Angewandte Chemie International Edition

Cover image for Vol. 45 Issue 3

January 9, 2006

Volume 45, Issue 3

Pages 327–519

    1. Cover Picture: Nanohybrids Composed of Quantum Dots and Cytochrome P450 as Photocatalysts (Angew. Chem. Int. Ed. 3/2006) (page 327)

      Binil Itty Ipe and Christof M. Niemeyer

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200690007

      Sunlight does chemistry in nanohybrids composed of CdS quantum dots (QDs) and enzyme P450BSβ. The hybrids, which are self-assembled through electrostatic interactions between the negatively charged QDs and the positively charged His6-marked P450, produce hydroxyl and superoxide radicals upon irradiation. In their Communication on page 504 ff., B. I. Ipe and C. M. Niemeyer report that these reactive oxygen species activate P450 to catalyze the monooxygenation of myristic acid. (Graphic prepared by P. Alhorn, B. Ipe, and K. Rabe.)

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      Aqueous FeIV[DOUBLE BOND]O: Spectroscopic Identification and Oxo-Group Exchange (page 340)

      Oleg Pestovsky, Sebastian Stoian, Emile L. Bominaar, Xiaopeng Shan, Eckard Münck, Lawrence Que Jr. and Andreja Bakac

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200690009

      This article corrects:

      Aqueous FeIV[DOUBLE BOND]O: Spectroscopic Identification and Oxo-Group Exchange1

      Vol. 44, Issue 42, 6871–6874, Version of Record online: 5 OCT 2005

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      Organocatalytic Asymmetric α-Halogenation of 1,3-Dicarbonyl Compounds (page 340)

      Giuseppe Bartoli, Marcella Basco, Armando Carlone, Manuela Locatelli, Paolo Melchiorre and Letizia Sambri

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200690011

      This article corrects:

      Organocatalytic Asymmetric α-Halogenation of 1,3-Dicarbonyl Compounds1

      Vol. 44, Issue 38, 6219–6222, Version of Record online: 1 SEP 2005

    4. Chembiogenesis 2005 and Systems Chemistry Workshop (pages 342–344)

      Johanna Stankiewicz and Lars Henning Eckardt

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200504139

    5. Silicon-Mediated Transformations of Functional Groups. By Helmut Vorbrüggen. (page 346)

      Thomas Müller and Norbert Auner

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200485258

    6. Catalytic Enantioselective Cross-Mannich Reaction of Aldehydes (pages 348–352)

      Maria Manuel B. Marques

      Version of Record online: 12 DEC 2005 | DOI: 10.1002/anie.200502630

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      A wide variety of optically active compounds as well as active compounds such as amino acid derivatives can be accessed by the cross-Mannich reaction of aldehydes, particularly by the direct catalytic asymmetric version, in which C[BOND]C bonds are formed. Remarkable advancements have been reported, including one-pot, three-component procedures with absolute stereocontrol and high yields (see example, NMP=N-methylpyrrolidine).

    7. Catalytic Asymmetric Tandem Transformations Triggered by Conjugate Additions (pages 354–366)

      Hong-Chao Guo and Jun-An Ma

      Version of Record online: 15 NOV 2005 | DOI: 10.1002/anie.200500195

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      Conjugate additions lead the way in catalytic asymmetric tandem transformations, which allow rapid access to complex molecular structures from readily available starting compounds. The advantage of such transformations is the formation of several bonds and the creation of two or more contiguous stereogenic centers by using a single catalyst in one pot (see scheme).

    8. Chemistry of Superheavy Elements (pages 368–401)

      Matthias Schädel

      Version of Record online: 19 DEC 2005 | DOI: 10.1002/anie.200461072

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      Man-made atoms: Experimental techniques, such as hot fusion (see scheme) and theoretical calculations on the superheavy elements (the transactinides) are now shedding light on the chemistry of these elements. Nuclear chemistry, performed at the ultimate one-atom-at-a-time limit, has reached element 108, hassium, and the elements 112 and beyond are now under investigation.

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      Elucidation of the Electrochemical Activation of Water over Pd by First Principles (pages 402–406)

      Jean-Sébastien Filhol and Matthew Neurock

      Version of Record online: 24 NOV 2005 | DOI: 10.1002/anie.200502540

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      Structural changes that occur at the palladium(111)/water interface during the electrocatalytic oxidation and reduction of water (see picture) have been calculated by ab initio methods. These results have been used to construct an electrochemical phase diagram, and demonstrate the influence of the polarization of the water/metal interface on surface properties.

    10. Fine Size Control of Platinum on Carbon Nanotubes: From Single Atoms to Clusters (pages 407–411)

      Yong-Tae Kim, Kazuyoshi Ohshima, Koichi Higashimine, Tomoya Uruga, Masaki Takata, Hiroyoshi Suematsu and Tadaoki Mitani

      Version of Record online: 9 DEC 2005 | DOI: 10.1002/anie.200501792

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      Bond formation between single Pt atoms and surface thiol groups is the result of the reduction of a Pt precursor in the presence of surface-thiolated carbon nanotubes. By setting the temperature of the following heat treatment, finely size-controlled and monodispersed Pt clusters were obtained from the dispersed single atoms (see picture).

    11. Trimethylamine as a Gas-Phase Promoter: Highly Efficient Epoxidation of Propylene over Supported Gold Catalysts (pages 412–415)

      Biswajit Chowdhury, Juan. J. Bravo-Suárez, Masakazu Daté, Susumu Tsubota and Masatake Haruta

      Version of Record online: 9 DEC 2005 | DOI: 10.1002/anie.200502382

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      The probable reaction pathways for propylene epoxidation with O2 and H2 in the presence of trimethylamine on trimethylsilylated Au-Ba(NO3)2/titanosilicate catalyst are discussed (see figure). The use of trimethylamine as a gas-phase promoter for nanoparticulate gold catalysts leads to a direct one-stage production of propylene oxide (PO) with steady space–time yields comparable to values for current industrial ethylene oxide production.

    12. Excited-State Triple Proton Transfer of 7-Hydroxyquinoline along a Hydrogen-Bonded Alcohol Chain: Vibrationally Assisted Proton Tunneling (pages 415–419)

      Oh-Hoon Kwon, Young-Shin Lee, Byung Kuk Yoo and Du-Jeon Jang

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200503209

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      Proton relay in cyclic 7-hydroxyquinoline–(alcohol)2 complexes (see picture) has been explored in nonpolar solvents. The asymmetric triple proton transfer has an unusually large, temperature-independent, and viscosity-dependent kinetic isotope effect. Heavy-atom motions (wavy arrow) of solvent and bridging molecules allow proton tunneling by assisting the complex to reach the optimal precursor configuration.

    13. Transition-Metal Doped Zinc Oxide Nanowires (pages 420–423)

      Benjamin D. Yuhas, David O. Zitoun, Peter J. Pauzauskie, Rongrui He and Peidong Yang

      Version of Record online: 12 DEC 2005 | DOI: 10.1002/anie.200503172

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      Bring in the substitute! Zn1−xCoxO nanowires are prepared by using a solution-based synthetic route. Structural, optical, and spectroscopic characterizations indicate that the cobalt atoms substitute the zinc cations in the host lattice as a result of the cobalt doping (the picture shows prepared Co-doped ZnO nanowires).

    14. Total Synthesis, NMR Solution Structure, and Binding Model of the Potent Histone Deacetylase Inhibitor FR235222 (pages 423–427)

      Manuela Rodriquez, Stefania Terracciano, Elena Cini, Giulia Settembrini, Ines Bruno, Giuseppe Bifulco, Maurizio Taddei and Luigi Gomez-Paloma

      Version of Record online: 28 NOV 2005 | DOI: 10.1002/anie.200501995

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      An alternative route: The fungal metabolite FR235222, a potent inhibitor of mammalian histone deacetylase (HDAC), has been synthesized. Key steps are the preparation of unusual amino acids Ahoda and (2R,4S)-MePro. A 3D model for cyclopeptide inhibitor interaction with the HDAC active site (see picture) highlights the differences between the binding mode of small-molecule and cyclopeptide inhibitors.

    15. “Perovskitization”-Assisted Electrochemical Reduction of Solid TiO2 in Molten CaCl2 (pages 428–432)

      Kai Jiang, Xiaohong Hu, Meng Ma, Dihua Wang, Guohong Qiu, Xianbo Jin and George Z. Chen

      Version of Record online: 12 DEC 2005 | DOI: 10.1002/anie.200502318

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      Speed up: In situ formation of perovskite phases (CaδTiOx, x/δ≥2) during electroreduction of porous TiO2 pellets to Ti metal in molten CaCl2 kinetically retards the process. Ex situ perovskitization of TiO2 with CaO (see picture) can prevent in situ perovskitization during electrolysis, thereby significantly increasing the electroreduction speed.

    16. CoII Chemistry of 2,6-Bis(2-pyridylcarbonyl)pyridine: An Icosanuclear Co Cluster Exhibiting Superparamagnetic Relaxation (pages 432–435)

      Athanassios K. Boudalis, Catherine P. Raptopoulou, Belén Abarca, Rafael Ballesteros, Mimoun Chadlaoui, Jean-Pierre Tuchagues and Aris Terzis

      Version of Record online: 12 DEC 2005 | DOI: 10.1002/anie.200502519

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      Giant clusters: Metal-assisted hydrolysis of 2,6-bis(2-pyridylcarbonyl)pyridine with Co(O2CMe)2⋅4 H2O in hot DMF yielded an icosanuclear CoII complex containing the triply deprotonated bis(gem-diol) form of the ligand and exhibiting superparamagnetic relaxation of its magnetization. The picture shows the central Co–O core of the complex (Co violet, O red).

    17. Designing Intermolecular Interactions between Halogenated Peripheries of Inorganic and Organic Molecules: Electrostatically Directed M[BOND]X⋅⋅⋅X′[BOND]C Halogen Bonds (pages 435–440)

      Guillermo Mínguez Espallargas, Lee Brammer and Paul Sherwood

      Version of Record online: 6 DEC 2005 | DOI: 10.1002/anie.200502586

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      Complementary electronic properties of inorganic and organic halogen species are exploited in the design of molecular networks that employ M[BOND]X⋅⋅⋅X′[BOND]C halogen bonds. The dominance of electrostatic effects in this type of interaction over other energy terms, such as charge transfer, is demonstrated by the study of a series of eight isostructural compounds (4-X′pyH)2[CoX4] (see picture; X=Cl, Cl/Br, Br, I; X′=Cl, Br).

    18. Unusual Structure and Reactivity of a Homoleptic “Super-Ate” Complex of Iron: Implications for Grignard Additions, Cross-Coupling Reactions, and the Kharasch Deconjugation (pages 440–444)

      Alois Fürstner, Helga Krause and Christian W. Lehmann

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502859

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      The additional molecule of methyllithium present in [(Me4Fe)(MeLi)][Li(OEt2)]2 (1), the first structurally characterized ate complex of FeII bearing only alkyl substituents without any further stabilizing ligands (see picture: Fe: magenta; Li: cyan; O: red; C and H: gray), is a particularly remarkable structural feature and contributes to the fascinating reactivity profile of 1 in the title reactions.

    19. Redox Behavior of Fe-Mo-O Catalysts Studied by Ultrarapid In Situ Diffraction (pages 445–448)

      S. D. M. Jacques, O. Leynaud, D. Strusevich, A. M. Beale, G. Sankar, C. M. Martin and P. Barnes

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502897

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      Hot air in a hurry: An industrial Fe-Mo-O catalyst, used in the production of formaldehyde has been studied under redox conditions using rapid in situ powder diffraction studies (see contour image). Surprisingly, the oxidation step is fastest as it is completed within 15 s at 472 °C.

    20. Direct Phenol Synthesis by Selective Oxidation of Benzene with Molecular Oxygen on an Interstitial-N/Re Cluster/Zeolite Catalyst (pages 448–452)

      Rajaram Bal, Mizuki Tada, Takehiko Sasaki and Yasuhiro Iwasawa

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502940

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      Remarkable selectivity (88 % in the steady-state reaction and 94 % in the pulse reaction) is observed in the direct synthesis of phenol from benzene with molecular oxygen over a Re/zeolite catalyst prepared by chemical-vapor deposition. The novel interstitial-N/Re clusters are formed with NH3 and are essential for the activity in the selective oxidation reaction.

    21. A Rhodium Complex with One Rh⋅⋅⋅C[BOND]C and One Rh⋅⋅⋅H[BOND]C Agostic Bond (pages 452–456)

      Simon K. Brayshaw, Jennifer C. Green, Gabriele Kociok-Köhn, Emma L. Sceats and Andrew S. Weller

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200503036

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      Hidden qualities: [Rh(PiPr3)(C14H16)][BArF4] (1; see picture of the cation; P violet, Rh olive green), which was synthesized by treatment of [RhCl(nbd)(PiPr3)] with Na[BArF4] (BArF4=B{C6H3(CF3)2}4) and norbornadiene (nbd) in fluorobenzene, contains an organic fragment derived from Binor-S as well as agostic Rh⋅⋅⋅CC and Rh⋅⋅⋅HC interactions. In solution, 1 undergoes rapid, reversible C[BOND]C activation/reductive elimination.

    22. Cholesterol-Aided Supramolecular Control over Chromophore Packing: Twisted and Coiled Helices with Distinct Optical, Chiroptical, and Morphological Features (pages 456–460)

      Ayyappanpillai Ajayaghosh, Chakkooth Vijayakumar, Reji Varghese and Subi Jacob George

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200503258

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      Good cholesterol: Oligo(p-phenylenevinylene)s (OPVs) that are mono- or disubstituted with cholesterol moieties form pseudo-J and pseudo-H aggregates, respectively (see picture), which lead to coiled and twisted helical structures with distinct optical, chiroptical, and morphological properties.

    23. “Gating” the Pores of a Metal Oxide Based Capsule: After Initial Cation Uptake Subsequent Cations Are Found Hydrated and Supramolecularly Fixed above the Pores (pages 460–465)

      Achim Müller, Yunshan Zhou, Hartmut Bögge, Marc Schmidtmann, Tamoghna Mitra, Erhard T. K. Haupt and Alois Berkle

      Version of Record online: 9 DEC 2005 | DOI: 10.1002/anie.200501994

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      Artificial cells: A polyoxomolybdate capsule, in which the cavity is linked to surface pores by channels, can take up Pr3+ ions. Each uptake reduces the negative charge on the capsule so that eventually no more Pr3+ ions enter the capsule, instead they remain bound on the surface (see structure: external hydrated Pr3+ green polyhedra, encapsulated Pr3+ light green, Mo blue, O red, SO42− yellow). This process models voltage gating of the ion channels of cells.

    24. Unsaturated Fatty Alcohol Derivatives as a Source of Substituted Allylzirconocene (pages 465–468)

      Nicka Chinkov, Anat Levin and Ilan Marek

      Version of Record online: 12 DEC 2005 | DOI: 10.1002/anie.200501946

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      From A to Z: Allylzirconocenes have been easily prepared in a one-pot procedure through a tandem allylic C[BOND]H activation–β-elimination reaction from unsaturated fatty alcohol and ether starting materials (see scheme). The reaction proceeds rapidly under mild condition and is insensitive to the length of the carbon tether between the double bond and the alcohol moiety.

    25. The Chemical Synthesis of Bioactive Glycosylphosphatidylinositols from Trypanosoma cruzi Containing an Unsaturated Fatty Acid in the Lipid (pages 468–474)

      Dmitry V. Yashunsky, Vladimir S. Borodkin, Michael A. J. Ferguson and Andrei V. Nikolaev

      Version of Record online: 8 DEC 2005 | DOI: 10.1002/anie.200502779

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      Protection strategy: Glycosylphosphatidylinositols (GPIs) from the Trypanosoma cruzi parasite (a causative agent of Chagas' disease) that contain an unsaturated fatty acid in the lipid moiety (see partial structure of 1, R=(CH2)7CH[DOUBLE BOND]CH(CH2)7CH3, and 2, R=(CH2)7CH[DOUBLE BOND]CHCH2CH[DOUBLE BOND]CH(CH2)4CH3) were prepared by a strategy that employs non-benzyl-type protecting groups. The synthetic GPIs show similar biological activity to their natural counterparts.

    26. Formation of Iridabenzenes by Coupling of Iridacyclopentadienes and Alkenes (pages 474–477)

      Eleuterio Álvarez, Margarita Paneque, Manuel L. Poveda and Nuria Rendón

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502437

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      A new synthesis of iridabenzene species involves the coupling of MeCH[DOUBLE BOND]CH2 with iridacycles 1 and 2. Surprisingly, the structure of the coupling product of the iridacyclopentadienes with propene (3 or 4) is highly susceptible to the nature of the substituents in the starting metallacycle.

    27. Efficient Solid-Phase Lipopeptide Synthesis Employing the Ellman Sulfonamide Linker (pages 477–481)

      Jose M. Palomo, Maria Lumbierres and Herbert Waldmann

      Version of Record online: 6 DEC 2005 | DOI: 10.1002/anie.200503298

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      Anchored down: Long lipopeptides (up to 26 amino acids) that carry multiple sensitive lipid residues as well as different reporter groups and tags can be synthesized efficiently by employing the Ellman sulfonamide linker as an anchoring group to the solid support (SPPS=solid-phase peptide synthesis).

    28. Convenient and Efficient Pd-Catalyzed Regioselective Oxyfunctionalization of Terminal Olefins by Using Molecular Oxygen as Sole Reoxidant (pages 481–485)

      Takato Mitsudome, Takuya Umetani, Naoya Nosaka, Kohsuke Mori, Tomoo Mizugaki, Kohki Ebitani and Kiyotomi Kaneda

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502886

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      Just the one: The combination of palladium dichloride and N,N-dimethylacetamide (DMA) constitutes a highly efficient and reusable catalytic system, which uses molecular oxygen as the sole reoxidant for liquid-phase Wacker oxidation and acetoxylation of terminal olefins to the corresponding methyl ketones and linear allylic acetates, respectively (see scheme).

    29. Cleavage of the C[TRIPLE BOND]N Bond on a Triruthenium Cluster: Synthesis and Structure of a Triruthenium Complex Containing a μ3-Nitrido Ligand (pages 485–488)

      Takashi Kawashima, Toshiro Takao and Hiroharu Suzuki

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200503267

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      Broken bonds: The reaction of [(Cp*Ru)3(μ-H)33-H)2] (1, Cp*=η5-C5Me5) with an equimolar amount of benzonitrile yields the μ3-nitrido-μ3-allyl complex 2 as a result of the C[TRIPLE BOND]N bond cleavage (see scheme). The C[TRIPLE BOND]N bond cleavage proceeds through the formation of μ3(⊥)-iminoacyl complex [(Cp*Ru)3322(⊥)-PhCNH)(μ-H)2].

    30. Ir-Catalyzed Borylation of C[BOND]H Bonds in N-Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters (pages 489–491)

      Ibraheem A. I. Mkhalid, David N. Coventry, David Albesa-Jove, Andrei S. Batsanov, Judith A. K. Howard, Robin N. Perutz and Todd B. Marder

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200503047

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      Blocking the way: Substitution at the 2-position in pyridines and other N-heterocycles blocks N-coordination to an Ir center. This steric hindrance provides a substrate-design criterion that allows the Ir-catalyzed borylation of C[BOND]H bonds, which can be followed by Suzuki–Miyaura cross-coupling in a one-pot reaction (see scheme; B2pin2=bis(pinacolato-O,O′)diboron, dtbpy=4,4′-tBu2-2,2′-bipyridine).

    31. Reactions of Nitrogen Oxides with Heme Models: Spectral Characterization of an Elusive Five-Coordinate FeIII(porphyrin) Nitrito Intermediate (pages 492–496)

      Tigran S. Kurtikyan and Peter C. Ford

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200502409

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      The famous five: The elusive five-coordinate nitrito complexes [FeIII(por)(ONO)] (por=meso-tetraphenylporphyrinato dianion or meso-tetra-p-tolylporphyrinato dianion) have been obtained by interaction of low-pressure NO2 with sublimed layers of [FeII(por)]. Spectral data confirm that the NO2 ligand prefers to bind through O coordination but adopts the N-bonded configuration when the second axial site is occupied (R=Ph, p-tolyl).

    32. Soluble Lanthanide Salts (LnCl3⋅2 LiCl) for the Improved Addition of Organomagnesium Reagents to Carbonyl Compounds (pages 497–500)

      Arkady Krasovskiy, Felix Kopp and Paul Knochel

      Version of Record online: 5 JAN 2006 | DOI: 10.1002/anie.200502485

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      Easy-to-prepare solutions of LnCl3⋅2 LiCl (Ln=La, Ce, Nd) (0.3–0.5 M in THF) are a unique source of soluble lanthanide salts with versatile applications in organic synthesis. These salts can serve as promoters or catalysts for the addition of organometallic compounds to sterically hindered, enolizable or α,β-unsaturated ketones or imines.

    33. Crown Ether–Gramicidin Hybrid Ion Channels: Dehydration-Assisted Ion Selectivity (pages 501–504)

      Jochen R. Pfeifer, Philipp Reiß and Ulrich Koert

      Version of Record online: 8 DEC 2005 | DOI: 10.1002/anie.200502570

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      Predictable ion selectivity is a major goal for the use of synthetic channels in biological systems. Gramicidin A (gA) is a suitable lead structure for the design of such channels. The crown ether–gA hybrid structure shown forms ion channels with a higher ion selectivity for K+ than for Cs+.

    34. Nanohybrids Composed of Quantum Dots and Cytochrome P450 as Photocatalysts (pages 504–507)

      Binil Itty Ipe and Christof M. Niemeyer

      Version of Record online: 19 DEC 2005 | DOI: 10.1002/anie.200503084

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      Synthesis with light: CdS quantum dots (QDs) generate superoxide and hydroxyl radicals upon UV irradiation in aqueous solution. The radicals are used for activating P450BSβ enzymes attached at the QD surface, effecting the catalytic transformation of myristic acid into α- and β-hydroxymyristic acid (see picture, R=(CH2)10CH3).

    35. A Small-Molecule FRET Probe To Monitor Phospholipase A2 Activity in Cells and Organisms (pages 508–512)

      Oliver Wichmann, Jochen Wittbrodt and Carsten Schultz

      Version of Record online: 2 DEC 2005 | DOI: 10.1002/anie.200500751

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      Watching live: The FRET reporter PENN/SATE (see picture; FRET=fluorescence resonance energy transfer) is membrane permeant and enters cells and small organisms by using a prodrug approach. Once inside cells the reporter is cleaved by phospholipases, which results in a 30-fold change in the emission ratio

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