ChemBioChem

Cover image for Vol. 12 Issue 6

April 11, 2011

Volume 12, Issue 6

Pages 813–971

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Cover Picture: Design, Synthesis and Characterization of a New Anionic Cell-Penetrating Peptide: SAP(E) (ChemBioChem 6/2011) (page 813)

      Irene Martín, Dr. Meritxell Teixidó and Prof. Dr. Ernest Giralt 

      Article first published online: 6 APR 2011 | DOI: 10.1002/cbic.201190021

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      The cover picture shows a rocket representing the anionic cell-penetrating peptide (CPP) SAP(E) reported by E. Giralt, M. Teixidó and I. Martín on p. 896 ff. The “moon” is a confocal microscopy image of HeLa cells after 3 hours of coincubation with CF-SAP and Rd-SAP(E). To the best of our knowledge, SAP(E) is one of the first anionic CPPs to be described. It adopts a polyproline II secondary structure in aqueous buffer and self-assembles to form aggregated structures able to internalize different cell lines with almost no toxic effects. The internalization mechanism proposed for SAP(E) is clathrin-independent. Much can be achieved from a negatively charged CPP, for example, the spectrum of possible cargoes increases enormously. Positively charged cargoes could now be added to the list of molecules with the capacity to be delivered by these promising vectors. Illustration made with the valuable help of José Alberto Santos.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Inside Cover: Inhibition of Influenza Virus Activity by Multivalent Glycoarchitectures with Matched Sizes (ChemBioChem 6/2011) (page 814)

      Ilona Papp, Christian Sieben, Dr. Adam L. Sisson, Johanna Kostka, Dr. Christoph Böttcher, Dr. Kai Ludwig, Prof. Andreas Herrmann and Prof. Rainer Haag

      Article first published online: 6 APR 2011 | DOI: 10.1002/cbic.201190022

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      The inside cover picture shows polyglycerol-based nanogels (~50 nm, blue) functionalized with sialic acid residues (orange). These glycocalyx mimetics are excellent inhibitors of influenza virus (green) binding and fusion. The optimal multivalent inhibitor reduces viral activity by up to 80 %; this emphasizes the importance of particle dimension and polyvalency for efficient competition with the cell surface (yellow). For further information, see the paper by R. Haag et al. on p. 887 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Graphical Abstract: ChemBioChem 6/2011 (pages 815–822)

      Article first published online: 6 APR 2011 | DOI: 10.1002/cbic.201190023

  4. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
  5. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Strategies and Perspectives in Ion-Channel Engineering (pages 830–839)

      Wolfgang Grosse, Prof. Dr. Lars-Oliver Essen and Prof. Dr. Ulrich Koert

      Article first published online: 6 APR 2011 | DOI: 10.1002/cbic.201000793

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      Opening channels: Ion-channel engineering, a reprogramming and re-engineering of pores and channels, becomes possible by combining structural biology with chemical/biological synthesis. Different functional and synthetic strategies are presented and discussed.

  6. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Open Season for Hunting and Trapping Post-translational Cysteine Modifications in Proteins and Enzymes (pages 841–844)

      Prof. Claus Jacob and Dr. Lalla A. Ba

      Article first published online: 28 MAR 2011 | DOI: 10.1002/cbic.201100068

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      The state that sulfur's in: A recently developed isotope-coded dimedone and iododimedone method for a more precise detection of sulfenic acid modifications in proteins and enzymes might reveal some of the secrets of post-translational cysteine modifications in cellular signalling and regulation.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Dye-Free MicroRNA Quantification by Using Pyrosequencing with a Sequence-Tagged Stem–loop RT Primer (pages 845–849)

      Hua Jing, Prof. Qinxin Song, Zhiyao Chen, Bingjie Zou, Chen Chen, Prof. Minsheng Zhu, Prof. Guohua Zhou, Tomoharu Kajiyama and Prof. Hideki Kambara

      Article first published online: 18 MAR 2011 | DOI: 10.1002/cbic.201100023

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      Micro-sensitive: A novel dye-free method to quantify femtomolar miRNA expression levels was developed. The miRNA was detected by reverse transcription with sequence-tagged stem–loop RT primers. Pyrosequencing technology was employed to quantify the microRNAs by detecting the tagged sequence labels in RT products of miRNA.

    2. Biosynthesis of 2-Alkyl-4(1H)-Quinolones in Pseudomonas aeruginosa: Potential for Therapeutic Interference with Pathogenicity (pages 850–853)

      Dominik Pistorius, Dr. Angelika Ullrich, Dr. Simon Lucas, Prof. Dr. Rolf W. Hartmann, Prof. Dr. Uli Kazmaier and Prof. Dr. Rolf Müller

      Article first published online: 18 MAR 2011 | DOI: 10.1002/cbic.201100014

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      Targeting quorum sensing: The Pseudomonas quinolone signal (PQS) and its direct precursor HHQ are important quorum-sensing signal molecules in P. aeruginosa that contribute to the pathogenicity of this bacterium. In vitro reconstitution of HHQ biosynthesis employing recombinant PqsD protein has shed light on this enzyme and its substrates, and led to a test system for identifying inhibitors.

    3. Small-Molecule Regulators of Human Stem Cell Self-Renewal (pages 854–857)

      Dr. Laure C. Bouchez, Dr. Anthony E. Boitano, Lorenzo de Lichtervelde, Russell Romeo, Dr. Michael P. Cooke and Prof. Dr. Peter G. Schultz

      Article first published online: 4 MAR 2011 | DOI: 10.1002/cbic.201000734

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      A cell-based phenotypic screen using primary CD34+ cells identified novel regulators of hematopoietic stem cell (HSC) fate. These compounds expand cord-blood-derived HSCs by acting as potent antagonists of the aryl hydrocarbon receptor.

    4. The Last Step of the Biosynthesis of the Cyanotoxins Cylindrospermopsin and 7-epi-Cylindrospermopsin is Catalysed by CyrI, a 2-Oxoglutarate-Dependent Iron Oxygenase (pages 858–862)

      Rabia Mazmouz, Dr. Florence Chapuis-Hugon, Prof. Dr. Valérie Pichon, Dr. Annick Méjean and Prof. Dr. Olivier Ploux

      Article first published online: 14 MAR 2011 | DOI: 10.1002/cbic.201000726

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      Unstereoselective by nature: CyrI is a 2-oxoglutarate-dependent iron oxygenase that catalyses the last step of the biosynthesis of the cyanobacterial cytotoxin cylindrospermopsin, by hydroxylating 7-deoxy-cylindrospermopsin. The stereoselectivity of this enzyme varies from strain to strain, which suggests that 7-epi-cylindrospermopsin should be considered a new member of the cyanobacterial toxin family.

    5. ELDOR Spectroscopy Reveals that Energy Landscapes in Human Methionine Synthase Reductase are Extensively Remodelled Following Ligand and Partner Protein Binding (pages 863–867)

      Dr. Stephen E. J. Rigby, Xiaodong Lou, Dr. Helen S. Toogood, Dr. Kirsten R. Wolthers and Prof. Nigel S. Scrutton

      Article first published online: 25 FEB 2011 | DOI: 10.1002/cbic.201000630

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      ELDOR roadmap: ELDOR spectroscopy gives access to the energy landscape of an electron transfer protein. In human methionine synthase reductase (MSR) this landscape is rugged and is remodelled through effector ligand and protein binding. The mobility of flavin-binding domains suggests that large-scale motion underpins electron transfer across multiple redox cofactors in the MSR–methionine synthase protein complex (see figure).

    6. Design and Synthesis of Selenazole-Containing Peptides for Cocrystallization with P-Glycoprotein (pages 868–873)

      Dr. Houchao Tao, Yue Weng, Dr. Rupeng Zhuo, Prof. Dr. Geoffrey Chang, Prof. Dr. Ina L. Urbatsch and Prof. Dr. Qinghai Zhang

      Article first published online: 8 MAR 2011 | DOI: 10.1002/cbic.201100048

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      Small changes for better X-rays: The synthesis of all 20 natural amino acid-derived selenazole units now makes it possible to create diverse selenium-labeled peptides as X-ray crystallographic tools with which to map the polyspecific binding sites of P-glycoprotein.

    7. Rational Design of Oncocin Derivatives with Superior Protease Stabilities and Antibacterial Activities Based on the High-Resolution Structure of the Oncocin-DnaK Complex (pages 874–876)

      Daniel Knappe, Michael Zahn, Ute Sauer, Dr. Guido Schiffer, Prof. Dr. Norbert Sträter and Prof. Dr. Ralf Hoffmann

      Article first published online: 8 MAR 2011 | DOI: 10.1002/cbic.201000792

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      Countering MDR pathogens: The proline-rich designer peptide oncocin is highly active against a number of antibiotic-resistant, Gram-negative pathogens. Here we deduce residues critical to its activity and the crystal structure of an oncocin–DnaK complex from a positional Ala scan. New lead compounds were highly resistant against serum and E. coli proteases.

    8. Ruthenium(II) Metallo-intercalators: DNA Imaging and Cytotoxicity (pages 877–880)

      Dr. Martin R. Gill, Hanan Derrat, Prof. Carl G. W. Smythe, Dr. Giuseppe Battaglia and Dr. Jim A. Thomas

      Article first published online: 23 MAR 2011 | DOI: 10.1002/cbic.201000782

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      Dead or alive: We report the successful cellular uptake of two ruthenium polypyridyl DNA light switch complexes that function as multifunctional cellular DNA imaging agents and display potent cytotoxicity against cancer cells. The cytotoxic properties of one complex are of great interest as it offers a potential lead for the development of a new class of anticancer drug in addition to its use as a cellular DNA imaging agent.

    9. Multiple-Catalytic Sensing of Nucleic Acid Sequences by Utilising a DNA–RNA–DNA Chimeric Antisense Probe and RNase H with a Eukaryotic Cell-Free Translation System (pages 881–885)

      Dr. Atsushi Ogawa

      Article first published online: 7 MAR 2011 | DOI: 10.1002/cbic.201000744

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      Double sense: A novel multiple-catalytic DNA sensing method utilises a chimeric probe that targets both the DNA and reporter mRNA. The technique uses just probe, RNase H, luciferase mRNA and wheat germ extract. With its four discrete catalytic processes including cycling probe technology, this method shows relatively high sensitivity and specificity despite requiring neither labelling nor nucleic acid amplification.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Inhibition of Influenza Virus Activity by Multivalent Glycoarchitectures with Matched Sizes (pages 887–895)

      Ilona Papp, Christian Sieben, Dr. Adam L. Sisson, Johanna Kostka, Dr. Christoph Böttcher, Dr. Kai Ludwig, Prof. Andreas Herrmann and Prof. Rainer Haag

      Article first published online: 7 MAR 2011 | DOI: 10.1002/cbic.201000776

      Thumbnail image of graphical abstract

      Polyglycerol nanoparticles of diameter 50–70 nm were coated with sialic acid residues to afford excellent inhibitors of influenza virus binding and fusion, and hence infectivity of erythrocytes. This approach highlights the versatility and potential of a growing class of biocompatible, branched, polyether nanogels that benefit from a highly functionalizable, hydrophilic surface.

    2. Design, Synthesis and Characterization of a New Anionic Cell-Penetrating Peptide: SAP(E) (pages 896–903)

      Irene Martín, Dr. Meritxell Teixidó and Prof. Dr. Ernest Giralt 

      Article first published online: 1 MAR 2011 | DOI: 10.1002/cbic.201000679

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      A SAP delivery: SAP(E) is an amphipathic proline-rich peptide derived from sweet arrow peptide (SAP) and adopts a defined PPII secondary structure in solution. Despite its overall negative charge it can be internalized into different cell lines without toxicity (see scheme). By making use of the noncationic nature of SAP(E) intracellular delivery of new cargoes might be possible.

    3. Engineering an Allosteric Binding Site for Aminoglycosides into TEM1-β-Lactamase (pages 904–913)

      Dr. Alexander N. Volkov, Dr. Humberto Barrios, Dr. Pascale Mathonet, Dr. Christine Evrard, Prof. Marcellus Ubbink, Prof. Jean-Paul Declercq, Prof. Patrice Soumillion and Prof. Jacques Fastrez

      Article first published online: 18 MAR 2011 | DOI: 10.1002/cbic.201000568

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      Evolving regulation: An allosteric binding site for aminoglycoside antibiotics has been created in TEM1-β-lactamase by directed evolution. Aminoglycosides binding activates the enzyme by expulsion of an inhibitor, and allows their detection at low concentration. Interactions with several ligands offer opportunities for complex allosteric regulation.

    4. Peptide Structure Stabilization by Membrane Anchoring and its General Applicability to the Development of Potent Cell-Permeable Inhibitors (pages 914–921)

      Liv Johannessen, Jarrett Remsberg, Prof. Vadim Gaponenko, Dr. Kristie M. Adams, Dr. Joseph J. Barchi Jr., Dr. Sergey G. Tarasov, Dr. Sheng Jiang and Dr. Nadya I. Tarasova

      Article first published online: 1 MAR 2011 | DOI: 10.1002/cbic.201000563

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      Keep in shape: Membrane anchoring through lipidation allows the cell membrane to function as a scaffold in stabilizing the native folds of short protein fragments. As a result, lipopeptides derived from motifs involved in essential interactions can function as protein inhibitors. They can be designed and developed rationally even in the absence of tertiary structure data for the target protein.

    5. Mining the Cinnabaramide Biosynthetic Pathway to Generate Novel Proteasome Inhibitors (pages 922–931)

      Dr. Shwan Rachid, Liujie Huo, Jennifer Herrmann, Dr. Marc Stadler, Dr. Bärbel Köpcke, Dr. Jens Bitzer and Prof. Dr. Rolf Müller

      Article first published online: 8 MAR 2011 | DOI: 10.1002/cbic.201100024

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      Mutasynthesis as chlorination tool: Cinnabaramides, in contrast to salinosporamides, are produced by terrestrial microorganisms, exhibit a unique hexyl side chain, and lack the chlorination required for potent activity as proteasome inhibitors. Deciphering of the biosynthesis of cinnabaramides revealed the biosynthetic origin of the side chain, leading to a successful strategy for the generation of chlorinated cinnabaramide analogues by mutasynthesis.

    6. Unusual Transglycosylation Activity of Flavobacterium meningosepticum Endoglycosidases Enables Convergent Chemoenzymatic Synthesis of Core Fucosylated Complex N-Glycopeptides (pages 932–941)

      Dr. Wei Huang, Dr. Jie Li and Prof. Dr. Lai-Xi Wang

      Article first published online: 4 MAR 2011 | DOI: 10.1002/cbic.201000763

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      Expanding the endoglycosidases' repertoire for transglycosylation: The F. meningosepticum endo-β-N-acetylglucosaminidases were found to have specific transglycosylation activities, being capable of transferring oligosaccharides from sugar oxazolines to a Fucα1,6GlcNAc-peptide to form a core-fucosylated N-glycopeptide. This provides an efficient method for complex glycopeptide synthesis and potentially for glycoprotein glycosylation remodeling.

    7. Potent and Selective Synthetic Modulators of a Quorum Sensing Repressor in Pseudomonas aeruginosa Identified from Second-Generation Libraries of N-Acylated L-Homoserine Lactones (pages 942–949)

      Dr. Margrith E. Mattmann, Patrick M. Shipway, Nicole J. Heth and Prof. Dr. Helen E. Blackwell

      Article first published online: 1 MAR 2011 | DOI: 10.1002/cbic.201000708

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      A little de-quorum: Non-native molecules that can intercept bacterial quorum sensing signals represent useful tools to study the mechanism of this complex cell–cell signaling process. The iterative design, synthesis, and screening of focused libraries of N-acylated homoserine lactones has revealed highly potent and selective modulators of the novel Pseudomonas aeruginosa quorum sensing repressor, QscR (see figure).

    8. Coupling Proteomics and Transcriptomics for the Identification of Novel and Variant Forms of Mollusk Shell Proteins: A Study with P. margaritifera (pages 950–961)

      Dr. Sophie Berland, Dr. Arul Marie, Dr. Denis Duplat, Dr. Christian Milet, Dr. Jean Yves Sire and Dr. Laurent Bédouet

      Article first published online: 14 MAR 2011 | DOI: 10.1002/cbic.201000667

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      Pulling proteins from a shell: Proteomic and transcriptomic methods were combined for the analysis of proteins in mollusk shell. Some sequences exhibited interesting variation among the mollusk species. A novel sequence (see figure) is described and regions with chitin-binding motifs are retrieved from several peptides nested in the shell; this indicates protein involvement in shell patterning.

    9. In Vitro Selection of Proteins that Undergo Covalent Labeling with Small Molecules by Thiol-Disulfide Exchange by Using Ribosome Display (pages 962–969)

      Dr. Hayato Yanagida, Dr. Tomoaki Matsuura, Dr. Yasuaki Kazuta and Dr. Tetsuya Yomo

      Article first published online: 7 MAR 2011 | DOI: 10.1002/cbic.201000620

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      The generation of proteins that undergo covalent labeling with small molecules was demonstrated through in vitro selection by using ribosome display technology. Selected cysteine mutants of the WW domain were biotin-labeled by disulfide exchange with a biotinylated peptide. This covalent-labeling technique is suitable for fusion proteins with a variety of small molecules.

  9. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Handbook of Epigenetics: The New Molecular and Medical Genetics. Edited by Trygve Tollefsbol. (page 970)

      Albert Jeltsch

      Article first published online: 25 FEB 2011 | DOI: 10.1002/cbic.201100065

      Academic Press, San Diego 2011, XIII+624 pp., hardcover $ 150.00.—ISBN 978-0-12-375709-8

    2. Functional Biochemistry in Health and Disease. By Eric Newsholme and Anthony Leech. (page 970)

      Dylan Thompson

      Article first published online: 4 MAR 2011 | DOI: 10.1002/cbic.201100008

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      Wiley–Blackwell Oxford 2010, 560 pp., softcover $ 75.00.—ISBN 978-0-471-93165-2

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. You have free access to this content
      Preview: ChemBioChem 7/2011 (page 971)

      Article first published online: 6 APR 2011 | DOI: 10.1002/cbic.201190025

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