Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

February 13, 2012

Volume 51, Issue 7

Pages 1491–1728

  1. Cover Picture

    1. Top of page
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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Cover Picture: Meter-Long and Robust Supramolecular Strands Encapsulated in Hydrogel Jackets (Angew. Chem. Int. Ed. 7/2012) (page 1491)

      Dr. Daisuke Kiriya, Dr. Masato Ikeda, Dr. Hiroaki Onoe, Dr. Masahiro Takinoue, Dr. Harunobu Komatsu, Yuto Shimoyama, Prof. Itaru Hamachi and Prof. Shoji Takeuchi

      Article first published online: 8 DEC 2011 | DOI: 10.1002/anie.201108163

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      Supramolecular self-assembly is used for the fabrication of nanofibers in a microfluidic channel on a macroscopic scale. In their Communication on page 1553 ff., S. Takeuchi et al. report meter-long supramolecular strands that are encapsulated in a robust polymer gel matrix. The strands are aligned under laminar flow conditions. Their mechanical strength is sufficiently high to allow their patterning onto a substrate and use as a template for synthesizing conductive polymers.

  2. Inside Cover

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    3. Inside Cover
    4. Inside Back Cover
    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Inside Cover: Dynamically Tunable Protein Microlenses (Angew. Chem. Int. Ed. 7/2012) (page 1492)

      Yun-Lu Sun, Prof. Dr. Wen-Fei Dong, Rui-Zhu Yang, Xiang Meng, Lu Zhang, Prof. Dr. Qi-Dai Chen and Prof. Dr. Hong-Bo Sun

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201108618

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      Proteins have been used to construct biocompatible microdevices by using maskless femtosecond laser direct writing. In their Communication on page 1558 ff., W. F. Dong, H. B. Sun, and co-workers report their strategy to produce microlenses from bovine serum albumin. The microlenses have controllable geometry as well as excellent imaging performance, and the focal length can be dynamically tuned by changing the pH of the surrounding solution.

  3. Inside Back Cover

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    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Inside Back Cover: Hydrogen Production Coupled to Hydrocarbon Oxygenation from Photocatalytic Water Splitting (Angew. Chem. Int. Ed. 7/2012) (page 1729)

      Dr. Wangkheimayum Marjit Singh, Derek Pegram, Haifeng Duan, Dr. Diganta Kalita, Prof. Dr. Paul Simone, Prof. Dr. Gary L. Emmert and Prof. Dr. Xuan Zhao

      Article first published online: 30 DEC 2011 | DOI: 10.1002/anie.201108619

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      The evolution of H2 and the oxygenation of hydrocarbons from photocatalytic water splitting are reported by X. Zhao et al. in their Communication on page 1653 ff. A homogeneous system for simultaneous hydrogen production and hydrocarbon oxidation, in which water is the source of both oxygen and hydrogen, has been developed. Two photosensitizers allow the coupling of the hydrocarbon oxygenation reaction to the H2 production process. (Photo courtesy of Rachel Wang.)

  4. Back Cover

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    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
    1. Back Cover: Switching the Targeting Pathways of a Therapeutic Antibody by Nanodesign (Angew. Chem. Int. Ed. 7/2012) (page 1730)

      Dr. Sanjib Bhattacharyya, Dr. Raman Deep Singh, Dr. Richard Pagano, Dr. J. David Robertson, Dr. Resham Bhattacharya and Dr. Priyabrata Mukherjee

      Article first published online: 16 DEC 2011 | DOI: 10.1002/anie.201108403

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      Gold nanoparticles can be used as a scaffold to elucidate the mechanism of endocytosis of cetuximab and its nanoconjugates, as well as the switching of endocytic pathways (caveolar versus pinocytotic) in pancreatic cancer cells, as demonstrated by P. Mukherjee and co-workers in their Communication on page 1563 ff. Tailoring the mechanism of endocytosis may be useful for targeting specific intracellular pathways to minimize the side effects of pharmaceutical compounds.

  5. Graphical Abstract

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    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Graphical Abstract: Angew. Chem. Int. Ed. 7/2012 (pages 1495–1507)

      Article first published online: 7 FEB 2012 | DOI: 10.1002/anie.201290010

  6. News

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    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
    16. Preview
  7. Author Profile

    1. Top of page
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    5. Back Cover
    6. Graphical Abstract
    7. News
    8. Author Profile
    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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    1. Michael Müller (page 1514)

      Article first published online: 3 JAN 2012 | DOI: 10.1002/anie.201107517

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      “My favorite place on earth is where my family is. My best investment was a Colnago racing bike. …” This and more about Michael Müller can be found on page 1514.

  8. News

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    6. Graphical Abstract
    7. News
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    9. News
    10. Obituary
    11. Book Reviews
    12. Highlights
    13. Minireview
    14. Review
    15. Communications
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  9. Obituary

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    8. Author Profile
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    11. Book Reviews
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    13. Minireview
    14. Review
    15. Communications
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    1. Har Ghobind Khorana (19222011) (pages 1516–1517)

      Peter H. Seeberger

      Article first published online: 20 JAN 2012 | DOI: 10.1002/anie.201200221

  10. Book Reviews

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    11. Book Reviews
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    13. Minireview
    14. Review
    15. Communications
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    1. Homogeneous Catalysts. Activity—Stability—Deactivation. By Piet W. N. M. van Leeuwen and John C. Chadwick. (page 1518)

      George J. P. Britovsek

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201108293

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      Wiley-VCH, Weinheim, 2011. 404 pp., hardcover, € 139.00.—ISBN 978-3527323296

    2. Micro Reaction Technology in Organic Synthesis. By Charlotte Wiles and Paul Watts. (pages 1518–1519)

      Kevin D. Nagy and Klavs F. Jensen

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201107992

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      CRC Press, Boca Raton, 2011. 453 pp., hardcover, £ 89.00.—ISBN 978-1439824719

  11. Highlights

    1. Top of page
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    6. Graphical Abstract
    7. News
    8. Author Profile
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    10. Obituary
    11. Book Reviews
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    13. Minireview
    14. Review
    15. Communications
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    1. Aryne Chemistry

      Arynes in Transition-Metal-Free Multicomponent Coupling Reactions (pages 1520–1522)

      Sachin Suresh Bhojgude and Dr. Akkattu T. Biju

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201106984

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      Let's couple together! The multicomponent reactions involving arynes offer direct access to unusual heterocyclic scaffolds and 1,2-disubstituted arenes. This transition-metal-free, one-pot construction of molecular complexity is likely to play a pivotal role in various carbon–carbon and carbon–heteroatom bond-forming reactions.

    2. Organic Frustrated Lewis Pairs

      Fullerenes as Neutral Carbon-Based Lewis Acids (pages 1523–1524)

      Dr. Javier Iglesias-Sigüenza and Dr. Manuel Alcarazo

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201107399

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      Lewis adducts between N-heterocyclic carbenes and fullerenes have been isolated and their structures confirmed by X-ray crystallography. This work shows that simple fullerenes such as C60 or C70 can act as Lewis acids. This result not only opens new perspectives in fullerene chemistry but might also have strong implications in emerging fields such as the metal-free activation of small molecules.

  12. Minireview

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    11. Book Reviews
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    13. Minireview
    14. Review
    15. Communications
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    1. Asymmetric Catalysis

      The Even-Handed Approach: Strategies for the Deployment of Racemic Chiral Catalysts (pages 1526–1533)

      Dr. Louise A. Evans, Dr. Neil S. Hodnett and Prof. Dr. Guy C. Lloyd-Jones

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201106836

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      Twin set: Our obsession for (enantio)selectivity in catalysis means we tend to analyze and graphically communicate our findings in the form of single-handed cycles. However, dual-cycle racemic catalysts are of distinct utility in polymerization, prediction of stereoselectivity, and mechanistic study.

  13. Review

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    14. Review
    15. Communications
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    1. Self-Assembly

      Learning from “Coffee Rings”: Ordered Structures Enabled by Controlled Evaporative Self-Assembly (pages 1534–1546)

      Wei Han and Prof. Zhiqun Lin

      Article first published online: 23 DEC 2011 | DOI: 10.1002/anie.201104454

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      Drying out: The evaporation of solutions of nonvolatile solutes is one way to generate complex ordered structures. An array of facile and robust preparative strategies based on controlled evaporative self-assembly (CESA) of confined solutions have been exploited to rationally assemble various soft and hard materials into spatially ordered structures (see picture) with engineered properties and functionality over large surface areas.

  14. Communications

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    1. Synthetic Methods

      Diisobutylaluminum Hydride Mediated Regioselective O Desilylations: Access to Multisubstituted Cyclodextrins (pages 1548–1552)

      Dr. Ramprasad Ghosh, Dr. Ping Zhang, Dr. Aixia Wang and Prof. Dr. Chang-Chun Ling

      Article first published online: 18 OCT 2011 | DOI: 10.1002/anie.201105737

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      A face off: Diisobutylaluminum hydride (DIBAL-H) has been found to be an effective O-desilylating reagent at the primary face of cyclodextrins. This methodology shows high chemo- and regioselectivity and provides an effective route to orthogonally protected, multisubstituted cyclodextrin derivatives.

    2. Supramolecular Strands

      Meter-Long and Robust Supramolecular Strands Encapsulated in Hydrogel Jackets (pages 1553–1557)

      Dr. Daisuke Kiriya, Dr. Masato Ikeda, Dr. Hiroaki Onoe, Dr. Masahiro Takinoue, Dr. Harunobu Komatsu, Yuto Shimoyama, Prof. Itaru Hamachi and Prof. Shoji Takeuchi

      Article first published online: 15 NOV 2011 | DOI: 10.1002/anie.201104043

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      Jacketed supramolecular strand: Meter-long supramolecular strands were obtained by encapsulating them in polymer gels using a microfluidic channel (see picture). The nanofibers in the strands are self-assembled and aligned under the laminar flow conditions. Their mechanical strength was sufficiently high to allow their patterning onto a substrate and use them as a template for synthesizing an insoluble, conductive polymer.

    3. Protein Microdevices

      Dynamically Tunable Protein Microlenses (pages 1558–1562)

      Yun-Lu Sun, Prof. Dr. Wen-Fei Dong, Rui-Zhu Yang, Xiang Meng, Lu Zhang, Prof. Dr. Qi-Dai Chen and Prof. Dr. Hong-Bo Sun

      Article first published online: 12 DEC 2011 | DOI: 10.1002/anie.201105925

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      Proteins in focus: Dynamically tunable protein microdevices were built up by a simple “top-down”, maskless, femtosecond laser direct writing approach with bovine serum albumin. This technique was used to produce biocompatible microlenses that swell and shrink reversibly in response to changes in the pH of the surrounding solution. These responses to environmental stimuli can be used to focus the microlenses.

    4. Drug Delivery

      Switching the Targeting Pathways of a Therapeutic Antibody by Nanodesign (pages 1563–1567)

      Dr. Sanjib Bhattacharyya, Dr. Raman Deep Singh, Dr. Richard Pagano, Dr. J. David Robertson, Dr. Resham Bhattacharya and Dr. Priyabrata Mukherjee

      Article first published online: 1 DEC 2011 | DOI: 10.1002/anie.201105432

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      On the right path: The mechanisms of endocytosis of cetuximab (C225) and its nanoconjugates have been elucidated in a pancreatic cancer cell line. By using gold nanoparticles as a scaffold, it is possible to switch the pathway for endocytosis from a Dyn-2-dependent caveolar mechanism to Cdc42-dependent pinocytosis/phagocytosis. Tailoring endocytotic mechanisms may enable specific intracellular pathways to be targeted.

    5. Carbon Composite Electrodes

      Composite Carbon Nanotube/Carbon Electrodes for Electrical Double-Layer Super Capacitors (pages 1568–1571)

      Malachi Noked, Sivan Okashy, Dr. Tomer Zimrin and Prof. Doron Aurbach

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201104334

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      Carbon in charge: A straightforward method is presented for the synthesis of carbon nanotube (CNT)/porous carbon composite electrodes with uniform distribution of the CNTs and high surface area of the carbon material. The crystallinity of the CNTs is not affected by the high-temperature activation process. Monolithic CNT/activated carbon composite electrodes that do not need binder or current collector were also developed.

    6. Heterogeneous Catalysis

      You have full text access to this OnlineOpen article
      Origin of Low CO2 Selectivity on Platinum in the Direct Ethanol Fuel Cell (pages 1572–1575)

      Richard Kavanagh, Dr. Xiao-Ming Cao, Dr. Wen-Feng Lin, Prof. Christopher Hardacre and Prof. P. Hu

      Article first published online: 2 JAN 2012 | DOI: 10.1002/anie.201104990

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      Calculated answer: First-principles calculations have been applied to calculate the energy barrier for the key step in CO formation on a Pt surface (see picture; Pt blue, Pt atoms on step edge yellow) to understand the low CO2 selectivity in the direct ethanol fuel cell. The presence of surface oxidant species such as O (brown bar) and OH (red bar) led to an increase of the energy barrier and thus an inhibition of the key step.

    7. Solid-State NMR spectroscopy

      Structural Basis of β-Amyloid-Dependent Synaptic Dysfunctions (pages 1576–1579)

      Dr. Christian Haupt, Dr. Jörg Leppert, Dr. Raik Rönicke, Dr. Jessica Meinhardt, Dr. Jay K. Yadav, Dr. Ramadurai Ramachandran, Dr. Oliver Ohlenschläger, Prof. Dr. Klaus G. Reymann, Dr. Matthias Görlach and Priv.-Doz. Dr. Marcus Fändrich

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201105638

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      Learn about Alzheimer: The molecular conformation of a toxic β-amyloid oligomer structure was determined by NMR spectroscopy (see picture). The measurements show a N-terminal β strand that controls the partitioning between oligomer and protofibril formation. Targeting the N-terminus of the peptide neutralizes Aβ-dependent neuronal dysfunctions. The data have important implications for understanding the structural basis of Alzheimer's disease.

    8. Gas Storage

      A Highly Porous and Robust (3,3,4)-Connected Metal–Organic Framework Assembled with a 90° Bridging-Angle Embedded Octacarboxylate Ligand (pages 1580–1584)

      Dr. Weigang Lu, Dr. Daqiang Yuan, Trevor A. Makal, Dr. Jian-Rong Li and Prof. Dr. Hong-Cai Zhou

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201106615

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      Picky cage: A dicopper(II)-paddle-wheel-based metal–organic framework (PCN-80, see picture) with a rare (3,3,4)-connected topology has been synthesized by using a unique octatopic ligand featuring 90° bridging-angle dicarboxylate moieties. PCN-80 has Brunauer-Emmett-Teller (BET) and Langmuir surface areas of 3850 and 4150 m2 g−1, respectively. It exhibits high gas-uptake capacity for H2 and large adsorption selectivity of CO2 over N2.

    9. Nanocages

      Calixarene-Based Nanoscale Coordination Cages (pages 1585–1588)

      Mei Liu, Prof. Dr. Wuping Liao, Dr. Chunhua Hu, Shangchao Du and Prof. Dr. Hongjie Zhang

      Article first published online: 30 DEC 2011 | DOI: 10.1002/anie.201106732

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      Molecular shuttlecocks: The introduction of tripodal ternary acids (red; see picture) to the cobalt/calixarene (green) systems led to the formation of four unprecedented calixarene-based nanoscale coordination cages through a [6+8] condensation. The overall periphery diameters of the nanocages ranged from 3.3 to 4.7 nm, and there were two sizes for the internal cavities (1.1 and 1.7 nm).

    10. Endohedral Fullerenes

      A Co-Crystal Composed of the Paramagnetic Endohedral Metallofullerene La@C82 and a Nickel Porphyrin with High Electron Mobility (pages 1589–1591)

      Dr. Satoru Sato, Dr. Hidefumi Nikawa, Prof. Dr. Shu Seki, Dr. Lu Wang, Dr. Guangfu Luo, Prof. Dr. Jing Lu, Dr. Masayuki Haranaka, Dr. Takahiro Tsuchiya, Prof. Dr. Shigeru Nagase and Prof. Dr. Takeshi Akasaka

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201106912

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      Ball and plane: The structure of La@C82 was clarified by single-crystal X-ray diffraction of samples co-crystallized with [NiII(OEP)] (OEP=octaethylporphyrin; see structure La red, N blue, Ni yellow, H pink). The charge-carrier mobility of the co-crystal was determined using flash-photolysis time-resolved microwave conductivity measurements. The material exhibited an anisotropic and high electron mobility of up to 0.9 cm2 V−1 s−1.

    11. Quantum Electrodynamics

      Modifying Chemical Landscapes by Coupling to Vacuum Fields (pages 1592–1596)

      Dr. James A. Hutchison, Dr. Tal Schwartz, Dr. Cyriaque Genet, Dr. Eloïse Devaux and Prof. Thomas W. Ebbesen

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201107033

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      Electromagnetic vacuum fields are omnipresent in our universe, inducing many events such as spontaneous emission, Lamb shift, and Van der Waals forces. As demonstrated here, a chemical reaction can be influenced by strongly coupling the energy landscape governing the reaction pathway to vacuum fields in an optical cavity (see picture; MC=merocyanine).

    12. Porous Materials

      Three-Dimensional Ordered Arrays of 58×58×58 Å3 Hollow Frameworks in Ionic Crystals of M2Zn2-Substituted Polyoxometalates (pages 1597–1601)

      Dr. Kosuke Suzuki, Dr. Yuji Kikukawa, Dr. Sayaka Uchida, Dr. Hiroko Tokoro, Kenta Imoto, Prof. Dr. Shin-ichi Ohkoshi and Prof. Dr. Noritaka Mizuno

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201107041

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      A void in the issue: A one-step self-assembly of γ-Keggin sandwich-type silicotungstates with M2Zn2 (M=Co, Ni, Zn) tetranuclear cores and tetrabutylammonium cations gave porous ionic crystals. These porous crystals are hollow frameworks containing large voids (ca. 38×38×38 Å3, see picture, voids yellow), between which guest molecules can be exchanged through the connecting channels.

    13. Borylenes

      The Parent Borylene: Betwixt and Between (pages 1602–1605)

      Prof. Dennis P. Curran, Dr. Anne Boussonnière, Dr. Steven J. Geib and Dr. Emmanuel Lacôte

      Article first published online: 4 JAN 2012 | DOI: 10.1002/anie.201107238

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      Still elusive: The reduction of dimethylimidazol-2-ylidene dichloroborane by sodium naphthalenide has been suggested to provide a borylene that cycloadds to naphthalene to make a borirane. Evidence has been provided that this borirane instead arises from coupling of a boryl radical and sodium naphthalenide. In contrast, reduction of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene dichloroborane and the related dimesityl derivative provide novel C[BOND]H insertion products that may have arisen from a borylene.

    14. Single-Molecule Magnets

      Magnetic Anisotropy in a Dysprosium/DOTA Single-Molecule Magnet: Beyond Simple Magneto-Structural Correlations (pages 1606–1610)

      Giuseppe Cucinotta, Mauro Perfetti, Dr. Javier Luzon, Dr. Mael Etienne, Dr. Pierre-Emmanuel Car, Prof. Dr. Andrea Caneschi, Dr. Guillaume Calvez, Dr. Kevin Bernot and Prof. Dr. Roberta Sessoli

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201107453

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      Magnetic moments: The orientation of the title single-molecule magnet was investigated by magnetic single crystal and luminescence characterization, supported by ab initio calculations, and was found to be governed by the position of the hydrogen atoms of the apical water molecules. This finding suggests that simple magneto-structural correlations can give misleading clues for research in molecular magnetism as well as in the design of MRI contrast agents.

    15. Molecular Devices

      Photoinduced Memory Effect in a Redox Controllable Bistable Mechanical Molecular Switch (pages 1611–1615)

      Tommaso Avellini, Hao Li, Dr. Ali Coskun, Gokhan Barin, Dr. Ali Trabolsi, Ashish N. Basuray, Dr. Sanjeev K. Dey, Prof. Alberto Credi, Dr. Serena Silvi, Prof. J. Fraser Stoddart and Prof. Margherita Venturi

      Article first published online: 2 JAN 2012 | DOI: 10.1002/anie.201107618

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      Something to remember: A rotaxane could be operated as a bistable memory element under kinetic control (see picture). Data was written on the molecule by an oxidation stimulus and locked by UV light irradiation. After the writing session, the oxidized species was reduced back to the original form without losing the written data for a few hours. Light irradiation also protects nonoxidized rotaxanes from accidental writing.

    16. Heterogeneous Catalysis

      Structural Requirements in Lithium Cobalt Oxides for the Catalytic Oxidation of Water (pages 1616–1619)

      Graeme P. Gardner, Dr. Yong Bok Go, David M. Robinson, Paul F. Smith, Prof. Joke Hadermann, Prof. Artem Abakumov, Prof. Martha Greenblatt and Prof. G. Charles Dismukes

      Article first published online: 11 JAN 2012 | DOI: 10.1002/anie.201107625

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      Who can split water? Two polymorphs of nanocrystalline cubic spinel and rhombohedral layered lithium cobalt oxides have been prepared and their application in the photocatalytic oxidation of water examined. The main factor that determines the catalytic activity of the different phases is the presence of a Co4O4 cubic core, which is present in the cubic form of the catalyst, but not in the layered structure (see scheme).

    17. Cooperative Catalysis

      Urea/Transition-Metal Cooperative Catalyst for anti-Selective Asymmetric Nitroaldol Reactions (pages 1620–1624)

      Kai Lang, Jongwoo Park and Prof. Sukwon Hong

      Article first published online: 4 JAN 2012 | DOI: 10.1002/anie.201107785

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      A cooperative catalyst that features urea H-bonding and a cobalt center was developed for anti-selective asymmetric Henry reactions (see scheme). The H-bonds of urea play a crucial role in the improvement in yield (from 30 % to 84 %), enantioselectivity (from 78 % to 96 %), and anti diastereoselectivity (from 3:1 to 48:1). A short synthesis of (1R,2S)-methoxamine hydrochloride was also accomplished with this catalyst.

    18. Nanosensors

      Multiplex Imaging of an Intracellular Proteolytic Cascade by using a Broad-Spectrum Nanoquencher (pages 1625–1630)

      Dr. Xinglu Huang, Magdalena Swierczewska, Dr. Ki Young Choi, Dr. Lei Zhu, Dr. Ashwinkumar Bhirde, Dr. Jinwoo Park, Dr. Kwangmeyung Kim, Prof. Jin Xie, Dr. Gang Niu, Prof. Kang Choon Lee, Dr. Seulki Lee and Dr. Xiaoyuan Chen

      Article first published online: 2 JAN 2012 | DOI: 10.1002/anie.201107795

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      Turn off the lights! A universal nanoquencher that quenches a broad range of visible to near-infrared dyes by using a series of dark quenchers incorporated into a cell-permeable mesoporous silica nanoparticle has been developed. In combination with dye-labeled substrates, this nanoquencher boosts multiple fluorescence signals upon specific proteolysis, which allows real-time imaging of proteolytic cascades (see scheme).

    19. Histone Demethylase Inhibition

      Linking of 2-Oxoglutarate and Substrate Binding Sites Enables Potent and Highly Selective Inhibition of JmjC Histone Demethylases (pages 1631–1634)

      Dr. Esther C. Y. Woon, Dr. Anthony Tumber, Dr. Akane Kawamura, Dr. Lars Hillringhaus, Dr. Wei Ge, Dr. Nathan R. Rose, Jerome H. Y. Ma, Mun Chiang Chan, Louise J. Walport, Ka Hing Che, Dr. Stanley S. Ng, Dr. Brian D. Marsden, Prof. Udo Oppermann, Dr. Michael A. McDonough and Prof. Christopher J. Schofield

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201107833

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      Select an isoform: Linking of cosubstrate and substrate binding sites enables highly selective inhibiton of isoforms of human histone lysine demethylases. The results should provide a basis for the development of potent and selective JmjC inhibitors, possibly suitable for clinical use.

    20. Porous Materials

      Inverse and High CO2/C2H2 Sorption Selectivity in Flexible Organic–Inorganic Ionic Crystals (pages 1635–1639)

      Ryo Eguchi, Dr. Sayaka Uchida and Prof. Dr. Noritaka Mizuno

      Article first published online: 3 JAN 2012 | DOI: 10.1002/anie.201107906

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      Highly selective CO2 sorption and inverse CO2/C2H2 sorption selectivity (4.8 at 278 K, 100 kPa) were achieved with an organic–inorganic ionic crystal. The key for the high affinity toward CO2 is the combination of structural flexibility and strong binding sites (K+) characteristic of organic–inorganic ionic crystals.

    21. Mechanochemistry

      A Mechanochemical Approach to Deracemization (pages 1640–1643)

      Kelly M. Wiggins and Prof. Christopher W. Bielawski

      Article first published online: 4 JAN 2012 | DOI: 10.1002/anie.201107937

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      Good combination: Enantioselective enzymatic hydrolysis was combined with a mechanically facilitated racemization process to prepare (S)-1,1′-binapthol ((S)-binol) in high yield and enantiopurity from a racemic precursor in a single step (see scheme). The enzyme cholesterol esterase stereoselectively hydrolyzes esters of (S)-binol and ultrasound was applied to achieve mechanically facilitated racemization of the precursor material.

    22. Synthetic Methods

      Catalytic Asymmetric anti-Selective Nitroaldol Reaction En Route to Zanamivir (pages 1644–1647)

      Tatsuya Nitabaru, Dr. Naoya Kumagai and Prof. Dr. Masakatsu Shibasaki

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201108153

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      Battling the flu: Zanamivir (Relenza) is widely prescribed as an anti-influenza drug. It contains a vicinal amino alcohol, which is in an anti orientation, and is readily accessed by an anti-selective catalytic asymmetric nitroaldol (Henry) reaction promoted by a heterobimetallic complex (see scheme; PMB=p-methoxybenzyl). Additional synthetic manipulation of the nitroaldol product allowed the enantioselective synthesis of zanamivir.

    23. Catalysis

      Cooperative Ligand Effects in Phase-Switching Homogeneous Catalysts (pages 1648–1652)

      Molise Mokhadinyana, Simon L. Desset, Prof. D. Bradley G. Williams and Prof. David J. Cole-Hamilton

      Article first published online: 11 JAN 2012 | DOI: 10.1002/anie.201108200

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      It takes two: Xantphos ligands that contain amidate groups are selective for the linear versus the branched-chain products in the rhodium-catalyzed hydroformylation of 1-octene. However, the catalyst only undergoes CO2-mediated phase switching in the presence of amidine-substituted triphenylphosphine (see scheme).

    24. Photocatalysis

      Hydrogen Production Coupled to Hydrocarbon Oxygenation from Photocatalytic Water Splitting (pages 1653–1656)

      Dr. Wangkheimayum Marjit Singh, Derek Pegram, Haifeng Duan, Dr. Diganta Kalita, Prof. Dr. Paul Simone, Prof. Dr. Gary L. Emmert and Prof. Dr. Xuan Zhao

      Article first published online: 16 NOV 2011 | DOI: 10.1002/anie.201106494

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      On the sunny side: A homogeneous system for H2 production and hydrocarbon oxidation was developed in the absence of any sacrificial reagent. This system consists of [Ru(TPA)(H2O)2]2+ and [Fe3(CO)12] as catalysts and [Ru(bpy)3]2+ and [Ir(bpy)(ppy)2]+ as photosensitizers (PS). Water is the oxygen source as well as the source for H2 formation (see picture; Sub=organic substrate).

    25. Molecular Recognition

      C[BOND]H⋅⋅⋅O Hydrogen Bonding Induced Triazole Foldamers: Efficient Halogen Bonding Receptors for Organohalogens (pages 1657–1661)

      Dr. Li-Yan You, Dr. Shi-Gui Chen, Prof. Xin Zhao, Prof. Yi Liu, Dr. Wen-Xian Lan, Ying Zhang, Prof. Hao-Jie Lu, Prof. Chun-Yang Cao and Prof. Zhan-Ting Li

      Article first published online: 11 JAN 2012 | DOI: 10.1002/anie.201106996

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      Into the fold: Intramolecular C[BOND]H⋅⋅⋅O hydrogen bonding has been utilized to create new aromatic triazole foldamers. Remarkably, all the triazole units of the foldamers are guided to orientate inward to form a nitrogen ring. As a result, they can efficiently bind neutral tri- and didentate organohalogens through multiple N⋅⋅⋅X (X=Cl, Br, I) halogen bonds to form stable 1:1 complexes.

    26. Homogeneous Catalysis

      Two Iron Catalysts are Better than One: A General and Convenient Reduction of Aromatic and Aliphatic Primary Amides (pages 1662–1666)

      Dr. Shoubhik Das, Bianca Wendt, Dr. Konstanze Möller, Dr. Kathrin Junge and Prof. Dr. Matthias Beller

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201108155

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      It takes two: For the reduction of amides to amines iron catalysts were developed. A combination of two different iron catalysts made possible the challenging reduction of primary amides (see picture).

    27. Hydrogen Production

      A Nickel Thiolate Catalyst for the Long-Lived Photocatalytic Production of Hydrogen in a Noble-Metal-Free System (pages 1667–1670)

      Zhiji Han, Dr. William R. McNamara, Dr. Min-Sik Eum, Prof. Patrick L. Holland and Prof. Richard Eisenberg

      Article first published online: 11 JAN 2012 | DOI: 10.1002/anie.201107329

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      A question of nobility: A biomimetic nickel thiolate complex (see scheme; TEA=triethylamine) exhibits unprecedented activity for the title reaction. By using a low concentration of a sacrificial donor, the system maintains significant activity for at least 60 hours. The enhanced stability of the system is ascribed to the ability to proceed through an oxidative quenching pathway.

    28. CO2 Reduction

      Borane-Mediated Carbon Dioxide Reduction at Ruthenium: Formation of C1 and C2 Compounds (pages 1671–1674)

      Dr. Sébastien Bontemps, Dr. Laure Vendier and Dr. Sylviane Sabo-Etienne

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201107352

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      One and two: The C2 compound pinBOCH2OCHO (see scheme; HBpin=pinacolborane) and several C1 compounds have been obtained from the borane-mediated reduction of CO2 under mild conditions with the catalyst precursor [RuH2(H2)2(PCy3)2]. Mechanistic investigation highlights the role of a series of new carbonyl ruthenium complexes that were characterized by multinuclear NMR spectroscopy, IR spectroscopy, and X-ray diffraction studies.

    29. Palladium-Catalyzed Cyclization

      Highly Efficient Narasaka–Heck Cyclizations Mediated by P(3,5-(CF3)2C6H3)3: Facile Access to N-Heterobicyclic Scaffolds (pages 1675–1679)

      Adele Faulkner and Dr. John F. Bower

      Article first published online: 9 JAN 2012 | DOI: 10.1002/anie.201107511

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      N-heterobicyclic scaffolds: Highly efficient palladium-catalyzed cyclizations of oxime esters with cyclic alkenes were used as a general entry to perhydroindole and related scaffolds. The chemistry is reliant upon the use of P(3,5-(CF3)2C6H3)3 for the key C(sp3)[BOND]N bond-forming process and this facilitates cyclizations with enhanced levels of efficiency across a range of sterically and electronically distinct substrates.

    30. Stereospecific Migration

      Enantioselective Synthesis of Spiro Cyclopentane-1,3′-indoles and 2,3,4,9-Tetrahydro-1H-carbazoles by Iridium-Catalyzed Allylic Dearomatization and Stereospecific Migration (pages 1680–1683)

      Qing-Feng Wu, Chao Zheng and Prof. Dr. Shu-Li You

      Article first published online: 5 JAN 2012 | DOI: 10.1002/anie.201107677

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      Rings with a twist: The highly enantioselective construction of five-membered spiroindolenines has been realized by the iridium-catalyzed intramolecular allylic dearomatization of indoles. The stereospecific migration of these spiro cyclopentane-1,3′-indole products provides enantioenriched 2,3,4,9-tetrahydro-1H-carbazoles.

    31. Electrochemistry

      Heat-Assisted Electrodissolution of Platinum in an Ionic Liquid (pages 1684–1688)

      Prof. Dr. Jing-Fang Huang and Hao-Yuan Chen

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201107997

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      Dissolving platinum: A noncorrosive, basic ionic liquid has been developed as a solvent system for the electrodissolution of platinum (see image). The metal was dissolved at an ultrahigh rate, and the facile recovery of pure platinum and platinum alloys from the same solution was achieved without any additional treatment of the solution or exchange of the medium.

    32. Sensing DNA Repair

      Direct Fluorescence Monitoring of DNA Base Excision Repair (pages 1689–1692)

      Dr. Toshikazu Ono, Dr. Shenliang Wang, Dr. Chi-Kin Koo, Lisa Engstrom, Prof. Dr. Sheila S. David and Prof. Dr. Eric T. Kool

      Article first published online: 12 JAN 2012 | DOI: 10.1002/anie.201108135

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      Uracil is a common form of DNA damage resulting from hydrolysis of cytosine, and cellular uracil DNA glycosylases (UDG) have evolved to remove it specifically. The use of nonnatural pyrene deoxyriboside in short DNA oligomers to directly report on UDG enzymatic activity is described. The mechanism relies on the use of uracil as a strong quencher of pyrene, and enzyme repair activity can be directly imaged with bacterial cells in real time.

    33. Heterocycles

      Highly Regioselective Migration of the Sulfonyl Group: Easy Access to Functionalized Pyrroles (pages 1693–1697)

      Xiaoyi Xin, Dr. Dongping Wang, Dr. Xincheng Li and Prof. Dr. Boshun Wan

      Article first published online: 11 JAN 2012 | DOI: 10.1002/anie.201108144

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      Good migrations: The highly regioselective migration of a sulfonyl group for the synthesis of functionalized pyrroles is reported (see scheme; DMF=N,N-dimethylformamide). The migration of the sulfonyl group to different positions can be controlled with high selectivity, thus allowing the formation of both α- and β-(arylsulfonyl)methyl pyrroles with high yields.

    34. Alcohol Oxidation

      Oxygen-Mediated Coupling of Alcohols over Nanoporous Gold Catalysts at Ambient Pressures (pages 1698–1701)

      Dr. Kathryn M. Kosuda, Dr. Arne Wittstock, Prof. Cynthia M. Friend and Prof. Marcus Bäumer

      Article first published online: 3 JAN 2012 | DOI: 10.1002/anie.201107178

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      Unsupported catalyst for green chemistry: The aerobic oxidation and coupling of primary alcohols (methanol, ethanol, n-butanol) to give the corresponding aldehydes and esters at temperatures below 100 °C is facilitated by unsupported nanoporous gold catalysts. The experimental conditions employed allow a close comparison to model experiments and open the door to a molecular-level understanding of the reaction.

    35. Planar B6 Ring

      All-Boron Planar B6 Ring in the Solid-State Phase Ti7Rh4Ir2B8 (pages 1702–1705)

      Priv.-Doz. Dr. Boniface P. T. Fokwa and Dipl.-Chem. Martin Hermus

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201106798

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      Now we are six: Planar B6 rings embedded in one-dimensional Ti7 wheels have been found in the crystal structure of a solid-state phase (Ti7Rh4Ir2B8) for the first time. First-principles calculations indicated strong B[BOND]B bonding but also significant interactions with the surrounding titanium atoms (see picture).

    36. Anti-Malaria Drugs

      Continuous-Flow Synthesis of the Anti-Malaria Drug Artemisinin (pages 1706–1709)

      Dr. François Lévesque and Prof. Dr. Peter H. Seeberger

      Article first published online: 16 JAN 2012 | DOI: 10.1002/anie.201107446

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      Malaria is a serious global health issue. Artemisinin combination treatments are the first-line drugs, but supplies are limited because artemisinin is obtained solely by extraction from Artemisia annua. A continuous-flow process that converts dihydroartemisinic acid into artemisinin (see scheme) was shown to be an inexpensive and scalable process that can ensure a steady, affordable supply of artemisinin.

    37. Asymmetric Hydrogenation

      Ruthenium NHC Catalyzed Highly Asymmetric Hydrogenation of Benzofurans (pages 1710–1713)

      Dr. Nuria Ortega, Slawomir Urban, Bernhard Beiring and Prof. Dr. Frank Glorius

      Article first published online: 3 JAN 2012 | DOI: 10.1002/anie.201107811

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      H2-O-T! Aromatic O-heterocycles are a challenging substrates for asymmetric hydrogenation (H2). An in situ formed chiral N-heterocyclic carbene (NHC) ruthenium complex allows the high yielding, completely regioselective, and highly asymmetric hydrogenation of substituted benzofurans at room Temperature, giving valuable 2,3-dihydrobenzofurans (see scheme).

    38. Redox Active Complexes

      A Halide-Induced Copper(I) Disulfide/Copper(II) Thiolate Interconversion (pages 1714–1718)

      Dr. Adam Neuba, Dr. Roxana Haase, Dr. Wolfram Meyer-Klaucke, Dr. Ulrich Flörke and Prof. Dr. Gerald Henkel

      Article first published online: 10 JAN 2012 | DOI: 10.1002/anie.201102714

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      One to two and back again: A disulfide–thiolate interconversion process in a dinuclear copper complex is induced by chloride ions (see scheme). Within this compound, the coordinating copper atoms serve either as electron source or as electron sink and thus oscillate between the oxidation states +I and +II.

    39. Glycopeptide Vaccines

      Variation of the Glycosylation Pattern in MUC1 Glycopeptide BSA Vaccines and Its Influence on the Immune Response (pages 1719–1723)

      Hui Cai, Zhi-Hua Huang, Lei Shi, Zhan-Yi Sun, Prof. Dr. Yu-Fen Zhao, Prof. Dr. Horst Kunz and Prof. Dr. Yan-Mei Li

      Article first published online: 13 JAN 2012 | DOI: 10.1002/anie.201106396

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      A shot in the arm for anticancer vaccines: Synthetic MUC1 glycopeptides bearing the STn and 2,6-ST antigens were conjugated covalently to BSA (see scheme). The obtained synthetic vaccines induced very strong immune responses in Balb/c mice. Predominant IgG isotype antibodies were induced. The antibodies exhibited strong binding to breast cancer cells of the MCF-7 cell line.

    40. Lightning Terminators

      You have full text access to this OnlineOpen article
      Stereochemistry of Benzylic Carbon Substitution Coupled with Ring Modification of 2-Nitrobenzyl Groups as Key Determinants for Fast-Cleaving Reversible Terminators (pages 1724–1727)

      Brian P. Stupi, Dr. Hong Li, Jinchun Wang, Dr. Weidong Wu, Sidney E. Morris, Prof. Vladislav A. Litosh, Jesse Muniz, Dr. Megan N. Hersh and Prof. Michael L. Metzker

      Article first published online: 9 JAN 2012 | DOI: 10.1002/anie.201106516

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      A complete set of 2-nitrobenzyl-modified reversible terminators have been developed, which upon exposure to UV light generate natural hydroxymethyl nucleotides (see scheme). The combination of a stereospecific (S)-tert-butyl group (R) at the benzylic carbon and a 5-OMe group (R′) on the 2-nitrobenzyl ring substantially increase the rate of photochemical cleavage. For 7-deaza-7-hydroxymethyl-2′-deoxyguanosine, these modifications led to a rate increase of more than one order of magnitude.

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      Preview: Angew. Chem. Int. Ed. 8/2012 (page 1728)

      Article first published online: 7 FEB 2012 | DOI: 10.1002/anie.201290011

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