ChemBioChem

Cover image for Vol. 12 Issue 5

March 21, 2011

Volume 12, Issue 5

Pages 653–811

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: STD and trNOESY NMR Study of Receptor–Ligand Interactions in Living Cancer Cells (ChemBioChem 5/2011) (page 653)

      Dr. Donatella Potenza, Dr. Francesca Vasile, Dr. Laura Belvisi, Dr. Monica Civera and Dr. Elena M. V. Araldi

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/cbic.201190015

      Thumbnail image of graphical abstract

      The cover picture shows a schematic NMR tube in which our cyclic RGD mimic (targeting integrin αvβ3) interacts with a suspension of intact bladder cancer cells. The integrin αvβ3 overexpressed on the cell membrane is labelled in red. The interaction between small ligands and membrane-bound proteins can be observed by NMR techniques directly on living cells, without the need to isolate the protein receptor. The saturation transfer difference (STD) spectrum, shown on the right, identifies the epitope of the mimic. The insight provided by NMR spectroscopy is completed by docking calculations, thus defining the ligand's integrin-bound conformation and the ligand–receptor interactions at a molecular level. The binding mode of our RGD mimic into the crystal structure of the αvβ3 integrin is shown at the bottom. For further information, see the communication by D. Potenza et al. on p. 695 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Inside Cover: Different Active-Site Loop Orientation in Serine Hydrolases versus Acyltransferases (ChemBioChem 5/2011) (page 654)

      Dr. Yun Jiang, Dr. Krista L. Morley, Dr. Joseph D. Schrag and Prof. Dr. Romas J. Kazlauskas

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/cbic.201190016

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      The inside cover picture shows a hydrolysis on–off gate. The oxyanion loop conformation near the active site distinguishes a hydrolase (Pseudomonas fluorescens esterase) from an acyltransferase (mycolyltransferase from Mycobacterium tuberculosis). For further details, see the paper by R. J. Kazlauskas et al. on p. 768 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    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. Review
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Corrigendum: A Route to Novel Functional Metalloproteins via Hybrids of Cytochrome P450 and Cytochrome c (page 662)

      Dr. Tianlei Ying, Fangfang Zhong, Dr. Zhong-Hua Wang, Wei Li, Prof. Xiangshi Tan and Prof. Zhong-Xian Huang

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/cbic.201190018

      This article corrects:

      A Route to Novel Functional Metalloproteins via Hybrids of Cytochrome P450 and Cytochrome c

      Vol. 12, Issue 5, 707–710, Version of Record online: 3 FEB 2011

  5. News

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

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
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    1. Biosynthesis of Vitamin B2: A Unique Way to Assemble a Xylene Ring (pages 670–680)

      Prof. Dr. Markus Fischer and Prof. Dr. Dr. Adelbert Bacher

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/cbic.201000681

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      The tricyclic isoalloxazine chromophore, which is the hallmark of flavocoenzymes, arises from a highly unusual dismutation of two 6,7-dimethyl-8-ribityllumazine molecules via a pentacyclic adduct. Two different classes of riboflavin synthases utilize different diastereomers of the pentacyclic adduct whose formation has been proposed to involve a hydride transfer step followed by a [4+2] cycloaddition.

  7. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
    10. Full Papers
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    1. Transformation with Tryptophan Halogenase Genes Leads to the Production of New Chlorinated Alkaloid Metabolites by a Medicinal Plant (pages 681–683)

      Prof. Karl-Heinz van Pée

      Version of Record online: 23 FEB 2011 | DOI: 10.1002/cbic.201100016

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      Catharanthus roseus produces chlorinated monoterpene indole alkaloids after the introduction of bacterial tryptophan halogenase genes into this medicinal plant. In the case of chlorination in the 5-position, the substrate specificity of an enzyme further downstream in the pathway also had to be changed. The background image is taken from Wikimedia Commons.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
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    1. Chemical Synthesis of a Bisphosphorylated Mannose-6-Phosphate N-Glycan and its Facile Monoconjugation with Human Carbonic Anhydrase II for in vivo Fluorescence Imaging (pages 685–690)

      Dr. Yunpeng Liu, Yan Mei Chan, Dr. Jianhui Wu, Dr. Chen Chen, Prof. Dr. Alan Benesi, Jing Hu, Prof. Dr. Yanming Wang and Prof. Dr. Gong Chen

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cbic.201000785

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      Red-ily made: The first chemical synthesis of a fully elaborated bisphosphorylated triantennary M6P N-glycan was achieved through a highly efficient late-stage phosphorylation strategy. A human carbonic anhydrase II-based fluorescently tagged neoglycoprotein platform was successfully constructed in order to evaluate the M6P N-glycan-directed protein internalization process in cell-based assays by confocal fluorescence imaging.

    2. Intense Blue Fluorescence in a Leucine Zipper Assembly (pages 691–694)

      Dr. Hiroshi Tsutsumi , Seiichiro Abe , Tomoaki Mino , Dr. Wataru Nomura and Prof. Hirokazu Tamamura 

      Version of Record online: 8 FEB 2011 | DOI: 10.1002/cbic.201000692

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      Fluorescence switching of 7-diethylaminocoumarin-3-carboxylic acid (DEAC) from a dark state to bright blue was achieved through the formation of a 3α-helical bundle structure. The DEAC unit in the leucine zipper assembly showed fluorescence 50 times stronger than that of the DEAC unit alone. The stable 3α-helical bundle structure was essential for the great enhancement of the DEAC fluorescence.

    3. STD and trNOESY NMR Study of Receptor–Ligand Interactions in Living Cancer Cells (pages 695–699)

      Dr. Donatella Potenza, Dr. Francesca Vasile, Dr. Laura Belvisi, Dr. Monica Civera and Dr. Elena M. V. Araldi

      Version of Record online: 3 FEB 2011 | DOI: 10.1002/cbic.201000756

      Thumbnail image of graphical abstract

      Integrin antagonists: Saturation transfer difference (STD) and transferred NOE provided useful information on membrane-bound receptor–ligand interactions in living cells in which the integrin αvβ3 is highly expressed. The epitopes of two cyclic RGD mimics were identified by STD. The different activities of these compounds were interpreted in terms of different binding modes. The experimental evidence was confirmed by docking calculations.

    4. Homoisoleucine: A Translationally Active Leucine Surrogate of Expanded Hydrophobic Surface Area (pages 700–702)

      James A. Van Deventer, Prof. John D. Fisk and Prof. David A. Tirrell

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/cbic.201000731

      Thumbnail image of graphical abstract

      Hil of a strong peptide! Homoisoleucine (Hil) serves as an effective surrogate for leucine with respect to protein translation in bacterial cells. Replacement of Leu by Hil stabilizes coiled-coil peptides, as shown by the elevation of the thermal denaturation temperature. The increase in denaturation temperature is larger than that observed previously for replacement of Leu by trifluoroleucine.

    5. Flavin-Induced DNA Photooxidation and Charge Movement Probed by Ultrafast Transient Absorption Spectroscopy (pages 703–706)

      Matthias Wenninger, Danila Fazio, Uwe Megerle, Christian Trindler, Stefan Schiesser, Prof. Dr. Eberhard Riedle and Prof. Dr. Thomas Carell

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cbic.201000730

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      Quantum yields of up to 14 % for the formation of a long-lived, charge-separated state can be achieved in flavin-capped DNA hairpins. The excited flavin state is quenched by electron-transfer processes from adjacent DNA bases. The introduction of multiple (dG:dC) base pairs leads to efficient hole trapping that competes with the charge recombination through dA-hopping processes.

    6. A Route to Novel Functional Metalloproteins via Hybrids of Cytochrome P450 and Cytochrome c (pages 707–710)

      Dr. Tianlei Ying, Fangfang Zhong, Dr. Zhong-Hua Wang, Wei Li, Prof. Xiangshi Tan and Prof. Zhong-Xian Huang

      Version of Record online: 3 FEB 2011 | DOI: 10.1002/cbic.201000631

      Thumbnail image of graphical abstract

      Novel hybrid proteins based on cytochrome c (Cyt c) and cytochrome P450 (CYP450) were constructed. They retain the good stability of Cyt c and acquire the catalytic activity of CYP450. More strikingly, the peroxidase activity of one particular hybrid protein is more than 40 times greater than that of Cyt c.

    7. Gene Disruption and Biochemical Characterization of Verruculogen Synthase of Aspergillus fumigatus (pages 711–714)

      Dr. Naoki Kato, Dr. Hirokazu Suzuki , Hiroshi Takagi, Dr. Masakazu Uramoto, Dr. Shunji Takahashi and Dr. Hiroyuki Osada

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cbic.201000562

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      Three in one: Verruculogen synthase FtmF is a key enzyme to diversify the fumitremorgin biosynthetic pathway in Aspergillus fumigatus: FtmF catalyzes not only endoperoxide bond formation of verruculogen but also the deprenylation and oxidation of fumitremorgin B to yield 12α,13α-dihydroxyfumitremorgin C and 13-oxoverruculogen, respectively.

    8. A Library Approach for the Discovery of Customized Yeast Three-Hybrid Counter Selections (pages 715–717)

      Laura M. Wingler and Prof. Virginia W. Cornish

      Version of Record online: 25 FEB 2011 | DOI: 10.1002/cbic.201000543

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      Developing effective new reporter genes for synthetic biology: Here we demonstrate that we can readily develop a robust counter selection for the yeast three-hybrid assay by screening libraries of genes not traditionally used as reporters, rather than by adapting classic reporter genes.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Targeting Bacterial Membranes: Identification of Pseudomonas aeruginosaD-Arabinose-5P Isomerase and NMR Characterisation of its Substrate Recognition and Binding Properties (pages 719–727)

      Dr. Cristina Airoldi, Dr. Silvia Sommaruga, Silvia Merlo, Dr. Paola Sperandeo, Prof. Laura Cipolla, Prof. Alessandra Polissi and Prof. Francesco Nicotra

      Version of Record online: 17 FEB 2011 | DOI: 10.1002/cbic.201000754

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      Rational design of antibacterial drugs: The identification and characterisation of P. aeruginosa API, which is involved in the biosynthesis of lipopolysaccharides, are reported. Structural requirements for substrate recognition and binding and the effects of mutations of the key residues have been evaluated by STD NMR spectroscopy. This information is essential for the rational design of new potential antibacterial drugs.

    2. Influence of Substrate Dideuteration on the Reaction of the Bifunctional Heme Enzyme Psi Factor Producing Oxygenase A (PpoA) (pages 728–737)

      Dr. André Nadler, Christian Koch, Dr. Florian Brodhun, Jan-Dirk Wehland, Prof. Dr. Kai Tittmann, Prof. Dr. Ivo Feussner and Prof. Dr. Ulf Diederichsen

      Version of Record online: 1 MAR 2011 | DOI: 10.1002/cbic.201000669

      Thumbnail image of graphical abstract

      Probing an enzyme: PpoA is an enzyme that catalyzes the dioxygenation of oleic acid to 8-hydroperoxyoleic acid and the rearrangement of this intermediate to 5,8-dihydroxyoleic acid. By using specifically deuterated OA derivatives that were synthesized by a novel protocol, we present new kinetic data that allow insight into the reaction mechanism and to determine the rate-limiting step.

    3. A Site-Saturated Mutagenesis Study of Pentaerythritol Tetranitrate Reductase Reveals that Residues 181 and 184 Influence Ligand Binding, Stereochemistry and Reactivity (pages 738–749)

      Dr. Helen S. Toogood, Dr. Anna Fryszkowska, Martyn Hulley, Michiyo Sakuma, Dr. David Mansell, Prof. Gill M. Stephens, Dr. John M. Gardiner and Prof. Nigel S. Scrutton

      Version of Record online: 4 MAR 2011 | DOI: 10.1002/cbic.201000662

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      Divergent evolution: A site-saturation study of PETN reductase was performed at conserved substrate binding residues H181 and H184. These residues were shown to dramatically alter the ratio of alkene versus nitro-group reduction in favour of oxime by-product formation, as summarised in the picture.

    4. Spacer Effects on in vivo Properties of DOTA-Conjugated Dimeric [Tyr3]Octreotate Peptides Synthesized by a “CuI-Click” and “Sulfo-Click” Ligation Method (pages 750–760)

      Cheng-Bin Yim , Berend van der Wildt, Dr. Ingrid Dijkgraaf, Lieke Joosten, Annemarie Eek, Cees Versluis, Dr. Dirk T. S. Rijkers, Prof. Dr. Otto C. Boerman and Prof. Dr. Rob M. J. Liskamp

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/cbic.201000639

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      Double click on tumor: This study reports the prolonged tumor-retention of a [Tyr3]octreotate dimer, synthesized by using a combination of CuI-catalyzed 1,3-dipolar cycloaddition (“copper-click”) and thio acid/sulfonyl azide amidation (“sulfo-click”), and shows that modification of the spacer between the two [Tyr3]octreotate motifs affects its pharmacokinetic profile.

    5. Heparin Inhibits Membrane Interactions and Lipid-Induced Fibrillation of a Prion Amyloidogenic Determinant (pages 761–767)

      Ehud Bazar, Dr. Tania Sheynis, Dr. Jerzy Dorosz and Prof. Raz Jelinek

      Version of Record online: 18 FEB 2011 | DOI: 10.1002/cbic.201000486

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      Blocking membrane binding: Glycosaminoglycans (GAGs) exhibit high affinities towards an amyloidogenic fragment of the prion peptide, suppress interactions of the peptide with lipid vesicles, and promote fibril formation in aqueous solutions irrespective of the presence of lipid bilayers. We suggest that GAGs' attenuation of amyloid toxicity is through blocking membrane interactions of the amyloidogenic proteins.

    6. Different Active-Site Loop Orientation in Serine Hydrolases versus Acyltransferases (pages 768–776)

      Dr. Yun Jiang, Dr. Krista L. Morley, Dr. Joseph D. Schrag and Prof. Dr. Romas J. Kazlauskas

      Version of Record online: 23 FEB 2011 | DOI: 10.1002/cbic.201000693

      Thumbnail image of graphical abstract

      All in the loop: A structure comparison of hydrolases and acyl transferases revealed a different conformation of the main chain in the oxyanion loop. Hydrolases point a C[DOUBLE BOND]O, whereas acytransferase point a NH, toward the active site. An X-ray structure of a hydrolase containing a sulfonate transition-state analogue show how this loop interacts with the attacking water.

    7. Myo-InositolTrisPyroPhosphate Treatment Leads to HIF-1α Suppression and Eradication of Early Hepatoma Tumors in Rats (pages 777–783)

      Dr. Marc Aprahamian , Dr. Gaétan Bour, Dr. Chérif Y. Akladios, Prof. Konstantina Fylaktakidou , Dr. Ruth Greferath , Prof. Luc Soler, Prof. Jacques Marescaux, Dr. Jean-Marc Egly, Prof. Jean-Marie Lehn and Prof. Claude Nicolau

      Version of Record online: 2 MAR 2011 | DOI: 10.1002/cbic.201000619

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      Up with oxygen, down with the tumor! Myo-inositol trispyrophosphate (ITPP) induces increased oxygen release from hemoglobin thereby causing downregulation of the hypoxia-inducible factor-1α and leading to eradication of early hepatocarcinoma tumors in rats.

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      Synthesis and Pro-Apoptotic Activity of Novel Glycyrrhetinic Acid Derivatives (pages 784–794)

      Dr. Evgeniya B. Logashenko, Dr. Oksana V. Salomatina, A. V. Markov, Dr. Dina V. Korchagina, Prof. Nariman F. Salakhutdinov, Prof. Genrikh A. Tolstikov, Prof. Valentin V. Vlassov and Prof. Marina A. Zenkova

      Version of Record online: 15 FEB 2011 | DOI: 10.1002/cbic.201000618

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      A new killer of cancer: Glycyrrhetinic acid derivatives were screened for their potential as inducers of human cancer cell death. Compound 1 displayed potent single-agent activity at micromolar concentrations, and induced death in various human cancer cells. Further analysis indicated that cell death was caused by the intrinsic caspase-dependent apoptosis pathway.

    9. Induction of Cell–Cell Connections by Using in situ Laser Lithography on a Perfluoroalkyl-Coated Cultivation Platform (pages 795–801)

      Dr. Kazunori Okano , David Yu, Ai Matsui, Yasuyo Maezawa, Prof. Dr. Yoichiroh Hosokawa, Dr. Atsushi Kira, Mie Matsubara, Prof. Dr. Ian Liau, Prof. Dr. Hiroshi Tsubokawa and Prof. Dr. Hiroshi Masuhara

      Version of Record online: 21 FEB 2011 | DOI: 10.1002/cbic.201000497

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      To make channels for cell-to-cell connections on a platform, an intense femtosecond laser pulse train was focused on the perfluoroalkyl (Rf) polymer layer during the cell culture process. This treatment modified the Rf polymer surface to create a cell-adhesive region. Cells elongated or migrated along the modified area and made cell–cell connections.

    10. Design and Synthesis of Conformationally Constrained Cyclophilin Inhibitors Showing a Cyclosporin-A Phenotype in C. elegans (pages 802–810)

      Dr. Colin J. Dunsmore , Dr. Kirk J. Malone , Dr. Kevin R. Bailey , Dr. Martin A. Wear, Dr. Hannah Florance, Dr. Sally Shirran , Dr. Perdita E. Barran, Prof. Antony P. Page, Prof. Malcolm D. Walkinshaw and Prof. Nicholas J. Turner 

      Version of Record online: 17 FEB 2011 | DOI: 10.1002/cbic.201000413

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      Small but effective: We describe the design and synthesis of small-molecule inhibitors for cyclophilin A, based upon a dimedone template. Mass spectrometry was used as an initial screen to quantify the affinity of the ligands for the protein. The biological role of cyclophilins in the nematode Caenorhabditis elegans was investigated with active inhibitors and fluorescent derivatives as chemical probes.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Preview: ChemBioChem 6/2011 (page 811)

      Version of Record online: 15 MAR 2011 | DOI: 10.1002/cbic.201190020

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