Angewandte Chemie International Edition

Cover image for Vol. 53 Issue 15

April 7, 2014

Volume 53, Issue 15

Pages 3751–4005

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. You have free access to this content
      Cover Picture: Interaction with the Surrounding Water Plays a Key Role in Determining the Aggregation Propensity of Proteins (Angew. Chem. Int. Ed. 15/2014) (page 3751)

      Dr. Song-Ho Chong and Prof. Sihyun Ham

      Article first published online: 3 APR 2014 | DOI: 10.1002/anie.201401101

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      Interaction with the surrounding water was shown to play a crucial role in determining the aggregation propensity of proteins. In their Communication on page 3961 ff., S.-H. Chong and S. Ham shown that the overall protein hydrophobicity, defined by the hydration free energy of the protein, is the predominant determinant of protein aggregation propensity in aqueous solutions. This result paves the way for the design of aggregation-resistant proteins as biotherapeutics.

    2. You have free access to this content
      Inside Cover: Confining Phosphanes Derived from Cyclodextrins for Efficient Regio- and Enantioselective Hydroformylation (Angew. Chem. Int. Ed. 15/2014) (page 3752)

      Matthieu Jouffroy, Dr. Rafael Gramage-Doria, Prof. Dominique Armspach, Dr. David Sémeril, Dr. Werner Oberhauser, Dr. Dominique Matt and Dr. Loic Toupet

      Article first published online: 25 MAR 2014 | DOI: 10.1002/anie.201401124

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      Metal confinement can make the difference, as shown by D. Matt, D. Armspach et al. in their Communication on page 3937 ff. The use of cyclodextrin derivatives with an introverted PIII donor atom in the rhodium-catalyzed hydroformylation of styrene leads to high iso- and enantioselectivity. This result is due to the selective formation of monophosphane complexes in which the cyclodextrin cavity tightly wraps around the metal center, like Russian nesting dolls (artwork: Katia Gradt).

    3. You have free access to this content
      Inside Back Cover: Site-Selective Synthesis of Janus-type Metal-Organic Framework Composites (Angew. Chem. Int. Ed. 15/2014) (page 4007)

      Sudarat Yadnum, Dr. Jérome Roche, Eric Lebraud, Philippe Négrier, Patrick Garrigue, Dr. Darren Bradshaw, Dr. Chompunuch Warakulwit, Prof. Jumras Limtrakul and Prof. Alexander Kuhn

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201401103

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      Janus metal–organic frameworks can be electrogenerated by site-selective deposition on the surface of conducting substrates, as demonstrated by A. Kuhn, D. Bradshaw, et al. in their Communication on page 4001 ff. This is the first time that such hybrid asymmetric materials have been obtained with high spatial control and without a physical connection between the modified object and the electrode. This approach should be useful for the synthesis of other types of particles with a mixed surface composition.

    4. You have free access to this content
      Back Cover: Nanosized Heterostructures of Au@Prussian Blue Analogues: Towards Multifunctionality at the Nanoscale (Angew. Chem. Int. Ed. 15/2014) (page 4008)

      Guillaume Maurin-Pasturel, Dr. Jérôme Long, Dr. Yannick Guari, Franck Godiard, Dr. Marc-Georg Willinger, Prof. Dr. Christian Guerin and Prof. Dr. Joulia Larionova

      Article first published online: 3 MAR 2014 | DOI: 10.1002/anie.201401097

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      Core–shell gold@Prussian blue analogue nanoparticles that exhibit plasmonic and magnetic properties can be synthesized according to a novel and rational approach that is described by Y. Guari and co-workers in their Communication on page 3872 ff. The synthetic concept also includes a smart way to hollow Prussian blue analogue nanoparticles (artwork: Tania Louis).

  2. Editorial

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. You have free access to this content
  3. Graphical Abstract

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. You have free access to this content
      Corrigendum: Synthetic Studies on Chartelline C: Stereoselective Construction of the Core Skeleton (page 3768)

      Dr. Kotaro Iwasaki, Rentaro Kanno, Dr. Toshiharu Morimoto, Dr. Tohru Yamashita, Dr. Satoshi Yokoshima and Prof. Tohru Fukuyama

      Article first published online: 3 APR 2014 | DOI: 10.1002/anie.201401113

      This article corrects:

      Synthetic Studies on Chartelline C: Stereoselective Construction of the Core Skeleton1

      Vol. 51, Issue 36, 9160–9163, Article first published online: 2 AUG 2012

  5. News

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

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. Wen-Jing Xiao (page 3774)

      Article first published online: 26 NOV 2013 | DOI: 10.1002/anie.201309507

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      “My favorite saying is ‘Where there's a will, there's a way’. My favorite drink is green tea. …” This and more about Wen-Jing Xiao can be found on page 3774.

  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. Self-Healing Polymers. From Principles to Applications. Edited by Wolfgang H. Binder. (page 3775)

      Marek W. Urban

      Article first published online: 19 FEB 2014 | DOI: 10.1002/anie.201310868

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      Wiley-VCH, Weinheim, 2013. 446 pp., hardcover, € 139.00.—ISBN 978-3527334391

  8. Highlight

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. Ras Inhibitors

      Selective Inhibition of Mutant Ras Protein through Covalent Binding (pages 3777–3779)

      Dr. Joachim Rudolph and Dr. David Stokoe

      Article first published online: 3 MAR 2014 | DOI: 10.1002/anie.201400233

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      One of the first oncogenes to be discovered and one of the most prevalently mutated tumor genes is Ras. Shokat et al. and Gray et al. have succeeded in discovering allosteric inhibitors and inhibitory nucleotide analogues, respectively, of K-Ras proteins (see scheme) that covalently and selectively bind G12C-mutant K-Ras. These strategies of specifically targeting a mutant form of Ras may offer an opportunity for cancer–selective therapies that spare normal tissue.

  9. Reviews

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. Phase-Change Materials

      Emerging Applications of Phase-Change Materials (PCMs): Teaching an Old Dog New Tricks (pages 3780–3795)

      Dr. Dong Choon Hyun, Nathanael S. Levinson, Prof. Unyong Jeong and Younan Xia

      Article first published online: 27 JAN 2014 | DOI: 10.1002/anie.201305201

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      PCMs on the rise: As a result of their sharp melting points and large heats of fusion during phase transition, phase-change materials (PCMs) have already found commercial use in thermal management. The vast potential of this class of fascinating materials has recently been tapped in a diverse array of high-tech applications such as controlled release, information storage, sensing/detection, and barcoding.

    2. Targeted Cancer Therapy

      Antibody–Drug Conjugates: An Emerging Concept in Cancer Therapy (pages 3796–3827)

      Dr. Ravi V. J. Chari, Dr. Michael L. Miller and Dr. Wayne C. Widdison

      Article first published online: 20 FEB 2014 | DOI: 10.1002/anie.201307628

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      Fight together: Antibody–drug conjugates (ADCs) are an emerging new class of targeted cancer therapeutics, with validation provided by the recent marketing approvals of the ADCs brentuximab vedotin and ado-trastuzumab emtansine. Key considerations in the design of ADCs, pre-clinical and clinical data of various ADCs in development, along with the current status and emerging advances are reviewed.

  10. Communications

    1. Top of page
    2. Cover Pictures
    3. Editorial
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Author Profile
    8. Book Review
    9. Highlight
    10. Reviews
    11. Communications
    1. Antimicrobial Polymers

      Antimicrobial Poly(2-methyloxazoline)s with Bioswitchable Activity through Satellite Group Modification (pages 3830–3834)

      Dipl.-Ing. Christian Krumm, Dipl.-Chem. Simon Harmuth, Montasser Hijazi, Britta Neugebauer, Anne-Larissa Kampmann, Helma Geltenpoth, Prof. Dr. Albert Sickmann and Prof. Dr. Joerg C. Tiller

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201311150

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      Biocides are widely used for preventing the spread of microbial infections and the fouling of materials. Since their application can build up microbial resistance and cause unpredictable long-term environmental problems, new biocidal agents are required. In a novel approach an antimicrobial polymer is deactivated by hydrolysis of an ester group through the action of a lipase. The crucial feature is the mutual interaction of the two endgroups of the polymer.

    2. Photopatterning

      Direct UV-Induced Functionalization of Surface Hydroxy Groups by Thiol–Ol Chemistry (pages 3835–3839)

      Linxian Li, Junsheng Li, Xin Du, Dr. Alexander Welle, Prof. Dr. Michael Grunze, Prof. Dr. Oliver Trapp and Dr. Pavel A. Levkin

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201310692

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      When thiols meet alcohols: A method based on thiol–alcohol chemistry is used for the direct photochemical modification and patterning of hydroxy-functionalized surfaces with different thiol-containing functional molecules (see picture).

    3. Intrinsically Disordered Proteins

      Compensatory Adaptations of Structural Dynamics in an Intrinsically Disordered Protein Complex (pages 3840–3843)

      Dr. Dennis Kurzbach, Thomas C. Schwarz, Gerald Platzer, Simone Höfler, Prof. Dariush Hinderberger and Prof. Robert Konrat

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201308389

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      Well-balanced: The binding of heparin to the intrinsically disordered protein (IDP) osteopontin was studied by a combination of NMR and EPR spectroscopy. The results offer insight into the interplay between structure and thermodynamics which results in low energy barriers and facilitates rapid substrate-binding and -release events in IDP interaction networks.

    4. Functional Microspheres

      Inverse Opal Spheres Based on Polyionic Liquids as Functional Microspheres with Tunable Optical Properties and Molecular Recognition Capabilities (pages 3844–3848)

      Jiecheng Cui, Wei Zhu, Ning Gao, Jian Li, Haowei Yang, Yin Jiang, Philipp Seidel, Prof. Dr. Bart Jan Ravoo and Prof. Dr. Guangtao Li

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201308959

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      Broad spectrum: Based on the combination of the unique features of both polyionic liquids and spherical colloidal crystals, a new class of optical spheres with a series of distinct properties was fabricated. Such photonic spheres could not only be used as stimuli-responsive photonic microgels, but also serve as functional microspheres that mimic the main characteristics of small molecules, including intrinsic optical properties, specific molecular recognition, reactivity and derivatization, and anisotropy.

    5. Bioactive Peptides

      Filaggrin Peptides with β-Hairpin Structure Bind Rheumatoid Arthritis Antibodies (pages 3849–3853)

      Sabrina Fischer and Prof. Armin Geyer

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201309873

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      Form follows function: A filaggrin peptide in a constricted β-hairpin conformation binds autoantibodies against rheumatoid arthritis. The binding affinity of these peptides is comparable to those of the flexible filaggrin peptides in ELISA tests. NMR spectroscopy identifies the homogeneity of peptide folding and supports the proposed antibody-bound conformation of the epitope.

    6. Gold Catalysis

      Cyclization of Gold Acetylides: Synthesis of Vinyl Sulfonates via Gold Vinylidene Complexes (pages 3854–3858)

      M. Sc. Janina Bucher, M. Sc. Thomas Wurm, Dr. Kumara Swamy Nalivela, Dr. Matthias Rudolph, Dr. Frank Rominger and Prof. Dr.  A. Stephen K. Hashmi

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201310280

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      Gold vinylidene intermediates are generated by the cyclization of gold acetylides that carry a sulfonate leaving group. This result demonstrates for the first time that the formation of these species is not restricted to a dual activation mode. The cyclization products obtained herein contain a vinyl sulfonate moiety, which makes them useful building blocks for cross-coupling reactions.

    7. Total Synthesis

      Light-Mediated Total Synthesis of 17-Deoxyprovidencin (pages 3859–3862)

      Dr. Nina Toelle, Dr. Harald Weinstabl, Dr. Tanja Gaich and Prof. Dr. Johann Mulzer

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201400617

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      Photochemistry is the key: An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photoinduced Z/E isomerization to a highly strained conformationally restricted ring system, and the stereoselective formation of two epoxides on the macrocycle.

    8. Ligand-Field States

      The Role of Ligand-Field States in the Ultrafast Photophysical Cycle of the Prototypical Iron(II) Spin-Crossover Compound [Fe(ptz)6](BF4)2 (pages 3863–3867)

      Andrea Marino, Dr. Pradip Chakraborty, Dr. Marina Servol, Dr. Maciej Lorenc, Prof. Eric Collet and Prof. Andreas Hauser

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201310884

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      The path of LIESST resistance: Ultrafast transient absorption with an infrared pump and a UV probe allows for a detailed elucidation of the sequence of events on irradiation into the spin-allowed ligand-field transition of the high-spin species of a prototypical iron(II) spin-crossover complex, thereby identifying the lowest-energy triplet state as a short-lived intermediate state with a lifetime of 39 ps in the passage from the excited quintet to the singlet ground state.

    9. C[BOND]H Activation

      Iron-Catalyzed C(sp2)[BOND]H and C(sp3)[BOND]H Arylation by Triazole Assistance (pages 3868–3871)

      Dr. Qing Gu, Dr. Hamad H. Al Mamari, M. Sc. Karolina Graczyk, Emelyne Diers and Prof. Dr. Lutz Ackermann

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201311024

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      With a little help: A versatile iron catalyst allows the arylation of C(sp2)[BOND]H and C(sp3)[BOND]H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide–alkyne cycloadditions.

    10. Prussian Blue Nanoparticles

      Nanosized Heterostructures of Au@Prussian Blue Analogues: Towards Multifunctionality at the Nanoscale (pages 3872–3876)

      Guillaume Maurin-Pasturel, Dr. Jérôme Long, Dr. Yannick Guari, Franck Godiard, Dr. Marc-Georg Willinger, Prof. Dr. Christian Guerin and Prof. Dr. Joulia Larionova

      Article first published online: 26 FEB 2014 | DOI: 10.1002/anie.201310443

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      Prussian gold: A method for the synthesis of single- and double-layer core–shell heterostructures that are based on a well-defined gold core and shells of Prussian blue analogues has been developed. These materials feature magneto-optical properties and may be considered as multifunctional nanoobjects.

    11. Synthetic Methods

      Regio- and Stereoselective 1,2-Dihydropyridine Alkylation/Addition Sequence for the Synthesis of Piperidines with Quaternary Centers (pages 3877–3880)

      Simon Duttwyler, Shuming Chen, Colin Lu, Brandon Q. Mercado, Prof. Dr. Robert G. Bergman and Prof. Dr. Jonathan A. Ellman

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201310517

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      Pipe up: Alkylation of readily prepared 1,2-dihydropyridines with alkyl triflates and Michael acceptors introduces quaternary carbon centers with high regio- and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeds with high diastereoselectivity. For carbon nucleophile addition, an unprecedented level of substitution is achieved to provide piperidine rings with contiguous tetrasubstituted carbon atoms.

    12. Main-Group Ligands

      Syntheses and Structures of Terminal Arylalumylene Complexes (pages 3881–3884)

      Koichi Nagata, Dr. Tomohiro Agou and Prof. Dr. Norihiro Tokitoh

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201310559

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      Quite a character: A terminal arylalumylene complex of platinum was obtained by the reaction of a dialumene–benzene adduct and [Pt(PCy3)2]. Reduction of 1,2-dibromodialumanes in the presence of [Pt(PCy3)2] also afforded the terminal arylalumylene complexes. DFT calculations suggest that the Al[BOND]Pt bonds in the arylalumylene complexes have a significantly high electrostatic character.

    13. Asymmetric Catalysis

      Catalytic, Enantioselective Synthesis of 1,2-anti-Diols by Asymmetric Ring-Opening/Cross-Metathesis (pages 3885–3888)

      Dr. John Hartung and Prof. Robert H. Grubbs

      Article first published online: 19 FEB 2014 | DOI: 10.1002/anie.201310767

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      Rather fetching: Chiral vicinal diols are found in natural products and ligands used for asymmetric catalysis. The enantioselective ring-opening/cross-metathesis of disubstituted cyclobutenes has been carried out with an enantiopure ruthenium metathesis catalyst to afford 1,2-anti-diols with high enantiopurity. The synthetic versatility of the products was demonstrated in the synthesis of insect pheromone (+)-endo-brevicomin and a monosaccharide ribose.

    14. Molecular Electronics

      Replacing AgTSSCH2-R with AgTSO2C-R in EGaIn-Based Tunneling Junctions Does Not Significantly Change Rates of Charge Transport (pages 3889–3893)

      Dr. Kung-Ching Liao, Dr. Hyo Jae Yoon, Dr. Carleen M. Bowers, Dr. Felice C. Simeone and Prof. Dr. George M. Whitesides

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201308472

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      Either way: For junctions comprising thiolate- and carboxylate-anchored self-assembled monolayers (SAMs) the role of the metal–SAM interface in charge transport by tunneling was investigated and the charge-transport rates were measured. The data suggest that Ag–SAM interfaces having either a thiolate or carboxylate anchoring group may be directly comparable.

    15. Radical Reactions

      Repairing the Thiol-Ene Coupling Reaction (pages 3894–3898)

      Dr. Guillaume Povie, Dr. Anh-Tuan Tran, Prof. David Bonnaffé, Jacqueline Habegger, Zhaoyu Hu, Dr. Christine Le Narvor and Prof. Philippe Renaud

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201309984

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      In good repair: Undesired hydrogen-atom transfers are responsible for the lack of efficiency in thiol-ene coupling reactions involving allyl glycosides. This competing reaction cannot be prevented but can be very efficiently repaired by carrying out the reaction in the presence of triethylborane and catechol.

    16. C[BOND]H Borylation

      Direct Borylation of Primary C[BOND]H Bonds in Functionalized Molecules by Palladium Catalysis (pages 3899–3903)

      Li-Sheng Zhang, Guihua Chen, Xin Wang, Qing-Yun Guo, Xi-Sha Zhang, Fei Pan, Kang Chen and Prof. Dr. Zhang-Jie Shi

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201310000

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      Crucial additives: A simple palladium-based system catalyzes the conversion of primary C(sp3)[BOND]H bonds in complex organic molecules into alkyl boronate esters. Amino acids, amino alcohols, alkyl amines, and a series of bioactive molecules that are modified with readily available directing groups are functionalized in the presence of commercially available additives, simple ligands, and oxygen as the terminal oxidant.

    17. Synthetic Methods

      Practical Metal-Free C(sp3)[BOND]H Functionalization: Construction of Structurally Diverse α-Substituted N-Benzyl and N-Allyl Carbamates (pages 3904–3908)

      Zhiyu Xie, Prof. Lei Liu, Wenfang Chen, Hongbo Zheng, Qingqing Xu, Prof. Huiqing Yuan and Prof. Hongxiang Lou

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201310193

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      Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

    18. Natural Products

      Omaezallene from Red Alga Laurencia sp.: Structure Elucidation, Total Synthesis, and Antifouling Activity (pages 3909–3912)

      Dr. Taiki Umezawa, Yuko Oguri, Dr. Hiroshi Matsuura, Shohei Yamazaki, Masahiro Suzuki, Erina Yoshimura, Dr. Takeshi Furuta, Dr. Yasuyuki Nogata, Dr. Yukihiko Serisawa, Dr. Kazuyo Matsuyama-Serisawa, Dr. Tsuyoshi Abe, Prof. Dr. Fuyuhiko Matsuda, Dr. Minoru Suzuki and Dr. Tatsufumi Okino

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201311175

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      Omaezallene, a new brominated antifouling natural product isolated from the red alga Laurencia sp., was synthesized and its structure elucidated through NMR experiments. The antifouling activities of omaezallene and its isomers against the cypris larvae of the barnacle Amphibalanus amphitrite were also evaluated.

    19. Asymmetric Catalysis

      Enantioselective N[BOND]H Insertion Reaction of α-Aryl α-Diazoketones: An Efficient Route to Chiral α-Aminoketones (pages 3913–3916)

      Bin Xu, Prof. Shou-Fei Zhu, Xiao-Dong Zuo, Zhi-Chao Zhang and Prof. Qi-Lin Zhou

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201400236

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      Spiro inspiration: A highly enantioselective N[BOND]H insertion reaction of α-diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in the organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions.

    20. Synthetic Methods

      Oxidative Cross-Coupling of Allenyl Ketones and Organoboronic Acids: Expeditious Synthesis of Highly Substituted Furans (pages 3917–3921)

      Ying Xia, Dr. Yamu Xia, Rui Ge, Zhen Liu, Dr. Qing Xiao, Dr. Yan Zhang and Prof. Dr. Jianbo Wang

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201400500

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      Migration patterns: Allenyl ketones are employed as a coupling partner in a palladium-catalyzed oxidative cross-coupling reaction with organoboronic acids. This reaction constitutes an efficient methodology for the synthesis of highly substituted furan derivatives. Palladium-carbene migratory insertion is proposed as the key step in this transformation. BQ=1,4-benzoquinone.

    21. Natural Products Synthesis

      Divergent Total Syntheses of Lyconadins A and C (pages 3922–3925)

      Dr. Yang Yang, Christopher W. Haskins, Wandi Zhang, Pui Leng Low and Prof. Dr. Mingji Dai

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201400416

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      Like-a-podium: Divergent total syntheses of the two Lycopodium alkaloids lyconadins A and C were developed from the intermediate 1. The synthesis of lyconadin A features a highly efficient ketal removal/formal aza-[4+2] cyclization to form the core structure. A ketal removal/Mannich reaction was used to construct the core structure of lyconadin C. The concise and flexible synthetic route offers a platform for the development of anti-neurodegenerative agents.

    22. Lithium–Oxygen Battery

      Superior Rechargeability and Efficiency of Lithium–Oxygen Batteries: Hierarchical Air Electrode Architecture Combined with a Soluble Catalyst (pages 3926–3931)

      Hee-Dae Lim, Hyelynn Song, Jinsoo Kim, Hyeokjo Gwon, Youngjoon Bae, Kyu-Young Park, Jihyun Hong, Haegyeom Kim, Taewoo Kim, Prof. Yong Hyup Kim, Xavier Lepró, Raquel Ovalle-Robles, Prof. Ray H. Baughman and Prof. Kisuk Kang

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201400711

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      Outstanding storage performance: A lithium–oxygen battery that uses a soluble catalyst combined with a hierarchical nanoporous air electrode shows high reversibility and good energy efficiency. Through the porous three-dimensional network of the air electrode, not only lithium ions and oxygen but also soluble catalysts can be rapidly transported, enabling significantly enhanced catalytic activity (CNT=carbon nanotube).

    23. Protein Engineering

      Genetically Encoding Photoswitchable Click Amino Acids in Escherichia coli and Mammalian Cells (pages 3932–3936)

      Dr. Christian Hoppmann, Dr. Vanessa K. Lacey, Dr. Gordon V. Louie, Jing Wei, Prof. Joseph P. Noel and Prof. Lei Wang

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201400001

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      Click and switch: Photoswitchable click amino acids (PSCaas) contain a photoisomerizable azobenzene and an additional click functional group. After being incorporated into proteins, the PSCaa spontaneously generates a protein bridge with a nearby cysteine residue through proximity-enabled bioreactivity. The bridge isomerizes in response to light, thereby altering protein conformation. These PSCaas may enable optogenetic control of proteins in situ.

    24. Homogeneous Catalysis

      Confining Phosphanes Derived from Cyclodextrins for Efficient Regio- and Enantioselective Hydroformylation (pages 3937–3940)

      Matthieu Jouffroy, Dr. Rafael Gramage-Doria, Prof. Dominique Armspach, Dr. David Sémeril, Dr. Werner Oberhauser, Dr. Dominique Matt and Dr. Loic Toupet

      Article first published online: 3 MAR 2014 | DOI: 10.1002/anie.201311291

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      Rhodium in confinement: α- and β-cyclodextrin derivatives bearing introverted PIII donor atoms readily form monophosphane complexes in which the cyclodextrin cavity tightly wraps around the metal center. When used as ligands in the rhodium-catalyzed hydroformylation of styrene, they lead to both high isoselectivity and enantioselectivity.

    25. Iridium Anticancer Drugs

      You have full text access to this OnlineOpen article
      The Potent Oxidant Anticancer Activity of Organoiridium Catalysts (pages 3941–3946)

      Dr. Zhe Liu, Dr. Isolda Romero-Canelón, Bushra Qamar, Jessica M. Hearn, Dr. Abraha Habtemariam, Dr. Nicolas P. E. Barry, Dr. Ana M. Pizarro, Dr. Guy J. Clarkson and Prof. Dr. Peter J. Sadler

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201311161

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      Protective pyridine: A novel half-sandwich organoiridium(III) complex with a pyridine ligand is more potent than both its chloride analogue and cisplatin towards a wide range of cancer cells. The pyridine ligand protects the iridium complex from rapid reactions with glutathione, and its potency correlates with a substantial increase in the amount of reactive oxygen species in the cancer cells.

    26. Protein Synthesis

      Total Synthesis of Homogeneous Variants of Hirudin P6: A Post-Translationally Modified Anti-Thrombotic Leech-Derived Protein (pages 3947–3951)

      Yves S. Y. Hsieh, Dr. Lakshmi C. Wijeyewickrema, Dr. Brendan L. Wilkinson, Prof. Robert N. Pike and Prof. Richard J. Payne

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201310777

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      Modifications matter: Hirudin P6 is a leech-derived anti-thrombotic protein that is natively O-glycosylated and sulfated on tyrosine. Ligation chemistry was employed to assemble a library of homogeneously modified hirudin P6 proteins with variation in glycosylation at Thr-43 and sulfation at Tyr-61. The type of post-translational modification present was shown to have a dramatic effect on inhibitory activity against both the fibrinogenolytic and amidolytic activities of thrombin.

    27. Metallacycles

      The Isolation and Characterization of a Rhodacycle Intermediate Implicated in Metal-Catalyzed Reactions of Alkylidenecyclopropanes (pages 3952–3956)

      Dr. Phillip A. Inglesby, Dr. John Bacsa, Daniela E. Negru and Prof. P. Andrew Evans

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201310232

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      A rhodacycle intermediate implicated in rhodium-catalyzed reactions of alkylidenecyclopropanes (ACPs) was isolated and characterized. The structure of the metallacycle, which was unambiguously determined by X-ray crystallography, is catalytically competent in the rhodium-catalyzed carbocyclization and ene-cycloisomerization reactions of ACPs.

    28. Porous Materials

      Templated Synthesis of Nitrogen-Enriched Nanoporous Carbon Materials from Porogenic Organic Precursors Prepared by ATRP (pages 3957–3960)

      Prof. Dr. Dingcai Wu, Zhenghui Li, Dr. Mingjiang Zhong, Prof. Dr. Tomasz Kowalewski and Prof. Dr. Krzysztof Matyjaszewski

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201309836

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      Nanocarbons from all-organic hairy nanoparticles: A versatile ATRP-based templating method has been developed to prepare nitrogen-enriched nanoporous carbon materials using all-organic hairy xPMMA-g-PAN nanoparticles as covalently fixed building blocks. Such materials are characterized by well-defined templated mesoporosity, high surface area, and an abundance of nitrogen-containing functional groups.

    29. Protein Aggregation

      Interaction with the Surrounding Water Plays a Key Role in Determining the Aggregation Propensity of Proteins (pages 3961–3964)

      Dr. Song-Ho Chong and Prof. Sihyun Ham

      Article first published online: 24 FEB 2014 | DOI: 10.1002/anie.201309317

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      Water, water, everywhere: Understanding the causes of protein aggregation is a central issue for understanding and preventing protein-aggregation diseases. Most studies to date have focused on the protein sequences without fully addressing the role of the surrounding water molecules. In fact, the interaction of a protein with the water surrounding it was found to play a pivotal role in determining its hydrophobicity and thus its aggregation propensity.

    30. Biocatalysis

      Facile Chemoenzymatic Strategies for the Synthesis and Utilization of S-Adenosyl-L-Methionine Analogues (pages 3965–3969)

      Dr. Shanteri Singh, Dr. Jianjun Zhang, Tyler D. Huber, Manjula Sunkara, Katherine Hurley, Dr. Randal D. Goff, Dr. Guojun Wang, Wen Zhang, Prof. Chunming Liu, Prof. Jürgen Rohr, Prof. Steven G. Van Lanen, Prof. Andrew J. Morris and Prof. Jon S. Thorson

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201308272

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      Mix and MATch: Methionine adenosyltransferase (MAT) was used to synthesize S-adenosylmethionine (SAM) analogues in a method directly compatible with downstream SAM-utilizing enzymes. As a proof of concept for the feasibility of natural product “alkylrandomization” by using this method, a coupled strategy in which MAT was applied in conjunction with the methyltransferase RebM was used to generate a small set of indolocarbazole analogues.

    31. Hybrid Materials

      Formation and Thermal Stability of Gold–Silica Nanohybrids: Insight into the Mechanism and Morphology by Electron Tomography (pages 3970–3974)

      Dr. Paromita Kundu, Dr. Hamed Heidari, Prof. Sara Bals, Prof. N. Ravishankar and Prof. Dr. Gustaaf Van Tendeloo

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201309288

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      A simple approach to synthesize gold nanoparticles (AuNPs) decorated on SiO2 spheres is demonstrated and a rationale is discussed for the formation mechanism. Electron tomography is used to understand the morphology of and changes upon heating the hybrid (see picture). The hybrid nanoparticles show excellent thermal stability appropriate for several applications.

    32. Fluorescent Probes

      Long-Wavelength Fluorescent Reporters for Monitoring Protein Kinase Activity (pages 3975–3978)

      Nathan P. Oien, Luong T. Nguyen, Dr. Finith E. Jernigan, Prof. Melanie A. Priestman and Prof. David S. Lawrence

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201309691

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      Searching far and near: Fluorescent reporters for protein kinase activity were developed. The probing wavelength is preprogrammed by using readily available fluorophores, thereby enabling detection within the optical window of tissue, specifically in the far-red and near-IR region. These agents were used to monitor endogenous cAMP-dependent protein kinase activity 1) in erythrocyte lysates and 2) in intact erythrocytes when using a light-activatable reporter.

    33. DNA Objects

      You have full text access to this OnlineOpen article
      Functionalizing Designer DNA Crystals with a Triple-Helical Veneer (pages 3979–3982)

      Dr. David A. Rusling, Arun Richard Chandrasekaran, Dr. Yoel P. Ohayon, Prof. Dr. Tom Brown, Prof. Dr. Keith R. Fox, Dr. Ruojie Sha, Prof. Dr. Chengde Mao and Prof. Dr. Nadrian C. Seeman

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201309914

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      Not so crystal clear: A macroscopic DNA crystal is presented based on the 3-fold symmetrical tensegrity triangle that has been functionalized with a triplex-forming oligonucleotide at each of its double-helical edges. Attachment of a fluorescent dye to the oligonucleotide led to its incorporation within the asymmetric unit cell of the crystal and yielded colored DNA crystals.

    34. Protein Synthesis

      A Synthetic Route to Human Insulin Using Isoacyl Peptides (pages 3983–3987)

      Dr. Fa Liu, Ethan Y. Luo, David B. Flora and Dr. Adam R. Mezo

      Article first published online: 11 MAR 2014 | DOI: 10.1002/anie.201310735

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      Chain of command: A longstanding challenge in the chemical synthesis of human insulin has been solved by incorporating isoacyl dipeptide segments into the A and B chains to address the hydrophobicity-associated issues. This route affords human insulin with a yield of 68 % based on the starting A chain and represents the most efficient chemical insulin synthesis reported to date.

    35. Microreactor Arrays

      Microarrays Formed by Microfluidic Spinning as Multidimensional Microreactors (pages 3988–3992)

      Ling-Ling Xu, Dr. Cai-Feng Wang and Prof. Su Chen

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201310977

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      At a critical juncture: Well-defined fluorescent microarrays with various patterns were fabricated in a controlled manner by a rapid and straightforward microfluidic spinning technique. By the use of appropriately doped components, the intersections of the multidimensional microarrays served as microreactors for environmentally friendly chemical reactions to form fluorescent nanocrystals.

    36. Imaging Agents

      Ubiquinone-Rhodol (UQ-Rh) for Fluorescence Imaging of NAD(P)H through Intracellular Activation (pages 3993–3995)

      Dr. Hirokazu Komatsu, Dr. Yutaka Shindo, Prof. Dr. Kotaro Oka, Dr. Jonathan P. Hill and Prof. Dr. Katsuhiko Ariga

      Article first published online: 5 MAR 2014 | DOI: 10.1002/anie.201311192

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      Active detection: NADH and NADPH are critical components of cellular energy metabolism and operate as electron carriers. A novel fluorescent ubiquinone-rhodol derivative (UQ-Rh) was developed as a probe for NAD(P)H. By using the artificial promoter [(η5-C5Me5)Ir(phen)(H2O)]2+, intracellular activation and imaging of NAD(P)H were successfully demonstrated.

    37. Organic Solar Cells

      Twisted but Conjugated: Building Blocks for Low Bandgap Polymers (pages 3996–4000)

      Dr. Chien-Yang Chiu, Dr. Hengbin Wang, Dr. Fulvio G. Brunetti, Prof. Fred Wudl and Prof. Craig J. Hawker

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201400674

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      A simplified synthetic approach provided novel building blocks for conjugated polymers featuring a non-planar repeat unit and a distorted double bond. The resulting copolymers are characterized by a broad absorption profile and show promising results in solar cells.

    38. Wireless Electrodeposition

      Site-Selective Synthesis of Janus-type Metal-Organic Framework Composites (pages 4001–4005)

      Sudarat Yadnum, Dr. Jérome Roche, Eric Lebraud, Philippe Négrier, Patrick Garrigue, Dr. Darren Bradshaw, Dr. Chompunuch Warakulwit, Prof. Jumras Limtrakul and Prof. Alexander Kuhn

      Article first published online: 6 MAR 2014 | DOI: 10.1002/anie.201400581

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      Two-faced MOF: The site-selective in situ synthesis of metal–organic framework (MOF) structures can be accomplished through bipolar electrochemistry, allowing the deposit to be confined to a defined area of a substrate without using masks or templates. This method can generate hybrid particles that have different combined functionalities on the same particle.

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