Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 23

June 2, 2006

Volume 45, Issue 23

Pages 3717–3885

    1. Cover Picture: Identification of Pyridinylpyrimidines as Inhibitors of Human Methionine Aminopeptidases (Angew. Chem. Int. Ed. 23/2006) (page 3717)

      Xiaoyi Hu, Anthony Addlagatta, Brian W. Matthews and Jun O. Liu

      Version of Record online: 24 MAY 2006 | DOI: 10.1002/anie.200690079

      The evolutionarily conserved enzymes, the methionine aminopeptidases (MetAPs), remove N-terminal methionine during protein synthesis. J. O. Liu et al. describe in their Communication on page 3772 ff. a new class of inhibitors for MetAPs and the crystal structure of the inhibitor complexed with MetAP1. These findings should facilitate the development of MetAP1-specific inhibitors that can serve as molecular probes for the function of MetAP1 and as potential leads for inhibitors of cancer cell growth.

    2. A Closer Look at Nanoporous Materials (pages 3732–3733)

      Jörg Kärger and Farida Grinberg

      Version of Record online: 24 MAY 2006 | DOI: 10.1002/anie.200601629

    3. Olefin Metathesis: The Early Days (Nobel Lecture) (pages 3740–3747)

      Yves Chauvin

      Version of Record online: 24 MAY 2006 | DOI: 10.1002/anie.200601234

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      Metathesis reactions are among the most important processes in organic synthesis. The decisive breakthrough in making these reactions practical for industrial purposes, which range from the synthesis of polymers to pharmaceuticals, came with the discovery of the reaction mechanism by Yves Chauvin and the targeted development of transition-metal-based metathesis catalysts by Richard Schrock and Robert Grubbs. The winners of the Chemistry Nobel Prize in 2005 present first-hand accounts of these developments.

    4. Multiple Metal–Carbon Bonds for Catalytic Metathesis Reactions (Nobel Lecture) (pages 3748–3759)

      Richard R. Schrock

      Version of Record online: 16 MAY 2006 | DOI: 10.1002/anie.200600085

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      Metathesis reactions are among the most important processes in organic synthesis. The decisive breakthrough in making these reactions practical for industrial purposes, which range from the synthesis of polymers to pharmaceuticals, came with the discovery of the reaction mechanism by Yves Chauvin and the targeted development of transition-metal-based metathesis catalysts by Richard Schrock and Robert Grubbs. The winners of the Chemistry Nobel Prize in 2005 present first-hand accounts of these developments.

    5. Olefin-Metathesis Catalysts for the Preparation of Molecules and Materials (Nobel Lecture) (pages 3760–3765)

      Robert H. Grubbs

      Version of Record online: 24 MAY 2006 | DOI: 10.1002/anie.200600680

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      Metathesis reactions are among the most important processes in organic synthesis. The decisive breakthrough in making these reactions practical for industrial purposes, which range from the synthesis of polymers to pharmaceuticals, came with the discovery of the reaction mechanism by Yves Chauvin and the targeted development of transition-metal-based metathesis catalysts by Richard Schrock and Robert Grubbs. The winners of the Chemistry Nobel Prize in 2005 present first-hand accounts of these developments.

    6. Nickel(II) Thiolate Complexes with a Flexible cyclo-{Ni10S20} Framework (pages 3768–3772)

      Chi Zhang, Satoshi Takada, Michael Kölzer, Tsuyoshi Matsumoto and Kazuyuki Tatsumi

      Version of Record online: 19 APR 2006 | DOI: 10.1002/anie.200600319

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      A tale of two toroids: New cyclic nickel(II) thiolate complexes (see structures; Ni green, S red, C purple) were synthesized by stepwise introduction of two kinds of thiolates to a nickel(II) center. The flexible {Ni10S20} core configuration crystallizes in different forms, either circular or ellipsoidal, depending on the presence or absence of an encapsulated guest molecule.

    7. Identification of Pyridinylpyrimidines as Inhibitors of Human Methionine Aminopeptidases (pages 3772–3775)

      Xiaoyi Hu, Anthony Addlagatta, Brian W. Matthews and Jun O. Liu

      Version of Record online: 24 MAY 2006 | DOI: 10.1002/anie.200600757

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      High-throughput screening of a library of compounds has led to the identification of a new structural class of human methionine aminopeptidases inhibitors. They inhibited the processing of 14-3-3γ in cells and blocked proliferation of both endothelial cells and transformed cancer cell lines. The picture shows the crystal structure of the complex of one inhibitor (yellow) with the type 1 human methionine aminopeptidase (blue CoII, red H2O).

    8. Directed meta-Metalation Using Alkali-Metal-Mediated Zincation (pages 3775–3778)

      David R. Armstrong, William Clegg, Sophie H. Dale, Eva Hevia, Lorna M. Hogg, Gordon W. Honeyman and Robert E. Mulvey

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600720

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      Move over directed ortho-metalation, here comes directed meta-metalation. The unprecedented meta-zincation of two anilides by a synergic mixed sodium/zinc dialkyl–amide base is presented. The orientation of the deprotonation of the anilides is remarkably switched to the meta site using this heterometallic mixed-metal system.

    9. A Chemically Switchable Molecular Pinwheel (pages 3779–3781)

      Owain P. H. Vaughan, Federico J. Williams, Nick Bampos and Richard M. Lambert

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600683

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      Spinning around: By insertion of a bifunctional ligand that acts as an axle—one end tethered to a silver surface, the other bonded to the metal center of a metalloporphyrin—an entire population of porphyrin molecules can be induced to spin. Removal of the axle quenches the motion. The switching process may be repeated an indefinite number of times.

    10. Starbons: New Starch-Derived Mesoporous Carbonaceous Materials with Tunable Properties (pages 3782–3786)

      Vitaly Budarin, James H. Clark, Jeffrey J. E. Hardy, Rafael Luque, Krzysztof Milkowski, Stewart J. Tavener and Ashley J. Wilson

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600460

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      A star is born: The complex molecular architecture found in plants is used in the design of new nanostructured materials. Carbon-based mesoporous materials with tunable surfaces and bulk properties can be synthesized by the low-temperature carbonization of expanded natural starches that are in turn prepared by a simple gelatinization–retrogradation process.

    11. Hermaphroditic Chirality of a D2-Symmetric Saddle-Shaped Porphyrin in Multicomponent Spontaneous Optical Resolution: Inclusion Cocrystals with Double-Helical Porphyrin Arrays (pages 3786–3790)

      Yukitami Mizuno, Md. Akhtarul Alam, Akihiko Tsuda, Kazushi Kinbara, Kentaro Yamaguchi and Takuzo Aida

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200503054

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      The dynamic dual chirality of D2-symmetric saddle-shaped porphyrin 1 decreases the stereochemical complexity of cocrystallization with racemic mandelic acid derivatives, such as BrMA, and allows spontaneous optical resolution (see picture). Each resulting cocrystal is porous and consists of one-handed double-helical porphyrin arrays in which chiral guests are enantioselectively included.

    12. Discovery of Low-Molecular-Weight Ligands for the AF6 PDZ Domain (pages 3790–3795)

      Mangesh Joshi, Carolyn Vargas, Prisca Boisguerin, Annette Diehl, Gerd Krause, Peter Schmieder, Karin Moelling, Volker Hagen, Markus Schade and Hartmut Oschkinat

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200503965

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      In the groove: The “drugability” of protein–protein interaction domains is still a matter of debate. The 3D structure of a complex of a small organic ligand and the AF6 PDZ domain revealed the creation of a binding pocket by the ligand (see picture). The derived compound is able to compete with a natural peptide ligand of the domain and represents a basic building block for the generation of selective PDZ inhibitors.

    13. Magic and Antimagic Protonated Water Clusters: Exotic Structures with Unusual Dynamic Effects (pages 3795–3800)

      N. Jiten Singh, Mina Park, Seung Kyu Min, Seung Bum Suh and Kwang S. Kim

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200504159

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      It's a kinda magic! Contrary to conventional wisdom that O[BOND]H bonds associated with dangling hydrogen atoms and those in the H3O+ ion in molecular clusters display characteristic peaks in IR spectra, a dynamic effect makes such peaks disappear, even in the gas phase at low temperatures. This finding helps solve the long-standing problems of magic and antimagic protonated water clusters with 21 (top structures) and 22 (bottom structures) water molecules.

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      Chemical Sensing with Familiar Devices (pages 3800–3803)

      Daniel Filippini, Adriano Alimelli, Corrado Di Natale, Roberto Paolesse, Arnaldo D'Amico and Ingemar Lundström

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600050

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      Seeing sense: The detection of detailed absorption and emission responses caused by amines, CO, and NOx is possible using an inexpensive array of porphyrins as sensors combined with a computer screen and web camera. The computer-screen image shows the array in the presence of triethylamine. [Zn]=[Zn(tpp)], [Fe]=[Fe(tppCl)] (tpp=5,10,15,20-tetraphenylporphyrin), BD=2,3,17,18-tetraethyl-7,8,12,13-tetramethyl-a,c-biladiene dihydrobromide.

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      A Quantum Chemical Study of the Quintuple Bond between Two Chromium Centers in [PhCrCrPh]: trans-Bent versus Linear Geometry (pages 3804–3807)

      Marcin Brynda, Laura Gagliardi, Per-Olof Widmark, Philip P. Power and Björn O. Roos

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600110

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      High five: Multiconfigurational quantum chemical methods show that a quintuple bond is present between the two CrI units in the model complex [PhCrCrPh]. The Cr[BOND]Cr (1.75 Å) and Cr[BOND]Ph (2.02 Å) bonds are shorter than those in the recently reported compound [Ar′CrCrAr′] (Ar′=2,6-(2,6-iPr2C6H3)2C6H3; 1.83 and 2.15 Å, respectively). This difference is attributed to the additional Cr[BOND]Ar′ interactions.

    16. A Hybrid Water–Chloride Structure with Discrete Undecameric Water Moieties Self-Assembled in a Heptaprotonated Octaamino Cryptand (pages 3807–3811)

      P. S. Lakshminarayanan, Eringathodi Suresh and Pradyut Ghosh

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600254

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      Odd water clusters: An unprecedented propeller-shaped undecameric water motif is stabilized within the lattice of the heptahydrochloride of a homoditopic octaamino cryptand with C3 symmetry. The discrete water clusters are oriented symmetrically around the cryptand moiety and interact with encapsulated chloride inside the cavity (see structure; Cl green, O red, N blue).

    17. The Enantioselective Allylation and Crotylation of Sterically Hindered and Functionalized Aryl Ketones: Convenient Access to Unusual Tertiary Carbinol Structures (pages 3811–3813)

      Noah Z. Burns, Blaine M. Hackman, Pui Yee Ng, Ian A. Powelson and James L. Leighton

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600910

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      A strained allylsilane reagent is highly effective in the enantioselective allylation of hydroxyphenylketones. The method is uniquely tolerant both of sterically hindered aliphatic ketones and highly functionalized diaryl ketones and has been extended to include the first examples of highly diastereo- and enantioselective ketone crotylation, which provides access to both diastereomers.

    18. Catalytic Enantioselective and Diastereoselective Addition of Aldehyde-Derived Enecarbamates to α-Oxo Aldehydes (pages 3814–3816)

      Ryosuke Matsubara, Nobuyuki Kawai and Shū Kobayashi

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600471

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      Added benefits: Catalytic enantio- and diastereoselective addition of aldehyde-derived enecarbamates to aldehydes is reported (see scheme). A copper(I)–diimine complex works well as the catalyst and the catalyst loading is not more than 1 mol % in most cases. By taking advantage of this reaction, the total synthesis of (2S,3S,4S)-3-hydroxy-4-methylproline has been accomplished.

    19. With Molecular-Oxygen-Activated Lewis Acids: Dinuclear Molybdenum Complexes for Aza-Diels–Alder Reactions of Acyl Hydrazones (pages 3816–3819)

      Yasuhiro Yamashita, Matthew M. Salter, Kayoko Aoyama and Shū Kobayashi

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600801

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      Easy activation: A Lewis acid catalyst based on molybdenum relies on activation by molecular oxygen for its high catalytic activity. The novel complex catalyzes the aza-Diels–Alder reaction of acyl hydrazones with Danishefsky dienes (see scheme) and other Lewis acid mediated reactions, such as the Mukaiyama aldol addition, Mannich-type reactions, and the addition of trimethylsilylcyanide to imines.

    20. Ir- and Ru-Catalyzed Sequential Reactions: Asymmetric α-Alkylative Reduction of Ketones with Alcohols (pages 3819–3822)

      Gen Onodera, Yoshiaki Nishibayashi and Sakae Uemura

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600677

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      The compatibility between [{IrCl(cod)}2] and ruthenium complex 1 to achieve asymmetric α-alkylative reduction of prochiral ketones with primary alcohols is an essential factor in obtaining optically active alcohols with elongation of the carbon skeleton in good yields with a high enantioselectivity.

    21. In(OTf)3-Catalyzed Tandem Nucleophilic Addition and Cyclization of ortho-Alkynylarylaldimines to 1,2-Dihydroisoquinolines (pages 3822–3825)

      Reiko Yanada, Shingo Obika, Hideki Kono and Yoshiji Takemoto

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600408

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      Multitasking catalyst: 1,2-Dihydroisoquinoline derivatives are prepared in good yields by an In(OTf)3-catalyzed tandem annulation reaction. The catalyst activates both the imine and alkyne to the addition of various nucleophiles and the subsequent intramolecular cyclization (see picture; OTf=trifluoromethanesulfonate).

    22. Platinum-Functionalized Octahedral Silica Nanocages: Synthesis and Characterization (pages 3825–3829)

      Xiong Wen Lou, Chongli Yuan, Qing Zhang and Lynden A. Archer

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200600239

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      Hole in one! Octahedral silica nanocages are prepared by a facile one-step approach, which also enables controlled functionalization with Pt in the cavities. The strategy is based on mediated deposition of silica on simultaneously generated salt quasi-templates, which are simply removed by washing with water.

    23. Fluorescent Quantum Dots with Boronic Acid Substituted Viologens To Sense Glucose in Aqueous Solution (pages 3829–3832)

      David B. Cordes, Soya Gamsey and Bakthan Singaram

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200504390

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      A quantum leap in glucose sensing: Commercially available fluorescent quantum dots are used in combination with boronic acid modified viologens to sense glucose in aqueous solution. The signal response is optimized by adjusting the ratio of quantum dots to viologen quencher.

    24. A Highly Enantioselective, Pd–TangPhos-Catalyzed Hydrogenation of N-Tosylimines (pages 3832–3835)

      Qin Yang, Gao Shang, Wenzhong Gao, Jingen Deng and Xumu Zhang

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600263

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      A catalyst system composed of Pd(OCOCF3)2 complexed with the electron-donating, rigid chiral diphosphane TangPhos gives excellent enantioselectivities (up to 99 % ee) and conversions (up to >99 %) in the hydrogenation of N-tosylimines 1 (see scheme). A variety of aromatic, aliphatic, and cyclic chiral amines 2 can be prepared by this methodology.

    25. High Thermoelectric Figure of Merit and Nanostructuring in Bulk p-type Na1−xPbmSbyTem+2 (pages 3835–3839)

      Pierre F. P. Poudeu, Jonathan D'Angelo, Adam D. Downey, Jarrod L. Short, Timothy P. Hogan and Mercouri G. Kanatzidis

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200600865

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      Worthy of merit: The new class of nanostructured p-type thermoelectrics Na1−xPbmSbyTem+2 is reported. The exceptionally high thermoelectric figures of merit ZT of these materials (see graph), which exceed those of the state-of-the-art materials PbTe and (GeTe)1−x((Ag2Te)1−y(Sb2Te3)y)x (TAGS), derive from their very low lattice thermal conductivities.

    26. Construction of Enantiomerically Enriched Tertiary α-Hydroxycarboxylic Acid Derivatives by Phase-Transfer-Catalyzed Asymmetric Alkylation of Diaryloxazolidin-2,4-diones (pages 3839–3842)

      Takashi Ooi, Kazuhiro Fukumoto and Keiji Maruoka

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600470

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      Center of attention: The chiral ammonium bromide 1 has been used as a catalyst for the highly enantioselective alkylation of diaryloxazolidindiones 2 under mild phase-transfer conditions (TBME=tert-butyl methyl ether). This method provides practical access to a variety of optically active tertiary α-hydroxycarboxylic acid derivatives.

    27. Hydrogen-Bond-Directed Head-to-Tail Orientation of Dipolar Merocyanine Dyes: A Strategy for the Design of Electrooptical Materials (pages 3842–3846)

      Frank Würthner, Johann Schmidt, Matthias Stolte and Rüdiger Wortmann

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200504581

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      Two merocyanine dyes are assembled by multiple hydrogen bonds with summation of their dipole moments (see formula; R=2-ethylhexyl). It exhibits a strongly increased degree of dye alignment in an electric field according to electrooptical absorption spectroscopy.

    28. Optical Switching of Self-Assembly: Micellization and Micelle–Hollow-Sphere Transition of Hydrogen-Bonded Polymers (pages 3846–3850)

      Xikui Liu and Ming Jiang

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200504364

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      Light switch: Noncovalently connected micelles are formed by the photoisomerization of azobenzene groups in copolymer building blocks and the hydrogen-bonding interaction within the polymer pair. The UV-induced micellar structure can be fixed through core cross-linking, which allows the reversible optical switching of a micelle–hollow-sphere transition (see picture).

    29. Orthogonal Glycosylation Reactions on Solid Phase and Synthesis of a Library Consisting of a Complete Set of Fucosyl Galactose Isomers (pages 3851–3854)

      Osamu Kanie, Isao Ohtsuka, Takuro Ako, Shusaku Daikoku, Yoshimi Kanie and Rumiko Kato

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200600433

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      A dream team: Orthogonal glycosylation and solid-phase synthesis were shown to be an excellent combination for polysaccharide synthesis (see scheme). The method was applied to generate a complete library of structural isomers with an L-fucosyl-D-galactose sequence.

    30. A η4-Dithio-para-benzoquinone Metal Complex (pages 3854–3858)

      Jamal Moussa, Daniel A. Lev, Kamal Boubekeur, Marie Noelle Rager and Hani Amouri

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600414

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      Overcoming a long-standing challenge: A rational synthetic procedure allows the isolation of the first stable η4-dithio-para-benzoquinone complex (2; Cp*=C5Me5). The X-ray molecular structure of 2 confirms the coordination of the elusive intermediate 1 in an η4 manner. Computational analyses of 2 support the role of the {Cp*Ir} fragment in stabilizing this reactive intermediate.

    31. A Carbocyclic Carbene as an Efficient Catalyst Ligand for C[BOND]C Coupling Reactions (pages 3859–3862)

      Wolfgang A. Herrmann, Karl Öfele, Sabine K. Schneider, Eberhardt Herdtweck and Stephan D. Hoffmann

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200503589

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      A new player on the field: Carbocyclic carbenes are potentially better control ligands than N-heterocyclic carbenes (NHCs) in catalyzed C[BOND]C coupling reactions. PdII complexes of cycloheptatrienylidene (see picture), which are readily prepared, thermally stable, and highly stable towards acid, are as effective as the familiar NHC complexes in Suzuki and Heck reactions or perform even better.

    32. Siphonazole, an Unusual Metabolite from Herpetosiphon sp. (pages 3863–3867)

      Markus Nett, Özlem Erol, Stefan Kehraus, Matthias Köck, Anja Krick, Ekaterina Eguereva, Edith Neu and Gabriele M. König

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200504525

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      Deep and complex: The first representative (see picture) of a new structural class has been isolated from a deep-rooted filamentous bacterium of the genus Herpetosiphon. Feeding with 13C and 15N-labeled precursors showed the complex biosynthesis to involve shikimate, the polyketide, and the amino acid metabolism.

    33. Crystallographic Characterization of a Synthetic 1:1 End-On Copper Dioxygen Adduct Complex (pages 3867–3869)

      Christian Würtele, Ekaterina Gaoutchenova, Klaus Harms, Max C. Holthausen, Jörg Sundermeyer and Siegfried Schindler

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600351

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      No doubt: The high-quality crystal structure of [Cu(TMG3tren)(O2)]SbF6 (see picture) presents the first unambiguous characterization of a bioinorganic compound in which a dioxygen molecule coordinates end-on to a CuI ion. This species, which is best described as a superoxo copper(II) complex, serves as a model complex for initially formed Cu–O2 adducts present in a variety of active sites of copper enzymes.

    34. Towards a General Scale of Nucleophilicity? (pages 3869–3874)

      Thanh Binh Phan, Martin Breugst and Herbert Mayr

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200600542

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      One for all? The nucleophilicity parameters N, which have been derived from the rate constants k of reactions of nucleophiles with carbocations, also hold for SN2-type reactions (see scheme). A general equation is suggested which includes established correlations (Swain–Scott, Ritchie) as special cases.

    35. Details of the Partial Unfolding of T4 Lysozyme on Quartz Using Site-Directed Spin Labeling (pages 3874–3877)

      Kerstin Jacobsen, Wayne L. Hubbell, Oliver P. Ernst and Thomas Risse

      Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600008

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      Spin doctoring: Site-directed spin labeling was used to determine the structure of T4 lysozyme adsorbed on quartz. At high ionic strength significant changes of the backbone fold are limited to the region around the enzymatic cleft. In contrast, at low ionic strength the previously unperturbed parts of the protein interact with the surface. Hydrophobic interactions are thought to play an important role in the partial unfolding at high ionic strength.

    36. Ultrahigh Resolution in Proton Solid-State NMR Spectroscopy at High Levels of Deuteration (pages 3878–3881)

      Veniamin Chevelkov, Kristina Rehbein, Anne Diehl and Bernd Reif

      Version of Record online: 28 APR 2006 | DOI: 10.1002/anie.200600328

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      Slim peaks: Using a perdeuterated protein recrystallized from a 10:90 H2O:D2O mixture in magic-angle spinning (MAS) solid-state NMR spectroscopy experiments gives small 1H line widths at moderate spinning frequencies without application of homonuclear decoupling. This labeling strategy opens new perspectives for assignment of large protein spin systems.

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