Angewandte Chemie International Edition

Cover image for Vol. 46 Issue 14

March 26, 2007

Volume 46, Issue 14

Pages 2333–2543

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
    12. Preview
    1. Cover Picture: Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides and Oligodipeptoids Tagged with Triazines as Recognition Elements / Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides Tagged with 2,4-Disubstituted 5-Aminopyrimidines as Recognition Elements (Angew. Chem. Int. Ed. 14/2007) (page 2333)

      Gopi Kumar Mittapalli, Kondreddi Ravinder Reddy, Hui Xiong, Omar Munoz, Bo Han, Francesco De Riccardis, Ramanarayanan Krishnamurthy, Albert Eschenmoser, Yazmin M. Osornio and Miguel A. Guerrero

      Version of Record online: 16 MAR 2007 | DOI: 10.1002/anie.200790050

      2,4-Dioxo- and 2,4-diamino derivatives of the 5-aminopyrimidine nucleus, which are attached to an oligodipeptide backbone, display inverse base-pairing strengths with complementary DNA and RNA compared to the corresponding 2,4-diamino- and 2,4-dioxotriazine derivatives. In their Communications on pages 2470 and 2478 ff., R. Krishnamurthy, A. Eschenmoser, and co-workers point to a remarkable correlation between pairing strength and ΔpKa values of pairs of complementary bases.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. Inside Cover: Multiplication of Human Natural Killer Cells by Nanosized Phosphonate-Capped Dendrimers (Angew. Chem. Int. Ed. 14/2007) (page 2334)

      Laurent Griffe, Mary Poupot, Patrice Marchand, Alexandrine Maraval, Cédric-Olivier Turrin, Olivier Rolland, Pascal Métivier, Gérard Bacquet, Jean-Jacques Fournié, Anne-Marie Caminade, Rémy Poupot and Jean-Pierre Majoral

      Version of Record online: 16 MAR 2007 | DOI: 10.1002/anie.200790051

      Human peripheral blood mononuclear cells (white blood cells) cultured in the presence of dendrimers capped with phosphonate groups reveal a selective multiplication of natural killer (NK) cells. In their Communication on page 2523 ff., A.-M. Caminade, R. Poupot, J.-P. Majoral, and co-workers describe the synthesis of various phosphazene dendrimers and their effect on NK cells, which play a key role in anticancer immunity. The picture shows a fluorescence microscopy image of a NK cell (red) engaged with target cancer cells (green).

  3. Graphical Abstract

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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
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    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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  4. Corrigenda

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigenda
    6. News
    7. Book Reviews
    8. Highlight
    9. Minireview
    10. Review
    11. Communications
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    1. You have free access to this content
      Total Synthesis of Tubulysin U and V (pages 2347–2348)

      Alexander Dömling, Barbara Beck, Uwe Eichelberger, Sukumar Sakamuri, Sanjay Menon, Quin-Zene Chen, Yingchun Lu and Ludger A. Wessjohann

      Version of Record online: 16 MAR 2007 | DOI: 10.1002/anie.200790053

      This article corrects:

      Total Synthesis of Tubulysin U and V1

      Vol. 45, Issue 43, 7235–7239, Version of Record online: 2 OCT 2006

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  5. News

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    4. Graphical Abstract
    5. Corrigenda
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    9. Minireview
    10. Review
    11. Communications
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  6. Book Reviews

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    4. Graphical Abstract
    5. Corrigenda
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  7. Highlight

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    1. Looking Beyond the RNA Structural Neighborhood for Potentially Primordial Genetic Systems (pages 2354–2356)

      John D. Sutherland

      Version of Record online: 7 FEB 2007 | DOI: 10.1002/anie.200604374

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      A world of difference: The search for processes in which organic matter may be brought to life through self-organization is key in prebiotic chemistry. An experimental exploration of potentially primordial information-carrying oligomers differing from nucleic acids in both backbone and recognition elements is highlighted.

  8. Minireview

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    1. Alcohols as Electrophiles in C[BOND]C Bond-Forming Reactions: The Hydrogen Autotransfer Process (pages 2358–2364)

      Gabriela Guillena, Diego J. Ramón and Miguel Yus

      Version of Record online: 25 JAN 2007 | DOI: 10.1002/anie.200603794

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      . ‥ something new, something borrowed: The hydrogen autotransfer (borrowing) process involves a hydrogen abstraction/C[BOND]C coupling/hydrogen capture sequence for the alkylation of nucleophiles using primary alcohols as the source of electrophile (see scheme). The sequence proceeds with high chemical yields and atom efficiencies, with water as the only formal waste material produced.

  9. Review

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    1. Supramolecular Chemistry in Water (pages 2366–2393)

      Gennady V. Oshovsky, David N. Reinhoudt and Willem Verboom

      Version of Record online: 16 MAR 2007 | DOI: 10.1002/anie.200602815

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      Caught in the act: Supramolecular chemistry in aqueous media is not as violent as depicted in the scheme. However, as in natural aggregation processes, strongly bonded artificial host–guest complexes are formed in the presence of competing, polar solvents. There are numerous examples that illustrate the principles involved in the formation of the complex and the self-assembly events.

  10. Communications

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    1. A Hydrogen-Bonded Hexameric Nanotoroidal Assembly (pages 2394–2397)

      Robert M. McKinlay and Jerry L. Atwood

      Version of Record online: 21 FEB 2007 | DOI: 10.1002/anie.200604453

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      Mmm, doughnuts! Six calix[4]arene molecules self-assemble into a large hexameric torus-shaped structure through hydrogen bonds (see picture; Br yellow, O red, C gray, H white). The doughnut assembly shows a noteworthy structural similarity to cucurbit[6]uril in the solid state and therefore may be viewed as a noncovalent analogue.

    2. DNA-Based Carbohydrate Biochips: A Platform for Surface Glyco-Engineering (pages 2398–2402)

      Yann Chevolot, Camille Bouillon, Sébastien Vidal, François Morvan, Albert Meyer, Jean-Pierre Cloarec, Anne Jochum, Jean-Pierre Praly, Jean-Jacques Vasseur and Eliane Souteyrand

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604955

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      When the chips are down: A glycoarray consisting of oligonucleotide/carbohydrate conjugates hybridized onto a DNA chip can be used for the immobilization of oligosaccharides at extremely low concentrations (1 μM). With lectin, the lower detection limit of the device was 2–20 nm. The relative surface density of the conjugates was monitored by Cy3 fluorescence.

    3. Assessing the Terminal Glycosylation of a Glycoprotein by the Naked Eye (pages 2403–2407)

      Mads D. Sørensen, Rita Martins and Ole Hindsgaul

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604936

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      Lookin' for Gals: Treatment of a glycoprotein with β-galactosidase releases terminal galactose (Gal) that is captured on hydroxylaminated glass beads. The novel red fluorescent reagent TMR-B binds to the immobilized Gal rendering the beads bright red with the color intensity in proportion to the amount of captured Gal. Gln: GlcNAc, M: Man, SA: sialic acid, TMR: tetramethylrhodamine.

    4. Towards Biological Supramolecular Chemistry: A Variety of Pocket-Templated, Individual Metal Oxide Cluster Nucleations in the Cavity of a Mo/W-Storage Protein (pages 2408–2413)

      Jörg Schemberg, Klaus Schneider, Ulrike Demmer, Eberhard Warkentin, Achim Müller and Ulrich Ermler

      Version of Record online: 16 FEB 2007 | DOI: 10.1002/anie.200604858

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      Create and protect: The cavity shell of a molybdenum/tungsten-storage protein acts as a polytopic host for several types of polyoxotungstate guests, which occur as individual clusters (one shown: yellow W, red O, ribbons protein) that are noncovalently or weakly bonded to the host. The formation of the guests is templated by the specific functionalities of the protein pockets.

    5. One-Step Patterning of Aligned Nanowire Arrays by Programmed Dip Coating (pages 2414–2417)

      Jiaxing Huang, Rong Fan, Stephen Connor and Peidong Yang

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604789

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      Dip, stick, slip: Dip coating, a widely used industrial process for making thin films, is used to align and position nanowires by means of the stick–slip motion of the solvent meniscus. Nanowire arrays with predefined spacing can be readily “printed” on a large substrate with tunable wire density (see picture), thus providing a facile method for producing nanowire-based devices.

    6. Blue-Emitting Heteroleptic Iridium(III) Complexes Suitable for High-Efficiency Phosphorescent OLEDs (pages 2418–2421)

      Cheng-Han Yang, Yi-Ming Cheng, Yun Chi, Chia-Jung Hsu, Fu-Chuan Fang, Ken-Tsung Wong, Pi-Tai Chou, Chih-Hao Chang, Ming-Han Tsai and Chung-Chih Wu

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604733

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      Dyed-in-the-wool true blue: True-blue phosphorescent organic light-emitting diodes are fabricated by using an IrIII dopant (see picture; gray C; blue N; red Ir; green F). The Ir complex has an enhanced metal-to-ligand charge-transfer contribution, hence a shortened radiative lifetime in the excited state. The maximum external quantum efficiency of the fabricated device is 8.5 % and the main emission is around 450 nm.

    7. A Nickel(II) Gold(I) D-Penicillaminate Coordination System with Multiple Switching in Color, Magnetism, and Chirality (pages 2422–2425)

      Mai Taguchi, Asako Igashira-Kamiyama, Takashi Kajiwara and Takumi Konno

      Version of Record online: 19 FEB 2007 | DOI: 10.1002/anie.200604728

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      Red, blue, and green: A red NiIIAuI complex with a low-spin square-planar NiN2S2 configuration can be converted into a green high-spin octahedral NiO3S3 complex by lowering the pH (see scheme; pH change: red arrows). Increasing the Ni/Au ratio (Ni/Au change: blue arrows) gives a light blue octahedral NiN2O2S2 complex; increasing the pH or decreasing the Ni/Au ratio gives a blue octahedral NiN3S3 configuration.

    8. Self-Assembly of Methylzinc–Polyethylene Glycol Amphiphiles and Their Application to Materials Synthesis (pages 2426–2430)

      Sebastian Polarz, Romy Regenspurger and Jürgen Hartmann

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200602262

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      A new kind of amphiphiles containing an organometallic headgroup, an alkyl zinc alkoxide, self-assembles to form [MeZnOPEGn] gel (PEG: polyethylene glycol; n=400; see picture, left), which in turn serves as a precursor to afford nanoporous ZnO (right).

    9. Transition of Cationic Dipeptide Nanotubes into Vesicles and Oligonucleotide Delivery (pages 2431–2434)

      Xuehai Yan, Qiang He, Kewei Wang, Li Duan, Yue Cui and Junbai Li

      Version of Record online: 28 FEB 2007 | DOI: 10.1002/anie.200603387

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      Password?—Vesicle! A cationic dipeptide can self-assemble into nanotubes at physiological pH values. Such self-assembled cationic dipeptide nanotubes (CDPNTs) are able to convert into vesicles spontaneously upon dispersion dilution and thus carry single-stranded DNA into HeLa cells across the biomembrane (see picture).

    10. Multicomponent Cylindrical Assemblies Driven by Amidinium–Carboxylate Salt-Bridge Formation (pages 2435–2439)

      Hiroshi Katagiri, Yoshie Tanaka, Yoshio Furusho and Eiji Yashima

      Version of Record online: 19 FEB 2007 | DOI: 10.1002/anie.200603921

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      An unexpected twist: Three chiral amidine-functionalized strands and two benzenetricarboxylic acid molecules self-assemble into a 3:2 cylindrical complex with controlled helicity through amidinium–carboxylate salt-bridge formation. A related 4:2 cylindrical complex composed of two zinc porphyrin units and four chiral strands twists into one direction upon encapsulation of 4,4′-bipyridine through coordination to the zinc centers (see picture).

    11. Solvent-Reversible Poration in Ionic Liquid Copolymers (pages 2440–2443)

      Feng Yan and John Texter

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604127

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      An open and closed case: Polymerization of microemulsions stabilized by surfactants based on ionic liquids leads to cross-linked polymer gels which can be transformed into porous polymers by anion exchange of the ionic liquid moiety. These porous polymers can be converted back into polymer gels by immersion in organic solvents. Subsequent immersion of these gels in water then affords the porous polymers once more (see scheme).

    12. The Search for the Species with the Highest Coordination Number (pages 2444–2447)

      Andreas Hermann, Matthias Lein and Peter Schwerdtfeger

      Version of Record online: 21 FEB 2007 | DOI: 10.1002/anie.200604148

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      The Gregory–Newton problem of kissing hard spheres transferred to chemistry can be formulated as: what is the highest possible coordination number for an atom? First-principles quantum chemical simulations of the Pb2+–He interactions revealed a remarkably stable PbHe152+ with all He atoms in the first coordination sphere. The picture shows the HOMO of this ion.

    13. Synthesis of Silica-Coated Semiconductor and Magnetic Quantum Dots and Their Use in the Imaging of Live Cells (pages 2448–2452)

      S. Tamil Selvan, Pranab K. Patra, Chung Yen Ang and Jackie Y. Ying

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604245

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      Bifunctional nanocomposites comprising semiconductor and magnetic nanoparticles are of interest in biological applications for biolabeling, bioimaging, and cell separation. To this end, a nanocomposite system that consists of Fe2O3 magnetic nanoparticles and CdSe quantum dots and which exhibits superparamagnetism and tunable emission properties was prepared and used to label different live cell membranes (see picture).

    14. Light-Induced Reversible Formation of Polymeric Micelles (pages 2453–2457)

      Hyung-il Lee, Wei Wu, Jung Kwon Oh, Laura Mueller, Gizelle Sherwood, Linda Peteanu, Tomasz Kowalewski and Krzysztof Matyjaszewski

      Version of Record online: 20 FEB 2007 | DOI: 10.1002/anie.200604278

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      Reversible disruption and regeneration of block-copolymer micelles has been achieved by UV and visible-light irradiation and studied by atomic force microscopy (see picture). A hydrophobic dye encapsulated in the original polymeric micelles was released after UV irradiation. Remarkably, some of the released hydrophobic dye was re-encapsulated on regeneration of the micelles by irradiation with visible light.

    15. A Mesh-Adjustable Molecular Sieve for General Use in Gas Separation (pages 2458–2462)

      Shengqian Ma, Daofeng Sun, Xi-Sen Wang and Hong-Cai Zhou

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604353

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      Storage space: A mesh-adjustable molecular sieve (MAMS), based on a graphitic metal–organic framework obtained by the packing of trilayers, has been prepared and characterized. The MAMS can separate any two or more gases with kinetic diameters between 2.9 and 5.0 Å through temperature-controlled molecular gating to hydrophobic gas-storage chambers (see picture).

    16. Chirality-Controlled Formation of β-Turn Secondary Structures in Short Peptide Chains: Gas-Phase Experiment versus Quantum Chemistry (pages 2463–2466)

      Valérie Brenner, François Piuzzi, Iliana Dimicoli, Benjamin Tardivel and Michel Mons

      Version of Record online: 21 FEB 2007 | DOI: 10.1002/anie.200604416

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      Spontaneous formation of secondary structures (i.e., β-turns) by isolated capped dipeptides in the gas phase was investigated by laser spectroscopy following supersonic expansion, and by quantum chemical calculations. The two most stable calculated β-turn structures I and II′ of one of the dipeptides were related to species B and B′, respectively, identified in the near-UV spectrum (see figure).

    17. Two-Photon Uncaging with the Efficient 3,5-Dibromo-2,4-dihydroxycinnamic Caging Group (pages 2467–2469)

      Nathalie Gagey, Pierre Neveu and Ludovic Jullien

      Version of Record online: 20 FEB 2007 | DOI: 10.1002/anie.200604598

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      An optical syringe for targeted delivery of a substrate in vivo has been developed on the basis of the 3,5-dibromo-2,4-dihydroxycinnamic caging group. Two-photon excitation of the caged compound uncages the substrate (ethanol in the scheme) and forms a coumarin whose fluorescence allows the concentration of released substrate to be quantified. Single-cell release can be achieved with a focused laser (shown schematically for a zebrafish embryo).

    18. Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides and Oligodipeptoids Tagged with Triazines as Recognition Elements (pages 2470–2477)

      Gopi Kumar Mittapalli, Kondreddi Ravinder Reddy, Hui Xiong, Omar Munoz, Bo Han, Francesco De Riccardis, Ramanarayanan Krishnamurthy and Albert Eschenmoser

      Version of Record online: 17 NOV 2006 | DOI: 10.1002/anie.200603207

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      Pairing up: Oligodipeptide, oligodeoxydipeptide, or oligodipeptoid backbones tagged with the 2,4-diaminotriazine nucleus pair strongly with complementary DNA and RNA. This is in sharp contrast with the behavior of the 2,4-dioxotriazine nucleus, which does not act as a nucleobase in these systems.

    19. Mapping the Landscape of Potentially Primordial Informational Oligomers: Oligodipeptides Tagged with 2,4-Disubstituted 5-Aminopyrimidines as Recognition Elements (pages 2478–2484)

      Gopi Kumar Mittapalli, Yazmin M. Osornio, Miguel A. Guerrero, Kondreddi Ravinder Reddy, Ramanarayanan Krishnamurthy and Albert Eschenmoser

      Version of Record online: 17 NOV 2006 | DOI: 10.1002/anie.200603209

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      Bit different: 2,4-Dioxo- and 2,4-diamino-5-aminopyrimidine nuclei attached to an oligodipeptide backbone display a disparity in their base-pairing strength which is opposite to that shown by corresponding triazines. This behavior points to a remarkable correlation between pairing strength and ΔpKa values of pairs of complementary bases.

    20. Modulating the Reactivity of α-Isocyanoacetates: Multicomponent Synthesis of 5-Methoxyoxazoles and Furopyrrolones (pages 2485–2488)

      Damien Bonne, Mouloud Dekhane and Jieping Zhu

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200605005

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      A simple approach to complexity: The reactivity pattern of α-isocyanoacetates can be tuned by modulating the acidity of the α C[BOND]H bond(s) against the nucleophilicity of the conjugate base. The unique reactivity of the α-(p-nitrophenyl)-α-isocyanoacetate 1 was exploited in a three-component synthesis of 5-methoxyoxazoles 2 and four-component synthesis of furopyrrolones 3. R1,R2,R3=alkyl, aryl, benzyl; R4=aryl.

    21. Stereoselective Difluoromethylenation Using Me3SiCF2SPh: Synthesis of Chiral 2,4-Disubstituted 3,3-Difluoropyrrolidines (pages 2489–2492)

      Ya Li and Jinbo Hu

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604783

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      A radical synthon: Nucleophilic (phenylthio)difluoromethylation of (R)-N-(tert-butylsulfinyl)imines with 1, a difluoromethylene radical anion equivalent, afforded the corresponding products in good yields and with high diastereoselectivity (d.r.≥98:2). The resulting PhSCF2-containing sulfinamides can be further transformed into chiral 2,4-trans-disubstituted 3,3-difluoropyrrolidines through an intramolecular radical cyclization methodology.

    22. Chemical Variation of Natural-Product-Like Scaffolds: Design, Synthesis, and Biological Activity of Fused Bicyclic Acetal Derivatives (pages 2493–2496)

      Lech-Gustav Milroy, Giovanna Zinzalla, Giuseppe Prencipe, Patrick Michel, Steven V. Ley, Mekala Gunaratnam, Monica Beltran and Stephen Neidle

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604688

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      A clue from nature: Can the bicyclic acetal framework, which is present in many structurally diverse biologically active natural products, be considered a privileged scaffold? Scaffolds with this framework were synthesized and elaborated to give a collection of small-molecule derivatives as potential orally bioavailable lead compounds, and preliminary biological tests gave encouraging results.

    23. Structural Studies of Gold(I, II, and III) Compounds with Pentafluorophenyl and Tetrahydrothiophene Ligands (pages 2497–2500)

      Jacorien Coetzee, William F. Gabrielli, Karolien Coetzee, Oliver Schuster, Stefan D. Nogai, Stephanie Cronje and Helgard G. Raubenheimer

      Version of Record online: 28 FEB 2007 | DOI: 10.1002/anie.200604592

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      A golden opportunity was seized to prepare an unbridged, dinucleur gold(II) compound, [Au2(C6F5)4(tht)2] (tht=tetrahydrothiophene), without any stabilizing chelating ligands (see picture; Au orange, S yellow, F green, C black) and to crystallographically characterize the gold(I) and gold(III) complexes participating in this conversion. A unique ligand scrambling of the latter gold(III) compound occurs in solution.

    24. Enzymatic Synthesis of Phosphonomethyl Oligonucleotides by Therminator Polymerase (pages 2501–2504)

      Marleen Renders, Gert Emmerechts, Jef Rozenski, Marcela Krecmerová, Antonin Holý and Piet Herdewijn

      Version of Record online: 20 FEB 2007 | DOI: 10.1002/anie.200603435

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      Therminator is the hero when it comes to the enzymatic production of phosphonomethyl–threosyl oligonucleotides with a non-natural 3′–2′ linkage (see scheme). The ability of Therminator polymerase to catalyze the condensation of diphosphate derivatives of nucleosides to give modified oligomers promises to be quite general. Such oligonucleotides are useful tools in synthetic biology because of the innate stability of the phosphonate linkage.

    25. Direct and Stereoselective Synthesis of β-Linked 2,6-Deoxyoligosaccharides (pages 2505–2507)

      Hiroshi Tanaka, Atsushi Yoshizawa and Takashi Takahashi

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604031

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      Short and sweet: Glycosidation of 2-deoxyglycosyl imidates with I2 as shown in the scheme (Bn=benzyl, Bz=benzoyl, MS=molecular sieves) proceeds smoothly to provide the corresponding β-linked 2-deoxyglycosides in excellent yields and selectivity. This coupling method has been shown to be adaptable to the synthesis of various β-linked oligosaccharides containing 2,6-dideoxy- and 2,3,6-trideoxyglycosides.

    26. A Binol-Strapped Calix[4]pyrrole as a Model Chirogenic Receptor for the Enantioselective Recognition of Carboxylate Anions (pages 2508–2511)

      Hidekazu Miyaji, Seong-Jin Hong, Seung-Doo Jeong, Dae-Wi Yoon, Hee-Kyung Na, Jooyeon Hong, Sihyun Ham, Jonathan L. Sessler and Chang-Hee Lee

      Version of Record online: 19 FEB 2007 | DOI: 10.1002/anie.200604161

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      Binding straps: Chiral calix[4]pyrroles 1 bearing an (R)- or (S)-binol-derived strap on one side of the tetrapyrrolic core (see picture) were synthesized and characterized. The resulting systems bind selected chiral carboxylate anions (shown in red) with high affinity in acetonitrile while at the same time exhibiting enantiomeric discrimination. PB=2-phenylbutyrate.

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      A Well-Defined Hydrocarbon-Soluble Calcium Monofluoride, [{LCaF(thf)}2]: The Application of Soluble Calcium Derivatives for Surface Coating (pages 2512–2514)

      Sharanappa Nembenna, Herbert W. Roesky, Selvarajan Nagendran, Anja Hofmeister, Jörg Magull, Peter-J. Wilbrandt and Matthias Hahn

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604447

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      See-through coats: A hydrocarbonsoluble dimeric calcium monofluoride is prepared (see structure; green Ca, purple F, red O, blue N, orange C). This compound is a precursor for the preparation of thin layers of transparent CaF2 at room temperature by dip-coating.

    28. Light-Driven Conformational Switch of i-Motif DNA (pages 2515–2517)

      Huajie Liu, Yun Xu, Fengyu Li, Yang Yang, Wenxing Wang, Yanlin Song and Dongsheng Liu

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604589

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      Making the switch: A photoinduced DNA conformational switch between the i-motif and random-coil structures has been achieved by combination with a reversible photoirradiated pH-jump system (see picture; MGCB: malachite green carbinol base, MG: malachite green). Multiple cycling of this switch has also been demonstrated.

    29. Studies toward the Total Synthesis of Gambieric Acids A and C: Convergent Assembly of the Nonacyclic Polyether Skeleton (pages 2518–2522)

      Kazushi Sato and Makoto Sasaki

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604625

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      A solid approach to ethereal rings: Key features of a convergent synthesis of the nonacyclic polyether skeleton of gambieric acids A and C include the connection of the BCD and GHIJ ring systems by esterification, the construction of the E ring in the form of a lactone, a stereoselective allylation to establish the C26 stereocenter, and the formation of the F ring by ring-closing metathesis (see scheme; Bn=benzyl, NAP=2-naphthylmethyl).

    30. Multiplication of Human Natural Killer Cells by Nanosized Phosphonate-Capped Dendrimers (pages 2523–2526)

      Laurent Griffe, Mary Poupot, Patrice Marchand, Alexandrine Maraval, Cédric-Olivier Turrin, Olivier Rolland, Pascal Métivier, Gérard Bacquet, Jean-Jacques Fournié, Anne-Marie Caminade, Rémy Poupot and Jean-Pierre Majoral

      Version of Record online: 15 FEB 2007 | DOI: 10.1002/anie.200604651

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      Non-natural born killers: The addition of phosphorus-containing dendrimers capped with phosphonate end groups to cultures of human peripheral blood mononuclear cells (white blood cells) strongly stimulates the selective multiplication of functional natural killer (NK) cells (see picture), which play a key role in anticancer immunity. Both the generation of the dendrimer and the type of end groups are important criteria for the activity.

    31. Total Synthesis of Candicanoside A, a Potent Antitumor Saponin with a Rearranged Steroid Side Chain (pages 2527–2530)

      Pingping Tang and Biao Yu

      Version of Record online: 20 FEB 2007 | DOI: 10.1002/anie.200604761

      Thumbnail image of graphical abstract

      The fused-ring scaffold of candicanoside A (1), a potent antitumor agent with a unique differential pattern, has now been synthesized from inexpensive starting materials. Compound 1 has the potential to act as a lead compound for the synthesis of antitumor agents with a novel mode of action.

    32. Acylation of Electrophilic Olefins through Decatungstate-Photocatalyzed Activation of Aldehydes (pages 2531–2534)

      Silvia Esposti, Daniele Dondi, Maurizio Fagnoni and Angelo Albini

      Version of Record online: 23 FEB 2007 | DOI: 10.1002/anie.200604820

      Thumbnail image of graphical abstract

      With tungsten and lamp: Ketones were prepared by the photocatalytic generation of acyl radicals from aldehydes and trapping them with equimolar amounts of electrophilic alkenes. Photocatalysis with tetrabutylammonium decatungstate is effective also at low temperatures (−20 to −50 °C), thus minimizing radical decarbonylation and allowing acylation by highly substituted aldehydes. EWG=electron-withdrawing group.

    33. Palladium-Catalyzed, Sequential, Three-Component Cross-Coupling of Aryl Halides, Alkynes, and Arynes (pages 2535–2538)

      Zhijian Liu and Richard C. Larock

      Version of Record online: 27 FEB 2007 | DOI: 10.1002/anie.200604969

      Thumbnail image of graphical abstract

      Three's a crowd? Polycyclic aromatic hydrocarbons can be synthesized efficiently and in high yield using the first palladium-catalyzed, sequential, three-component coupling of alkynes and arynes with aryl halides (see scheme). This process appears to involve the catalytic, stepwise carbopalladation of an alkyne and an aryne to generate the three-component products.

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