ChemBioChem

Cover image for Vol. 14 Issue 18

December 16, 2013

Volume 14, Issue 18

Pages 2377–2520

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. You have free access to this content
      Cover Picture: Functionalized Bis-enol Acetates as Specific Molecular Probes for Esterases (ChemBioChem 18/2013) (page 2377)

      Phillipp Richter, Dr. Jerrit Weißflog, Dr. Natalie Wielsch, Dr. Aleš Svatoš and Prof. Dr. Georg Pohnert

      Article first published online: 9 DEC 2013 | DOI: 10.1002/cbic.201390066

      Thumbnail image of graphical abstract

      The cover picture shows the sesquiterpene caulerpenyne (top left), which is found in high amounts in many green algae of Caulerpa spp. These algae form a biopolymer after wounding, sealing their giant cells (bottom left). Rapid polymer formation is initiated by esterases that activate caulerpenyne to a protein-reactive 1,4-dialdehyde. Inspired by this process, G. Pohnert et al. tailored synthetic caulerpenyne analogues containing the masked reactive group as well as a fluorescent tag. On p. 2435 ff., they explain how these probes are activated by lipolytic enzymes and specifically label esterases without labeling related lipases. MS-sequencing of labeled porcine liver esterase revealed that eight out of 35 lysines, exclusively located around the active site, are covalently modified after incubation with the probe (below right). Selectivity in complex samples was demonstrated by selective detection of esterases in crude Candida lipolytica protein extracts. This strategy, modeled after a natural process, now provides a conceptual new solution for an old problem in molecular probe design.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Graphical Abstract: ChemBioChem 18/2013 (pages 2379–2385)

      Article first published online: 9 DEC 2013 | DOI: 10.1002/cbic.201390067

  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
  4. Review

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Dissecting the Molecular Basis of the Role of the O-Mannosylation Pathway in Disease: α-Dystroglycan and Forms of Muscular Dystrophy (pages 2392–2402)

      Dr. David Live, Prof. Dr. Lance Wells and Prof. Dr. Geert-Jan Boons

      Article first published online: 7 NOV 2013 | DOI: 10.1002/cbic.201300417

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      Defective glycoconjugate construction: α-Dystroglycan is modified by O-mannosyl-initiated glycans that carry the ligands for components of the extracellular matrix, such as laminin. Mutations in the enzymes that assemble this glycan result in dystroglycanopathies, inherited disorders that are associated with muscle weakness and wasting, heart defects, and cognitive impairment, often leading to premature death.

  5. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Polymerase Recognition of a Watson–Crick-Like Metal-Mediated Base Pair: Purine-2,6-Dicarboxylate⋅Copper(II)⋅ Pyridine (pages 2403–2407)

      Dr. Eun-Kyong Kim and Prof. Christopher Switzer

      Article first published online: 5 NOV 2013 | DOI: 10.1002/cbic.201300634

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      A new beginning: A Cu2+-mediated Watson–Crick-like base pair was recognized by nine out of ten DNA polymerases studied. The purine-2,6-dicarboxylateCu2+3-pyridine base pair was formed in the presence Cu2+ ions, but not in the absence of copper. It is concluded that metal-ion mediated bonding interactions are sufficient for non-canonical base-pair synthesis by enzymes.

    2. The Effect of the Length of Histone H3K4me3 on Recognition by Reader Proteins (pages 2408–2412)

      Bas Pieters, Roman Belle and Dr. Jasmin Mecinović

      Article first published online: 4 NOV 2013 | DOI: 10.1002/cbic.201300525

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      Thermodynamic analyses of associations between reader domain proteins and histone H3K4me3 peptides demonstrated that the shortest recognised histone substrate contains just the first four amino acids in histone 3. Deletion or addition at the N terminus resulted in a substantial decrease of binding affinity for most readers, thus verifying the importance of the H3A1 binding pocket.

    3. Simplified Deoxypropionate Acyl Chains for Mycobacterium tuberculosis Sulfoglycolipid Analogues: Chain Length is Essential for High Antigenicity (pages 2413–2417)

      Benjamin Gau, Aurélie Lemétais, Dr. Marco Lepore, Dr. Luis Fernando Garcia-Alles, Dr. Yann Bourdreux, Dr. Lucia Mori, Dr. Martine Gilleron, Prof. Dr. Gennaro De Libero, Dr. Germain Puzo, Prof. Jean-Marie Beau and Dr. Jacques Prandi

      Article first published online: 31 OCT 2013 | DOI: 10.1002/cbic.201300482

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      The longer, the better: Increasing the lengths of the 1,3-methyl-branched fatty acyl chain units in mycobacterial diacylated sulfoglycolipid (Acyl2SGL) analogues led to dramatic improvements in their antigenic properties and gave products more potent than the natural antigen Acyl2SGLs.

    4. Biocatalytic Synthesis of Quercetin 3-O-Glucoside-7-O-Rhamnoside by Metabolic Engineering of Escherichia coli (pages 2418–2422)

      Jonathon Roepke and Dr. Gale G. Bozzo

      Article first published online: 6 NOV 2013 | DOI: 10.1002/cbic.201300474

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      You are what you eat: Quercetin 3-O-glucoside-7-O-rhamnoside is a rare natural product with potential biological importance. We describe a strategy for the regioselective synthesis of this bisglycoside by feeding quercetin 3-O-glucoside, a naturally abundant precursor, to metabolically engineered Escherichia coli.

    5. An Unconventional Glycosyl Transfer Reaction: Glucansucrase GTFA Functions as an Allosyltransferase Enzyme (pages 2423–2426)

      Malte Timm, Julian Görl, Michael Kraus, Dr. Slavko Kralj, Dr. Hendrik Hellmuth, Dr. Raphael Beine, Prof. Dr. Klaus Buchholz, Prof. Dr. Lubbert Dijkhuizen and Prof. Dr. Jürgen Seibel

      Article first published online: 13 NOV 2013 | DOI: 10.1002/cbic.201300392

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      First reported allosyltransferase: The allopyranosyl analogue of sucrose (All-Fru) was used as donor for the glucansucrase GTFA from Lactobacillus reuteri 121. This enzyme is able to hydrolyse All-Fru and transfer allose to acceptor substrates such as sugars, amino acids and (−)-epicatechin, thus forming artificial α-linked allopyranosyl products. A triple GTFA mutant showed twofold increase in allosyl transfer.

    6. Enzymatic Aerobic Alkene Cleavage Catalyzed by a Mn3+-Dependent Proteinase A Homologue (pages 2427–2430)

      Dr. Aashrita Rajagopalan, Dr. Markus Schober, Anita Emmerstorfer, Lucas Hammerer, Anna Migglautsch, Dr. Birgit Seisser, Dr. Silvia. M. Glueck, Dr. Frank Niehaus, Dr. Juergen Eck, Dr. Harald Pichler, Prof. Dr. Karl Gruber and Prof. Dr. Wolfgang Kroutil

      Article first published online: 4 NOV 2013 | DOI: 10.1002/cbic.201300601

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      New clothes for Mn3+: Aerobic alkene cleavage of styrene-type substrates by Trametes hirsuta is attributed to an enzyme that is dependent on manganese in oxidation state three. The enzyme has a proteinase backbone and binds Mn3+ exclusively via oxygen atoms, in contrast to all known Mn3+ enzymes.

    7. Chemoselective Oxime Reactions in Proteins and Peptides by Using an Optimized Oxime Strategy: The Demise of Levulinic Acid (pages 2431–2434)

      Stijn M. Agten, Dennis Suylen, Dr. Hans Ippel, Dr. Maria Kokozidou, Dr. Guido Tans, Dr. Pieter van de Vijver, Dr. Rory R. Koenen and Prof. Tilman M. Hackeng

      Article first published online: 22 OCT 2013 | DOI: 10.1002/cbic.201300598

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      Selecting the right partner faster: In protein chemoselective conjugation, the use of levulinic acid for ketone introduction leads to slow oxime formation and poor yield because of internal cyclization, especially at low concentrations. A mechanism for cyclization is proposed and alternative keto-acids have been tested. These showed faster formation of oximes without side products.

    8. Functionalized Bis-enol Acetates as Specific Molecular Probes for Esterases (pages 2435–2438)

      Phillipp Richter, Dr. Jerrit Weißflog, Dr. Natalie Wielsch, Dr. Aleš Svatoš and Prof. Dr. Georg Pohnert

      Article first published online: 5 NOV 2013 | DOI: 10.1002/cbic.201300556

      Thumbnail image of graphical abstract

      Modeled after nature: The wound-sealing reaction of green algae guided the development of hydrolase-reactive probes for the specific labeling of esterases. These diagnostic tools react selectively with esterases (even in the presence of other hydrolytic enzymes) by forming covalent adducts.

    9. Biosynthesis and Mass Spectrometric Imaging of Tolaasin, the Virulence Factor of Brown Blotch Mushroom Disease (pages 2439–2443)

      Dr. Kirstin Scherlach, Dr. Gerald Lackner, Katharina Graupner, Dr. Sacha Pidot, Tom Bretschneider and Prof. Dr. Christian Hertweck

      Article first published online: 12 NOV 2013 | DOI: 10.1002/cbic.201300553

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      Killing them softly. The molecular basis for the biosynthesis of tolaasin, the Pseudomonas tolaasii-derived causative agent of mushroom (Agaricus bisporus) soft rot, was revealed by genome mining and analysis of the NRPS genes. Production of the toxic lipopeptides during infection was confirmed by imaging mass spectrometry.

    10. A Predicted Immunity Protein Confers Resistance to Pyocin S5 in a Sensitive Strain of Pseudomonas aeruginosa (pages 2444–2446)

      Bahareh Haji Rasouliha, Dr. Hua Ling, Chun Loong Ho and Prof. Dr. Matthew Wook Chang

      Article first published online: 12 NOV 2013 | DOI: 10.1002/cbic.201300410

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      Keeping it together: The putative S5 immunity (S5I) protein confers resistance to pyocin S5 in P. aeruginosa. We show that S5I prevents cellular lysis in cells expressing S5I protein. This paves the way to a better understanding of its role in cellular adaptation and could be used for therapeutic purposes in future.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Copper-Assisted Click Reactions for Activity-Based Proteomics: Fine-Tuned Ligands and Refined Conditions Extend the Scope of Application (pages 2447–2455)

      Georg C. Rudolf and Prof. Dr. Stephan A. Sieber

      Article first published online: 25 OCT 2013 | DOI: 10.1002/cbic.201300551

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      Business as usual: We introduce a customised ABPP click methodology that preserves the native protein fold, accelerates catalysis and is compatible with a greater range of buffers. Requiring no alteration of the established azide/alkyne CuAAC substrates, it is a powerful tool for use in biochemical and proteomic procedures without major alterations to the established protocols.

    2. Identification of a Molecular Target of a Novel Fungal Metabolite, Pyrrolizilactone, by Phenotypic Profiling Systems (pages 2456–2463)

      Dr. Yushi Futamura, Dr. Makoto Kawatani, Dr. Makoto Muroi, Harumi Aono, Dr. Toshihiko Nogawa and Prof. Dr. Hiroyuki Osada

      Article first published online: 25 OCT 2013 | DOI: 10.1002/cbic.201300499

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      A novel trypsin-like proteasome inhibitor: Pyrrolizilactone, a novel fungal metabolite, was identified from our microbial metabolite fraction library. With the aid of two phenotype profiling systems—MorphoBase and ChemProteoBase—we established that pyrrolizilactone is a unique proteasome inhibitor targeting trypsin-like activity of the proteasome.

    3. Chemoselective Immobilization of Proteins by Microcontact Printing and Bio-orthogonal Click Reactions (pages 2464–2471)

      Dr. Zachary P. Tolstyka, Wade Richardson, Dr. Erhan Bat, Caitlin J. Stevens, Dayanara P. Parra, Jonathan K. Dozier, Prof. Dr. Mark D. Distefano, Prof. Dr. Bruce Dunn and Prof. Dr. Heather D. Maynard

      Article first published online: 25 OCT 2013 | DOI: 10.1002/cbic.201300478

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      Don't move! Chemoselective immobilization of site-specifically modified proteins on surfaces through bio-orthogonal click reactions is demonstrated. The presented approach involves microcontact printing of aminooxy- or azide-functionalized alkanethiols and subsequent immobilization of proteins.

    4. Synthesis and Structure–Activity Relationship Study of Organometallic Bioconjugates of the Cyclic Octapeptide Octreotate (pages 2472–2479)

      Dr. Annika Gross, Daniel Habig and Prof. Dr. Nils Metzler-Nolte

      Article first published online: 11 NOV 2013 | DOI: 10.1002/cbic.201300450

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      With added mettle: Metal moieties (Cp2Fe, Cp2Ru, Cp2Co+, Co2(CO)6) were added to octreotate, and toxicity and cellular uptake were investigated. Enhanced uptake of ferrocenoyl-octreotate compared to other metallocene-peptides and an acetylated compound was demonstrated, and improved uptake into SSTR-expressing cells was shown.

    5. Mushroom Hunting by Using Bioinformatics: Application of a Predictive Framework Facilitates the Selective Identification of Sesquiterpene Synthases in Basidiomycota (pages 2480–2491)

      Dr. Maureen B. Quin, Christopher M. Flynn, Grayson T. Wawrzyn, Dr. Swati Choudhary and Prof. Claudia Schmidt-Dannert

      Article first published online: 24 OCT 2013 | DOI: 10.1002/cbic.201300349

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      Ringing up: Several putative sesquiterpene synthases from Stereum hirsutum have been discovered through phylogenetic analyses. Clustering based on sequence conservation and shared cyclization mechanisms allows the directed isolation and characterization of 1,6-, 1,10- and 1,11-cyclizing enzymes. Three new Δ6-protoilludene synthases are described and kinetically characterized.

    6. Iterative Antimicrobial Candidate Selection from Informed D-/L-Peptide Dimer Libraries (pages 2492–2499)

      Dr. Roman J. Lichtenecker, Dr. Bernhard Ellinger, Dr. Hong-Mei Han, Kirtikumar B. Jadhav, Dr. Sascha Baumann, Dr. Oliwia Makarewicz, Dr. Markus Grabenbauer and Prof. Dr. Hans-Dieter Arndt

      Article first published online: 22 OCT 2013 | DOI: 10.1002/cbic.201300243

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      Perfecting peptides: An iterative strategy for the transposition of antimicrobial activity from an α-helical all-L-peptide to a new D-/L-peptide was implemented by employing a library of D-/L-peptide disulfide dimers that were iteratively optimized. By using this unique concept, new antimicrobial candidate compounds could be selected from a previously unexplored chemical space.

    7. Concerted Electron/Proton Transfer Mechanism in the Oxidation of Phenols by Laccase (pages 2500–2505)

      Prof. Carlo Galli, Dr. Catherine Madzak, Dr. Raffaella Vadalà, Prof. Claude Jolivalt and Prof. Patrizia Gentili

      Article first published online: 22 OCT 2013 | DOI: 10.1002/cbic.201300531

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      Oxidation efficiency towards phenolic substrates by Trametes villosa and Trametes versicolor laccases and the D206A mutant of this latter was studied at two pH values. By the Hammett approach and Marcus analysis, we obtained unambiguous evidence that the oxidation takes place by a concerted electron/proton transfer (EPT) mechanism.

    8. Time-Resolved in-Situ Observation of Starch Polysaccharide Degradation Pathways (pages 2506–2511)

      Dr. Sophie R. Beeren, Bent O. Petersen, Dr. Marie Bøjstrup, Prof. Dr. Ole Hindsgaul and Dr. Sebastian Meier

      Article first published online: 24 OCT 2013 | DOI: 10.1002/cbic.201300461

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      Direct observations of starch remodeling should facilitate our understanding and control of processes of biotechnological, medical, and environmental relevance. Here, analytical challenges in time-resolved in situ observation of starch metabolism are addressed by means of resolution-optimized multidimensional NMR experiments.

    9. Contextual Compound Screening for Improved Therapeutic Discovery (pages 2512–2518)

      Dr. Lasse Evensen, Dr. Kristin Odlo, Dr. David R. Micklem, Dr. Amanda Littlewood-Evans, Dr. Jeanette Wood, Dr. Christian Kuzniewski, Prof. Dr. Karl-Heinz Altmann, Prof. Dr. Trond Vidar Hansen and Prof. Dr. James B. Lorens

      Article first published online: 12 NOV 2013 | DOI: 10.1002/cbic.201300409

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      Context is everything: Microenvironmental factors that regulate cellular responses influence drug sensitivity. Organotypic model systems combined with temporal live-cell imaging can detect and quantify cellular dynamics; this can be used to quantify the contextual activity of compound inhibitors and identify novel compounds with potent activity in vivo.

  7. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Review
    6. Communications
    7. Full Papers
    8. Book Reviews
    1. Bacterial Toxins: Genetics, Cellular Biology and Practical Applications. Edited by Thomas Proft. (page 2519)

      Alison Weiss

      Article first published online: 20 NOV 2013 | DOI: 10.1002/cbic.201300696

      Caister Academic, Norwich, 2013, VIII+234 pp., hardcover, £ 159.00.—ISBN 978-1-908230-28-7

    2. Chemical Synthesis of Nucleoside Analogues. Edited by Pedro Merino. (page 2520)

      Rick Cosstick

      Article first published online: 27 NOV 2013 | DOI: 10.1002/cbic.201300703

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      Wiley, Hoboken 2013, XVI+895 pp., hardcover, $ 175.00.—ISBN 978-1-1180-0751-8

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