ChemBioChem

Cover image for Vol. 13 Issue 12

August 13, 2012

Volume 13, Issue 12

Pages 1701–1827

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Biosynthesis and Cellular Localization of Functional Polyketides in the Gastropod Mollusc Scaphander lignarius (ChemBioChem 12/2012) (page 1701)

      Dr. Adele Cutignano, Prof. Conxita Avila, Dr. Annamaria Rosica, Dr. Giovanna Romano, Dr. Bruna Laratta, Anna Domenech-Coll, Dr. Guido Cimino, Dr. Ernesto Mollo and Dr. Angelo Fontana

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201290048

      Thumbnail image of graphical abstract

      The cover picture shows the biosynthesis, in the specialized tissue of the opisthobranch mollusc Scaphander lignarius, of the aromatic semiochemical lignarenones. Opisthobranchs are a special group of marine invertebrates that are very well known as an extraordinary source of bioactive natural products. In the article on p. 1759 ff., A. Fontana et al. show that the biosynthesis of lignarenones takes place in specialized mantle cells, the Blochmann's glands, by an unprecedented benzenoid pathway. Synthesis of the polyketide skeleton requires a mixed acetate–propionate assembly that is primed by benzoic acid derived from L-phenylalanine. This last process is gated by enzymatic nonoxidative deamination of the amino acid; this is reminiscent of the transformation catalyzed by phenylalanine ammonia lyases (PALs) in plants and fungi. The article suggests that marine invertebrates possess their own competence for the biosynthesis of natural products, thus challenging the present view on the universal role of microorganisms as the source of functional products in marine benthos.

    2. Inside Cover: Fluorescent Aplyronine A: Intracellular Accumulation and Disassembly of Actin Cytoskeleton in Tumor Cells ChemBioChem 12/2012) (page 1702)

      Prof. Dr. Masaki Kita, Kozo Yoneda, Yuichiro Hirayama, Kota Yamagishi, Yuki Saito, Yuka Sugiyama, Dr. Yoshihiro Miwa, Dr. Osamu Ohno, Maho Morita, Prof. Dr. Kiyotake Suenaga and Prof. Dr. Hideo Kigoshi

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201290049

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      The inside cover picture shows HEp-2 cells (expressing GFP-tagged cytoplasmic actin) treated with the fluorescent derivative of aplyronine A (ApAFL, bottom). ApA is an antitumor and apoptogenic macrolide of marine origin. M. Kita, H. Kigoshi, et al. (see article on p. 1754 ff.) have established that ApA accumulates throughout the cytoplasm and causes the rapid disassembly of the actin cytoskeleton in tumor cells.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Graphical Abstract: ChemBioChem 12/2012 (pages 1703–1710)

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201290050

  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Corrigendum: Dimerization Determines Substrate Specificity of a Bacterial Prenyltransferase (page 1710)

      David Peterhoff, Dr. Hermann Zellner, Dr. Harald Guldan, Dr. Rainer Merkl, Prof. Dr. Reinhard Sterner and Dr. Patrick Babinger

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201200473

      This article corrects:

      Dimerization Determines Substrate Specificity of a Bacterial Prenyltransferase

      Vol. 13, Issue 9, 1297–1303, Article first published online: 21 MAY 2012

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
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    1. Patterned Self-Assembled Monolayers: Efficient, Chemically Defined Tools for Cell Biology (pages 1717–1724)

      Justin T. Koepsel and William L. Murphy

      Article first published online: 17 JUL 2012 | DOI: 10.1002/cbic.201200226

      Thumbnail image of graphical abstract

      SAM patterning can be used to fabricate cell culture substrates with arrays of chemically defined conditions. This Minireview highlights microfluidic, photochemical, localized removal, and backfilling techniques, which can be used to locally pattern SAM substrates with biomolecules, and also describes how these approaches have been applied in SAM-based biological screening systems.

  6. Highlights

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
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    1. Going Non-native To Improve Oxidative Protein Folding (pages 1725–1727)

      Prof. Watson J. Lees

      Article first published online: 4 JUL 2012 | DOI: 10.1002/cbic.201200288

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      Chemical origami: Protein folding rates and yields can be limited by the presence of kinetic traps. By replacing two cysteines with selenocysteines in bovine pancreatic trypsin inhibitor, Hilvert and co-workers increased the folding rate and removed two traps from the oxidative-folding pathway, even though the resulting diselenide would correspond to a non-native disulfide bond.

    2. Moving Pd-Mediated Protein Cross Coupling to Living Systems (pages 1728–1731)

      Jie Li and Prof. Peng R. Chen

      Article first published online: 4 JUL 2012 | DOI: 10.1002/cbic.201200353

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      Palladium goes live: Palladium-mediated carbon–carbon bond formation plays a revolutionary role in advancing organic synthesis. Recently developed biocompatible Pd catalysts have now allowed some of these reactions, such as Suzuki–Miyaura and copper-free Sonogashira cross coupling, to be performed on proteins in living E. coli cells.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
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    1. C-Glycosphingolipids with an exo-Methylene Substituent: Stereocontrolled Synthesis and Immunostimulation of Mouse and Human Natural Killer T Lymphocytes (pages 1733–1737)

      Dr. Zheng Liu, Dr. Amy N. Courtney, Prof. Dr. Leonid S. Metelitsa and Prof. Dr. Robert Bittman

      Article first published online: 10 JUL 2012 | DOI: 10.1002/cbic.201200374

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      Introduction of an exo-methylene group into the C-glycoside analogue of KRN7000 was found to afford a new glycosphingolipid ligand with potent agonistic activity for both human and mouse invariant natural killer T lymphocytes. The key synthetic strategy utilized the Nozaki–Hiyama–Kishi reaction to achieve a high-yield coupling between an α-galactosyl aldehyde and a vinyl iodide.

    2. Terretonin Biosynthesis Requires Methylation as Essential Step for Cyclization (pages 1738–1741)

      Yudai Matsuda, Dr. Takayoshi Awakawa, Dr. Takayuki Itoh, Dr. Toshiyuki Wakimoto, Prof. Dr. Tetsuo Kushiro, Prof. Dr. Isao Fujii, Prof. Dr. Yutaka Ebizuka and Prof. Dr. Ikuro Abe

      Article first published online: 10 JUL 2012 | DOI: 10.1002/cbic.201200369

      Thumbnail image of graphical abstract

      Unexpected methylation: Terretonin is a fungal meroterpenoid derived from 3,5-dimethylorsellinic acid (DMOA). Trt1 is a terpene cyclase involved in terretonin biosynthesis and only accepts the methylated compound as a substrate to produce the cyclized product. Methylation is a common requirement for the cyclization steps in DMOA-derived meroterpenoid biosynthesis.

    3. You have full text access to this OnlineOpen article
      Selective Desulfurization Significantly Expands Sequence Variety of 3′-Peptidyl–tRNA Mimics Obtained by Native Chemical Ligation (pages 1742–1745)

      Anna-Skrollan Geiermann and Prof. Dr. Ronald Micura

      Article first published online: 11 JUL 2012 | DOI: 10.1002/cbic.201200368

      Thumbnail image of graphical abstract

      Accessible: Functionally complex 3′-peptidyl–RNA conjugates can be efficiently desulfurized under free radical reaction conditions as demonstrated here. One-pot procedures for native chemical ligation (NCL) and desulfurization enable sequences for this class of bioconjugates that are inaccessible by other methods.

    4. Exploring the Pharmacology and Action Spectra of Photochromic Open-Channel Blockers (pages 1746–1749)

      Timm Fehrentz, Christian A. Kuttruff, Florian M. E. Huber, Dr. Michael A. Kienzler, Dr. Peter Mayer and Prof. Dr. Dirk Trauner

      Article first published online: 13 JUL 2012 | DOI: 10.1002/cbic.201200216

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      Light control of voltage-gated ion channels: We have developed red-shifted derivatives of QAQ, a powerful doubly charged photochromic blocker. These derivatives allow for remote control of Kv and Nav channel conductance with light and offer the opportunity to silence neuronal activity reversibly.

      Corrected by:

      Corrigendum: Corrigendum: Exploring the Pharmacology and Action Spectra of Photochromic Open-Channel Blockers

      Vol. 14, Issue 10, 1157, Article first published online: 1 JUL 2013

    5. Metabolic Labeling of DNA by Purine Analogues in Vivo (pages 1750–1753)

      Anne B. Neef, Dr. Florent Samain and Prof. Dr. Nathan W. Luedtke

      Article first published online: 20 JUL 2012 | DOI: 10.1002/cbic.201200253

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      DNA tracking: The 2′-deoxyadenosine analogue “EdA” efficiently labels newly synthesized DNA with alkyne groups in vivo without inhibiting cell cycle progression or embryonic development. This provides the first demonstration that a bio-orthogonal functional group can be metabolically incorporated into DNA through endogenous pathways by addition of a purine analogue to cells.

    6. Fluorescent Aplyronine A: Intracellular Accumulation and Disassembly of Actin Cytoskeleton in Tumor Cells (pages 1754–1758)

      Prof. Dr. Masaki Kita, Kozo Yoneda, Yuichiro Hirayama, Kota Yamagishi, Yuki Saito, Yuka Sugiyama, Dr. Yoshihiro Miwa, Dr. Osamu Ohno, Maho Morita, Prof. Dr. Kiyotake Suenaga and Prof. Dr. Hideo Kigoshi

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cbic.201200385

      Thumbnail image of graphical abstract

      Nonstick: Aplyronine A (ApA) is an antitumor and apoptogenic macrolide of marine origin. We prepared a fluorescent derivative of ApA that accumulated strongly throughout the cytoplasm and caused the rapid disassembly of the actin cytoskeleton in tumor cells. We also established that ApA caused malfunction of cell adhesion and dephosphorylation of focal adhesion kinase with apoptosis.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Biosynthesis and Cellular Localization of Functional Polyketides in the Gastropod Mollusc Scaphander lignarius (pages 1759–1766)

      Dr. Adele Cutignano, Prof. Conxita Avila, Dr. Annamaria Rosica, Dr. Giovanna Romano, Dr. Bruna Laratta, Anna Domenech-Coll, Dr. Guido Cimino, Dr. Ernesto Mollo and Dr. Angelo Fontana

      Article first published online: 24 JUL 2012 | DOI: 10.1002/cbic.201200287

      Thumbnail image of graphical abstract

      Lignarenones are structurally simple polyketides of the mollusc Scaphander lignarius that are synthesised in a specialised eukaryotic tissue by Blochmann's glands. Polyketide assembly requires acetate/propionate as elongation units, and is primed by benzoic acid derived from the conversion of L-phenylalanine. Benzoate synthesis involves a novel PAL activity that has not previously been seen in animals.

    2. You have full text access to this OnlineOpen article
      Inhibition of Lipopolysaccharide Transport to the Outer Membrane in Pseudomonas aeruginosa by Peptidomimetic Antibiotics (pages 1767–1775)

      Martina Werneburg, Katja Zerbe, Mario Juhas, Laurent Bigler, Urs Stalder, Andres Kaech, Urs Ziegler, Daniel Obrecht, Leo Eberl and John A. Robinson

      Article first published online: 17 JUL 2012 | DOI: 10.1002/cbic.201200276

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      Traffic jam: The β-hairpin antibiotic L27–11 binds to the outer membrane (OM) protein LptD in Pseudomonas sp. New evidence suggests that the antibiotic inhibits the essential LPS-transport function of LptD. The OM proteins LptD and LptE form a complex in the OM and transport lipopolysaccharide from the periplasm into the outer leaflet of the outer cell membrane.

    3. Production of the Quorum-Sensing Molecules N-Acylhomoserine Lactones by Endobacteria Associated with Mortierella alpina A-178 (pages 1776–1784)

      Dr. Kenji Kai, Kana Furuyabu, Ayaka Tani and Prof. Hideo Hayashi

      Article first published online: 17 JUL 2012 | DOI: 10.1002/cbic.201200263

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      Bacterial quorum sensing: We have isolated N-acylhomoserine lactones (AHLs), bacterial quorum-sensing (QS) compounds, from the culture broth of the zygomycete fungus Mortierella alpina. The fungus harbors bacterial endosymbionts that are the true producers of the AHLs. This finding raises the possibility that QS plays a role in the development of fungus–endobacterium symbiosis.

    4. You have full text access to this OnlineOpen article
      Enzyme-Specific Activation versus Leaving Group Ability (pages 1785–1790)

      Roseri J. A. C. de Beer, Berry Bögels, Dr. Gijs Schaftenaar, Barbara Zarzycka, Dr. Peter J. L. M. Quaedflieg, Dr. Floris L. van Delft, Dr. Sander B. Nabuurs and Prof. Floris P. J. T. Rutjes

      Article first published online: 23 JUL 2012 | DOI: 10.1002/cbic.201200227

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      Activation by the enzyme or just a good leaving group? The guanidinophenyl (OGp) ester is a key activating group in substrate mimetics and chemoenzymatic peptide bond formation. We show that the leaving group ability of the ester is at least as important in this process as the specific interactions of the activating group with the enzyme.

    5. Lys53 of Ribosomal Protein L36AL and the CCA End of a tRNA at the P/E Hybrid Site Are in Close Proximity on the Human Ribosome (pages 1791–1797)

      Prof. Codjo Hountondji, Dr. Konstantin Bulygin, Dr. Anne Woisard, Dr. Pierre Tuffery, Dr. Jean-Bernard Créchet, Dr. Markus Pech, Prof. Dr. Knud H. Nierhaus, Prof. Galina Karpova and Dr. Soria Baouz

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201200208

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      RNA–protein interactions: C74/75 of a P/E tRNA can be crosslinked to K53 of L44e, the only protein adjacent to the CCA end of a ribosomal bound tRNA. L44e has remarkable features: for example, a universally conserved GGQ motif—the Q residue—contains one of seven identified modifications, thus suggesting that this protein might be a preferential target for regulation.

    6. Characterization of the Suillus grevillei Quinone Synthetase GreA Supports a Nonribosomal Code for Aromatic α-Keto Acids (pages 1798–1804)

      Barbara Wackler, Dr. Gerald Lackner, Dr. Yit Heng Chooi and Prof. Dr. Dirk Hoffmeister

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cbic.201200187

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      The keto being accepted: The atromentin synthase GreA represents a peptide synthetase-like enzyme from the basidiomycete Suillus grevillei. The GreA adenylation domain preferably accepts 4-hydroxyphenylpyruvic acid. Through in silico simulation of the adenylation domain structure a nonribosomal code emerged which appears specific to aromatic α-keto acids.

    7. Cardiotoxin-I: An Unexpectedly Potent Insulinotropic Agent (pages 1805–1812)

      Thi Tuyet Nhung Nguyen, Dr. Benjamin Folch, Myriam Létourneau, Dr. David Vaudry, Prof. Nam Hai Truong, Prof. Nicolas Doucet, Dr. David Chatenet and Prof. Alain Fournier

      Article first published online: 16 JUL 2012 | DOI: 10.1002/cbic.201200081

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      Virtues of venom: Cardiotoxin-I, isolated from Naja kaouthia snake venom, is able to produce concentration-dependent insulin release from INS-1E cells both in the presence and absence of glucose. Further evaluation showed that this toxin does not have hemolytic or cytotoxic characteristics, thus suggesting its potential as a tool to study insulin secretion or as a new therapeutic agent.

    8. Precursor-Directed Syntheses and Biological Evaluation of New Elansolid Derivatives (pages 1813–1817)

      Heinrich Steinmetz, Wiebke Zander, Muftah A. M. Shushni, Rolf Jansen, Klaus Gerth, Richard Dehn, Gerald Dräger, Andreas Kirschning and Rolf Müller

      Article first published online: 17 JUL 2012 | DOI: 10.1002/cbic.201200228

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      Importent alternatives: Elansolid A is an antibiotic secreted by Chitinophaga sancti. We synthesized a library of derivatives from the natural precursor elansolid C1 that was obtained by fermentation with anthranilic acid. The new compounds were tested for inhibitory activity against Staphylococcus aureus and Micrococcus luteus. None was as potent as the natural antibiotic, but stability was significantly increased.

    9. Mushroom Tyrosinase Oxidizes Tyrosine-Rich Sequences to Allow Selective Protein Functionalization (pages 1818–1825)

      Marcus J. C. Long and Prof. Lizbeth Hedstrom

      Article first published online: 17 JUL 2012 | DOI: 10.1002/cbic.201100792

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      Mushroom tyrosinase is a multifaceted chemical biology tool: This enzyme catalyzes the formation of o-quinones in tyrosine-rich peptide sequences such as the HA tag. These o-quinones can be selectively functionalized with hydrazine dyes to create labeled proteins. Under different reaction conditions, the o-quinones induce protein cleavage or crosslinking.

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireview
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Preview: ChemBioChem 13/2012 (page 1827)

      Article first published online: 3 AUG 2012 | DOI: 10.1002/cbic.201290052

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