ChemBioChem

Cover image for Vol. 10 Issue 15

October 12, 2009

Volume 10, Issue 15

Pages 2405–2543

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Cover Picture: Making Epothilones Fluoresce: Design, Synthesis, and Biological Characterization of a Fluorescent N12-Aza-Epothilone (Azathilone) (ChemBioChem 15/2009) (page 2405)

      Jürg Gertsch , Fabian Feyen , Alexander Bützberger, Barbara Gerber, Bernhard Pfeiffer and Karl-Heinz Altmann

      Version of Record online: 7 OCT 2009 | DOI: 10.1002/cbic.200990065

      Thumbnail image of graphical abstract

      The cover picture shows cells with a green fluorescent microtubule network after treatment with the fluorescent epothilone analogue NBD-azathilone. Docking studies indicate that the NBD moiety of the tubulin-bound analogue is located in a hydrophobic pocket that is not utilized by natural epothilones and directly contributes to tubulin binding. For further information on elucidating the binding and cellular effects of this analogue, see the article by K. H. Altmann et al. on p. 2513 ff.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Inside Cover: Cyclodextrin Aldehydes are Oxidase Mimics (ChemBioChem 15/2009) (page 2406)

      Thomas Hauch Fenger, Jeannette Bjerre and Mikael Bols

      Version of Record online: 7 OCT 2009 | DOI: 10.1002/cbic.200990066

      Thumbnail image of graphical abstract

      The inside cover picture shows the catalytic cycle for a cyclodextrin 6-aldehyde that catalyses the oxidation of 2-aminophenol to 2-aminophenoxazin-3-one in the presence of hydrogen peroxide. In this reaction, the cyclodextrin behaves like an oxidase with the rate of reaction inside the cavity much higher than the rate in solution. For more information, see the article by M. Bols et al. on p. 2494 ff.

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. You have free access to this content
  5. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Chemical Approaches to DNA Nanotechnology (pages 2420–2443)

      Masayuki Endo and Hiroshi Sugiyama

      Version of Record online: 27 AUG 2009 | DOI: 10.1002/cbic.200900286

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      The power of DNA: In this review, we focus on the intersection of DNA chemistry and nanotechnology and describe the potential of synthetic chemistry and its contribution to DNA nanotechnology. We also describe recent progress relating to the construction of DNA assemblies, nanoscale structures, and programmed arrangements of functional molecules and materials.

  7. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Protein Conjugates of SH3-Domain Ligands and ATP-Competitive Inhibitors as Bivalent Inhibitors of Protein Kinases (pages 2445–2448)

      Rakesh Tiwari and Keykavous Parang

      Version of Record online: 3 SEP 2009 | DOI: 10.1002/cbic.200900462

      Thumbnail image of graphical abstract

      Double trouble: Designing bivalent inhibitors of protein kinases by using a protein (hAGT) as a spacer between SH3-domain-binding ligands and an ATP-binding-site inhibitors is described.

  8. Concept

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Delivery of Therapeutic RNAi by Nanovehicles (pages 2449–2454)

      Huricha Baigude and Tariq M. Rana

      Version of Record online: 17 AUG 2009 | DOI: 10.1002/cbic.200900252

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      Designer packaging: Nanovehicles created from cationic polymers and anionic oligonucleotides through electrostatic interaction play a most important role in nonviral siRNA delivery. The type and content of amine in the polymer determine the hydrophobicity, surface charge, and particle size of resulting nanovehicle. Targeted delivery may be achieved by modifying the nanovehicle by coupling moieties that bind specific cell surface receptors.

  9. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
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    1. Mechanistic Insights into Water Activation in SAM Hydroxide Adenosyltransferase (duf-62) (pages 2455–2459)

      Hai Deng, Stephen A. McMahon, Alessandra S. Eustáquio, Bradley S. Moore, James H. Naismith and David O'Hagan

      Version of Record online: 8 SEP 2009 | DOI: 10.1002/cbic.200900369

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      Breaking waters: The substrate analogue S-adenosyl-L-homocysteine (SAH) was co-crystallised with SAM hydroxide adenosyltransferase from Pyrococcus horikoshii. Of the two active site water molecules one appears to be structural and the other is a candidate for nucleophilic attack, to become the C5′ adenosyl hydroxyl group. The data support a mechanism in which the Arg–Asp ion pair is important for positioning both water molecules.

    2. N-Terminal Specific Point-Immobilization of Active Proteins by the One-Pot NEXT-A Method (pages 2460–2464)

      Keitaro Ebisu, Hiroaki Tateno, Hiroyuki Kuroiwa, Koshi Kawakami, Megumi Ikeuchi, Jun Hirabayashi, Masahiko Sisido and Masumi Taki

      Version of Record online: 8 SEP 2009 | DOI: 10.1002/cbic.200900430

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      Who's NEXT-A: Combination of the NEXT-A method and noncatalytic Huisgen reaction enabled us to immobilize proteins onto a solid support. Lectin-immobilized gel made by using this novel method, was subjected to frontal affinity chromatography to detect sugar–lectin interactions. Immobilization of a target protein directly from cell lysates was also demonstrated.

    3. Biofunction-Assisted Sensors Based on a New Method for Converting Aptazyme Activity into Reporter Protein Expression with High Efficiency in Wheat Germ Extract (pages 2465–2468)

      Atsushi Ogawa

      Version of Record online: 11 SEP 2009 | DOI: 10.1002/cbic.200900497

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      Sensible wheat germ: I have developed novel biosensors based on a new method for converting aptazyme activity into easily detectable protein expression by translating aptazyme-fused mRNA in eukaryotic wheat germ extract. Some newly elucidated unique features of the wheat germ translation system make the sensitivity of this method much higher than that of previously reported aptazyme-based biosensors.

    4. Phosphoroselenoate Dinucleotides for Modification of mRNA 5′ End (pages 2469–2473)

      Joanna Kowalska, Maciej Lukaszewicz, Joanna Zuberek, Edward Darzynkiewicz and Jacek Jemielity

      Version of Record online: 8 SEP 2009 | DOI: 10.1002/cbic.200900522

      Thumbnail image of graphical abstract

      Beginning from the end (5′ end): Analogues of the messenger RNA 5′ end (cap) bearing an oxygen-to-selenium substitution at the β position of triphosphate bridge, which could be useful for X-ray crystallography, were synthesised. They were also incorporated into transcripts to demonstrate that such a small change of the mRNA 5′ end can improve properties of the whole mRNA molecule, for example, its translation efficiency.

  10. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Development of New and Selective Trypanosoma cruzi trans-Sialidase Inhibitors from Sulfonamide Chalcones and Their Derivatives (pages 2475–2479)

      Jin Hyo Kim , Hyung Won Ryu, Jae Hoon Shim, Ki Hun Park and Stephen G. Withers

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/cbic.200900108

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      Killer catechols: A series of sulfonamide-containing hydroxylated chalcones and quinolinone derivatives was synthesized and tested as inhibitors of the trans-sialidase from T. cruzi. Full kinetic analyses of inhibition were performed for these catechol derivatives, both for the transglycosylation reaction in the presence of lactose and for the hydrolysis reaction in its absence. Ki values in the low and submicromolar range were found.

    2. In vitro Characterization of Enzymes Involved in the Synthesis of Nonproteinogenic Residue (2S,3S)-β-Methylphenylalanine in Glycopeptide Antibiotic Mannopeptimycin (pages 2480–2487)

      Yu-Ting Huang, Syue-Yi Lyu, Pei-Hsuan Chuang, Ning-Shian Hsu, Yi-Shan Li, Hsiu-Chien Chan, Chuen-Jiuan Huang, Yu-Chen Liu, Chang-Jer Wu, Wen-Bin Yang and Tsung-Lin Li

      Version of Record online: 3 SEP 2009 | DOI: 10.1002/cbic.200900351

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      Mannopeptimycin contains the nonproteinogenic amino acid (2S,3S)-β-methylphenylalanine. The biosynthesis of this amino acid was unknown until now. In vitro biochemical results suggest phenylpyruvic acid is the precursor that is methylated at its β-position by MppJ to (3S)-β-methylphenylpyruvic acid at the expense of one molecule of SAM. The formation of (2S,3S)-β-methylphenylalanine requires an additional enzyme, TyrB.

    3. Transition from EcoDam to T4Dam DNA Recognition Mechanism without Loss of Activity and Specificity (pages 2488–2493)

      Hany Elsawy, Sveatoslav Podobinschi, Sanjay Chahar and Albert Jeltsch

      Version of Record online: 1 SEP 2009 | DOI: 10.1002/cbic.200900441

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      Kissing cousins: The EcoDam and T4Dam DNA methyltransferase are related, but deviate in their contact to the first base pair of the target sequence. We have successfully “transplanted” T4Dam DNA recognition into EcoDam and show that one intermediate of this transition is fully active; this indicates that a smooth evolutionary pathway exists between EcoDam and T4Dam. The EcoDam to T4Dam transition might have been driven by selective pressure towards increased catalytic activity.

    4. Cyclodextrin Aldehydes are Oxidase Mimics (pages 2494–2503)

      Thomas Hauch Fenger, Jeannette Bjerre and Mikael Bols

      Version of Record online: 8 SEP 2009 | DOI: 10.1002/cbic.200900448

      Thumbnail image of graphical abstract

      Just like the real thing: Enzyme-like oxidations of amines and alcohols are catalysed by cyclodextrin derivatives in aqueous solution containing H2O2. The catalysis followed Michaelis–Menten kinetics, and 2-O-ethoxy-2-al-β-cyclodextrin was found to be the best catalyst.

    5. Passage of Trojan Peptoids into Plant Cells (pages 2504–2512)

      Kai Eggenberger, Esther Birtalan, Tina Schröder, Stefan Bräse and Peter Nick

      Version of Record online: 8 SEP 2009 | DOI: 10.1002/cbic.200900331

      Thumbnail image of graphical abstract

      Sneaking into plant cells: Trojan peptoids represent novel carrier systems for the insertion of cargoes into tobacco BY-2 cells. Polyarginine-like but not polylysine-like peptoids were found to enter plant cells (see figure) significantly faster than the endocytosis tracer dextrane, and uptake kinetics could be clearly discriminated from receptor-mediated endocytosis.

    6. Making Epothilones Fluoresce: Design, Synthesis, and Biological Characterization of a Fluorescent N12-Aza-Epothilone (Azathilone) (pages 2513–2521)

      Jürg Gertsch , Fabian Feyen , Alexander Bützberger, Barbara Gerber, Bernhard Pfeiffer and Karl-Heinz Altmann

      Version of Record online: 16 SEP 2009 | DOI: 10.1002/cbic.200900376

      Thumbnail image of graphical abstract

      Lighting up microtubules: A green fluorescent 12-aza-epothilone (NBD-azathilone) has been prepared that specifically binds to cellular microtubules (MTs). This suggests that cancer cell growth inhibition by azathilones is a result of direct interference with MT functionality, as it is for natural epothilones. NBD-azathilone is a new tool for labeling the cellular MT network.

    7. Potent Fluoro-oligosaccharide Probes of Adhesion in Toxoplasmosis (pages 2522–2529)

      Sarah A. Allman, Henrik H. Jensen, Balakumar Vijayakrishnan, James A. Garnett, Ester Leon, Yan Liu, Daniel C. Anthony, Nicola R. Sibson, Ten Feizi, Stephen Matthews and Benjamin G. Davis

      Version of Record online: 11 SEP 2009 | DOI: 10.1002/cbic.200900425

      Thumbnail image of graphical abstract

      Spiked candy: An unnatural fluorinated sugar probe (see figure), designed and synthesised to bind to the pathogenic protein TgMIC1, was found to display binding potency equal to and above that of the natural ligand. Dissection of its binding mechanism demonstrated that it is possible to create effective fluorinated probe ligands for the study of, and perhaps intervention in, sugar–protein binding events.

    8. Structure and Replication of yDNA: A Novel Genetic Set Widened by Benzo-Homologation (pages 2530–2538)

      Haige Lu, Stephen R. Lynch, Alex H. F. Lee and Eric T. Kool

      Version of Record online: 24 SEP 2009 | DOI: 10.1002/cbic.200900434

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      Expanding horizons: The first solution structure of the “yDNA” alternative genetic set, and studies of polymerase replication of yDNA pairs in vitro are described. The structure reveals an antiparallel, base-paired helix. Replication experiments show the extent and limits of the three yDNA pairings.

  11. Book Reviews

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. Bacterial Polysaccharides: Current Innovations and Future Trends. Edited by Matthias Ullrich. (pages 2539–2540)

      Chang-Chun Ling

      Version of Record online: 7 OCT 2009 | DOI: 10.1002/cbic.200900501

      Caister, Norwich 2009, XII+358 pp., hardcover £ 150.00.—ISBN 978-1-904455-45-5

    2. Quantum Tunnelling in Enzyme-Catalysed Reactions. Edited by Rudolf K. Allemann and Nigel S. Scrutton. (page 2541)

      Troy Wymore

      Version of Record online: 7 OCT 2009 | DOI: 10.1002/cbic.200900473

      RSC, Cambridge 2009, XXV+385 pp., hardcover £ 119.95.—ISBN 978-0-85404-122-0

  12. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Review
    8. Highlight
    9. Concept
    10. Communications
    11. Full Papers
    12. Book Reviews
    13. Preview
    1. You have free access to this content
      Preview: ChemBioChem 16/2009 (page 2543)

      Version of Record online: 7 OCT 2009 | DOI: 10.1002/cbic.200990070

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