ChemBioChem

Cover image for Vol. 11 Issue 2

January 25, 2010

Volume 11, Issue 2

Pages 133–279

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
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    1. Cover Picture: Crystal Structure of the Human Monoacylglycerol Lipase, a Key Actor in Endocannabinoid Signaling (ChemBioChem 2/2010) (page 133)

      Geoffray Labar, Cédric Bauvois, Franck Borel, Jean-Luc Ferrer, Johan Wouters and Didier M. Lambert

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/cbic.201090000

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      The cover picture shows the crystal structure of the human monoacylglycerol lipase (MAGL). This enzyme constitutes the most relevant pathway that terminates the action of 2-arachidonoylglycerol, which is one of the main representatives of a family of signaling lipids known as “endocannabinoids”. These messengers act by activating the CB1 and CB2 cannabinoid receptors, the molecular targets of the psychoactive constituent of Cannabis sativa, D9-THC, thereby modulating synaptic transmission in the brain. For more information, see the paper by D. M. Lambert et al. on p. 218 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
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    1. Inside Cover: Peptoid–Peptide Hybrid Backbone Architectures (ChemBioChem 2/2010) (page 134)

      Christian A. Olsen

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/cbic.201090001

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      The inside cover picture shows fragments of oligomeric hybrid structures containing α-amino acids in combination with peptoid or β-peptoid residues. For further information on the future of such compounds in targeting biological systems see the Minireview by C. A. Olsen on p. 152 ff. (Photo of the Little Mermaid by Jesper Rosenberg, www.calbo.dk)

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    9. Preview
  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    9. Preview
  5. Minireviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
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    1. FRET-Based Activity Biosensors to Probe Compartmentalized Signaling (pages 147–151)

      Xinxin Gao and Jin Zhang

      Version of Record online: 11 DEC 2009 | DOI: 10.1002/cbic.200900594

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      Illuminating compartmentalized signaling: We discuss the applications of FRET-based biosensors with a focus on understanding compartmentalized signaling of kinase and second-messenger dynamics. With their unique features of genetic encodability and targetability, these biosensors allow real-time tracking of activity dynamics with high spatiotemporal resolution.

    2. Peptoid–Peptide Hybrid Backbone Architectures (pages 152–160)

      Christian A. Olsen

      Version of Record online: 16 DEC 2009 | DOI: 10.1002/cbic.200900618

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      The right blend: Peptidomimetics with hybrid backbone architectures (i.e., those containing at least two different types of monomers) have received increased attention recently. This article provides an overview of the literature concerning hybrid peptidomimetics containing peptoid (N-alkylated glycine) or β-peptoid (N-alkylated β-alanine) residues in combination with α-amino acids, and shows that these types of structures have potential as ligands in a wide variety of biological systems.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
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    1. Haloacetamidine-Based Inactivators of Protein Arginine Deiminase 4 (PAD4): Evidence that General Acid Catalysis Promotes Efficient Inactivation (pages 161–165)

      Bryan Knuckley, Corey P. Causey, Perry J. Pellechia, Paul F. Cook and Paul R. Thompson

      Version of Record online: 11 DEC 2009 | DOI: 10.1002/cbic.200900698

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      Dropping acid: Dysregulated protein arginine deiminase (PAD) activity is associated with rheumatoid arthritis. pH studies indicate that the PAD inhibitors F- and Cl-amidine inactivate the PADs through a multistep mechanism that involves the protonation and stabilization of the tetrahedral intermediate formed upon nucleophilic attack by the active-site cysteine.

    2. Structural Features of Apramycin Bound at the Bacterial Ribosome A Site as Detected by NMR and CD Spectroscopy (pages 166–169)

      Duccio Balenci, Nicola D'Amelio, Elena Gaggelli, Nicola Gaggelli, Luciano Cellai, Elena Molteni and Gianni Valensin

      Version of Record online: 18 DEC 2009 | DOI: 10.1002/cbic.200900629

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      What a site! The interaction of apramycin (see figure) with an RNA fragment mimicking the bacterial ribosomal A site was investigated by NMR spectroscopy, mainly by using the transferred NOE technique. The fact that only the RNA-bound antibiotic shows nonzero NOE effects, allowed us to gain structural details of bound apramycin despite the fast exchange conditions between the free and RNA-bound forms. The dissociation constant of the apramycin–RNA complex was evaluated by CD spectroscopy.

    3. Neisseria meningitidis Serogroup B Polysialyltransferase: Insights into Substrate Binding (pages 170–174)

      Raphael Böhm, Friedrich Freiberger, Katharina Stummeyer, Rita Gerardy-Schahn, Mark von Itzstein and Thomas Haselhorst

      Version of Record online: 8 DEC 2009 | DOI: 10.1002/cbic.200900659

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      On the loose: We report an STD NMR spectroscopic study of the polysialyltransferase from Neisseria meningitidis serogroup B (NmB-polyST). The spectra reveal that the cytosine and ribose moiety receive more saturation than the sialic acid residue of CMP-Neu5Ac. This loose binding enables a fast and efficient sialyl transfer to the acceptor substrate. Our analysis offers a view of the structural determinants necessary for binding to NmB-polyST that provide the basis for the development of novel NmB-polyST inhibitors.

    4. Protein Incorporation in Giant Lipid Vesicles under Physiological Conditions (pages 175–179)

      Paige M. Shaklee, Stefan Semrau, Maurits Malkus, Stefan Kubick, Marileen Dogterom and Thomas Schmidt

      Version of Record online: 10 DEC 2009 | DOI: 10.1002/cbic.200900669

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      Life's construction zone: Proteins were incorporated into giant vesicles (GVs) under physiological conditions by using electroformation. The figure shows these fluorescently labeled GVs in which proteins are encapsulated. Our method opens doors to investigating the membrane properties of native, intracellular membranes.

    5. Strong and Reversible Monovalent Supramolecular Protein Immobilization (pages 180–183)

      Jacqui F. Young , Hoang D. Nguyen , Lanti Yang, Jurriaan Huskens, Pascal Jonkheijm and Luc Brunsveld 

      Version of Record online: 20 NOV 2009 | DOI: 10.1002/cbic.200900599

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      Proteins with an iron clasp: Site-selective incorporation of a ferrocene molecule into a protein allows for easy, strong, and reversible supramolecular protein immobilization through a selective monovalent interaction of the ferrocene with a cucurbit[7]uril immobilized on a gold surface. The proteins can be printed in a uniform monolayer that is resistant to washing conditions, but can be removed through competition with an excess of ferrocene ligand.

    6. The Biosynthesis of Liposidomycin-like A-90289 Antibiotics Featuring a New Type of Sulfotransferase (pages 184–190)

      Masanori Funabashi, Satoshi Baba, Koichi Nonaka, Masahiko Hosobuchi, Yoko Fujita, Tomoyuki Shibata and Steven G. Van Lanen

      Version of Record online: 30 DEC 2009 | DOI: 10.1002/cbic.200900665

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      Lip reading: The biosynthetic gene cluster for A-90289, a fatty acid nucleoside antibiotic, was cloned and sequenced. The sulfotransferase LipB is demonstrated to be essential for A-90289 biosynthesis, and in vitro characterization revealed LipB utilizes p-nitrophenylsulfate as an aryl sulfate donor and a variety of nonaryl acceptors including caprazamycin A to give the 2′-O-sulfated product, A-90289A.

    7. Analysis of the Liposidomycin Gene Cluster Leads to the Identification of New Caprazamycin Derivatives (pages 191–196)

      Leonard Kaysser, Stefanie Siebenberg, Bernd Kammerer and Bertolt Gust

      Version of Record online: 28 DEC 2009 | DOI: 10.1002/cbic.200900637

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      En route: The liposidomycin biosynthetic gene cluster has been identified, cloned and heterologously expressed. A comparison with the gene cluster of the structurally related caprazamycins supports the proposed pathway to liponucleoside formation and led to the identification of new sulfated caprazamycin derivatives.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
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    1. Biocatalysis with Thermostable Enzymes: Structure and Properties of a Thermophilic ‘ene’-Reductase related to Old Yellow Enzyme (pages 197–207)

      Björn V. Adalbjörnsson, Helen S. Toogood, Anna Fryszkowska, Christopher R. Pudney, Thomas A. Jowitt, David Leys and Nigel S. Scrutton

      Version of Record online: 26 NOV 2009 | DOI: 10.1002/cbic.200900570

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      A hot, new Old Yellow Enzyme: We describe the X-ray crystal structure of a new thermostable Old Yellow Enzyme, and report its kinetic properties, thermo- and solvent stability, and biocatalytic potential. The markedly improved solvent stability of the enzyme shows great potential for applications in industrial-scale biotransformations.

    2. Chemically Induced Cardiomyogenesis of Mouse Embryonic Stem Cells (pages 208–217)

      Albrecht Berkessel, Bianca Seelig, Silke Schwengberg, Jürgen Hescheler and Agapios Sachinidis

      Version of Record online: 28 DEC 2009 | DOI: 10.1002/cbic.200900345

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      A heartbeat away: The screening of diversity oriented and focused libraries of (thio)ureas and cinchona alkaloid derivatives by using a transgenic murine embryonic stem cell lineage expressing enhanced green fluorescent protein under the control of α-myosine heavy chain promoter (pα-MHC-EGFP) was carried out, and novel cardiomyogenesis inducing substances were identified. Two cationic quinidine derivatives (see figure) showed the strongest cardiomyogenesis inducing activities.

    3. Crystal Structure of the Human Monoacylglycerol Lipase, a Key Actor in Endocannabinoid Signaling (pages 218–227)

      Geoffray Labar, Cédric Bauvois, Franck Borel, Jean-Luc Ferrer, Johan Wouters and Didier M. Lambert

      Version of Record online: 2 DEC 2009 | DOI: 10.1002/cbic.200900621

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      MAG(ica)L crystal: The crystal structure of human monoacylglycerol lipase (MAGL) has been elucidated. The enzyme catalyzes the hydrolysis of the endocannabinoid 2-arachidonoylglycerol, thus stopping its action at CB1 and CB2 cannabinoid receptors.

    4. Galectin-1–Asialofetuin Interaction Is Inhibited by Peptides Containing the Tyr-Xxx-Tyr Motif Acting on the Glycoprotein (pages 228–234)

      Edit Wéber, Anasztázia Hetényi , Balázs Váczi, Éva Szolnoki, Roberta Fajka-Boja, Vilmos Tubak, Éva Monostori and Tamás A. Martinek

      Version of Record online: 24 NOV 2009 | DOI: 10.1002/cbic.200900502

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      Monitoring protein–ligand interactions by NMR spectroscopy revealed that peptides containing the Tyr-Xxx-Tyr motif bind to asialofetuin (ASF), whereas no sign of galectin-1–peptide interaction was found. The findings suggest that these peptides modify the presentation of the carbohydrate chains of the glycoprotein thereby inhibiting the galectin-1–glycoprotein interaction.

    5. Preparation of Biomolecule Microstructures and Microarrays by Thiol–ene Photoimmobilization (pages 235–247)

      Dirk Weinrich, Maja Köhn, Pascal Jonkheijm, Ulrika Westerlind, Leif Dehmelt, Hans Engelkamp, Peter C. M. Christianen, Jürgen Kuhlmann, Jan C. Maan, Dirk Nüsse, Hendrik Schröder, Ron Wacker, Edgar Voges , Rolf Breinbauer, Horst Kunz, Christof M. Niemeyer and Herbert Waldmann

      Version of Record online: 30 DEC 2009 | DOI: 10.1002/cbic.200900559

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      Light=flexibility! Taking advantage of the photoactivatable thiol–ene reaction, biomolecules such as biotin, oligonucleotides, peptides, and glycopeptides were photoimmobilized to generate both microarrays and microstructured biochips. The use of light grants flexibility in terms of microstructure geometry and size. The obtained biochips were successfully used to profile antibody specificity in serum.

    6. Phosphopantetheinylation and Specificity of Acyl Carrier Proteins in the Mupirocin Biosynthetic Cluster (pages 248–255)

      Jennifer A. Shields, Ayesha S. Rahman, Christopher J. Arthur, John Crosby, Joanne Hothersall, Thomas J. Simpson and Christopher M. Thomas

      Version of Record online: 10 DEC 2009 | DOI: 10.1002/cbic.200900565

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      MupN protein, the essential Sfp-like PPTase of the mupirocin biosynthetic cluster, is shown to efficiently phosphopantetheinylate representatives of both type I and type II acyl carrier proteins from the cluster. Bioassays with hybrid and mutant ACPs (see Figure) implicate the C-terminal half of the type II ACPs in specificity.

    7. Synthesis of S-Adenosyl-L-homocysteine Capture Compounds for Selective Photoinduced Isolation of Methyltransferases (pages 256–265)

      Christian Dalhoff, Michael Hüben, Thomas Lenz, Peter Poot, Eckhard Nordhoff, Hubert Köster and Elmar Weinhold

      Version of Record online: 4 JAN 2010 | DOI: 10.1002/cbic.200900349

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      Fisherman's friends: Molecular fishing hooks were developed to selectively tag and isolate methyltransferases. These capture compounds contain the cofactor product S-adenosyl-L-homocysteine for directed, noncovalent prebinding to the enzymes (1), a photoreactive group for covalent crosslinking (2) and biotin for isolation with streptavidin-coated magnetic beads (3).

    8. The Thioesterase Bhp is Involved in the Formation of β-Hydroxytyrosine during Balhimycin Biosynthesis in Amycolatopsis balhimycina (pages 266–271)

      Sri Mulyani, Ellen Egel, Claudia Kittel, Suada Turkanovic, Wolfgang Wohlleben, Roderich D. Süssmuth and Karl-Heinz van Pée

      Version of Record online: 8 DEC 2009 | DOI: 10.1002/cbic.200900600

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      The identification of Bhp as a thioesterase that catalyses the hydrolysis of the thioester bond of β-OH-Tyr-SNAC is the last piece of evidence required to fully understand the formation of β-OH-Tyr as a precursor in balhimycin and other β-OH-Tyr-containing glycopeptide antibiotics.

    9. Biomimetic Formation of 2-Tropolones by Dioxygenase-Catalysed Ring Expansion of Substituted 2,4-Cyclohexadienones (pages 272–276)

      Meite Xin and Timothy D. H. Bugg

      Version of Record online: 10 DEC 2009 | DOI: 10.1002/cbic.200900631

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      At sixes and sevens: We have demonstrated experimentally the proposed ring expansion in the biosynthesis of substituted 2-tropolones. Treatment of four cyclohexa-2,4-dienones with the non-haem iron(II)-dependent extradiol catechol dioxygenase MhpB from E. coli resulted in the formation of 2-tropolones through a pinacol-type rearrangement. This ring expansion could also be effected nonenzymatically by treatment with 1,4,7-triazacyclononane and FeCl2.

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    9. Preview
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      Preview: ChemBioChem 3/2010 (page 279)

      Version of Record online: 20 JAN 2010 | DOI: 10.1002/cbic.201090004

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