pressure Chemistry

      Pressure-Driven Assembly of Spherical Nanoparticles and Formation of 1D-Nanostructure Arrays (pages 8431–8434)

      Dr. Huimeng Wu, Dr. Feng Bai, Dr. Zaicheng Sun, Raid E. Haddad, Prof. Daniel M. Boye, Prof. Zhongwu Wang and Prof. Hongyou Fan

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/anie.201001581

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      Forced into line: External pressure was used to engineer nanoparticle assembly. Reversible manipulation of the unit-cell dimensions of a 3D ordered nanoparticle array under a hydrostatic pressure field enabled the fine-tuning of the interparticle distance. Under a uniaxial pressure field, nanoparticles were forced to contact and coalesce into nanorods or nanowires and ordered ultrahigh-density arrays (see picture; small arrows denote pressure).

    19. Chiral Resolution

      The Driving Mechanism Behind Attrition-Enhanced Deracemization (pages 8435–8438)

      Dr. Wim L. Noorduin, Dr. Willem J. P. van Enckevort, Dr. Hugo Meekes, Dr. Bernard Kaptein, Prof. Dr. Richard M. Kellogg, Prof. Dr. John C. Tully, Prof. Dr. J. Michael McBride and Prof. Dr. Elias Vlieg

      Version of Record online: 21 SEP 2010 | DOI: 10.1002/anie.201002036

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      Change of heart: A solution-phase enantiomeric excess that has the handedness of the minor population of the solid phase is observed during grinding of a slurry of racemic conglomerate crystals. This excess is the driving force for a net flux of molecules from crystals of the minor handedness to crystals of the major handedness, thus explaining the complete deracemization of the solid phase (see picture: blue: S form, red: R form).

    20. Macroporous Catalysts

      Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex (pages 8439–8443)

      Abdel-Moneim Abu-Elfotoh, Dr. Kesiny Phomkeona, Prof. Kazutaka Shibatomi and Prof. Seiji Iwasa

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201002240

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      Along came poly: A novel macroporous polymer-supported chiral RuII/pheox catalyst (1, see SEM image) afforded excellent reactivity and enantioselectivity in inter- and intramolecular cyclopropanation reactions with a broad range of substrates. The catalyst showed no leaching and could be reused up to 11 times, even after storage.

    21. Lithium Batteries

      Polyimides: Promising Energy-Storage Materials (pages 8444–8448)

      Zhiping Song, Dr. Hui Zhan and Prof. Yunhong Zhou

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201002439

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      Plastic batteries: Polyimides are proposed as cathode materials for rechargeable lithium batteries. Although they are regarded as insulators, five polyimides with different structures all show good electrochemical activity and some of them show promising performance, which could allow their use in a new generation of “green battery” applications.

    22. Oxo Complexes

      A Low-Spin Ruthenium(IV)–Oxo Complex: Does the Spin State Have an Impact on the Reactivity? (pages 8449–8453)

      Prof. Dr. Takahiko Kojima, Yuichirou Hirai, Dr. Tomoya Ishizuka, Dr. Yoshihito Shiota, Prof. Dr. Kazunari Yoshizawa, Dr. Kenichiro Ikemura, Prof. Dr. Takashi Ogura and Prof. Dr. Shunichi Fukuzumi

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201002733

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      Spin doesn't matter: A ruthenium(II)–aqua complex bearing a pentadentate pyridylamine with a carboxylate group as a ligand affords a seven-coordinate low-spin (S=0) ruthenium(IV)–oxo complex (see structure) by oxidation through proton-coupled electron transfer. Comparison of the reactivity of the low-spin and an intermediate-spin (S=1) RuIV–oxo complexes revealed that the spin state does not affect the reactivity of catalytic oxidation of organic compounds.

    23. Biological Assays

      Amplified Aptamer-Based Assay through Catalytic Recycling of the Analyte (pages 8454–8457)

      Chun-Hua Lu, Juan Li, Mei-Hua Lin, Yi-Wei Wang, Prof. Huang-Hao Yang, Prof. Xi Chen and Prof. Guo-Nan Chen

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201002822

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      Turn up the volume: In a simple and highly sensitive aptamer-based assay that relies on the ability of nanomaterials to protect DNA from nuclease cleavage, the aptamer is released from the nanomaterial when challenged with a target. The nuclease then cleaves the free aptamer and releases the target, which can initiate a new cycle. Recycling of the target in this way leads to significant signal amplification (see diagram).

    24. Protein Biology

      Precise Control of Protein Concentration in Living Cells (pages 8458–8461)

      Hubert D. Lau, Junko Yaegashi, Balyn W. Zaro and Prof. Matthew R. Pratt

      Version of Record online: 27 SEP 2010 | DOI: 10.1002/anie.201003073

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      Rapamycin to the rescue: Native protein concentration was precisely controlled in living cells by using the small molecule rapamycin. The addition of rapamycin “shielded” a destabilization domain from degradation and induced complementation of split ubiquitin (UbN and UbC); as a result, proteins (Pro) of interest were released. This technology enables the investigation of native protein biology over a broad concentration range.

    25. Antimicrobial Peptides

      Role of the Conformational Rigidity in the Design of Biomimetic Antimicrobial Compounds (pages 8462–8465)

      Andrey Ivankin, Liran Livne, Prof. Amram Mor, Prof. Gregory A. Caputo, Prof. William F. DeGrado, Dr. Mati Meron, Dr. Binhua Lin and Prof. David Gidalevitz

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/anie.201003104

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      When structural flexibility is a plus: A link between structural flexibility of biomimetic antimicrobials and their ability to penetrate into the hydrophobic core and disrupt the integrity of bacterial lipid model membranes has been established using liquid surface X-ray scattering techniques. Results indicate that the modes of interaction of flexible and conformationally restrained antimicrobials with the bacterial membranes are different (see picture).

    26. Homogeneous Catalysis

      Elementary Steps in Gold Catalysis: The Significance of gem-Diauration (pages 8466–8470)

      Ing. Günter Seidel, Prof. Christian W. Lehmann and Prof. Alois Fürstner

      Version of Record online: 18 AUG 2010 | DOI: 10.1002/anie.201003349

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      Disturbing neighbors: Alkenylgold species with a heteroatom substituent are thought to be key intermediates in gold-catalyzed trans additions of protic nucleophiles to alkynes. One reason for the scarcity of such compounds lies in the non-innocence of the neighboring heteroatom, which may enforce the uptake of a second gold fragment with formation of surprisingly robust species with a gem-digold unit adjacent to a largely cationic center (see scheme).

    27. Self-Assembly

      Self-Dissociating Tubules from Helical Stacking of Noncovalent Macrocycles (pages 8471–8475)

      Ho-Joong Kim, Seong-Kyun Kang, Youn-Kyoung Lee, Prof. Chaok Seok, Jeong-Kyu Lee, Prof. Wang-Cheol Zin and Prof. Myongsoo Lee

      Version of Record online: 22 SEP 2010 | DOI: 10.1002/anie.201003779

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      Donuts anyone? Molecules based on a meta-linked aromatic segment self-assemble into hexameric macrocycles that, in turn, stack on top of each other to from elongated tubular helical suprastructures. The formed tubules dissociate into discrete stacks of toroids in response to the addition of silver salt (see picture).

    28. Imaging Agents

      One-Pot Synthesis of Highly Magnetically Sensitive Nanochains Coated with a Highly Cross-Linked and Biocompatible Polymer (pages 8476–8479)

      Dr. Junfeng Zhou, Dr. Lingjie Meng, Dr. Xinliang Feng, Dr. Xiaoke Zhang and Prof. Qinghua Lu

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201003820

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      Neptune's necklace: Fe3O4 colloidal nanocrystal clusters (ca. 200 nm in diameter) were organized into one-dimensional nanochains and coated with a highly cross-linked polymer in a facile one-pot synthesis (see picture). The nanochains have enhanced hydrogen T2 relaxation rates, facile magnetic manipulation, good water dispersivity, and excellent biocompatibility.

    29. Biomass

      Production of Calcium Carbide from Fine Biochars (pages 8480–8483)

      Guodong Li, Qingya Liu, Prof. Dr. Zhenyu Liu, Dr. Z. Conrad Zhang, Chengyue Li and Weize Wu

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201004169

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      Rising from the ashes: Fine chars produced from biomass can be used as a feedstock for the production of CaC2 in an autothermal process that operates at a temperature 500 °C lower than the traditional electric arc process and with greatly reduced reaction time (see scheme for the reaction of CaO and C forming CaC2).

    30. Enzyme Inhibition

      A Myosin V Inhibitor Based on Privileged Chemical Scaffolds (pages 8484–8488)

      Dr. Kabirul Islam, Harvey F. Chin, Adrian O. Olivares, Lauren P. Saunders, Prof. Dr. Enrique M. De La Cruz and Prof. Dr. Tarun M. Kapoor

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201004026

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      Switching the motor off: Privileged chemical scaffolds were used as a starting point for the development of a specific chemical inhibitor 1 of myosin V, a key motor protein required for intracellular transport (see picture; ADP=adenosine diphosphate, ATP=adenosine triphosphate). The potency of 1, which does not compete directly with nucleotide binding, is comparable to that of other known motor-protein inhibitors used as probes in chemical biology.

    31. Porous Materials

      A Highly Porous Metal–Organic Framework with Open Nickel Sites (pages 8489–8492)

      Kristina Gedrich, Dr. Irena Senkovska, Nicole Klein, Ulrich Stoeck, Antje Henschel, Martin R. Lohe, Dr. Igor A. Baburin, Dr. Uwe Mueller and Prof. Dr. Stefan Kaskel

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/anie.201001735

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      A healthy appetite: A new metal–organic framework (DUT-9; see picture) has an unprecedented topology that contains {Ni53-O)2(CO2)6} clusters (green polyhedra; C gray, O red). DUT-9 has very high storage capacities for methane, hydrogen, and carbon dioxide because of the presence of open metal sites (marked by stars).

    32. Nanosheets

      Janus Nanomembranes: A Generic Platform for Chemistry in Two Dimensions (pages 8493–8497)

      Dr. Zhikun Zheng, Dr. Christoph T. Nottbohm, Priv.-Doz. Dr. Andrey Turchanin, Heiko Muzik, Priv.-Doz. Dr. André Beyer, Dr. Mike Heilemann, Prof. Dr. Markus Sauer and Prof. Dr. Armin Gölzhäuser

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/anie.201004053

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      Buttered side up: A one nanometer thick membrane with different functional groups on each side was fabricated from self-assembled monolayers of aromatic molecules. The amino side of this Janus membrane was modified with tetramethylrhodamine (TMR) fluorescent dye, and the thiol side with ATTO647N (see picture). The functionalization and functionality of the nanomembrane were demonstrated by X-ray photoelectron spectroscopy and fluorescence microscopy.

    33. Antitumor Vaccines

      Synthetic Antitumor Vaccines from Tetanus Toxoid Conjugates of MUC1 Glycopeptides with the Thomsen–Friedenreich Antigen and a Fluorine-Substituted Analogue (pages 8498–8503)

      Prof. Dr. Anja Hoffmann-Röder, Anton Kaiser, Sarah Wagner, Nikola Gaidzik, Danuta Kowalczyk, Dr. Ulrika Westerlind, Bastian Gerlitzki, Prof. Dr. Edgar Schmitt and Prof. Dr. Horst Kunz

      Version of Record online: 28 SEP 2010 | DOI: 10.1002/anie.201003810

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      A “shot in the arm” for cancer therapy: Coupling of synthetic glycopeptide tandem-repeat sequences of the epithelial mucin MUC1 with the Thomsen–Friedenreich (T) antigen (A) or a difluoro analogue (B) to tetanus toxoid (TTox) affords synthetic vaccines, which induce very strong immune responses in mice overriding the natural tolerance of the immune system. The induced antibodies are selectively directed against the tumor-associated MUC1 structures and strongly bind to breast cancer cells of the MCF-7 cell line.

    34. DNA Enzymes

      Combinatorial Mutation Interference Analysis Reveals Functional Nucleotides Required for DNA Catalysis (pages 8504–8508)

      Falk Wachowius, Fatemeh Javadi-Zarnaghi and Dr. Claudia Höbartner

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/anie.201003940

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      Completeanalysis! Combinatorial mutation interference analysis (CoMA) is a highly efficient method to identify catalytically essential nucleotides in deoxyribozymes by the simultaneous assessment of all possible mutations in the active site of the catalyst. The application of CoMA for two different deoxyribozymes revealed indispensable guanosine nucleotides for DNA-catalyzed RNA ligation.

    35. Spin Crossover

      Significant Variation of the Singlet–Quintet Intersystem Crossing Rate Constant in an Iron(II) High-Spin Complex as a Function of Temperature (pages 8509–8512)

      Dr. Itana Krivokapic, Pradip Chakraborty, Dr. Robert Bronisz, Dr. Cristian Enachescu and Prof. Dr. Andreas Hauser

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/anie.201004500

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      Relax! In the dilute mixed-crystal system [Zn1−xFex(bbtr)3](ClO4)2, x=2 % (bbtr=1,4-di(1,2,3-triazol-1-yl)butane), the iron(II) centers are predominantly in the high-spin state. The low-spin state can be populated as a metastable state by irradiation with near-IR light; the rate constant of the low-spin[RIGHTWARDS ARROW]high-spin relaxation spans 14 orders of magnitude between 40 and 220 K (see picture).

    36. Allylic Substitution

      Copper-Catalyzed Si[BOND]B Bond Activation in Branched-Selective Allylic Substitution of Linear Allylic Chlorides (pages 8513–8515)

      Devendra J. Vyas and Prof. Dr. Martin Oestreich

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/anie.201004658

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      The harder they come, the better they leave! Chloride is superior to all common leaving groups in the γ-selective allylic substitution of linear precursors. This approach involves a novel copper-catalyzed Si[BOND]B bond activation (see scheme; γ/α≥98:2, 7 examples; Si=SiMe2Ph and B=Bpin with pin=pinacolato).

    37. Aluminum Reagents

      Diastereoselective Synthesis of Homoallylic Alcohols with Adjacent Tertiary and Quaternary Centers by Using Functionalized Allylic Aluminum Reagents (pages 8516–8519)

      Zhihua Peng, Tobias D. Blümke, Dr. Peter Mayer and Prof. Dr. Paul Knochel

      Version of Record online: 6 SEP 2010 | DOI: 10.1002/anie.201003813

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      Al be there for you: Sensitive functional groups, including ester and cyano groups, can be present in allylic aluminum reagents prepared by aluminum insertion in the presence of InCl3. These aluminum organometallic compounds undergo addition reactions to various functionalized aldehydes or ketones with remarkable diastereoselectivities allowing the construction of two adjacent quaternary and tertiary centers (see scheme).

    38. Directed Zirconation

      tmp4Zr: An Atom-Economical Base for the Metalation of Functionalized Arenes and Heteroarenes (pages 8520–8524)

      Dr. Masilamani Jeganmohan and Prof. Dr. Paul Knochel

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/anie.201003558

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      Zirconium bases reach lots of places: Only 25 % of zirconium metal is required for the metalation of various functionalized aromatic compounds and heterocycles. All four 2,2,6,6-tetramethylpiperidyl (tmp) groups of the new base tmp4Zr⋅4 MgCl2⋅6 LiCl (1) are used up in the metalation process. The resulting zirconium species smoothly undergo palladium-catalyzed cross-couplings and addition to CO2 and epoxides (see scheme).

    39. Natural Product Synthesis

      Total Synthesis and Determination of the Absolute Configuration of (−)-Dolabriferol (pages 8525–8527)

      Sylvain Laclef, Prof. Dr. Maris Turks and Prof. Dr. Pierre Vogel

      Version of Record online: 23 SEP 2010 | DOI: 10.1002/anie.201003735

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      A reaction cascade combining sulfur dioxide with a 1-oxy-1,3-diene and (E)-silyl enol ether formed the basis of a short total synthesis of (−)-dolabriferol (see scheme; TMS=trimethylsilyl). The absolute configuration of this natural product, which was first extracted from a gastropod mollusc in 1996, was established unequivocally.

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