ChemBioChem

Cover image for Vol. 15 Issue 3

February 10, 2014

Volume 15, Issue 3

Pages 337–474

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Cover Picture: Acetylcholine Promotes Binding of α-Conotoxin MII at α3β2 Nicotinic Acetylcholine Receptors (ChemBioChem 3/2014) (page 337)

      Somisetti V. Sambasivarao, Jessica Roberts, Vivek S. Bharadwaj, Jason G. Slingsby, Conrad Rohleder, Chris Mallory, Prof. James R. Groome, Prof. Owen M. McDougal and Prof. C. Mark Maupin

      Article first published online: 2 FEB 2014 | DOI: 10.1002/cbic.201490004

      Thumbnail image of graphical abstract

      The cover picture shows the binding of α-conotoxin MII to the C-loop of an α3β2 neuronal acetylcholine receptor residing in the post-synaptic phospholipid bilayer, which comprises a 3:1:1 ratio of POPC, POPA, and cholesterol. Docking studies and voltage clamp experiments show that the presence of acetylcholine in the C-loop region enhances the binding of toxin, slowing its washout. These observations indicate that α-conotoxin MII might preferentially target active synaptic clefts, which would be an evolutionary advantage. On p. 413 ff., O. M. McDougal, C. M. Maupin, et al. describe the creation of two heteropentameric α3β2 neuronal acetylcholine receptor homology models that were used in docking studies of acetylcholine, α-conotoxin, and both neurotransmitter and toxin to the various C-loop regions (i.e., α3–β2, β2–α3, and β2–β2). Subsequent voltage clamp experiments confirmed that the presence of acetylcholine enhanced the binding of toxin prolonging its effect on the ligand-gated ion channel. (Cover art designed by C.M.M.).

    2. Inside Cover: Long Residence Times Revealed by Aurora A Kinase-Targeting Fluorescent Probes Derived from Inhibitors MLN8237 and VX-689 (ChemBioChem 3/2014) (page 338)

      Dr. Darja Lavogina, Dr. Erki Enkvist, Dr. Kaido Viht and Dr. Asko Uri

      Article first published online: 2 FEB 2014 | DOI: 10.1002/cbic.201490005

      Thumbnail image of graphical abstract

      The inside cover picture shows fluorescent probes based on well-known inhibitors MLN8237 and VX-689 (MK-5108) that revealed slow association/dissociation kinetics in inhibition and binding assays with Aurora A kinase. For more details see the paper by D. Lavõgina et al. on p. 443 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Graphical Abstract: ChemBioChem 3/2014 (pages 339–345)

      Article first published online: 2 FEB 2014 | DOI: 10.1002/cbic.201490006

  3. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Spotlights on our sister journals: ChemBioChem 3/2014 (pages 346–349)

      Article first published online: 2 FEB 2014 | DOI: 10.1002/cbic.201490007

  4. Highlights

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Structure Elucidation of DNA–Protein Crosslinks by Using Reductive Desulfurization and Liquid Chromatography–Tandem Mass Spectrometry (pages 353–355)

      Susith Wickramaratne and Prof. Natalia Y. Tretyakova

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300757

      Thumbnail image of graphical abstract

      Easier with ethyl: Guengerich and co-workers have developed a powerful new approach to the structure elucidation of hydrolytically stable AGT–DNA crosslinks by reductive desulfurization of the thioether linkage between AGT and DNA to convert cysteine DPCs to the corresponding ethyl–DNA adducts, which can be readily characterized by LC-MSn.

    2. The Selenocysteine Incorporation Machinery Allows the Dual Use of Sense Codons: A New Strategy for Expanding the Genetic Code? (pages 356–358)

      Dr. Thorsten Stafforst

      Article first published online: 20 DEC 2013 | DOI: 10.1002/cbic.201300735

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      Sense and Secis: Even though selenocysteine, Sec, is naturally incorporated by suppressing UAG stop codons, it was recently shown that sense codons such as UAC can efficiently code for Sec. This article highlights the implications of using such a strategy to introduce unnatural amino acids site-selectively into proteins. Please note: ChemBioChem will be accepting submissions of original research for a special issue on “Expanding the Genetic Code” in January 2014.

  5. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Red Fluorescent Turn-On Ligands for Imaging and Quantifying G Protein-Coupled Receptors in Living Cells (pages 359–363)

      Iuliia A. Karpenko, Rémy Kreder, Christel Valencia, Dr. Pascal Villa, Dr. Christiane Mendre, Dr. Bernard Mouillac, Prof. Dr. Yves Mély, Prof. Dr. Marcel Hibert, Dr. Dominique Bonnet and Dr. Andrey S. Klymchenko

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300738

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      Receptor, you can turn me on: The first red fluorescent turn-on ligands for a G protein-coupled receptor (oxytocin) are reported. The molecular design, a fluorogenic dye connected to a peptide agonist by a polar spacer, ensures a strong specific turn-on response, thus enabling imaging and rapid quantification of receptors at the cell surface.

    2. Identification of Fluorinases from Streptomyces sp MA37, Norcardia brasiliensis, and Actinoplanes sp N902-109 by Genome Mining (pages 364–368)

      Dr. Hai Deng, Dr. Long Ma, Nouchali Bandaranayaka, Zhiwei Qin, Greg Mann, Dr. Kwaku Kyeremeh, Dr. Yi Yu, Dr. Thomas Shepherd, Prof. James H. Naismith and Prof. David O'Hagan

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300732

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      Get on the fluor! The fluorinase enzyme from Streptomyces cattleya was identified in 2002 as the only fluorination enzyme known in biochemistry. Three additional fluorinases expressed through bacterial genome mining are now reported. These new fluorinases extend the range of genes available for developing fluorination biotechnology.

    3. Biosynthesis of the Insecticidal Xenocyloins in Xenorhabdus bovienii (pages 369–372)

      Anna Proschak, Qiuqin Zhou, Tim Schöner, Dr. Aunchalee Thanwisai, Darko Kresovic, Dr. Andrea Dowling, Prof. Dr. Richard ffrench-Constant, Prof. Dr. Ewgenij Proschak and Prof. Dr. Helge B. Bode

      Article first published online: 2 FEB 2014 | DOI: 10.1002/cbic.201300694

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      There's more than one: The biosynthesis of the insecticidal xenocyloins has been identified, as well as the second example of an acylating ketosynthase (KS). Phylogenetic analysis indicated that these related enzymes represent a new subclass of KSs found in different bacteria; acylating KSs might be more widespread than thought.

    4. Control of Plant Defense Mechanisms and Fire Blight Pathogenesis through the Regulation of 6-Thioguanine Biosynthesis in Erwinia amylovora (pages 373–376)

      Dr. Sébastien Coyne, Agnieszka Litomska, Dr. Cornelia Chizzali, Dr. Mohammed N. A. Khalil, Dr. Klaus Richter, Prof. Dr. Ludger Beerhues and Prof. Dr. Christian Hertweck

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300684

      Thumbnail image of graphical abstract

      Blight relief: Analysis of the regulation of 6-thioguanine (6TG) biosynthesis in the pathogen Erwinia amylovora sheds new light on the pathogenesis of fire blight. Surprisingly, at low 6TG titers, apple trees are capable of activating the abscission machinery to excise infected tissue and to dam further pathogen dissemination, thus preventing full infection of the tree.

    5. Redox-Driven Host–Guest Interactions Allow the Controlled Release of Captured Cells on RGD-Functionalized Surfaces (pages 377–381)

      Dhruv Thakar, Dr. Liliane Coche-Guérente, Michaël Claron, Dr. Christiane H. F. Wenk, Dr. Jérôme Dejeu, Prof. Pascal Dumy, Prof. Pierre Labbé and Dr. Didier Boturyn

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300636

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      Exclusive! A new redox-driven method enabling selective cell isolation is described. To illustrate this strategy, we exploited a sophisticated macromolecule encompassing an RGD-containing cyclic peptide as the ligand of an αvβ3 receptor that is overexpressed in metastatic cells, as well as a supramolecular system, a β-cyclodextrin–ferrocene complex, which dissociates under electrochemical polarization.

    6. On One Leg: Trehalose Monoesters Activate Macrophages in a Mincle-Dependant Manner (pages 382–388)

      Dr. Bridget L. Stocker, Dr. Ashna A. Khan, Stephanie H. Chee, Dr. Faustin Kamena and Dr. Mattie S. M. Timmer

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300674

      Thumbnail image of graphical abstract

      Optimised Mincle agonists: We show for the first time that trehalose monoesters can activate macrophages in a Mincle-dependent manner. The activities of the monoesters parallel those of their diester counterparts, both in the presence and in the absence of priming agents. As such, these studies provide important insight for the rational design of further Mincle agonists.

    7. Catalytic Scope of the Thiamine-Dependent Multifunctional Enzyme Cyclohexane-1,2-dione Hydrolase (pages 389–392)

      Sabrina Loschonsky, Simon Waltzer, Dr. Sonja Fraas, Tobias Wacker, Prof. Dr. Susana L. A. Andrade, Prof. Dr. Peter M. H. Kroneck and Prof. Dr. Michael Müller

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300673

      Thumbnail image of graphical abstract

      Back together: Recombinant cyclohexane-1,2-dione hydrolase (CDH) catalyzes the asymmetric cross-benzoin reaction of aromatic aldehydes and pyruvate (up to quantitative conversion and 92–99 % ee). Notably, CDH accepts several aldehydes, such as hydroxybenzaldehydes, nitrobenzaldehydes, and naphthaldehydes; previously, these have only in rare cases been known as substrates of other thiamine-dependent enzymes.

  6. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Unique Crystal Structure of a Novel Surfactant Protein from the Foam Nest of the Frog Leptodactylus vastus (pages 393–398)

      Dr. Denise Cavalcante Hissa, Dr. Gustavo Arruda Bezerra, Dr. Ruth Birner-Gruenberger, Dr. Luciano Paulino Silva, Dr. Isabel Usón, Prof. Dr. Karl Gruber and Prof. Dr. Vânia Maria Maciel Melo

      Article first published online: 17 JAN 2014 | DOI: 10.1002/cbic.201300726

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      Making the perfect egg: Frog eggs and sperm are matured in “foam nests” that are stabilized by the naturally occurring surfactant protein ranaspumin. We report the amino acid sequence, crystal structure (which corresponds to a novel fold), and biochemical properties of Lv-RSN-1, the uncommon ranaspumin from the frog Leptodactylus vastus.

    2. An Integrated Computational and Experimental Approach to Gaining Selectivity for MMP-2 within the Gelatinase Subfamily (pages 399–412)

      Benjamin Fabre, Kamila Filipiak, Dr. Natalia Díaz, Dr. José María Zapico, Dr. Dimas Suárez, Prof. Ana Ramos and Prof. Beatriz de Pascual-Teresa

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300698

      Thumbnail image of graphical abstract

      Rational MMP-2 inhibitor design: Several hydroxamic-derived compounds have been designed, synthesised and characterised as potent MMP-2 inhibitors. Among them, 11 b presents an increased MMP-2/MMP-9 selectivity with an IC50 ratio over 102. Computational analyses based on extensive molecular dynamics simulations and free energy calculations explain the observed differences in the inhibition profiles.

    3. Acetylcholine Promotes Binding of α-Conotoxin MII at α3β2 Nicotinic Acetylcholine Receptors (pages 413–424)

      Somisetti V. Sambasivarao, Jessica Roberts, Vivek S. Bharadwaj, Jason G. Slingsby, Conrad Rohleder, Chris Mallory, Prof. James R. Groome, Prof. Owen M. McDougal and Prof. C. Mark Maupin

      Article first published online: 13 JAN 2014 | DOI: 10.1002/cbic.201300577

      Thumbnail image of graphical abstract

      Electrostatically driven antagonist properties: The selective antagonist α-Conotoxin MII (stick representation) is shown bound and unbound under the C-loop near the acetylcholine binding pocket of the heteropentameric α3β2 nicotinic acetylcholine receptor. The two α3-subunits are depicted in orange, and the three β2-subunits are depicted in yellow.

    4. Lipochitin Oligosaccharides Immobilized through Oximes in Glycan Microarrays Bind LysM Proteins (pages 425–434)

      Dr. Nicolai N. Maolanon, Dr. Mickael Blaise, Dr. Kasper K. Sørensen, Prof. Mikkel B. Thygesen, Dr. Emiliano Cló, Dr. John T. Sullivan, Prof. Clive W. Ronson, Prof. Jens Stougaard, Prof. Ola Blixt and Prof. Knud J. Jensen

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300520

      Thumbnail image of graphical abstract

      Hold still! Complex lipochitin oligosaccharides were immobilized by oxime linkages to form a glycan microarray to evaluate binding of proteins containing LysM domains. Array functionality was evaluated by using LysM domain-containing protein autolysin p60, which targets bacterial peptidoglycan. Specific binding to Nod factors and chitin oligosaccharides was observed, with increasing affinity corresponding to increasing chitin oligomer length.

    5. Active Efflux Influences the Potency of Quorum Sensing Inhibitors in Pseudomonas aeruginosa (pages 435–442)

      Joseph D. Moore, Joseph P. Gerdt, Dr. Nora R. Eibergen and Prof. Dr. Helen E. Blackwell

      Article first published online: 29 JAN 2014 | DOI: 10.1002/cbic.201300701

      Thumbnail image of graphical abstract

      Get pumped: Small molecules capable of inhibiting bacterial cell–cell signaling (quorum sensing, QS) are of significant interest as potential anti-infective agents. Here we show that AHL-derived QS inhibitors are substrates of the efflux pump MexAB-OprM in Pseudomonas aeruginosa; however, an aminobenzimidazole derivative did not display efflux-induced reduction in potency.

      Corrected by:

      Corrigendum: Corrigendum: Active Efflux Influences the Potency of Quorum Sensing Inhibitors in Pseudomonas aeruginosa

      Vol. 15, Issue 5, 634, Article first published online: 17 MAR 2014

    6. Long Residence Times Revealed by Aurora A Kinase-Targeting Fluorescent Probes Derived from Inhibitors MLN8237 and VX-689 (pages 443–450)

      Dr. Darja Lavogina, Dr. Erki Enkvist, Dr. Kaido Viht and Dr. Asko Uri

      Article first published online: 8 JAN 2014 | DOI: 10.1002/cbic.201300613

      Thumbnail image of graphical abstract

      Illuminating the night sky: Fluorescent probes based on well-known inhibitors of Aurora A target either only the ATP site, or both the ATP and substrate sites of the kinase. MLN8237, VX-689 (MK-5108) and their fluorescent derivatives show low-nanomolar affinity and long residence times in binding and inhibition studies with Aurora A and its activator, TPX2.

    7. The Cyclic Cystine Ladder of Theta-Defensins as a Stable, Bifunctional Scaffold: A Proof-of-Concept Study Using the Integrin-Binding RGD Motif. (pages 451–459)

      Anne C. Conibear, Dr. Alexander Bochen, Dr. K. Johan Rosengren, Petar Stupar, Dr. Conan Wang, Prof. Dr. Horst Kessler and Prof. Dr. David J. Craik

      Article first published online: 2 JAN 2014 | DOI: 10.1002/cbic.201300568

      Thumbnail image of graphical abstract

      The ladder to success: The RGD integrin-binding epitope was incorporated into the cyclic cystine ladder of theta-defensins to give stable and selective integrin-binding peptides, thus demonstrating the potential of the cyclic cystine ladder as a peptide drug scaffold.

    8. Solid-Phase Synthesis and Biological Evaluation of N-Dipeptido L-Homoserine Lactones as Quorum Sensing Activators (pages 460–465)

      Dr. Mette R. Hansen, Dr. Sebastian T. Le Quement, Tim H. Jakobsen, Dr. Søren Skovstrup, Prof. Olivier Taboureau, Prof. Tim Tolker-Nielsen, Prof. Michael Givskov and Prof. Thomas E. Nielsen

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300533

      Thumbnail image of graphical abstract

      Behind the screen: A virtual screening approach identified a number of N-dipeptido L-homo-serine lactones as potential quorum sensing modulators. Selected compounds were synthesized and identified as activators of LasR, a protein regulating quorum sensing in Pseudomonas aeruginosa; EC50 values were in the low micromolar range.

    9. Probing Bacterial Uptake of Glycosylated Ciprofloxacin Conjugates (pages 466–471)

      Dr. Stephen J. Milner, Christopher T. Carrick, Prof. Kevin G. Kerr, Dr. Anna M. Snelling, Dr. Gavin H. Thomas, Dr. Anne-Kathrin Duhme-Klair and Dr. Anne Routledge

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201300512

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      More is not always better: Mono- and disaccharide-functionalised ciprofloxacin conjugates have been synthesised and used as chemical probes of the bacterial uptake of glycosylated ciprofloxacin. The data suggest a lack of active uptake through sugar transporters and that the addition of a disaccharide results in a significant decrease in antimicrobial activity.

  7. Book Reviews

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlights
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Protein–Protein Interactions in Drug Discovery. Edited by Alexander Dömling. (pages 472–473)

      Birgit Strodel

      Article first published online: 16 JAN 2014 | DOI: 10.1002/cbic.201300761

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      Wiley-VCH, Weinheim 2013, XXI+314 pp., hardcover, € 139.00.—ISBN 978-3-527-33107-9

    2. Metal Ions in Life Sciences, Vol. 12: Metallomics and the Cell. Edited by Lucia Banci. (pages 473–474)

      Artur Krezel

      Article first published online: 21 JAN 2014 | DOI: 10.1002/cbic.201400005

      Springer, Dordrecht 2013, XXXVI+609 pp., hardcover, € 181.85.—ISBN 978-94-007-5560-4

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