Angewandte Chemie International Edition

Cover image for Vol. 48 Issue 41

September 28, 2009

Volume 48, Issue 41

Pages 7453–7705

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: In Situ Assembly and Screening of Enzyme Inhibitors with Surface-Tension Microarrays (Angew. Chem. Int. Ed. 41/2009) (page 7453)

      Laurent Mugherli, Olga N. Burchak, Larissa A. Balakireva, Aline Thomas, François Chatelain and Maxim Y. Balakirev

      Article first published online: 2 SEP 2009 | DOI: 10.1002/anie.200904018

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      The formation of rain droplets … on a leaf surface reflects a fundamental property of water: high surface tension. An artificial array of highly uniform droplets can be created on a lithographically patterned glass surface with a differential surface energy. In their Communication on page 7639 ff., M. Y. Balakirev and co-workers describe the use of arrayed droplets for the solution-phase synthesis of small molecules and subsequent high-throughput quantitative analysis of enzyme kinetics.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Inside Cover: Total Synthesis of (+)-Haplophytine (Angew. Chem. Int. Ed. 41/2009) (page 7454)

      Hirofumi Ueda, Hitoshi Satoh, Koji Matsumoto, Kenji Sugimoto, Tohru Fukuyama and Hidetoshi Tokuyama

      Article first published online: 2 SEP 2009 | DOI: 10.1002/anie.200904021

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      An oxidative rearrangment and the Fischer indole synthesis are key processes in the first total synthesis of (+)-haplophytine, which is described by H. Tokuyama, T. Fukuyama, and co-workers in their Communication on page 7600 ff. The cover picture shows a photograph of Haplophyton cimicidum (T. Beth Kinsey, www.fireflyflrest.com/flowers), which is the source of (+)-haplophytine.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Graphical Abstract: Angew. Chem. Int. Ed. 41/2009 (pages 7457–7469)

      Article first published online: 23 SEP 2009 | DOI: 10.1002/anie.200990216

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Book Reviews
    7. Highlights
    8. Essay
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Landmarks in Organo-Transition Metal Chemistry. A Personal View. Series: Profiles in Inorganic Chemistry. By Helmut Werner. (pages 7477–7478)

      Alexander Filippou

      Article first published online: 23 SEP 2009 | DOI: 10.1002/anie.200903542

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      Springer Verlag, Heidelberg 2009. 354 pp., hardcover € 85.55.—ISBN 978-0387098470

    2. Chemical Vapour Deposition. Precursors, Processes and Applications. Edited by Anthony C. Jones and Michael L. Hitchman. (pages 7478–7479)

      Graziella Malandrino

      Article first published online: 23 SEP 2009 | DOI: 10.1002/anie.200903570

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      Royal Society of Chemistry, Cambridge 2008. 600 pp., hardcover £ 199.95.—ISBN 978-0854044658

  6. Highlights

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

      Total Syntheses of (+)-Haplophytine (pages 7480–7483)

      Eric Doris

      Article first published online: 11 SEP 2009 | DOI: 10.1002/anie.200903468

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      Yes they can! The Fukuyama and Tokuyama research groups recently achieved the first total synthesis of haplophytine, followed soon after by the report from Nicolaou, Chen, et al. This concludes the story that began several decades ago with its isolation from a Mexican plant and its identification. These syntheses are discussed in the context of five total syntheses of aspidophytine, the lower portion of halophytine.

    2. Nanostructures

      All-Inorganic Nanocrystal Arrays (pages 7484–7486)

      Stephanie L. Brock

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903989

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      Snuggle up: Nanocrystals have long been known to form ordered arrays and superlattices, but traditional organic capping ligands keep the nanocrystals separated, precluding conductivity. Now researchers have used molecular metal chalcogenide caps to form 2D and 3D nanocrystal arrays (see picture) with closer packing and much improved conductivity.

      Corrected by:

      Corrigendum: All-Inorganic Nanocrystal Arrays

      Vol. 49, Issue 7, 1183, Article first published online: 1 FEB 2010

  7. Essay

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

      What is Cooperativity? (pages 7488–7499)

      Christopher A. Hunter and Harry L. Anderson

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200902490

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      The lamprey holds the clue to the link between supramolecular self-assembly and allosteric ligand binding. Chelate cooperativity in self-assembled structures results in denaturation behavior that is indistinguishable from allosteric ligand binding. The chelate effect is the most common origin of positive cooperativity, yet its significance has been widely overlooked.

  8. Minireview

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

      Metal–Organic Frameworks: Opportunities for Catalysis (pages 7502–7513)

      David Farrusseng, Sonia Aguado and Catherine Pinel

      Article first published online: 18 AUG 2009 | DOI: 10.1002/anie.200806063

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      MOFing ventured, MOFing gained: Thanks to their multifunctional features (see picture; rectangle=Lewis center), metal–organic frameworks are of great potential value for catalysis, including photocatalysis. Their design is described in light of challenges in catalysis, and current challenges and perspectives are discussed.

  9. Review

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

      Chemical, Electrochemical, and Structural Properties of Endohedral Metallofullerenes (pages 7514–7538)

      Manuel N. Chaur, Frederic Melin, Angy L. Ortiz and Luis Echegoyen

      Article first published online: 23 SEP 2009 | DOI: 10.1002/anie.200901746

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      Guests welcome: The chemical and electrochemical properties of endohedral metallofullerenes, that is, fullerenes that encapsulate a metallic moiety in their interior, depend on the size and structure of the fullerene cage, their exohedral functionalization, as well as the type of metallic unit (see example; blue N, red Sc). The properties can be fine-tuned and offer potential applications in molecular electronics and medicine, for example.

  10. Communications

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

      Biocompatible Functionalized Polyglycerol Microgels with Cell Penetrating Properties (pages 7540–7545)

      Adam L. Sisson, Dirk Steinhilber, Torsten Rossow, Pia Welker, Kai Licha and Rainer Haag

      Article first published online: 20 AUG 2009 | DOI: 10.1002/anie.200901583

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      Gels for cells: A new method to produce biocompatible polyglycerol microgel nanoparticles with controllable size (25–100 nm, see picture, top) and a readily functionalizable surface is developed. Fluorescence imaging shows clear evidence for particle uptake by cells through endocytotic pathways and localization of the particles in the perinuclear region.

    2. Catalytically Active MOFs

      Heterogeneous Catalytic Oxidation by MFU-1: A Cobalt(II)-Containing Metal–Organic Framework (pages 7546–7550)

      Markus Tonigold, Ying Lu, Björn Bredenkötter, Bernhard Rieger, Stefan Bahnmüller, Julia Hitzbleck, Gerhard Langstein and Dirk Volkmer

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200901241

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      Structurally related to MOF-5, the cobalt(II)-containing metal–organic framework MFU-1 is stable to hydrolysis. Catalytic turnover is achieved in oxidation reactions with redox-active MFU-1, and the solid catalyst is easily recovered from the reaction mixture. Catalytic transformations have been shown to occur inside the pores of the microporous solid.

    3. Antitumor Vaccines

      A Synthetic Vaccine Consisting of a Tumor-Associated Sialyl-TN-MUC1 Tandem-Repeat Glycopeptide and Tetanus Toxoid: Induction of a Strong and Highly Selective Immune Response (pages 7551–7555)

      Anton Kaiser, Nikola Gaidzik, Ulrika Westerlind, Danuta Kowalczyk, Alexandra Hobel, Edgar Schmitt and Horst Kunz

      Article first published online: 15 AUG 2009 | DOI: 10.1002/anie.200902564

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      An ideal combination: The vaccine A is obtained by conjugation of the synthetic tumor-associated sialyl-TN-MUC1 glycopeptide antigen to tetanus toxoid (molecular weight >150 000). Vaccine A induces a very strong and selective immune response against the glycopeptide structure in wild-type mice (Balb/c).

    4. Asymmetric Synthesis

      Efficient Enantioselective Synthesis of Optically Active Diols by Asymmetric Hydrogenation with Modular Chiral Metal Catalysts (pages 7556–7559)

      Renat Kadyrov, René M. Koenigs, Claus Brinkmann, David Voigtlaender and Magnus Rueping

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902835

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      Valuable vicinal 1,2-diols can be prepared with high enantioselectivity by the asymmetric ruthenium-catalyzed hydrogenation of aryl- and alkyl-substituted α-hydroxy ketones (see scheme). The ligands, which are distinguished by their modular construction, display excellent enantioface differentiation.

    5. Enzyme Inhibitors

      Potent and Selective Inhibition of Acid Sphingomyelinase by Bisphosphonates (pages 7560–7563)

      Anke G. Roth, Daniela Drescher, Yang Yang, Susanne Redmer, Stefan Uhlig and Christoph Arenz

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200903288

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      More than mending bones: A simple geminal aminobisphosphonate (see picture) is the most potent selective inhibitor of the acid sphingomyelinase known to date. It can be synthesized in a one-step procedure and inhibits cell death in vitro. Since the acid sphingomyelinase is a putative drug target for inflammatory lung diseases, bisphosphonates may find application in the treatment of pulmonary diseases.

    6. RNA Technology

      Small-Molecule-Dependent Regulation of Transfer RNA in Bacteria (pages 7564–7567)

      Barbara Berschneider, Markus Wieland, Marina Rubini and Jörg S. Hartig

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200900851

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      External influence: Transfer RNA can be regulated by fusing a ligand-dependent ribozyme to the tRNA, resulting in disruption of the functional tRNA structure. Upon small-molecule-dependent activation of ribozyme cleavage, the tRNA is released and can be processed to act in translation.

    7. Copper Catalysis

      Discrimination of Diazo Compounds Toward Carbenoids: Copper(I)-Catalyzed Synthesis of Substituted Cyclobutenes (pages 7569–7572)

      José Barluenga, Lorena Riesgo, Luis A. López, Eduardo Rubio and Miguel Tomás

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903902

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      With perfect exe-Cu-tion: Copper(I) catalyzes several processes in an ordered manner. First it is able to transform substrate 2 into a copper(I) furylcarbene by isomerization/cyclization, which then reacts with 1 to produce a cyclopropyldiazo derivative, which undergoes copper(I)-catalyzed, regioselective ring enlargement to cyclobutene 3.

    8. Polycyclic Hydrocarbons

      9-Stannafluorenes: 1,4-Dimetal Equivalents for Aromatic Annulation by Double Cross-Coupling (pages 7573–7576)

      Ikuhiro Nagao, Masaki Shimizu and Tamejiro Hiyama

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903779

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      Double or nothing! A straightforward and high-yielding approach to a variety of polycyclic aromatic hydrocarbons has been achieved through palladium-catalyzed annulation of 9,9-dimethyl-9-stannafluorenes and dithienostannole with 1,2-dihaloarenes (see scheme). In addition, 1,1-dibromo-1-alkenes can also be applied to this annulation to produce dibenzofulvenes in excellent yields.

    9. Natural Product Synthesis

      Stereoselective Synthesis of 2,6-cis-Tetrahydropyrans through a Tandem Allylic Oxidation/Oxa-Michael Reaction Promoted by the gem-Disubstituent Effect: Synthesis of (+)-Neopeltolide Macrolactone (pages 7577–7581)

      Hyoungsu Kim, Yongho Park and Jiyong Hong

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903690

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      The minimal use of protecting groups is one highlight of a concise and efficient synthesis of (+)-neopeltolide macrolactone on the basis of the title tandem reaction and dithiane coupling reactions (see scheme). The gem-disubstituent effect of the dithiane moiety promoted the oxa-Michael reaction following allylic oxidation to ensure the efficient synthesis of the 2,6-cis-tetrahydropyran and high diastereoselectivity.

    10. Solid Electrolytes

      High Proton Conductivity in Anodic ZrO2/WO3 Nanofilms (pages 7582–7585)

      Damian Kowalski, Yoshitaka Aoki and Hiroki Habazaki

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903598

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      Amorphous double-oxide nanofilm (ZrO2/WO3) is a new class of proton-conducting electrolyte that can be simply fabricated by physical vapor deposition (PVD) and anodic oxidation of Zr/W alloy film (see schematic). The practical area-specific resistivity of 0.2 Ω cm2 is reached at a temperature as low as 100 °C for a 60 nm thick oxide film.

    11. Microreformer Design

      Nanostructured Zinc Oxide Nanorods with Copper Nanoparticles as a Microreformation Catalyst (pages 7586–7590)

      Yan-Gu Lin, Yu-Kuei Hsu, San-Yuan Chen, Yu-Kai Lin, Li-Chyong Chen and Kuei-Hsien Chen

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902907

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      A microreformer that consists of arrayed zinc oxide nanorods (ZnO NRs) with copper nanoparticles (Cu NPs; see picture) is an active catalyst for the conversion of methanol into hydrogen.

    12. Chemical Ligation

      Triblock Peptide and Peptide Thioester Synthesis With Reactivity-Differentiated Sulfonamides and Peptidyl Thioacids (pages 7591–7594)

      David Crich and Indrajeet Sharma

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903050

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      One after the other: Triblock peptide synthesis was achieved at ambient temperature by sequential reaction of sulfonamide-protected peptidyl thioacids first with highly reactive 2,4-dinitrobenzenesulfonamides and second with more moderately reactive sulfonamides to produce the oligopeptides in good yields. The method is compatible with C-terminal thioesters and thus presents a new approach for native chemical ligation strategies.

    13. Palladium Catalysis

      Palladium-Catalyzed Hydroxylation of Aryl Halides under Ambient Conditions (pages 7595–7599)

      Alexey G. Sergeev, Thomas Schulz, Christian Torborg, Anke Spannenberg, Helfried Neumann and Matthias Beller

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902148

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      Turning down the heat: The first room temperature Pd-catalyzed synthesis of phenols from aryl bromides and chlorides is presented. Stoichiometric studies of Pd-mediated hydroxylation of aryl halides employing a bulky imidazolyl-phosphine ligand and the novel palladium precursor [Pd(cod)(CH2SiMe3)2] led to development of efficient catalytic synthesis of phenols under ambient conditions (see scheme; Ad=adamantyl, cod=1,5-cyclooctadiene).

      Corrected by:

      Corrigendum: Palladium-Catalyzed Hydroxylation of Aryl Halides under Ambient Conditions

      Vol. 48, Issue 50, 9391, Article first published online: 30 NOV 2009

    14. Natural Product Synthesis

      Total Synthesis of (+)-Haplophytine (pages 7600–7603)

      Hirofumi Ueda, Hitoshi Satoh, Koji Matsumoto, Kenji Sugimoto, Tohru Fukuyama and Hidetoshi Tokuyama

      Article first published online: 3 JUL 2009 | DOI: 10.1002/anie.200902192

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      Advancing alkaloid synthesis: (+)-Haplophytine (see structure) was the target of a total synthesis featuring a highly stereoselective intramolecular Mannich reaction, Friedel–Crafts alkylation, oxidative rearrangement, and Fischer indole synthesis.

    15. Asymmetric Catalysis

      Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst (pages 7604–7607)

      Xiao Han, Jacek Kwiatkowski, Feng Xue, Kuo-Wei Huang and Yixin Lu

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903635

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      Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β-lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).

      Corrected by:

      Corrigendum: Corrigendum: Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst

      Vol. 50, Issue 12, 2664, Article first published online: 8 MAR 2011

    16. Emissive Siloles

      Structural Modulation of Solid-State Emission of 2,5-Bis(trialkylsilylethynyl)-3,4-diphenylsiloles (pages 7608–7611)

      Zujin Zhao, Zhiming Wang, Ping Lu, Carrie Y. K. Chan, Dandan Liu, Jacky W. Y. Lam, Herman H. Y. Sung, Ian D. Williams, Yuguang Ma and Ben Zhong Tang

      Article first published online: 4 SEP 2009 | DOI: 10.1002/anie.200903698

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      Solidarity means strength: In new silole luminogens, the solid aggregates are stronger emitters than isolated molecules. The solid-state emission is tunable by varying molecular structures of the luminogens. Increasing bulkiness of the substituents weakens intermolecular interactions and restricts intramolecular rotations, leading to a blue shift in emission color and a great increase in emission efficiency (see examples in picture).

    17. Palladium Catalysis

      The Newman–Kwart Rearrangement of O-Aryl Thiocarbamates: Substantial Reduction in Reaction Temperatures through Palladium Catalysis (pages 7612–7615)

      Jeremy N. Harvey, Jesús Jover, Guy C. Lloyd-Jones, Jonathan D. Moseley, Paul Murray and Joseph S. Renny

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200903908

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      Much cooler: The development of a catalyst for the Newman–Kwart rearrangement allows an escape from the harsh thermal conditions of the standard uncatalyzed reaction (see scheme). Mechanistic investigations, employing kinetic, isotopic labelling (2H, 18O, 34S) and DFT studies, suggest that the reaction proceeds through a five-centred Pd–S coordinated oxidative addition, with intermolecular exchange of aryl and thiocarbamate moieties through dimerization of the resting state.

    18. Natural Product Synthesis

      Total Synthesis of (+)-Haplophytine (pages 7616–7620)

      K. C. Nicolaou, Stephen M. Dalby, Shuoliang Li, Takahiro Suzuki and David Y.-K. Chen

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200904588

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      A problem solved: Haplophytine (1) yields to total synthesis through a convergent strategy employing modern synthetic methods. Key steps include hypervalent iodine mediated oxidative coupling, semi-pinacol type oxidative skeletal rearrangement, Suzuki–Miyaura coupling, and radical cyclisation.

    19. Liquid Crystals

      Supramolecular Polymers and Chromonic Mesophases Self-Organized from Phosphorescent Cationic Organoplatinum(II) Complexes in Water (pages 7621–7625)

      Wei Lu, Yong Chen, V. A. L. Roy, Stephen Sin-Yin Chui and Chi-Ming Che

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200903109

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      Soft matter with a hard core: Through PtII⋅⋅⋅PtII and hydrophobic interactions, planar organoplatinum(II) cations with chloride or sulfate as counterions self-organize themselves in water into red-emissive, chromonic, and viscoelastic mesophases from which aligned films and discrete uniaxial microfibers with cofacial molecular orientations can be readily prepared.

    20. Protein Nanoarrays

      Multiplexed Protein Arrays Enabled by Polymer Pen Lithography: Addressing the Inking Challenge (pages 7626–7629)

      Zijian Zheng, Weston L. Daniel, Louise R. Giam, Fengwei Huo, Andrew J. Senesi, Gengfeng Zheng and Chad A. Mirkin

      Article first published online: 3 SEP 2009 | DOI: 10.1002/anie.200902649

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      High-end printer: A novel way of using a polymer pen lithography (PPL) array mould to localize different inks on the pens of a PPL array has been developed. This technique allows for rapid pen inking and subsequent generation of multiplexed patterns of up to 150 000 nano- and microscale protein features per second (see picture). It is a general approach, which in principle can be extended to any substance that can be transported by PPL.

    21. Multimetal Oxide Catalysts

      The ReaxFF Monte Carlo Reactive Dynamics Method for Predicting Atomistic Structures of Disordered Ceramics: Application to the Mo3VOx Catalyst (pages 7630–7634)

      Kimberly Chenoweth, Adri C. T. van Duin and William A. Goddard III

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902574

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      What's your occupation? The ReaxFF computational approach is used to resolve partial or mixed occupation of crystallographic sites of the Mo3VOx multimetal oxide (MMO) catalyst. It provides insight into the oxidation state and coordination environment of the metal sites, identifies donor–acceptor networks in the catalyst, and predicts selectivity for molecular diffusion into channels of the framework (see picture).

    22. Constitutional Dynamic Chemistry

      Structural and Functional Evolution of a Library of Constitutional Dynamic Polymers Driven by Alkali Metal Ion Recognition (pages 7635–7638)

      Shunsuke Fujii and Jean-Marie Lehn

      Article first published online: 23 JUL 2009 | DOI: 10.1002/anie.200902512

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      Aptly folded: Dynamic polymer libraries were generated by polycondensation through reversible imine bonds and can undergo driven evolution under the double stimuli of donor–acceptor stacking and metal-ion binding (see picture). The specific binding modes of alkali metal ions are associated with specific constitutional changes and with different optical natures that reflect the presence and the positions of donor and acceptor units within the folded dynamer.

    23. Droplet Microarrays

      In Situ Assembly and Screening of Enzyme Inhibitors with Surface-Tension Microarrays (pages 7639–7644)

      Laurent Mugherli, Olga N. Burchak, Larissa A. Balakireva, Aline Thomas, François Chatelain and Maxim Y. Balakirev

      Article first published online: 6 JUL 2009 | DOI: 10.1002/anie.200901139

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      Hundreds of reactions were conducted in parallel in droplets maintained on a glass slide through differential surface tension in a new approach to submicroliter-scale synthesis. This “surface-tension microarray” was applied to the in situ assembly of thousands of derivatives of phenylboronic acid and their profiling against the NS3/4A protease of the hepatitis C virus. Several potent inhibitors of the enzyme were identified.

    24. Zeolites

      Selective Petroleum Refining Over a Zeolite Catalyst with Small Intracrystal Mesopores (pages 7645–7648)

      Dong Ho Park, Seong Su Kim, Hui Wang, Thomas J. Pinnavaia, Maria C. Papapetrou, Angelos A. Lappas and Kostas S. Triantafyllidis

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200901551

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      Cracking good cracking: Mesoporous ZSM-5 zeolite catalysts (see TEM image) made by soft templating methods show higher gas–oil cracking activity and greatly enhanced product selectivity than conventional ZSM-5. The cracking of large hydrocarbons to gasoline and diesel fuel occurs in intracrystal mesopores, while the conversion of smaller molecules into feedstock olefins occurs in framework micropores.

    25. Analytical Methods

      Quantitative Detection of Bioassays with a Low-Cost Image-Sensor Array for Integrated Microsystems (pages 7649–7654)

      Daynene M. Vykoukal, Gregory P. Stone, Peter R. C. Gascoyne, Eckhard U. Alt and Jody Vykoukal

      Article first published online: 4 SEP 2009 | DOI: 10.1002/anie.200901814

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      Portable assay systems require inexpensive detectors that can be integrated with microfluidic sample handling. Now a mass-produced digital-camera sensor has been interfaced with different lab-on-a-chip architectures to image nanoliter reagent droplets and for quantitative photometry of colorimetric and bioluminescence assays (see contact images of the fluid-handling electrode array (right), and colorimetric (top) and bioluminescent samples (bottom)).

    26. Carbon Nanotubes

      Experimentally Determined Redox Potentials of Individual (n,m) Single-Walled Carbon Nanotubes (pages 7655–7659)

      Yasuhiko Tanaka, Yasuhiko Hirana, Yasuro Niidome, Koichiro Kato, Susumu Saito and Naotoshi Nakashima

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902468

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      Nanotubes reveal their potential: The fabrication of a thin film that retains isolated single-walled nanotubes (SWNTs) allows the experimental determination of the redox potentials of many individual SWNTs that have different chirality indexes (n,m). The method is simple and applicable to all individual SWNTs whose near-IR photoluminescence (PL) is detectable (see picture).

    27. DNA Nanostructures

      A pH-Triggered, Fast-Responding DNA Hydrogel (pages 7660–7663)

      Enjun Cheng, Yongzheng Xing, Ping Chen, Yang Yang, Yawei Sun, Dejian Zhou, Lijin Xu, Qinghua Fan and Dongsheng Liu

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200902538

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      Y switch? A fast, pH-responsive DNA hydrogel (see picture; right) was prepared by a three-armed DNA nanostructure (left) assembling together through the formation of intermolecular i-motif structures (middle). The hydrogel can be switched to the non-gel state in minutes by simply using environmental pH changes.

    28. Dynamic Nanostructures

      Constitutional Adaptation of Dynamic Polymers: Hydrophobically Driven Sequence Selection in Dynamic Covalent Polyacylhydrazones (pages 7664–7667)

      J. Frantz Folmer-Andersen and Jean-Marie Lehn

      Article first published online: 11 SEP 2009 | DOI: 10.1002/anie.200902487

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      Hydrophobic selection: Reversible polymerization and folding of amphiphilic dialdehyde and dihydrazide monomers yields nanostructured rods. The resulting dynamers are stable enough to resist the incorporation of excess dihydrazide. In water, a more hydrophobic dihydrazide component (see picture, green) is favored over a less hydrophobic one (purple). This selectivity is lost when MeCN is added, implicating that hydrophobicity drives selectivity.

    29. Drug Delivery

      Supramolecular Stacking of Doxorubicin on Carbon Nanotubes for In Vivo Cancer Therapy (pages 7668–7672)

      Zhuang Liu, Alice C. Fan, Kavya Rakhra, Sarah Sherlock, Andrew Goodwin, Xiaoyuan Chen, Qiwei Yang, Dean W. Felsher and Hongjie Dai

      Article first published online: 16 SEP 2009 | DOI: 10.1002/anie.200902612

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      The evidence is stacking up: Many therapeutic advantages such as prolonged circulation in the blood, increased tumor drug uptake, enhanced therapeutic efficacy, and markedly reduced toxic side effects are provided by a carbon nanotube based chemotherapeutic formulation (see picture). In this system, doxorubicin (DOX) is loaded onto the sidewalls of functionalized single-walled carbon nanotubes by supramolecular π–π stacking.

    30. Carbohydrate Recognition

      A Synthetic Lectin for β-Glucosyl (pages 7673–7676)

      Nicholas P. Barwell, Matthew P. Crump and Anthony P. Davis

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903104

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      Evolving tastes: Addition of alkoxy groups (green; see picture) to macrotricyclic carbohydrate receptors yields improved affinities and new selectivities. Notably, the propoxy-substituted receptor shows a strong preference for β-glucosyl. Glucose is bound both in water and reconstituted blood plasma, which holds promise for applications in blood glucose monitoring.

    31. Janus Particles

      Janus Particles with Controllable Patchiness and Their Chemical Functionalization and Supramolecular Assembly (pages 7677–7682)

      Xing Yi Ling, In Yee Phang, Canet Acikgoz, M. Deniz Yilmaz, Mark A. Hempenius, G. Julius Vancso and Jurriaan Huskens

      Article first published online: 10 SEP 2009 | DOI: 10.1002/anie.200903579

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      Seeing the right face: Mono- and bifunctionalized Janus particles with controllable chemical patchiness are prepared by a general masking/unmasking technique and subsequent chemical functionalization (see picture). Supramolecular “host”- and “guest”-functionalized Janus particles were prepared, and specific noncovalent host–guest interactions were used to controllably assemble heterogeneous particles.

    32. Cooperative Catalysis

      Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications (pages 7683–7686)

      Ji Woong Lee, Hailong Yan, Hyeong Bin Jang, Hong Ki Kim, Sung-Woo Park, Sungyul Lee, Dae Yoon Chi and Choong Eui Song

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903903

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      Achiral polyether derivatives have been shown to dramatically accelerate SN2 reactions by the simultaneous activation of both the nucleophile (KF) and electrophile (sulfonate; see picture). By using chiral variants as catalysts, the desilylative kinetic resolution of the silyl ethers of racemic secondary alcohols has been achieved. Density functional calculations provide detailed insight into the modes of action of this type of organic promoter.

    33. Synthetic Methods

      The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties, and Metal Chelation (pages 7687–7690)

      Paul A. Wender, Justin P. Christy, Adam B. Lesser and Marc T. Gieseler

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200903859

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      All-kynes of COTs: A Ni0-catalyzed [2+2+2+2] cycloaddition of 1,6-diynes yields highly functionalized hexa- and octa-substituted cyclooctatetraenes (COTs; see picture) along with the first example of a fully intramolecular [2+2+2+2] cycloaddition product. The regioselectivity of this process is studied and the initial use of COT ligands is shown in the formation of a ZnII complex with a bis(oxazoline) COT.

    34. Enzyme Mechanisms

      Structure-Guided Directed Evolution of Alkenyl and Arylmalonate Decarboxylases (pages 7691–7694)

      Krzysztof Okrasa, Colin Levy, Matthew Wilding, Mark Goodall, Nina Baudendistel, Bernhard Hauer, David Leys and Jason Micklefield

      Article first published online: 8 SEP 2009 | DOI: 10.1002/anie.200904112

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      Rational enhancement: The X-ray crystal structure of an arylmalonate decarboxylase (AMDase) with a mechanism-based inhibitor bound to an active-site dioxyanion hole provides insight into the mechanism of this intriguing enzyme. The structure also guided the extension of the AMDase biocatalytic repertoire to include a wide range of α-alkenyl as well as α-arylmalonates.

    35. Bioorganic Chemistry

      DNA-Templated Homo- and Heterodimerization of Peptide Nucleic Acid Encoded Oligosaccharides that Mimick the Carbohydrate Epitope of HIV (pages 7695–7700)

      Katarzyna Gorska, Kuo-Ting Huang, Olivier Chaloin and Nicolas Winssinger

      Article first published online: 22 SEP 2009 | DOI: 10.1002/anie.200903328

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      All under control: The programmability of hybridization has been utilized to generate a combinatorial library of structures that emulate the topologies of complex carbohydrates interacting with an antibody that shows broad-spectrum activity against HIV. This simple method involves attaching oligosaccharides tagged with peptide nucleic acids onto DNA templates in a controlled manner (see schematic picture).

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      Article first published online: 23 SEP 2009 | DOI: 10.1002/anie.200990218

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