Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 34

August 25, 2006

Volume 45, Issue 34

Pages 5561–5715

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
    8. Communications
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    1. Cover Picture: Luminescent One-Dimensional Nanoscale Materials with PtII⋅⋅⋅PtII Interactions (Angew. Chem. Int. Ed. 34/2006) (page 5561)

      Yinghui Sun, Kaiqi Ye, Hongyu Zhang, Junhu Zhang, Lan Zhao, Bao Li, Guangdi Yang, Bai Yang, Yue Wang, Siu-Wai Lai and Chi-Ming Che

      Version of Record online: 21 AUG 2006 | DOI: 10.1002/anie.200690115

      Platinum(II)-to-platinum(II) interactions mediate and direct the formation of micro- and nanometer-scale molecular wires of [Pt(CNtBu)2(CN)2]. The cover picture depicts models and microscopy images of the wires. Y. Wang, C.-M. Che, and co-workers describe in their Communication on page 5610 ff. the formation and photophysical properties of these photoluminescent molecular wires. An X-ray crystallographic study provides a structural basis for rationalizing the photoluminescent responses.

  2. Graphical Abstract

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    7. Review
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  3. News

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    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
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  4. Book Reviews

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    3. Graphical Abstract
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    5. Book Reviews
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    7. Review
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  5. Highlights

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    5. Book Reviews
    6. Highlights
    7. Review
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    1. Blue, but Not a Mirage: Stable Aminoketenes by Carbene Carbonylation (pages 5580–5582)

      Thomas T. Tidwell

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601643

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      A true oasis: The preparation of the first isolable aminoketenes by carbon monoxide addition to nitrogen-substituted carbenes (see scheme; Ar=2,6-iPr2C6H3) fills a void in ketene chemistry in unexpected ways, and further provides a visual demonstration of ketene HOMO–LUMO interactions.

    2. The Search for Single DNA Damage among Millions of Base Pairs: DNA Glycosylases Trapped at Work (pages 5583–5585)

      Hans-Achim Wagenknecht

      Version of Record online: 4 AUG 2006 | DOI: 10.1002/anie.200602387

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      Flipped out? The location of base lesions by DNA glycosylases does not necessarily need complete base-flipping into the active site as recent structures of DNA-protein complexes show (see picture; oG=8-oxoguanine).

  6. Review

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    1. Biosynthetic Inorganic Chemistry (pages 5588–5601)

      Yi Lu

      Version of Record online: 10 AUG 2006 | DOI: 10.1002/anie.200600168

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      One hand washes the other: The methods of inorganic chemistry have for many years supported biology. It is now time to show what new biological techniques can do for inorganic chemistry.

  7. Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
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    1. Lone-Pair Interfaces That Divide Inorganic Materials into Ionic and Covalent Parts (pages 5602–5606)

      Zuzana Mayerová, Mats Johnsson and Sven Lidin

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200600861

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      The lone (ar)ranger: The structure of Cu20Sb35O44Cl37 is divided up into two parts: ionically bonded Cu+–Cl supertetrahedra (green) and covalently bonded clusters that resemble zeolite β cages. The Sb3+ ions (gray) lie at the vertices of the cages, while their lone pairs of electrons form surfaces that separate the covalent and ionic parts.

    2. Double Proton Coupled Charge Transfer in DNA (pages 5606–5609)

      Francesco Luigi Gervasio, Mauro Boero and Michele Parrinello

      Version of Record online: 3 AUG 2006 | DOI: 10.1002/anie.200602106

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      Double or nothing: Large-scale density functional calculations are used to study the formation of a large polaron on three proximal guanines (see picture). The formation was observed by step by step following of a proton-coupled charge transfer. The role played by the double proton transfer and a new and unexpected role for the tautomers of G and C were found.

    3. Luminescent One-Dimensional Nanoscale Materials with PtII⋅⋅⋅PtII Interactions (pages 5610–5613)

      Yinghui Sun, Kaiqi Ye, Hongyu Zhang, Junhu Zhang, Lan Zhao, Bao Li, Guangdi Yang, Bai Yang, Yue Wang, Siu-Wai Lai and Chi-Ming Che

      Version of Record online: 28 JUL 2006 | DOI: 10.1002/anie.200601588

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      Down to the wire: PtII⋅⋅⋅PtII interactions provide the cohesive driving force for the construction of micro- and nanometer-scale luminescent wires, such as nanowires of [Pt(CNtBu)2(CN)2] (see picture; Pt pink, N blue, C gray), which is a potential candidate for applications in nano-optical, electronic, and sensory devices.

    4. Self-Assembly of a Tetradecanuclear Iron Nitride Cluster (pages 5613–5616)

      Miriam V. Bennett and R. H. Holm

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601570

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      A novel construction: The reaction of [FeCl4] with (Me3Sn)3N leads to the cluster [Fe14N8(NSnMe3)4Cl12]4− (see picture; Fe red, N blue, Sn yellow, Cl green; Me groups omitted), which has a core built from 16 Fe2N2 rhombs. Mössbauer spectroscopy indicates the presence of 12 FeIII and 2 FeII ions, and magnetic measurements suggest an S=2 ground state for the cluster.

    5. Site-Selective Derivatization and Remodeling of Erythromycin A by Using Simple Peptide-Based Chiral Catalysts (pages 5616–5619)

      Chad A. Lewis and Scott J. Miller

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601490

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      Reversal: Simple peptide-based nucleophilic catalysts can perturb the inherent reactivity hierarchy of the polyol natural product erythromycin A (see picture). Such catalyst-dependent modifications that reorganize natural product architecture may be of utility for generation of natural product analogs.

    6. Constraints on the Structure of (CUG)97 RNA from Magic-Angle-Spinning Solid-State NMR Spectroscopy (pages 5620–5623)

      Kerstin Riedel, Christian Herbst, Sabine Häfner, Jörg Leppert, Oliver Ohlenschläger, Maurice S. Swanson, Matthias Görlach and Ramadurai Ramachandran

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200600769

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      Twists in a spin: RNA structural constraints have been obtained directly by exploiting the dependence of inter- and intranucleotide 1H–1H interactions on RNA conformation through the use of 13C MAS solid-state NMR spectroscopy. The data provide evidence that (CUG)97 RNA principally adopts an A-form helix conformation with a C3′-endo sugar pucker and an anti glycosidic torsion angle χ (see model).

    7. Mismatch-Binding Ligands Function as a Molecular Glue for DNA (pages 5623–5626)

      Tao Peng, Chikara Dohno and Kazuhiko Nakatani

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601190

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      A sticky end: Two DNA strands that produce three contiguous mismatches (5′-TGG-3′/5′-TGG-3′ sequence) do not hybridize spontaneously, but are adhered by the mismatch-binding ligand naphthyridine carbamate dimer (NC; see picture, red rectangles: naphthyridine rings).

    8. Non-Exponential Distance Dependence of Bridge-Mediated Electronic Coupling (pages 5626–5629)

      Mattias P. Eng and Bo Albinsson

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601379

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      Donor chromophores attached to oligo(phenyleneethynylene) molecular bridges of varying length have attenuation factors for electron tunneling β that vary systematically with the donor–bridge (DB) energy gap (see picture). Investigations show that for bridges with ethynylene and vinylene repeating subunits, the electronic coupling increases with increasing donor–acceptor (DA) distance. A simple model accounts for this unexpected observation.

    9. Nonlinear Self-Excited Oscillation of a Synthetic Ion-Channel-Inspired Membrane (pages 5630–5633)

      Taichi Ito and Takeo Yamaguchi

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200600298

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      In full swing: Nonlinear oscillations by molecular signals are one of the inherent properties of life. An artificial ion-gating membrane, which was synthesized from a thermosensitive polymer and a crown ether, generated a relaxation oscillation similar to that of neurons in response to a specific ion signal (see picture).

    10. Engineering Proteins with Novel Mechanical Properties by Recombination of Protein Fragments (pages 5633–5638)

      Deepak Sharma, Yi Cao and Hongbin Li

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200600382

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      The power of recombination: A DNA-shuffling-based recombination technique was used to recombine protein fragments from two parent proteins to generate hybrid proteins, which can fold into three-dimensional structures similar to those of the parent proteins. These designed hybrid proteins are mechanically stable and display novel mechanical properties.

    11. Towards a Structural Understanding of the Anti-Ulcer and Anti-Gastritis Drug Bismuth Subsalicylate (pages 5638–5642)

      Philip C. Andrews, Glen B. Deacon, Craig M. Forsyth, Peter C. Junk, Ish Kumar and Melissa Maguire

      Version of Record online: 25 JUL 2006 | DOI: 10.1002/anie.200600469

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      The action of Pepto-Bismol arising from the structure and hydrolysis of bismuth subsalicylate (BSS) is not yet understood. Two bismuth oxosalicylate clusters, [Bi38O44(HSal)26(Me2CO)16(H2O)2] (1) and [Bi9O7(HSal)13(Me2CO)5] (2), have been characterized which provide structural insight into the nature of BSS. A Bi9O7 cluster forms the core of 2 and is found at the heart of 1 (see picture; core Bi atoms: green, core O atoms: red).

    12. Room-Temperature Autoconversion of Free-Base Corrole into Free-Base Porphyrin (pages 5642–5645)

      Claude P. Gros, Jean-Michel Barbe, Enrique Espinosa and Roger Guilard

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200601580

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      As easy as AB2C: Irradiation of a solution of the free-base corrole 1 with a 400-W lamp led to its conversion into the corresponding trans-AB2C-porphyrin 2 and an open-chain biliverdin-type by-product.

    13. Ruthenium-Induced Allylcarbamate Cleavage in Living Cells (pages 5645–5648)

      Craig Streu and Eric Meggers

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200601752

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      Easy going: A ruthenium-catalyzed release of amines from their respective allylcarbamates is disclosed and is a step towards the design of catalysts as tools for cellular biology. The reaction tolerates the combination of water, air, and thiols and can be performed inside living mammalian cells. Cp*=pentamethylcyclopentadienyl, cod=1,5-cyclooctadiene.

    14. Small-Molecule Screening Made Simple for a Difficult Target with a Signaling Nucleic Acid Aptamer that Reports on Deaminase Activity (pages 5648–5652)

      Nadine H. Elowe, Razvan Nutiu, Abdellah Allali-Hassani, Jonathan D. Cechetto, Donald W. Hughes, Yingfu Li and Eric D. Brown

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200601695

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      Problem child: The application of signaling DNA-aptamer technology to the development and execution of a high-throughput screen for an otherwise problematic target, adenosine deaminase (ADA), is reported. The approach employed a signaling DNA aptamer that reports on adenosine concentration (see scheme). The assay was robust in a screen of more than 44 000 molecules and revealed a new competitive inhibitor of the deaminase.

    15. Glycosidation Promoted by a Reusable Solid Superacid in Supercritical Carbon Dioxide (pages 5652–5655)

      Xue-Bing Li, Masato Ogawa, Toshiki Monden, Takahiro Maeda, Eri Yamashita, Mariko Naka, Masao Matsuda, Hiroshi Hinou and Shin-Ichiro Nishimura

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200602161

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      Superduper: A practical and cleaner synthetic protocol for various glycosides was established by means of a recyclable solid superacid promoter in supercritical carbon dioxide (scCO2). Anomeric mixtures composed of α- and β-isomers were successfully separated by employing supercritical fluid chromatography (SFC) with scCO2 and methanol. L=leaving group, P=protecting group, ROH= sphingosine, sugar, etc.

    16. Nanostructured Bi2Se3 Films and Their Thermoelectric Transport Properties (pages 5656–5659)

      Xiaofeng Qiu, Leah N. Austin, Philip A. Muscarella, Jeffrey S. Dyck and Clemens Burda

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200600848

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      A new strategy to grow thermoelectric nanostructures on a wide variety of substrates is introduced. The synthesis involves the reduction of a selenium precursor to promote nucleation with bismuth ions to produce Bi2Se3 nanostructured films (see picture, scale bar 10 μm) under thermodynamic control. Thermoelectric transport measurements of the nanostructured films were performed from 6 to 300 K.

    17. Conformationally Rigid Trifluoromethyl-Substituted α-Amino Acid Designed for Peptide Structure Analysis by Solid-State 19F NMR Spectroscopy (pages 5659–5661)

      Pavel K. Mikhailiuk, Sergii Afonin, Alexander N. Chernega, Eduard B. Rusanov, Maxim O. Platonov, Galina G. Dubinina, Marina Berditsch, Anne S. Ulrich and Igor V. Komarov

      Version of Record online: 25 JUL 2006 | DOI: 10.1002/anie.200600346

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      Designing a sturdy label: The fluorinated amino acid l-CF3-Bpg (see picture), which was specifically designed as a 19F NMR label for structure analysis of membrane-bound peptides, does not display the drawbacks of previously used labels. The amino acid can be readily incorporated into peptides and is particularly suitable as a substitute for Leu, Ile, and Met.

    18. Superlattice Formation from Polydisperse Ag Nanoparticles by a Vapor-Diffusion Method (pages 5662–5665)

      Yang Yang, Shuman Liu and Keisaku Kimura

      Version of Record online: 26 JUL 2006 | DOI: 10.1002/anie.200601233

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      A self-correction process that is time- and pH-dependent results in growth of perfect superlattices from a bulk solution of hydrophilic Ag nanoparticles, despite their polydispersity, by a vapor-diffusion technique. After 12 weeks, three-dimensional rhombic superlattices are obtained (see picture).

    19. Synthesis, Structure, and Properties of 4,7-Dimethoxybenzo[c]tellurophene: A Molecular Pyroelectric Material (pages 5666–5670)

      Michael Pittelkow, Theis K. Reenberg, Kim T. Nielsen, Magnus J. Magnussen, Theis I. Sølling, Frederik C. Krebs and Jørn B. Christensen

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601298

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      More than just curiosities: The synthesis and characterization of a stable benzo[c]tellurophene are presented. Te[BOND]Te interactions are shown to be one of the main driving forces for the crystal-packing properties of this electron-rich benzo[c]tellurophene; furthermore, investigation of its pyroelectric properties reveals a secondary pyroelectric effect.

    20. Metal-Mediated C[BOND]H Bond Activation in a Carbon-Substituted Hemiporphyrazine (pages 5670–5673)

      Ruoqiu Wu, Anιl Çetin, William S. Durfee and Christopher J. Ziegler

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200601765

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      The expanded phthalocyanine dicarbahemiporphyrazine forms complexes in which the arene CH groups are in close proximity to the metal center. In the case of the copper adduct, one of the two C[BOND]H bonds is attacked by a solvent pyridine molecule, thereby forming a C[BOND]N bond (see picture; C gray, N blue, H light green). This reaction may proceed by oxidative nucleophilic substitution of hydrogen.

    21. Rhodium-Catalyzed Enantioselective Conjugate Silyl Transfer: 1,4-Addition of Silyl Boronic Esters to Cyclic Enones and Lactones (pages 5675–5677)

      Christian Walter, Gertrud Auer and Martin Oestreich

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601747

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      Missing linkage: A chiral cationic rhodium complex catalyzes the enantioselective conjugate addition of silyl anion equivalents to cyclic α,β-unsaturated ketones (X=CH2) and esters (X=O; see scheme). This unprecedented catalytic process enables the asymmetric formation of a carbon–silicon bond, thus providing a facile access to α-chiral organosilicon compounds.

    22. Enantioselective Reduction of Ketones with “Designer Cells” at High Substrate Concentrations: Highly Efficient Access to Functionalized Optically Active Alcohols (pages 5677–5681)

      Harald Gröger, Francoise Chamouleau, Nicolas Orologas, Claudia Rollmann, Karlheinz Drauz, Werner Hummel, Andrea Weckbecker and Oliver May

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200503394

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      Productive cells: In a simple, highly efficient process for the synthesis of optically active alcohols, ketones are reduced by “designer cells” at high substrate concentrations and without the addition of an “external” cofactor in aqueous reaction medium. A wide range of R and S alcohols can be prepared with conversions of >90 % and enantioselectivities of >99 % ee (scheme shows results from the application on a 10-L scale).

    23. Formation of an Aqueous Oxoiron(IV) Complex at pH 2–6 from a Nonheme Iron(II) Complex and H2O2 (pages 5681–5684)

      Jochen Bautz, Michael R. Bukowski, Marion Kerscher, Audria Stubna, Peter Comba, Achim Lienke, Eckard Münck and Lawrence Que Jr.

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601134

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      A ferryl cation in water: Iron(II) coordinated by the pentadentate ligand L reacts with H2O2 to form a low-spin FeIV[DOUBLE BOND]O complex with S=1 (2 in scheme) under conditions similar to those of the classical Fenton reaction. Complex 2 differs from a recently obtained high-spin aquated oxoiron(IV) species and demonstrates the role of the supporting polydentate ligand in controlling spin state and product formation.

    24. Premithramycinone G, an Early Shunt Product of the Mithramycin Biosynthetic Pathway Accumulated upon Inactivation of Oxygenase MtmOII (pages 5685–5689)

      Mohamed S. Abdelfattah and Jürgen Rohr

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200600511

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      The unusual dodecaketide premithramycinone G (see formula), which possesses a five-membered ring with two ketide chains in its tetracyclic structure, was accumulated upon inactivation of an early acting oxygenase of the mithramycin biosynthetic pathway. This unexpected structure allows novel hypothetic conclusions to be drawn regarding the early mithramycin pathway and suggestions for the involvement of three previously unassigned oxygenases.

    25. Reversible Formation of Polymeric Chains by Coordination of Pentaphosphaferrocene with Silver(I) Cations (pages 5689–5693)

      Manfred Scheer, Laurence J. Gregoriades, Alexander V. Virovets, Werner Kunz, Roland Neueder and Ingo Krossing

      Version of Record online: 24 JUL 2006 | DOI: 10.1002/anie.200601546

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      A fragile coordination polymer: The pentaphosphaferrocene [Cp*Fe(η5-P5)] reacts with the AgI salt of the weakly coordinating anion [Al{OC(CF3)3}4] to yield a polymer comprising cyclo-P5 moieties in an unprecedented 1,2,3-coordination mode (see figure). Analytical data and DFT calculations support the existence of a monomer/dimer/oligomer equilibrium in solution, which is entirely in favor of the monomer at room temperature and shifts to the dimer/oligomer at reduced temperatures.

    26. Practical, Highly Active, and Enantioselective Ferrocenyl–Imidazoline Palladacycle Catalysts (FIPs) for the Aza-Claisen Rearrangement of N-para-Methoxyphenyl Trifluoroacetimidates (pages 5694–5698)

      Matthias E. Weiss, Daniel F. Fischer, Zhuo-qun Xin, Sascha Jautze, W. Bernd Schweizer and René Peters

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601731

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      Just a pinch of catalyst: Just 0.05 mol % of a novel planar chiral ferrocenyl–imidazoline palladacycle catalyst (FIP) is sufficient to catalyze a highly efficient aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates and thereby provide access to chiral protected primary allylic amines with unprecedentedly high enantioselectivities (see scheme).

    27. A Trefoil Knot Made of Amino Acids and Steroids (pages 5698–5702)

      Martin Feigel, Rüdiger Ladberg, Simon Engels, Regine Herbst-Irmer and Roland Fröhlich

      Version of Record online: 20 JUL 2006 | DOI: 10.1002/anie.200601111

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      Tying up the loose ends: Cyclization of a linear hexapeptide made from alternating valine and α-aminodeoxycholanic acid units yielded two macrolactams: cyclo(valine-3-α-aminodeoxycholic acid amide)3 and cyclo(valine-3-α-aminodeoxycholic acid amide)6, the product of a cyclodimerization (see structure). X-Ray diffraction studies confirmed that the latter compound has the structure of a trefoil knot.

    28. Controlling the Activity of the 20S Proteasome Complex by Synthetic Gatekeepers (pages 5702–5705)

      Katrin Schulze, Alart Mulder, Ali Tinazli and Robert Tampé

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200600644

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      Open sesame: The proteasome complex is a nanodegradation machine that is essential for cellular protein turnover. A multivalent chelator head (MCH) was exploited for the specific binding to histidine-tagged proteasomes, even in crude cell lysates. Acting as synthetic gatekeepers, this MCH controls the access and thus the proteolytic activity of the nanomachinery.

    29. Low-Temperature Activation of Methane: It also Works Without a Transition Metal (pages 5705–5708)

      Detlef Schröder and Jana Roithová

      Version of Record online: 21 JUL 2006 | DOI: 10.1002/anie.200601273

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      Abstract art: Bare [MgO]+ ions can activate methane in a thermal ion/molecule reaction to afford [MgOH]++CH3. as major products and Mg++CH3OH in a side reaction. In conjunction with ab initio calculations, the results strongly support an hydrogen-atom abstraction mechanism which is assisted by a metal–carbon interaction (see scheme). Hydrocarbons (except methane) can also be activated by the magnesium-oxide cluster [Mg2O2]+.

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    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Book Reviews
    6. Highlights
    7. Review
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