ChemBioChem

Cover image for Vol. 14 Issue 17

November 25, 2013

Volume 14, Issue 17

Pages 2221–2371

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlight
    6. Communications
    7. Full Papers
    8. Book Review
    1. You have free access to this content
      Cover Picture: Synthesis and Characterization of Cell-Permeable Caged Phosphates that Can Be Photolyzed by Visible Light or 800 nm Two-Photon Photolysis (ChemBioChem 17/2013) (page 2221)

      Dr. Cyril Herbivo, Dr. Ziad Omran, Dr. Julia Revol, Dr. Hélène Javot and Dr. Alexandre Specht

      Version of Record online: 18 NOV 2013 | DOI: 10.1002/cbic.201390062

      Thumbnail image of graphical abstract

      The cover picture shows a membrane-permeable photolabile precursor of inorganic phosphate (Pi). The EANBP caged-Pi molecules can accumulate intracellularly by using acetoxymethyl (AM) groups for cell delivery. This principle is schematically represented here, as applied to root-tip cells from the plant Arabidopsis thaliana. The caged-Pi molecule is able to release Pi efficiently, either after visible light irradiation, or after two-photon excitation at 800 nm. Altogether, this membrane-permeable caged Pi allows the generation and maintenance of a considerable pool of intracellular Pi, thus making it suitable for the study of the Pi signal-transduction cascade in living cells, including plant cells. For further information, see the paper by H. Javot, A. Specht, et al. on p. 2277 ff.

    2. You have free access to this content
      Inside Cover: Reducing Product Inhibition in Nucleic Acid-Templated Ligation Reactions: DNA-Templated Cycligation (ChemBioChem 17/2013) (page 2222)

      Alexander Roloff and Prof. Dr. Oliver Seitz

      Version of Record online: 18 NOV 2013 | DOI: 10.1002/cbic.201390063

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      The inside cover picture shows a DNA-templated ligation–cyclization reaction sequence. On p. 2322 ff., O. Seitz and A. Roloff explain how, during this “cycligation”, product inhibition is reduced due to the decreased template affinity of the cyclic ligation products. Product cyclization could thus provide a generic tool to increase turnover in nucleic acid-templated chemistry.

  2. Graphical Abstract

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

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

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlight
    6. Communications
    7. Full Papers
    8. Book Review
    1. Biomimetic Assembly of the [FeFe] Hydrogenase: Synthetic Mimics in a Biological Shell (pages 2237–2238)

      Dr. Ulf-Peter Apfel and Prof. Dr. Wolfgang Weigand

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/cbic.201300523

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      Combining synthetic chemistry and biology: A new method that allows the incorporation of synthetic [FeFe] hydrogenase mimics into the apo-hydrogenase is highlighted. Azadithiolato-functionalized model complexes showed similar activity to wild-type enzymes when implemented into the protein.

  5. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlight
    6. Communications
    7. Full Papers
    8. Book Review
    1. Yeast Three-Hybrid Screening for Identifying Anti-Tuberculosis Drug Targets (pages 2239–2242)

      Dr. Simone Moser and Prof. Kai Johnsson

      Version of Record online: 16 OCT 2013 | DOI: 10.1002/cbic.201300472

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      Mycobacterium goes yeast: Target deconvolution of anti-tuberculosis drugs can be a very challenging task. Here we report a yeast 3-hybrid system that allows promising small molecules to be screened for protein targets of a pathogen in nontoxic yeast cells. The system employs libraries of randomly fragmented bacterial DNA and offers a technically simple alternative approach for target identification.

    2. Cell-Free Preparation of Functional and Triggerable Giant Proteoliposomes (pages 2243–2247)

      Dr. Yan-Jun Liu, Gregory P. R. Hansen, Anna Venancio-Marques and Prof. Damien Baigl

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300501

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      Heat, we leak: We express a membrane protein outside well-defined giant liposomes obtained by gravity-transferred sucrose-in-oil droplets into a cell-free, reconstituted expression system. We show that the presence of the liposome is necessary during expression for efficient protein insertion into the membrane and that temperature can trigger the resulting membrane function.

    3. Identification of Mureidomycin Analogues and Functional Analysis of an N-Acetyltransferase in Napsamycin Biosynthesis (pages 2248–2255)

      Dr. Xiaoyu Tang, Marcel Gross, Prof. Dr. Yunying Xie, Andreas Kulik and Dr. Bertolt Gust

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300287

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      Antibiotic abundance: Several new uridyl peptide antibiotics were identified from a heterologous producer strain containing the mureidomycin/napsamycin biosynthetic gene cluster by using HRMS and LC-ESI-MS/MS. Analysis of the new compounds and the corresponding gene cluster revealed NpsB, an N-acetyltransferase, to be responsible for acetylation of the uridyl peptide antibiotic.

    4. Cloning and Sequencing of the Chaetocin Biosynthetic Gene Cluster (pages 2256–2258)

      Dr. Thomas Gerken and Prof. Christopher T. Walsh

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300513

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      How a fungus does it: The epidithiodiketopiperazine (ETP) fungal alkaloids, which include gliotoxin, have garnered much attention since their initial isolation. The cloning and sequencing of the biosynthetic gene cluster for another ETP, chaetocin A (see figure) were used to suggest a route towards dimerization and sulfur incorporation in these molecules.

    5. Characterization of N-Demethyllincosamide Methyltransferases LmbJ and CcbJ (pages 2259–2262)

      Dr. Lucie Najmanová, Dr. Eva Kutejová, Dr. Jan Kadlec, Marek Polan, Dr. Jana Olšovská, Dr. Oldřich Benada, Dr. Jitka Novotná, Dr. Zdeněk Kameník, Dr. Petr Halada, Dr. Jacob Bauer and Dr. Jiří Janata

      Version of Record online: 25 OCT 2013 | DOI: 10.1002/cbic.201300389

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      Chemical diversity: Two SAM-dependent N-methyltransferases—LmbJ from the biosynthesis of the antibiotic lincomycin and CcbJ from celesticetin biosynthesis—have been characterized and compared. Both tested enzymes form multimers and are able to utilize N-demethyllincomycin, the natural substrate of LmbJ, with comparable efficiency.

    6. Dual Targeting of the Warburg Effect with a Glucose-Conjugated Lactate Dehydrogenase Inhibitor (pages 2263–2267)

      Emilia C. Calvaresi, Dr. Carlotta Granchi, Dr. Tiziano Tuccinardi, Dr. Valeria Di Bussolo, Dr. Robert W. Huigens III, Dr. Hyang Yeon Lee, Dr. Rahul Palchaudhuri, Prof. Marco Macchia, Prof. Adriano Martinelli, Prof. Filippo Minutolo and Prof. Paul J. Hergenrother

      Version of Record online: 31 OCT 2013 | DOI: 10.1002/cbic.201300562

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      Effective glucose diet: We report the development and activity of glucose-conjugated LDH-A inhibitors designed for dual targeting of the Warburg effect (elevated glucose uptake and glycolysis) in cancer cells. Glycoconjugation could be applied to inhibitors of many enzymes involved in glycolysis or tumor metabolism.

    7. New Biologically Active Hydrogen Sulfide Donors (pages 2268–2271)

      Thomas Roger, Dr. Francoise Raynaud, Dr. Frédéric Bouillaud, Céline Ransy, Dr. Serge Simonet, Christine Crespo, Dr. Marie-Pierre Bourguignon, Dr. Nicole Villeneuve, Dr. Jean-Paul Vilaine, Dr. Isabelle Artaud and Dr. Erwan Galardon

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300552

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      Generous donors: The dithioperoxyanhydrides (CH3COS)2, (PhCOS)2, CH3COSSCO2Me and PhCOSSCO2Me act as thiol-activated hydrogen sulfide donors in aqueous buffer solution. The most efficient donor (CH3COS)2 can induce a biological response in cells, and advantageously replace hydrogen sulfide in ex vivo vascular studies.

    8. Enzymes from the Haloacid Dehalogenase (HAD) Superfamily Catalyse the Elusive Dephosphorylation Step of Riboflavin Biosynthesis (pages 2272–2275)

      Dr. Ilka Haase, Sonja Sarge, Dr. Boris Illarionov, Dr. Dietmar Laudert, Dr. Hans-Peter Hohmann, Prof. Adelbert Bacher and Prof. Markus Fischer

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/cbic.201300544

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      The missing link: Studies on the biosynthesis of riboflavin have failed to characterise dephosphorylation of the intermediate 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione 5′-phosphate. We show that this reaction can be catalysed in Escherichia coli by YigB and YbjI and in plant chloroplasts by AtcpFHy1, which are members of the haloacid dehalogenase superfamily.

  6. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlight
    6. Communications
    7. Full Papers
    8. Book Review
    1. Synthesis and Characterization of Cell-Permeable Caged Phosphates that Can Be Photolyzed by Visible Light or 800 nm Two-Photon Photolysis (pages 2277–2283)

      Dr. Cyril Herbivo, Dr. Ziad Omran, Dr. Julia Revol, Dr. Hélène Javot and Dr. Alexandre Specht

      Version of Record online: 10 OCT 2013 | DOI: 10.1002/cbic.201300425

      Thumbnail image of graphical abstract

      Life of Pi: Membrane-permeable photolabile precursors of Pi, capable of releasing Pi efficiently either after visible light irradiation or after two-photon excitation at 800 nm, have been developed. These “caged-Pi” molecules are capable of intracellular accumulation, without requiring injection. This allows for a considerable pool of intracellularly available Pi, suitable for studying any living cell.

    2. A Single Mutation at the Ferredoxin Binding Site of P450 Vdh Enables Efficient Biocatalytic Production of 25-Hydroxyvitamin D3 (pages 2284–2291)

      Dr. Yoshiaki Yasutake, Dr. Taiki Nishioka, Dr. Noriko Imoto and Prof. Tomohiro Tamura

      Version of Record online: 24 SEP 2013 | DOI: 10.1002/cbic.201300386

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      Dramatic activity enhancement by a single mutation: A Highly active single mutant of P450 vitamin D3 hydroxylase (Vdh) was obtained by engineering the ferredoxin-binding surface. Biocatalytic production of 25-hydroxyvitamin D3 is reported, by using nisin-treated Rhodococcus erythropolis cells expressing the Vdh mutant.

    3. The ATP/ADP Substrate Specificity Switch between Toxoplasma gondii NTPDase1 and NTPDase3 is Caused by an Altered Mode of Binding of the Substrate Base (pages 2292–2300)

      Dr. Ulrike Krug, Robert Totzauer, Dr. Matthias Zebisch and Prof. Dr. Norbert Sträter

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300441

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      Reversal of enzyme specificity: Toxoplasma gondii NTPDases1 and -3 vary greatly in their ability to hydrolyze ADP and ATP. Here we show that this switch is mainly dependent on residues 492 and 493, which give rise to two different binding modes of the nucleotide base.

    4. Directed Evolution by Using Iterative Saturation Mutagenesis Based on Multiresidue Sites (pages 2301–2309)

      Dr. Loreto P. Parra, Dr. Rubén Agudo and Prof. Dr. Manfred T. Reetz

      Version of Record online: 18 OCT 2013 | DOI: 10.1002/cbic.201300486

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      More residues, less screening: Iterative saturation mutagenesis (ISM) of the Baeyer–Villiger monooxygenase PAMO at two five-residue sites leads to an active mutant in the diastereoselective Baeyer–Villiger reaction of 4-(bromomethylidene)cyclohexanone.

    5. Towards Functional Orthogonalisation of Protein Complexes: Individualisation of GroEL Monomers Leads to Distinct Quasihomogeneous Single Rings (pages 2310–2321)

      Dr. Sonja Billerbeck, Dr. Belén Calles, Dr. Christian L. Müller, Prof. Dr. Victor de Lorenzo and Prof. Dr. Sven Panke

      Version of Record online: 22 OCT 2013 | DOI: 10.1002/cbic.201300332

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      A functional permissive site within the essential folding machine GroEL was identified and used to individualise GroEL monomers through various peptide insertions. Co-expression of two biochemically distinct monomers revealed the assembly of quasi-homogenous single rings, and this can be used as basis for the orthogonal evolution of folding machines with new functions.

    6. Reducing Product Inhibition in Nucleic Acid-Templated Ligation Reactions: DNA-Templated Cycligation (pages 2322–2328)

      Alexander Roloff and Prof. Dr. Oliver Seitz

      Version of Record online: 9 OCT 2013 | DOI: 10.1002/cbic.201300516

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      Keep on rolling: A DNA-templated ligation–cyclization reaction yields cyclic ligation products with significantly decreased template affinity. Compared to ligation-only reactions, the “cycligation” method provides higher yields in shorter times. Product cycligation might provide a generic tool to reduce product inhibition in nucleic acid-templated chemistry.

    7. Novel Aeruginosin-865 from Nostoc sp. as a Potent Anti-inflammatory Agent (pages 2329–2337)

      Aleksandra Kapuścik, Dr. Pavel Hrouzek, Dr. Marek Kuzma, Simona Bártová, Dr. Petr Novák, Dr. Jouni Jokela, Maren Pflüger, Dr. Andreas Eger, Dr. Harald Hundsberger and Dr. Jiří Kopecký

      Version of Record online: 2 OCT 2013 | DOI: 10.1002/cbic.201300246

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      Calm down: Anti-inflammatory activity of the new aeruginosin Aer-865 is reported. In TNF-α-stimulated endothelial cells, Aer-865 downregulates IL-8 and ICAM-1 and is associated with inhibition of NF-κB translocation to the nucleus. In this respect Aer-865 can be considered an interesting immunomodulatory agent.

    8. Small-Molecule Mechanism of Action Studies in Caenorhabditis elegans (pages 2338–2344)

      Katherine Zlotkowski, Anders M. Eliasen, Aurpon Mitra and Prof. Dionicio Siegel

      Version of Record online: 7 OCT 2013 | DOI: 10.1002/cbic.201300399

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      Branch line: The mechanism of action of clovanemagnolol, a compound that promotes axonal branching in primary neuronal cultures and in Caenorhabditis elegans, was determined by using affinity reagents with soluble C. elegans proteome and genetic recapitulation of the observed branching phenotype.

    9. Volatile Terpenes from Actinomycetes: A Biosynthetic Study Correlating Chemical Analyses to Genome Data (pages 2345–2354)

      Patrick Rabe, Christian A. Citron and Dr. Jeroen S. Dickschat

      Version of Record online: 8 OCT 2013 | DOI: 10.1002/cbic.201300329

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      Bacterial terpenes: The volatile terpenes emitted by 24 actinomycetes, most with sequenced genomes, have been identified. The results of these chemical analyses were compared with a phylogenetic tree of bacterial terpene cyclases, thus revealing previously unrecognised side products of characterised bacterial terpene cyclases. The analytical data were used to suggest the functions of three new enzymes.

    10. Identification of New N-Acylhomoserine Lactone Signalling Compounds of Dinoroseobacter shibae DFL-12T by Overexpression of luxI Genes (pages 2355–2361)

      Alexander Neumann, Diana Patzelt, Prof. Dr. Irene Wagner-Döbler and Prof. Dr. Stefan Schulz

      Version of Record online: 11 NOV 2013 | DOI: 10.1002/cbic.201300424

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      Cell signalling: (2E,11Z)-N-Octadeca-2,11-dienoylhomoserine lactone was identified as the major quorum-sensing regulator in the marine bacterium Dinoroseobacter shibae DFL-12 by overexpression of a luxI gene in the host organisms. This quorum-sensing signal induces flagella formation and cell differentiation. Overexpression of the same gene in E. coli resulted in the formation of a different set of homoserine lactones.

    11. α-Crystallin Modulates its Chaperone Activity by Varying the Exposed Surface (pages 2362–2370)

      Dr. Valentina Palmieri, Dr. Giuseppe Maulucci, Dr. Alessando Maiorana, Dr. Massimiliano Papi and Prof. Marco De Spirito

      Version of Record online: 12 NOV 2013 | DOI: 10.1002/cbic.201300447

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      The eye lens guardian: The α-crystallin family, like other heat shock proteins, is known to have chaperone activity and protect cells from heat, drug cytotoxicity, and oxidative stress. Small-angle X-ray scattering conformational analysis shows a direct link between the α-crystallin quaternary structure and its chaperone activity, thus offering new prospects for misfolding pathologies and non-surgical treatment of cataracts.

  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Highlight
    6. Communications
    7. Full Papers
    8. Book Review
    1. Methods in Molecular Biology 969: Synthetic Messenger RNA and Cell Metabolism Modulation: Methods and Protocols. Edited by Peter M. Rabinovich. (page 2371)

      Johannes Grillari

      Version of Record online: 16 OCT 2013 | DOI: 10.1002/cbic.201300631

      Humana Press, Totowa 2013, XI+323 pp., hardcover, $ 139.00.—ISBN 978-1-62703-259-9

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