ChemBioChem

Cover image for Vol. 10 Issue 11

July 20, 2009

Volume 10, Issue 11

Pages 1741–1903

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: Selective Detection of Phosphotyrosine in the Presence of Various Phosphate-Containing Biomolecules with the Aid of a Terbium(III) Complex (ChemBioChem 11/2009) (page 1741)

      Hiroki Akiba, Jun Sumaoka and Makoto Komiyama

      Version of Record online: 13 JUL 2009 | DOI: 10.1002/cbic.200990041

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      The cover picture shows the selective detection of phosphotyrosine by using a terbium(III) complex. This strategy is a combination of Tyr-targeted energy transfer and phosphate-directed interaction, as indicated in the upper part of the picture. The phosphorylation of Tyr can easily be detected by its luminescence, which is dependent upon energy transfer from the Tyr residue to the TbIII center. When Tyr is not phosphorylated, the interaction with the TbIII complex is weak. The lower part of the picture shows the high selectivity among various biomolecules, such as nonphosphorylated Tyr, phosphorylated Ser or Thr, and nucleic acid species. In their communication on p. 1773 ff, J. Sumaoka, M. Komiyama, et al. discuss their detection of Tyr phosphorylation in nucleic acid-containing solutions.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Inside Cover: Primary Steps of pH-Dependent Insulin Aggregation Kinetics are Governed by Conformational Flexibility (ChemBioChem 11/2009) (page 1742)

      Jürgen Haas, Esteban Vöhringer-Martinez, Andreas Bögehold, Dirk Matthes, Ulf Hensen, Avishay Pelah, Bernd Abel and Helmut Grubmüller

      Version of Record online: 13 JUL 2009 | DOI: 10.1002/cbic.200990042

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      The inside cover picture shows, on the left, the structure of peptide hormone insulin; titrable groups between pH 1 to 7 are highlighted. On the right, structural ensembles from atomistic simulations show that pH-induced protonation changes of insulin critically affect its conformational flexibility. From top to bottom the number of protonated sites was increased to match displayed pH values. For more information, see the article by H. Grubmüller et al. on p. 1816 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
  4. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
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    1. You have free access to this content
      The Molecular Basis of Inhibition of Golgi α-Mannosidase II by Mannostatin A (page 1751)

      Douglas A. Kuntz , Wei Zhong , Jun Guo, David R. Rose and Geert-Jan Boons

      Version of Record online: 13 JUL 2009 | DOI: 10.1002/cbic.200990044

      This article corrects:

      The Molecular Basis of Inhibition of Golgi α-Mannosidase II by Mannostatin A

      Vol. 10, Issue 2, 268–277, Version of Record online: 19 DEC 2008

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
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  6. Minireview

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
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    1. Complex Oxidation Chemistry in the Biosynthetic Pathways to Vancomycin/Teicoplanin Antibiotics (pages 1757–1764)

      Paul F. Widboom and Steven D. Bruner

      Version of Record online: 16 JUN 2009 | DOI: 10.1002/cbic.200900117

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      O2can do: Investigations into the machinery responsible for the biosynthesis of the vancomycin/teicoplanin family of antibiotics have uncovered multiple examples of novel enzyme chemistry. In particular, oxidation chemistry plays key roles in constructing the complex structures of the natural products. From biosynthesis of rare amino acids to the tailoring of the peptide product, diverse enzyme-catalyzed reactions are discussed with a focus on structure and chemical mechanism.

  7. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
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    1. How Can Folded Biopolymers and Synthetic Foldamers Recognize Each Other? (pages 1765–1767)

      Benoit Baptiste, Frédéric Godde and Ivan Huc

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/cbic.200900295

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      Getting to know you better: The structure-based design of synthetic α-helix-mimicking foldamers targeted to biopolymer surfaces is still in its infancy, but key steps are being made.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
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    1. NMR Spectroscopic Investigation of Early Events in IAPP Amyloid Fibril Formation (pages 1769–1772)

      Rajesh Mishra, Matthias Geyer and Roland Winter

      Version of Record online: 2 JUL 2009 | DOI: 10.1002/cbic.200900237

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      Real-time, residue-specific transition monitoring: IAPP forms amyloid fibrillar deposits in type II diabetes under pathological conditions. The initial events of IAPP fibril formation and the transition from soluble to insoluble, fibrillated IAPP can be monitored by kinetic NMR spectroscopy.

    2. Selective Detection of Phosphotyrosine in the Presence of Various Phosphate-Containing Biomolecules with the Aid of a Terbium(III) Complex (pages 1773–1776)

      Hiroki Akiba, Jun Sumaoka and Makoto Komiyama

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/cbic.200900227

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      Finding phosphotyrosine: Phosphotyrosine (either in its monomeric form or as a component of oligopeptides) was selectively detected by using luminescence in the presence of a specialized terbium(III) complex, without any signals from nonphosphorylated tyrosine, phosphoserine, phosphothreonine, nucleotides, or nucleic acids. Tyrosine phosphorylation could clearly be distinguished even in the presence of single-stranded RNA.

    3. Very Fast Product Release and Catalytic Turnover of DNA Photolyase (pages 1777–1780)

      Agathe Espagne, Martin Byrdin, Andre P. M. Eker and Klaus Brettel

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/cbic.200900328

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      Repair champion: The substrate binding and product release of the light-driven DNA repair enzyme photolyase were followed by a novel fluorescence approach. Unexpectedly, release of repaired nucleobases from the substrate binding pocket appears to be as fast as 50 μs. Moreover, catalytic turnover under strong light is limited by substrate binding and can be more than 100 times faster than previously reported.

    4. DNA Monofunctionalization of Quantum Dots (pages 1781–1783)

      Helen M. J. Carstairs, Kostas Lymperopoulos, Achillefs N. Kapanidis, Jonathan Bath and Andrew J. Turberfield

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/cbic.200900300

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      Dots as pure as the driven snow: A method to purify streptavidin-coated quantum dots functionalized with a single short DNA duplex from an inhomogeneous population is presented. A high percentage (∼86 %) of the monofunctionalized quantum dots present in the original sample are recovered. Hybridization of the attached DNA after purification is demonstrated.

    5. Synthesis of Light-Responsive Bridged Nucleic Acid and Changes in Affinity with Complementary ssRNA (pages 1784–1788)

      Kunihiko Morihiro, Tetsuya Kodama, Masaru Nishida, Takeshi Imanishi and Satoshi Obika

      Version of Record online: 2 JUL 2009 | DOI: 10.1002/cbic.200900241

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      Turn on the light: We have designed a light-responsive bridged nucleic acid (BNA) with a photolabile group at the bridged structure that can change its affinity for a complementary single-stranded RNA (ssRNA) in two stages. Oligonucleotides containing light-responsive BNA lose their binding affinity for complementary ssRNA upon photoirradiation, but this affinity can be restored by treatment with nucleophile.

    6. Solid-State NMR Studies of Adenosine 5′-Triphosphate Freeze-Trapped in the Nucleotide Site of Na,K-ATPase (pages 1789–1792)

      David A. Middleton, Eleri Hughes, Natalya U. Fedosova and Mikael Esmann

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/cbic.200900167

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      Freeze frame: The ubiquitous ion pump, Na,K-ATPase (NKA), was discovered over half a century ago, yet atomic details of the native substrate ATP in the nucleotide site remain unavailable. Here, we use low-temperature solid-state NMR spectroscopy to detect uniformly 13C-labelled ATP bound to NKA in membrane preparations. Freeze-trapping the complex prevents ATP hydrolysis and allows the detection of specific nucleotide–enzyme contacts.

    7. Development of a Fluorescent Peptide for the Detection of Vascular Endothelial Growth Factor (VEGF) (pages 1793–1795)

      Yoshio Suzuki and Kenji Yokoyama

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/cbic.200900190

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      Held down and lit up: We report a new fluorescence-based reagent for the detection and quantification of VEGF. The fluorescence intensity of the reagent increased upon binding to VEGF, as illustrated here. Immobilization of the reagent onto a plate facilitated the successful detection of VEGF in serum by using fluorescence spectrometry. This reagent is a good VEGF indicator and could find wide applications for the convenient detection of VEGF.

    8. A Cytotoxic Ruthenium Tris(Bipyridyl) Complex that Accumulates at Plasma Membranes (pages 1796–1800)

      Olivier Zava, Shaik M. Zakeeruddin, Christophe Danelon, Horst Vogel, Michael Grätzel and Paul J. Dyson

      Version of Record online: 25 JUN 2009 | DOI: 10.1002/cbic.200900013

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      Shine a light: A ruthenium tris(bipyridyl) complex that was originally designed as a photosensitizer for solar cells has been found to adhere to plasma membranes.

    9. New, Highly Active Nonbenzoquinone Geldanamycin Derivatives by Using Mutasynthesis (pages 1801–1805)

      Simone Eichner, Heinz G. Floss, Florenz Sasse and Andreas Kirschning

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/cbic.200900246

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      You are what you eat: The feeding of aromatic and heteroaromatic amino acids to an AHBA-blocked mutant of S. hygroscopicus yielded new analogues of the highly potent Hsp90 inhibitor geldanamycin. Except for a “pyridine”-geldanamycin derivative, all new compounds had strong antiproliferative activity (IC50 values in the nM range).

    10. Multivalent Manno-Glyconanoparticles Inhibit DC-SIGN-Mediated HIV-1 Trans-Infection of Human T Cells (pages 1806–1809)

      Olga Martínez-Ávila, Luis M. Bedoya, Marco Marradi, Caroline Clavel, José Alcamí and Soledad Penadés

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/cbic.200900294

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      Gold simplifies matters: Gold manno-glyconanoparticles displaying different densities of linear and branched mannose oligosaccharides acted as inhibitors of DC-SIGN-mediated HIV trans-infection of human activated peripheral blood mononuclear cells. Presentation of simple linear di-, tri-, and tetraoligosaccharides on the nanoclusters resulted in efficiencies similar to those observed for complex branched penta- and heptamannosides.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Precisely Programmed and Robust 2D Streptavidin Nanoarrays by Using Periodical Nanometer-Scale Wells Embedded in DNA Origami Assembly (pages 1811–1815)

      Akinori Kuzuya, Mayumi Kimura, Kentaro Numajiri, Naohiro Koshi, Toshiyuki Ohnishi, Fuminori Okada and Makoto Komiyama

      Version of Record online: 27 JUN 2009 | DOI: 10.1002/cbic.200900229

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      A new punched DNA origami assembly with periodic, nanometer-scale wells has been successfully designed and constructed. Punched origami assemblies allow for the arrangement of fully distinguishable nanometer-scale wells in two dimensions. Through modification of the wells with two biotins, exactly one streptavidin (SA) tetramer can be captured in any predetermined well in the complex.

    2. Primary Steps of pH-Dependent Insulin Aggregation Kinetics are Governed by Conformational Flexibility (pages 1816–1822)

      Jürgen Haas, Esteban Vöhringer-Martinez, Andreas Bögehold, Dirk Matthes, Ulf Hensen, Avishay Pelah, Bernd Abel and Helmut Grubmüller

      Version of Record online: 16 JUN 2009 | DOI: 10.1002/cbic.200900266

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      The role of entropy: The pH-induced protonation changes of titrable groups of insulin (see figure) affect its structural fluctuations, and thus the entropic contributions to free energies of transition states and, hence, kinetics. These interrelations were quantified for the primary steps of insulin aggregation. Through a combined mass spectrometry, atomic force spectroscopy, and molecular dynamics simulations study we have obtained structural information of putative aggregation rate-determining transition states.

    3. Translational Diffusion and Interaction of a Photoreceptor and Its Cognate Transducer Observed in Giant Unilamellar Vesicles by Using Dual-Focus FCS (pages 1823–1829)

      Jana Kriegsmann, Ingo Gregor, Iris von der Hocht , Johann Klare, Martin Engelhard, Jörg Enderlein and Jörg Fitter

      Version of Record online: 23 JUN 2009 | DOI: 10.1002/cbic.200900251

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      How low can you go? A photoreceptor (NpSRII) and its related transducer (NpHtrII) were incorporated into the lipid membrane of giant unilamellar vesicles (GUV). Intermolecular binding of both membrane proteins was estimated by measuring the lateral diffusion of fluorescently labelled proteins by using dual-focus fluorescence correlation spectroscopy (2fFCS).

    4. Influence of the Nucleophile on the Candida antarctica Lipase B-Catalysed Resolution of a Chiral Acyl Donor (pages 1830–1838)

      Eduardo García-Urdiales, Nicolás Ríos-Lombardía, Juan Mangas-Sánchez, Vicente Gotor-Fernández and Vicente Gotor

      Version of Record online: 2 JUL 2009 | DOI: 10.1002/cbic.200900204

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      The size does matter! The employment of a bulkier nucleophile than ammonia, such as benzyl amine, in the CALB-catalysed resolution of methyl (±)-3-hydroxy-pentanoate, causes this chiral acyl donor to bind in a more restrictive area of the binding site, as illustrated here. The increased number of contacts with the amino acids of the site improves the enantioselectivity by threefold.

    5. Potent Triple Helix Stabilization by 5′,3′-Modified Triplex-Forming Oligonucleotides (pages 1839–1851)

      Nouha Ben Gaied, Zhengyun Zhao, Simon R. Gerrard, Keith R. Fox and Tom Brown

      Version of Record online: 24 JUN 2009 | DOI: 10.1002/cbic.200900232

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      Make it a triple: Simple anthraquinone and pyrene analogues were attached to both the 5′ and 3′ termini of triplex-forming oligonucleotides (TFOs), as demonstrated in the figure. They strongly stabilized parallel triplexes and gave an increase in melting temperature of around 30 °C in comparison to unmodified TFOs.

    6. Modification with Organometallic Compounds Improves Crossing of the Blood–Brain Barrier of [Leu5]-Enkephalin Derivatives in an In Vitro Model System (pages 1852–1860)

      Antonio Pinto, Ulrich Hoffmanns, Melanie Ott, Gert Fricker and Nils Metzler-Nolte

      Version of Record online: 30 JUN 2009 | DOI: 10.1002/cbic.200900157

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      Metals for lipophilicity: Enkephalin peptides are thought to be suitable vectors for passage through the blood–brain barrier (BBB). Here, we introduce derivatives of enkephalin that have been labeled with organometallic compounds, in particular with metallocenes such as ferrocene carboxylic acid. The introduction of the organometallic moiety enhances the uptake into cells and the permeation coefficient of [Leu5]-enkephalin in an in vitro model.

    7. New Structural Variants of Homoserine Lactones in Bacteria (pages 1861–1868)

      Verena Thiel, Brigitte Kunze, Pankaj Verma, Irene Wagner-Döbler and Stefan Schulz

      Version of Record online: 16 JUN 2009 | DOI: 10.1002/cbic.200900126

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      It's good to talk: N-Acylhomoserine lactones (AHLs) carrying a methyl branch in the side chain (1) occur in the bacterium Aeromonas culicicola, while in Jannaschia helgolandensis, which is a marine bacterium of the Roseobacter clade, a doubly unsaturated AHL (2) occurs. The varying response of these AHLs in sensor systems illustrates the need for detailed analysis of structure and biological response in order to understand chemical communication in bacteria.

    8. The Synechocystis sp. PCC6803 Sfp-Type Phosphopantetheinyl Transferase Does Not Possess Characteristic Broad-Range Activity (pages 1869–1877)

      Alexandra A. Roberts, Janine N. Copp, Mohamed A. Marahiel and Brett A. Neilan

      Version of Record online: 27 JUN 2009 | DOI: 10.1002/cbic.200900095

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      All fat, no flavour: Why would the cyanobacterium Synechocystis sp. PCC6803 possess a broad-range activity Sfp-type phosphopantetheinyl transferase (Sppt) when it does not synthesise NRPS/PKS natural products? This study reveals that Sppt is indeed a Sfp-type PPT, but with an uncharacteristic narrow specificity and poor catalytic activity. Accumulated mutations in the CoA/Mg2+ binding site might restrict the enzyme's activity to fatty acid synthesis, and might have resulted in the subsequent deletion of NRPS/PKS gene clusters.

    9. Selectivity of Competitive Multivalent Interactions at Interfaces (pages 1878–1887)

      Thomas André, Annett Reichel, Karl-Heinz Wiesmüller, Robert Tampé, Jacob Piehler and Roland Brock

      Version of Record online: 29 JUN 2009 | DOI: 10.1002/cbic.200900001

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      Controlling multivalency: Titration of hexa- and decahistidine with imidazole on multivalent chelator surfaces reveals surprising new characteristics of multivalent recognition at interfaces. In the presence of hexahistidine, the EC50 values for decahistidine increase considerably, leading to a sixfold increase in selectivity relative to the difference in EC50 values measured for either ligand alone.

    10. Characterisation of a Recombinant NADP-Dependent Glycerol Dehydrogenase from Gluconobacter oxydans and its Application in the Production of L-Glyceraldehyde (pages 1888–1896)

      Nina Richter, Markus Neumann, Andreas Liese, Roland Wohlgemuth, Thorsten Eggert and Werner Hummel

      Version of Record online: 3 JUL 2009 | DOI: 10.1002/cbic.200900193

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      It's elementary, dear Watson: We describe the characterisation of a NADP-dependent glycerol dehydrogenase from Gluconobacter oxydans (Gox1615), and show that the enzyme can be applied in the kinetic resolution of glyceraldehydes (see scheme), which is a versatile chiral building block in the production of fine chemicals, pharmaceuticals and natural products.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Minireview
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Preview: ChemBioChem 12/2009 (page 1903)

      Version of Record online: 13 JUL 2009 | DOI: 10.1002/cbic.200990046

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