Angewandte Chemie International Edition

Cover image for Vol. 54 Issue 10

March 2, 2015

Volume 54, Issue 10

Pages 2857–3149

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. You have free access to this content
      Cover Picture: The Catalytic Mechanism of Human Parainfluenza Virus Type 3 Haemagglutinin-Neuraminidase Revealed (Angew. Chem. Int. Ed. 10/2015) (page 2857)

      Larissa Dirr, Dr. Ibrahim M. El-Deeb, Dr. Patrice Guillon, Cindy J. Carroux, Dr. Leonard M. G. Chavas and Prof. Mark von Itzstein

      Article first published online: 9 FEB 2015 | DOI: 10.1002/anie.201500511

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      The human parainfluenza virus type 3 (hPIV-3) is one of the leading causes of lower respiratory tract disease in children. In their Communication on page 2936 ff., M. von Itzstein, I. M. El-Deeb, P. Guillon, L. M. G. Chavas, and co-workers investigate the catalytic mechanism of hPIV-3 haemagglutinin-neuraminidase (HN) and determine that it is a retaining glycohydrolase. Moreover hPIV-3 HN utilizes a highly conserved tyrosine residue to form a transient covalent bond with the anomeric carbon of the substrate. Finally a novel sialic acid derivative showed potency in virus blockade assays.

    2. You have free access to this content
      Inside Cover: A Complex Perovskite-Type Oxynitride: The First Photocatalyst for Water Splitting Operable at up to 600 nm (Angew. Chem. Int. Ed. 10/2015) (page 2858)

      Dr. Chengsi Pan, Dr. Tsuyoshi Takata, Mamiko Nakabayashi, Dr. Takao Matsumoto, Prof. Naoya Shibata, Prof. Yuichi Ikuhara and Prof. Kazunari Domen

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500325

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      Water splitting on a particulate-type photocatalyst using solar energy is expected to be a scalable and cost-effective route for hydrogen production. However, most of the photocatalysts developed to date can only utilize a small part of the spectrum of sunlight. In their Communication on page 2955 ff., T. Takata, K. Domen et al. describe the development of a novel water-splitting photocatalyst operable over a wide range of the visible-light spectrum.

    3. You have free access to this content
      Inside Back Cover: The Nucleoside Uridine Isolated in the Gas Phase (Angew. Chem. Int. Ed. 10/2015) (page 3151)

      Dr. Isabel Peña, Dr. Carlos Cabezas and Prof. José L. Alonso

      Article first published online: 16 FEB 2015 | DOI: 10.1002/anie.201501245

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      The nucleoside uridine has been placed in the gas phase by laser ablation and structurally characterized by Fourier transform microwave spectroscopy. In their Communication on page 2991 ff., J. L. Alonso et al. show that free from the bulk effects of their native environments, the anti/C2′-endo-g+ conformation is the most stable form. Intramolecular hydrogen bonds involving uracil and ribose moieties play an important role in the stabilization of the nucleoside.

    4. You have free access to this content
      Back Cover: A D-Peptide Ligand of Nicotine Acetylcholine Receptors for Brain-Targeted Drug Delivery (Angew. Chem. Int. Ed. 10/2015) (page 3152)

      Xiaoli Wei, Dr. Changyou Zhan, Qing Shen, Prof. Wei Fu, Cao Xie, Jie Gao, Chunmei Peng, Prof. Ping Zheng and Prof. Weiyue Lu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201500512

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      Peptide ligands efficiently aid brain-targeted drug delivery by hijacking cognate receptors expressed on brain capillary endothelial cells. However, enzymatic barriers inactivate L-peptides and undermine the transport efficiency. In their Communication on page 3023 ff., W. Lu, C. Zhan, et al. identified a D-peptide ligand of nicotine acetylcholine receptors that is resistant to proteolysis and verified its superiority for brain-targeted drug delivery in comparison to the L-peptide ligand.

  2. Frontispiece

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. You have free access to this content
      Frontispiece: Electron Transfer in Peptides: On the Formation of Silver Nanoparticles

      Sonja Kracht, Dr. Matthias Messerer, Dr. Matthieu Lang, Dr. Sonja Eckhardt, Dr. Miriam Lauz, Prof. Bernard Grobéty, Prof. Katharina M. Fromm and Prof. Bernd Giese

      Article first published online: 24 FEB 2015 | DOI: 10.1002/anie.201581061

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      Nanoparticles K. M. Fromm, B. Giese et al. report in their Communication on page 2912 ff. how shielding effects prevent the formation of Ag nanoparticles from Ag+–peptides. This problem was overcome by chloride ions first forming AgCl microcrystals.

  3. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 10/2015 (pages 2861–2875)

      Article first published online: 24 FEB 2015 | DOI: 10.1002/anie.201590009

  4. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
  5. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. Todd B. Marder (page 2882)

      Article first published online: 22 OCT 2014 | DOI: 10.1002/anie.201409785

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      “I advise my students to see the world and keep an open mind. My favorite quote is ‘Never try to discourage thinking for you are sure to succeed’ (Bertrand Russell) …” This and more about Todd B. Marder can be found on page 2882.

  6. News

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. Inorganic Chemical Biology. Principles, Techniques and Applications. Edited by Gilles Gasser. (page 2885)

      Peter J. Sadler

      Article first published online: 12 FEB 2015 | DOI: 10.1002/anie.201412172

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      John Wiley and Sons, Chichester, 2014. 432 pp., hardcover, € 142.00.—ISBN 978-1118510025

  8. Review

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. Liquid-Crystal Templates

      Functional Materials from Cellulose-Derived Liquid-Crystal Templates (pages 2888–2910)

      Dr. Michael Giese, Dr. Lina K. Blusch, Dr. Mostofa K. Khan and Prof. Mark J. MacLachlan

      Article first published online: 17 DEC 2014 | DOI: 10.1002/anie.201407141

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      Out of the woods: Novel mesoporous and nanostructured materials can be generated by templating approaches based on cellulose-based liquid crystals derived from trees. This Review focuses on materials templated by cellulose nanocrystals, since their chiral nematic order allows their use in various optical applications such as optical filters, sensors, and optoelectronics.

  9. Communications

    1. Top of page
    2. Cover Pictures
    3. Frontispiece
    4. Graphical Abstract
    5. News
    6. Author Profile
    7. News
    8. Book Review
    9. Review
    10. Communications
    1. Nanoparticles

      Electron Transfer in Peptides: On the Formation of Silver Nanoparticles (pages 2912–2916)

      Sonja Kracht, Dr. Matthias Messerer, Dr. Matthieu Lang, Dr. Sonja Eckhardt, Dr. Miriam Lauz, Prof. Bernard Grobéty, Prof. Katharina M. Fromm and Prof. Bernd Giese

      Article first published online: 6 FEB 2015 | DOI: 10.1002/anie.201410618

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      Interplay of peptides and silver: Shielding effects prevent the formation of Ag nanoparticles (AgNPs) from Ag+-peptides. How can nature overcome this problem and synthesize AgNPs through electron transfer processes over long distances?

    2. Protein Modification

      You have full text access to this OnlineOpen article
      Structure and Mechanism of an Aspartimide-Dependent Peptide Ligase in Human Legumain (pages 2917–2921)

      Dr. Elfriede Dall, M. Sc. Julia C. Fegg, Prof. Dr. Peter Briza and Prof. Dr. Hans Brandstetter

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201409135

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      Peptide bond (bio)synthesis requires ATP as a coupling reagent. By contrast, human legumain ligase exploits an endogenous energy reservoir that results from the conversion of a conserved aspartate to a metastable succinimide. Legumain's protease activity recharges the succinimide. This functional duality may account for the generation of three-dimensional epitopes for MHC presentation through the cleavage and splicing of sequentially distant epitopes.

    3. Heterogeneous Catalysis

      The Electronic Factor in Alkane Oxidation Catalysis (pages 2922–2926)

      Dr. Maik Eichelbaum, Dr. Michael Hävecker, Dr. Christian Heine, Anna Maria Wernbacher, Dr. Frank Rosowski, Dr. Annette Trunschke and Prof. Robert Schlögl

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410632

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      Decades-old concepts in semiconductor physics such as gas-phase-dependent band bending (see figure) could be proven in heterogeneous oxidation catalysis for selective alkane oxidation reactions on vanadium oxide based catalysts by near-ambient-pressure X-ray photoelectron spectroscopy. These “electronic factors” are discussed as descriptors for selective catalyst materials.

    4. Heteroarenes

      Sulfur-Annulated Hexa-peri-hexabenzocoronene Decorated with Phenylthio Groups at the Periphery (pages 2927–2931)

      Dr. Yuan-Zhi Tan, Dr. Silvio Osella, Yi Liu, Bo Yang, Prof. Dr. David Beljonne, Prof. Dr. Xinliang Feng and Prof. Dr. Klaus Müllen

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201409932

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      Sulfur annulation: The unprecedented sulfur-annulated hexa-peri-hexabenzocoronenes were synthesized and unambiguously characterized by X-ray diffraction, revealing the distinct sulfur-annulated peripheral structure. Associated with DFT calculations, the strain minimization of the aromatic carbon skeleton should be responsible for the regioselective sulfur annulation at the bay positions.

    5. Metal Hydrides

      An Anti CuO2-type Metal Hydride Square Net Structure in Ln2M2As2Hx (Ln=La or Sm, M=Ti, V, Cr, or Mn) (pages 2932–2935)

      Dr. Hiroshi Mizoguchi, SangWon Park, Dr. Haruhiro Hiraka, Dr. Kazutaka Ikeda, Prof. Toshiya Otomo and Prof. Hideo Hosono

      Article first published online: 10 NOV 2014 | DOI: 10.1002/anie.201409023

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      Using the strong donating nature of H, a new series of La2Fe2Se2O3-type layered mixed-anion arsenides, Ln2M2As2Hx (Ln=La or Sm, M=Ti, V, Cr, or Mn; x≈3), was synthesized. These contain an unusual M2H square net, which has anti CuO2 square net structures and strong metal–metal bonding with a distance of 2.80 Å confirmed in La2Ti2As2H2.3.

    6. Parainfluenza Virus

      The Catalytic Mechanism of Human Parainfluenza Virus Type 3 Haemagglutinin-Neuraminidase Revealed (pages 2936–2940)

      Larissa Dirr, Dr. Ibrahim M. El-Deeb, Dr. Patrice Guillon, Cindy J. Carroux, Dr. Leonard M. G. Chavas and Prof. Mark von Itzstein

      Article first published online: 10 FEB 2015 | DOI: 10.1002/anie.201412243

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      Antivirus update: 2,3-difluoro sialic acid derivatives were used to explore the catalytic mechanism of human parainfluenza type 3 haemagglutinin-neuraminidase. The enzyme is a retaining glycohydrolase and acts by a mechanism involving a covalent adduct formed between the key amino acid residue Tyr530 and the substrate. One sialic acid derivative showed potency in virus blockade assays and is thus a promising new lead in anti-parainfluenza virus inhibitor design.

    7. Gene Delivery

      A Tailor-Made Specific Anion-Binding Motif in the Side Chain Transforms a Tetrapeptide into an Efficient Vector for Gene Delivery (pages 2941–2944)

      Mao Li, Stefanie Schlesiger, Prof. Shirley K. Knauer and Prof. Carsten Schmuck

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410429

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      Cell-penetrating peptides are widely utilized as vectors for gene delivery. Guanidinocarbonylpyrrole groups, which are tailor-made anion binding sites, were introduced into the side chains of tetralysine to obtain 1. This enormously enhances the cellular uptake of the corresponding peptide/DNA polyplexes relative to peptides with natural amino acids. Tetrapeptide analogue 1 is a highly efficient transfection vector and also shows negligible cytotoxicity.

    8. Perfluorinated Alkoxides

      A Convenient Route to Tetraalkylammonium Perfluoroalkoxides from Hydrofluoroethers (pages 2945–2949)

      Benson J. Jelier, Dr. Jon L. Howell, Prof. Craig D. Montgomery, Prof. Daniel B. Leznoff and Prof. Chadron M. Friesen

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410639

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      Fluoride free! The preparation of a series of tetraalkylammonium perfluoroalkoxides under mild, fluoride-free conditions is achieved by the methylation of tertiary amines with commercially available, partially fluorinated ethers. This practical synthesis paves a new way to an underrepresented class of thermally stable compounds bearing α-fluorines.

    9. Ammonia Decomposition | Very Important Paper

      Lithium Imide Synergy with 3d Transition-Metal Nitrides Leading to Unprecedented Catalytic Activities for Ammonia Decomposition (pages 2950–2954)

      Jianping Guo, Peikun Wang, Prof. Dr. Guotao Wu, Prof. Dr. Anan Wu, Daqiang Hu, Prof. Dr. Zhitao Xiong, Prof. Dr. Junhu Wang, Pei Yu, Fei Chang, Zheng Chen and Prof. Dr. Ping Chen

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410773

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      Beyond an electronic promoter: Synergy between Li2NH and 3d transition-metal nitrides (TMNs) leads to unprecedented catalytic activities for NH3 decomposition. Li2NH acts as more than just an electronic promoter: it is an NH3 transmitting agent and favors the formation of a higher N-content intermediate, thereby altering the overall reaction energetics.

    10. Photocatalysis

      A Complex Perovskite-Type Oxynitride: The First Photocatalyst for Water Splitting Operable at up to 600 nm (pages 2955–2959)

      Dr. Chengsi Pan, Dr. Tsuyoshi Takata, Mamiko Nakabayashi, Dr. Takao Matsumoto, Prof. Naoya Shibata, Prof. Yuichi Ikuhara and Prof. Kazunari Domen

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410961

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      Overall water splitting was achieved on a new complex perovskite-type oxynitride photocatalyst, LaMgxTa1−xO1+3xN2−3x (x≥1/3), with an absorption edge at 600 nm. Coating the surface of the RhCrOy/LaMgxTa1−xO1+3xN2−3x photocatalyst particles with a layer of amorphous oxyhydroxide effectively prevented the reverse reaction and self-oxidation of the photocatalyst.

    11. Inhibitors | Hot Paper

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      Selective and Potent Proteomimetic Inhibitors of Intracellular Protein–Protein Interactions (pages 2960–2965)

      Dr. Anna Barnard, Dr. Kérya Long, Dr. Heather L. Martin, Dr. Jennifer A. Miles, Dr. Thomas A. Edwards, Dr. Darren C. Tomlinson, Dr. Andrew Macdonald and Prof. Andrew J. Wilson

      Article first published online: 4 FEB 2015 | DOI: 10.1002/anie.201410810

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      Picky mimics: Inhibition of protein–protein interactions represents a major challenge in chemical biology and drug discovery. By using a library of N-alkylated aromatic oligoamides, helix mimetics that reproduce their biophysical binding selectivity in a cellular context can be identified.

    12. DNA Nanotechnology

      Gold-Nanoparticle-Mediated Jigsaw-Puzzle-like Assembly of Supersized Plasmonic DNA Origami (pages 2966–2969)

      Guangbao Yao, Dr. Jiang Li, Dr. Jie Chao, Dr. Hao Pei, Dr. Huajie Liu, Prof. Yun Zhao, Dr. Jiye Shi, Dr. Qing Huang, Prof. Lianhui Wang, Prof. Wei Huang and Prof. Chunhai Fan

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410895

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      Over the limit: A jigsaw-puzzle-like assembly strategy mediated by gold nanoparticles (AuNPs) is used to break the size limit of classic DNA origami. DNA-functionalized AuNPs are used as universal joints to assemble triangular DNA origami (see picture; red arrow denotes AuNP binding site) to form higher-order super-origami plasmonic nanostructures.

    13. Carbon Dots

      Tunable Photoluminescence Across the Entire Visible Spectrum from Carbon Dots Excited by White Light (pages 2970–2974)

      Prof. Shengliang Hu, Dr. Adrian Trinchi, Paul Atkin and Prof. Ivan Cole

      Article first published online: 14 JAN 2015 | DOI: 10.1002/anie.201411004

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      Color tuning: Carbon dots whose peak fluorescence emission wavelengths are tunable across the entire visible spectrum from 400 to 710 nm are synthesized by simple adjustment of reagents and synthesis conditions. They exhibit multicolor emission upon excitation with white light.

    14. Electrochemistry

      Oxide-Supported IrNiOx Core–Shell Particles as Efficient, Cost-Effective, and Stable Catalysts for Electrochemical Water Splitting (pages 2975–2979)

      Hong Nhan Nong, Dr. Hyung-Suk Oh, Tobias Reier, Dr. Elena Willinger, Dr. Marc-Georg Willinger, Prof. Dr. Valeri Petkov, Dr. Detre Teschner and Prof. Dr. Peter Strasser

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411072

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      Water splitting: IrNiOx core–shell nanoparticles consisting of a thin IrOx shell and an Ir-low/Ir-free core supported on mesoporous antimony doped tin oxide are demonstrated to provide substantial advances toward more efficient, stable, and less expensive electrolytic water splitting catalysts.

    15. Photocatalysis | Hot Paper

      The Nature of Photocatalytic “Water Splitting” on Silicon Nanowires (pages 2980–2985)

      Dong Liu, Leilei Li, Yang Gao, Dr. Chengming Wang, Prof. Jun Jiang and Prof. Yujie Xiong

      Article first published online: 7 JAN 2015 | DOI: 10.1002/anie.201411200

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      The production of hydrogen gas by photocatalytic water splitting on silicon nanowires was investigated. It occurs through cleavage of Si[BOND]H bonds and formation of Si[BOND]OH bonds; the surface dangling bonds have a great impact on charge separation.

    16. Gas Adsorption

      You have full text access to this OnlineOpen article
      Two-Dimensional Covalent Organic Frameworks for Carbon Dioxide Capture through Channel-Wall Functionalization (pages 2986–2990)

      Ning Huang, Dr. Xiong Chen, Prof. Dr. Rajamani Krishna and Prof. Dr. Donglin Jiang

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411262

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      Efficient CO2 capture is achieved by converting a conventional two-dimensional covalent organic framework (COF) to an outstanding CO2 capture material with large capacity and high selectively. The nanopore walls are chemically engineered with functional groups in a controlled manner to enhance interactions with CO2, leading to the development of a new general way to design COFs for gas storage and separation.

    17. Microwave Spectroscopy | Hot Paper

      The Nucleoside Uridine Isolated in the Gas Phase (pages 2991–2994)

      Dr. Isabel Peña, Dr. Carlos Cabezas and Prof. José L. Alonso

      Article first published online: 12 FEB 2015 | DOI: 10.1002/anie.201412460

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      Intramolecular hydrogen bonds: The simplest nucleoside uridine has been placed in the gas phase by laser ablation and structurally characterized by Fourier transform microwave spectroscopy. Intramolecular hydrogen bonds involving uracil and ribose moieties (see picture) have been found to play an important role in the stabilization of the nucleoside.

    18. Imaging Agents | Hot Paper

      Highly Fluorescent and Water-Soluble Diketopyrrolopyrrole Dyes for Bioconjugation (pages 2995–2999)

      Dr. Elodie Heyer, Pauline Lory, Dr. Jérôme Leprince, Dr. Mathieu Moreau, Prof. Anthony Romieu, Prof. Massimo Guardigli, Prof. Aldo Roda and Dr. Raymond Ziessel

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411274

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      All-in-one solution! A simple but very effective synthetic strategy to make diketopyrrolopyrrole (DPP) dyes water-soluble and highly fluorescent in aqueous media for bioconjugation to proteins is presented. Bovine serum albumin-DPP conjugates with unprecedentedly high quantum yields were obtained, thus enabling detection of minute amounts of fluorescent proteins through epifluorescence microscopy.

    19. DNA Intercalators

      Tuning the Excited State of Water-Soluble IrIII-Based DNA Intercalators that are Isostructural with [RuII(NN)2(dppz)] Light-Switch Complexes (pages 3000–3003)

      Sasha Stimpson, Dan R. Jenkinson, Andrew Sadler, Dr. Mark Latham, Dr Ashley Wragg, Dr. Anthony J. H. M. Meijer and Dr. Jim A. Thomas

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411346

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      The same but different: Two new IrIII complexes, with IrIII(NN)2 moieties coordinated to either the DNA-intercalating ligand dipyridophenazine (dppz) or its cyclometalating analogue benzopyridophenazine (bppz), are reported. Experimental and computational studies show that the systems have very different excited states (see picture; dppz complex (top), bppz complex (bottom)) and both bind to DNA with affinities comparable to their RuII analogues.

    20. Alkaloid Biosynthesis | Very Important Paper

      Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids (pages 3004–3007)

      Dr. Hsiao-Ching Lin, Dr. Grace Chiou, Dr. Yit-Heng Chooi, Dr. Travis C. McMahon, Dr. Wei Xu, Prof. Neil K. Garg and Prof. Yi Tang

      Article first published online: 8 JAN 2015 | DOI: 10.1002/anie.201411297

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      Putting the whole family on the map: Communesins, a prominent class of complex indole alkaloids isolated from various Penicillium species, are shown to be biosynthesized from two different building blocks derived from L-tryptophan. The entire biosynthetic pathway was mapped by genetic inactivation studies, which led to the isolation of three new communesin analogues.

    21. Supramolecular Chemistry

      A C3-Symmetric Macrocycle-Based, Hydrogen-Bonded, Multiporous Hexagonal Network as a Motif of Porous Molecular Crystals (pages 3008–3012)

      Dr. Ichiro Hisaki, Shoichi Nakagawa, Dr. Norimitsu Tohnai and Prof. Mikiji Miyata

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411438

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      Construction of porous crystalline two-dimensional frameworks is achieved through non-interpenetrated stacking of a multiporous hexagonal network possessing three kinds of voids with different sizes and shapes. A cavity volume of up to 58 % is obtained.

    22. Biocatalysis

      Engineered L-Serine Hydroxymethyltransferase from Streptococcus thermophilus for the Synthesis of α,α-Dialkyl-α-Amino Acids (pages 3013–3017)

      Karel Hernandez, Igor Zelen, Giovanna Petrillo, Prof. Dr. Isabel Usón, Claudia M. Wandtke, Dr. Jordi Bujons, Dr. Jesús Joglar, Dr. Teodor Parella and Prof. Dr. Pere Clapés

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411484

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      Quaternary stereocenters are obtained with a stereoselective biocatalyst. Chirally pure α,α-dialkyl-α-amino acid derivatives were synthetized through aldol addition of D-Ala and D-Ser to a variety of acceptor aldehydes. This reaction is catalyzed by the engineered pyridoxal-5′-phosphate dependent biocatalyst SHMTSth Y55T. (SHMTSth is the L-serine hydroxymethyltransferase from Streptococcus thermophilus).

    23. Polymer Gels

      Photoreversible Gelation of a Triblock Copolymer in an Ionic Liquid (pages 3018–3022)

      Dr. Takeshi Ueki, Yutaro Nakamura, Ryoji Usui, Yuzo Kitazawa, Soonyong So, Prof. Dr. Timothy P. Lodge and Prof. Dr. Masayoshi Watanabe

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411526

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      Make or break: The reversible micellization and gel-to-sol transition of an ionic liquid/ABA block copolymer solution triggered by a photostimulus is described. Photorheology is employed to monitor the light-induced viscoelastic property changes of the functional liquid resulting from hierarchical changes in the microscopic substructure of the macromolecular building blocks.

    24. Blood–Brain Barrier | Very Important Paper

      A D-Peptide Ligand of Nicotine Acetylcholine Receptors for Brain-Targeted Drug Delivery (pages 3023–3027)

      Xiaoli Wei, Dr. Changyou Zhan, Qing Shen, Prof. Wei Fu, Cao Xie, Jie Gao, Chunmei Peng, Prof. Ping Zheng and Prof. Weiyue Lu

      Article first published online: 19 JAN 2015 | DOI: 10.1002/anie.201411226

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      A D-peptide ligand of nicotine acetylcholine receptors (nAChRs), termed DCDX, was developed. The function of DCDX as a D-peptide antagonist of nAChRs was experimentally and computationally validated. DCDX exhibits exceptional stability during nAChRs-mediated transcytosis and in blood circulation, offering potential for brain-targeted drug delivery in the treatment of central nervous system diseases.

    25. Gas Separation | Very Important Paper

      Remarkably Enhanced Gas Separation by Partial Self-Conversion of a Laminated Membrane to Metal–Organic Frameworks (pages 3028–3032)

      Dr. Yi Liu, Dr. Jia Hong Pan, Nanyi Wang, Frank Steinbach, Dr. Xinlei Liu and Prof. Jürgen Caro

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201411550

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      From LDH to MOF: The partial transformation of a ZnAl-NO3 layered double hydroxide (LDH) membrane to a ZIF-8 metal–organic framework (MOF) top layer led to the formation of the composite membrane ZIF-8-ZnAl-NO3 LDH. This membrane is characterized by remarkably enhanced H2/CH4 gas separation and H2 permeance.

    26. Asymmetric Cyclization | Hot Paper

      Enantioselective Palladium-Catalyzed Dearomative Cyclization for the Efficient Synthesis of Terpenes and Steroids (pages 3033–3037)

      Kang Du, Pan Guo, Yuan Chen, Zhen Cao, Dr. Zheng Wang and Prof. Dr. Wenjun Tang

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411817

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      One, two, three: An enantioselective palladium-catalyzed dearomative cyclization was developed for the efficient construction of a series of chiral tricyclic phenanthrenone derivatives bearing all-carbon quaternary centers. This method was applied in highly efficient syntheses of a kaurene intermediate, the skeleton of the anabolic steroid boldenone, and the antimicrobial diterpene (−)-totaradiol.

    27. Grignard Reactions

      Catalytic Asymmetric Alkylation of Acylsilanes (pages 3038–3042)

      Jiawei Rong, Rik Oost, Dr. Alaric Desmarchelier, Prof. Adriaan J. Minnaard and Prof. Syuzanna R. Harutyunyan

      Article first published online: 17 NOV 2014 | DOI: 10.1002/anie.201409815

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      Chiral silanes: The highly enantioselective addition of Grignard reagents to acylsilanes is catalyzed by copper diphosphine complexes. This transformation affords α-silylated tertiary alcohols in up to 97 % yield and 98:2 enantiomeric ratio.

    28. Organocatalysis

      Catalytic Enantioselective [5+2] Cycloaddition between Oxidopyrylium Ylides and Enals under Dienamine Activation (pages 3043–3046)

      Ane Orue, Dr. Uxue Uria, Prof. Efraim Reyes, Prof. Luisa Carrillo and Prof. Jose L. Vicario

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410723

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      By using all its powers of persuasion, a bifunctional secondary-amine/squaramide catalyst encouraged 1-acetoxyisochroman-4-ones to react as benzopyrylium ylides with α,β-unsaturated aldehydes in efficient [5+2] cycloaddition reactions with high diastereo- and enantioselectivity. The transformation proceeds by dienamine activation and involves β,γ-functionalization of the enal (see scheme).

    29. Photocatalysis

      Interface Engineering of a CoOx/Ta3N5 Photocatalyst for Unprecedented Water Oxidation Performance under Visible-Light-Irradiation (pages 3047–3051)

      Shanshan Chen, Dr. Shuai Shen, Guiji Liu, Yu Qi, Prof. Fuxiang Zhang and Prof. Can Li

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409906

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      Hydrophilic interface modification of a CoOx-modified Ta3N5 photocatalyst with a magnesia nanolayer significantly improves its water oxidation efficiency under visible light irradiation. The essential roles of the interface modification are proposed to enhance the interfacial coverage of the CoOx/Ta3N5 photocatalyst and to decrease the defect density of Ta3N5 semiconductor. AQE=apparent quantum efficiency.

    30. Synthetic Methods

      Intramolecular C[BOND]H Activation through Gold(I)-Catalyzed Reaction of Iodoalkynes (pages 3052–3055)

      Pablo Morán-Poladura, Dr. Eduardo Rubio and Prof. Dr. José M. González

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409970

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      Golden dance: The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes gives the corresponding 3-iodo-1-substituted-1H-indene. Gold(I) catalysis triggers a selective intramolecular carbon–carbon bond-forming event, which involves the insertion of benzylic C[BOND]H bonds in the catalytically assembled gold(I) iodovinylidene intermediate.

    31. Carbenes

      Transition-Metal-Free Intramolecular Carbene Aromatic Substitution/Büchner Reaction: Synthesis of Fluorenes and [6,5,7]Benzo-fused Rings (pages 3056–3060)

      Zhenxing Liu, Haocheng Tan, Long Wang, Tianren Fu, Ying Xia, Dr. Yan Zhang and Prof. Dr. Jianbo Wang

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201409982

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      Transition-metal-free: The synthesis of fluorenes and [6,5,7]benzo-fused rings is achieved through a transition-metal-free protocol of intramolecular aromatic substitution and Büchner reaction. The new synthetic method uses readily available aromatic N-tosylhydrazones as the diazo compound precursors and shows wide substrate scope.

    32. Carbohydrates

      Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions (pages 3061–3064)

      Dr. Angie Garcia, Douglas A. L. Otte, Dr. Walter A. Salamant, Jillian R. Sanzone and Prof. K. A. Woerpel

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410043

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      Making an approach: In contrast to observations with carbohydrates, alkoxy groups can accelerate acetal hydrolysis even though they are inductively electron withdrawing. The alkoxy group must be able to approach the acetal carbon atom without developing too much strain. The data are most consistent with the alkoxy group stabilizing the developing positive charge by electrostatic stabilization, not formation of a new covalent bond.

    33. Reaction Intermediates

      Dinuclear Copper Intermediates in Copper(I)-Catalyzed Azide–Alkyne Cycloaddition Directly Observed by Electrospray Ionization Mass Spectrometry (pages 3065–3068)

      Dr. Claudio Iacobucci, Dr. Samantha Reale, Prof. Jean-François Gal and Prof. Francesco De Angelis

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410301

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      Mechanistic aspects of the CuAAC reaction have been clarified by electrospray ionization mass spectrometry (ESI-MS). Dinuclear copper intermediates have been detected for the first time and characterized. Neutral and ion-tagged reactants provided complementary evidence for the reaction catalytic cycle.

    34. Macrocycles

      Zethrene and Dibenzozethrene: Masked Biradical Molecules? (pages 3069–3073)

      Ya-Chu Hsieh, Hau-Yu Fang, Yi-Ting Chen, Rong Yang, Prof. Chen-I Yang, Prof. Pi-Tai Chou, Prof. Ming-Yu Kuo and Prof. Yao-Ting Wu

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410316

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      Shelling out: Substituents and π-conjugation remarkably affect the structures and properties of zethrene series. The parent dibenzozethrene and zethrene are both singlet open-shell biradicals, but the former has stronger biradical characteristics than the latter, as verified experimentally and theoretically, whereas all substituted derivatives have a closed-shell ground state.

    35. Natural Product Synthesis

      Total Synthesis of Trioxacarcin DC-45-A2 (pages 3074–3078)

      Prof. Dr. K. C. Nicolaou, Dr. Quan Cai, Dr. Bo Qin, Mette T. Petersen, Remi J. T. Mikkelsen and Dr. Philipp Heretsch

      Article first published online: 12 JAN 2015 | DOI: 10.1002/anie.201410369

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      Zipping it all together: A monodentate Lewis acid was used to induce the stereoselective formation of the bicyclo[2.2.1]heptane structural motif of DC-45-A2 (1), the naturally occurring parent compound of the trioxacarcin class of antitumor agents.

    36. Battery Electrodes

      Wet-Chemical Synthesis of Phase-Pure FeOF Nanorods as High-Capacity Cathodes for Sodium-Ion Batteries (pages 3079–3083)

      Jian Zhu and Dr. Da Deng

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410572

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      Fair of phase: A new wet-chemical method was developed for the facile preparation of phase-pure FeOF nanorod structures (see SEM image). The as-prepared FeOF nanorods demonstrated a high sodium-ion-storage capacity of approximately 250 mAh g−1 and excellent cycling and rate performance (see graph).

    37. Multicomponent Reactions | Hot Paper

      Base-Promoted Coupling of Carbon Dioxide, Amines, and N-Tosylhydrazones: A Novel and Versatile Approach to Carbamates (pages 3084–3087)

      Wenfang Xiong, Dr. Chaorong Qi, Haitao He, Lu Ouyang, Prof. Dr. Min Zhang and Prof. Dr. Huanfeng Jiang

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410605

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      Carbene intermediate? No! An unprecedented strategy for the synthesis of a range of organic carbamates through the coupling of carbon dioxide, amines, and N-tosylhydrazones is reported. The base-promoted reaction is proposed to proceed via a carbocation intermediate and is characterized by excellent functional group tolerance and a wide substrate scope.

    38. Copper Arenes

      A Copper(I)–Arene Complex With an Unsupported η6 Interaction (pages 3088–3091)

      Dr. Ashley M. Wright, Dr. Benjamin J. Irving, Dr. Guang Wu, Dr. Anthony J. H. M. Meijer and Prof. Dr. Trevor W. Hayton

      Article first published online: 21 JAN 2015 | DOI: 10.1002/anie.201410948

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      Addition of PR3 (R=Ph or OPh) to [Cu(η2-Me6C6)2][PF6] results in the formation of [(η6-Me6C6)Cu(PR3)][PF6], the first copper–arene complexes to feature an unsupported η6 arene interaction. DFT analysis shows that the preference for the η6 binding mode is enforced by the steric clash between the methyl groups of the arene ligand and the phenyl rings of the phosphine co-ligand.

    39. Heterocycle Synthesis

      Palladium(0)-Catalyzed Iminohalogenation of Alkenes: Synthesis of 2-Halomethyl Dihydropyrroles and Mechanistic Insights into the Alkyl Halide Bond Formation (pages 3092–3096)

      Chen Chen, Longlei Hou, Mian Cheng, Prof. Jianhua Su and Dr. Xiaofeng Tong

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201410996

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      Eliminated: The use of electron-poor phosphine ligands proved to be crucial to promoting alkyl bromide and chloride reductive elimination in the title reaction with γ,δ-unsaturated oxime esters. Furthermore, SN2-type alkyl bromide and chloride reductive elimination has also been established.

    40. Helical Superstructures

      Design of Aromatic Helical Polymers for STM Visualization: Imaging of Single and Double Helices with a Pattern of π–π Stacking (pages 3097–3101)

      Dr. Junyan Zhu, Prof. Zeyuan Dong, Prof. Shengbin Lei, Dr. Lili Cao, Prof. Bing Yang, Dr. Wenfang Li, Yuanchao Zhang, Prof. Junqiu Liu and Prof. Jiacong Shen

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201410975

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      Seeing is believing: STM imaging of rationally designed helical polymers with a pattern of π–π stacking of the helical structures revealed single- and double-helical superstructures (see picture), including the smallest helical architecture observed to date, with a diameter of approximately 1.3 nm. The interconversion of single and double helices was further underpinned by experimental analyses.

    41. Metallacycles

      σ-Aromaticity in an Unsaturated Ring: Osmapentalene Derivatives Containing a Metallacyclopropene Unit (pages 3102–3106)

      Dr. Congqing Zhu, Xiaoxi Zhou, Hongjie Xing, Ke An, Dr. Jun Zhu and Prof. Dr. Haiping Xia

      Article first published online: 4 FEB 2015 | DOI: 10.1002/anie.201411220

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      World of Os: A series of osmapentalene derivatives with a metallacyclopropene unit were synthesized by treatment of complex 1 with various allenes at room temperature. Experimental observations and theoretical calculations reveal that σ-aromaticity dominates in the unsaturated three-membered ring.

    42. Conjugation

      Fused Corrole Dimers Interconvert between Nonaromatic and Aromatic States through Two-Electron Redox Reactions (pages 3107–3111)

      Shota Ooi, Dr. Takayuki Tanaka, Kyu Hyung Park, Sangsu Lee, Prof. Dr. Dongho Kim and Prof. Dr. Atsuhiro Osuka

      Article first published online: 8 JAN 2015 | DOI: 10.1002/anie.201411242

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      Doubled up: A singly linked corrole dimer was synthesized and oxidized to a meso–meso and ββ doubly linked 2H-corrole dimer, which was interconvertible with an aromatic 3H-corrole dimer upon two-electron redox reactions. The nonaromatic 2H-corrole dimer was rather stable, probably because of the double direct connection between the corrole units.

    43. 2D Semiconductors | Hot Paper

      Atomically Thin Arsenene and Antimonene: Semimetal–Semiconductor and Indirect–Direct Band-Gap Transitions (pages 3112–3115)

      Dr. Shengli Zhang, Prof. Zhong Yan, Prof. Dr. Yafei Li, Prof. Dr. Zhongfang Chen and Prof. Haibo Zeng

      Article first published online: 7 JAN 2015 | DOI: 10.1002/anie.201411246

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      Unlike black phosphorus, both arsenic and antimony are typical semimetals in their natural, layered bulk state. However, monolayered arsenene and antimonene are indirect wide-band-gap semiconductors, and under strain, they become direct band-gap semiconductors. Owing to these band-gap transitions, these materials could find applications in nano- and optoelectronic devices.

    44. β-Carbon Elimination

      Synthesis of Enantioenriched 5,6-Dihydrophenanthridine Derivatives through retro-Carbopalladation of Chiral o-Bromobenzylamines (pages 3116–3120)

      Dr. Juntao Ye, Aurore Limouni, Sonia Zaichuk and Prof. Dr. Mark Lautens

      Article first published online: 8 JAN 2015 | DOI: 10.1002/anie.201411276

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      Retro-carbopalladation of aldimines in the presence of a suitable β-hydrogen atom is a key step in the Pd-catalyzed homocoupling reactions of o-bromobenzylamines, providing an expeditious synthetic route to 5,6-dihydrophenanthridine derivatives. A highly enantioselective synthesis procedure was also achieved in a one-pot manner by taking advantage of Rh and Pd catalysis.

    45. Asymmetric Catalysis

      Asymmetric Rhodium-Catalyzed Addition of Thiols to Allenes: Synthesis of Branched Allylic Thioethers and Sulfones (pages 3121–3125)

      Adrian B. Pritzius and Prof. Dr. Bernhard Breit

      Article first published online: 16 JAN 2015 | DOI: 10.1002/anie.201411402

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      All about S: The rhodium-catalyzed enantioselective hydrothiolation of terminal monosubstituted allenes with aromatic and functionalized aliphatic thiols permits the atom-economic synthesis of valuable branched allylic thioethers and sulfones in high regio- and enantioselectivity. By varying the ligand and reaction conditions both aromatic and aliphatic thiols were tolerated.

    46. Drug Delivery

      Antitumor Drug Delivery Modulated by A Polymeric Micelle with an Upper Critical Solution Temperature (pages 3126–3131)

      Dr. Weishuo Li, Dr. Liwen Huang, Xiaoying Ying, Prof. Dr. You Jian, Prof. Dr. Yuan Hong, Prof. Dr. Fuqiang Hu and Prof. Dr. Yongzhong Du

      Article first published online: 28 JAN 2015 | DOI: 10.1002/anie.201411524

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      Smart device: Poly(AAm-co-AN)-g-PEG micelles were used as a temperature-triggered drug delivery system based on their upper critical solution temperature. The polymeric micelles displayed a good drug release profile both in vitro and in vivo. Additionally, an excellent antitumor efficiency was achieved. DOX=doxorubicin.

    47. Synthetic Methods

      Copper-Catalyzed Cyanomethylation of Allylic Alcohols with Concomitant 1,2-Aryl Migration: Efficient Synthesis of Functionalized Ketones Containing an α-Quaternary Center (pages 3132–3135)

      Dr. Ala Bunescu, Dr. Qian Wang and Prof. Dr. Jieping Zhu

      Article first published online: 16 JAN 2015 | DOI: 10.1002/anie.201411657

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      A shift in gear: Ketones with an α-quaternary center were synthesized by the title copper triflate catalyzed alkylation of alkenes with non-activated alkyl nitriles (see scheme; 1,10-Phen=1,10-phenanthroline). The reaction involves the copper-catalyzed formation of an alkyl nitrile radical, its addition to the alkene, and the migration of a vicinal aryl group with the concomitant generation of a carbonyl functionality.

    48. Natural Product Synthesis | Hot Paper

      Total Synthesis of (−)-Caprazamycin A (pages 3136–3139)

      Hugh Nakamura, Dr. Chihiro Tsukano, Motohiro Yasui, Shinsuke Yokouchi, Dr. Masayuki Igarashi and Prof. Dr. Yoshiji Takemoto

      Article first published online: 22 JAN 2015 | DOI: 10.1002/anie.201411954

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      Abra‘capraza’: Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features the scalable preparation of the syn-β-hydroxy amino acid with a thiourea-catalyzed diastereoselective aldol reaction, construction of a diazepanone with an unstable fatty-acid side chain, and global deprotection by hydrogenation.

    49. Gold Clusters

      Structure Determination of [Au18(SR)14] (pages 3140–3144)

      Anindita Das, Chong Liu, Hee Young Byun, Prof. Katsuyuki Nobusada, Shuo Zhao, Prof. Nathaniel Rosi and Prof. Rongchao Jin

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410161

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      Heart of gold: A decade after the first report of the [Au18(SR)14] cluster, its structure is finally obtained (see picture, gold pink, sulfur yellow, cyclohexyl groups as wire frame). It has a bi-octahedral (or hexagonal closing packing) Au9 kernel protected by staple-like surface motifs.

    50. The Structure and Optical Properties of the [Au18(SR)14] Nanocluster (pages 3145–3149)

      Shuang Chen, Shuxin Wang, Juan Zhong, Yongbo Song, Dr. Jun Zhang, Prof. Hongting Sheng, Prof. Yong Pei and Prof. Manzhou Zhu

      Article first published online: 23 JAN 2015 | DOI: 10.1002/anie.201410295

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      Gold mine: The X-ray crystallographic structure of cyclohexylthiolate-protected [Au18(SR)14] nanocluster shows it has a Au9 bi-octahedral kernel (Au gold, S pink, C gray). This Au9 core is formed by two octahedral Au6 units sharing one triangular face. A gold atom in the Au9 core, which can also be considered as part of the Au4(SR)5 staple motif offering new insight into the evolution from AuI complexes to larger Au nanoclusters.

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