ChemBioChem

Cover image for Vol. 9 Issue 4

March 3, 2008

Volume 9, Issue 4

Pages 477–650

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Communications
    7. Full Papers
    8. Book Reviews
    9. Preview
    1. Cover Picture: Surface Modification of Tobacco Mosaic Virus with “Click” Chemistry (ChemBioChem 4/2008) (page 477)

      Michael A. Bruckman, Gagandeep Kaur, L. Andrew Lee, Fang Xie, Jennifer Sepulveda, Rebecca Breitenkamp, Xiongfei Zhang, Maisie Joralemon, Thomas P. Russell, Todd Emrick and Qian Wang

      Version of Record online: 21 FEB 2008 | DOI: 10.1002/cbic.200890009

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      The cover picture shows tobacco mosaic virus (TMV) decorated with a wide array of compounds. These modifications are based on the synergistic combination of the highly efficient CuI-catalyzed azide–alkyne cycloaddition reaction, a prototypical “click” reaction, and the aryldiazonium coupling reaction. This combination provides an extremely efficient way to conjugate a wide spectrum of compounds to the phenolic groups of tyrosine residues presented on the TMV capsid. To highlight the modularity and efficiency of this click conjugation, a cell-adhesion assay was performed after TMV had been modified with functionalities that can promote or prevent cell adhesion and proliferation. The crystal structures shown in the background depict the structure of the TMV coat protein, which is self-assembled helically around a single-stranded genomic RNA. Nature propagates this assembly using the leaf of the tobacco plant host. Further details can be found in the article by Q. Wang et al. on p. 519 ff. The figure was prepared by Z. Niu.

  2. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Communications
    7. Full Papers
    8. Book Reviews
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    1. Enzymatic Synthesis of Optically Active Tertiary Alcohols: Expanding the Biocatalysis Toolbox (pages 491–498)

      Robert Kourist, Pablo Domínguez de María and Uwe T. Bornscheuer

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/cbic.200700688

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      Rational routes: Optically active tertiary alcohols are important compounds in organic synthesis. Recent achievements in the enzymatic synthesis of this compound class are reviewed. Whereas active biocatalysts were initially identified by trial and error, recent achievements in protein engineering now guide identification and substantially aid understanding and improvement of enzymes with respect to substrate range and enantioselectivity.

  5. Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Minireview
    6. Communications
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    8. Book Reviews
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    1. The Human Histone Acetyltransferase P/CAF is a Promiscuous Histone Propionyltransferase (pages 499–503)

      Hans Leemhuis, Len C. Packman, Karl P. Nightingale and Florian Hollfelder

      Version of Record online: 5 FEB 2008 | DOI: 10.1002/cbic.200700556

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      Catalytic promiscuity: The human histone acetyltransferase P/CAF can confer propionyl instead of acetyl marks onto peptides that mimic the H3 histone tail. Catalysis of propionyl transfer occurs with a kcat of 8.8 min−1 (versus a kcat of 12 min−1 observed for the transfer of an acetyl group) and with identical specificity for individual lysine residues in the H3 sequence.

    2. Flavoprotein Iodotyrosine Deiodinase Functions without Cysteine Residues (pages 504–506)

      James A. Watson Jr., Patrick M. McTamney, Jennifer M. Adler and Steven E. Rokita

      Version of Record online: 28 JAN 2008 | DOI: 10.1002/cbic.200700562

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      Iodotyrosine deiodinase provides a new precedent for flavin-dependent dehalogenation. Iodotyrosine deiodinase requires no standard redox-active amino acid to promote reductive deiodination of diiodotyrosine despite the precedence for such residues in other enzymes that catalyze analogous reactions. Three cysteines present in the native mammalian enzyme could be removed without significant loss of catalytic activity.

    3. Stepwise Combinatorial Evolution of Akt Bisubstrate Inhibitors (pages 507–509)

      Jung Hwan Lee, Sanjai Kumar and David S. Lawrence

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/cbic.200700583

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      Bisubstrate analogue inhibitors have recently received considerable attention as mechanistic and structural probes of protein kinases. A stepwise library-based strategy was employed to create a potent bisubstrate inhibitor of Akt from an extraordinarily weak nonphosphorylatable peptide. The combinatorial methodology offers a means to retain desirable properties during the directed evolution of inhibitory species.

    4. Ligand-Stabilized Hairpin Structures Interfere with Elongation of Human Telomere (pages 510–513)

      Masaki Hagihara , Yuki Goto and Kazuhiko Nakatani 

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/cbic.200700667

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      No way! Naphthyridine tetramer (NT) can bind to G–G mismatches produced by the pairing of two GGG units in hairpin secondary structures, which are a possible intermediate in the folding of telomeres into G quadruplexes. Here we report that NT-stabilized hairpin structures in the telomere can interfere with DNA synthesis by Taq DNA polymerase (see figure). With its unique sequence preference, NT could be used to gain deeper insight into the biological consequence of ligand–telomere interactions.

    5. Development of Bacteriophage P22 as a Platform for Molecular Display: Genetic and Chemical Modifications of the Procapsid Exterior Surface (pages 514–518)

      Sebyung Kang, Gabriel C. Lander, John E. Johnson and Peter E. Prevelige

      Version of Record online: 21 JAN 2008 | DOI: 10.1002/cbic.200700555

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      Loop regions on the external surface of the 420 coat protein molecules making up the icosahedral phage P22 procapsid (see figure) can be genetically modified to enable specific chemical modification. This makes it possible to symmetrically display organic and inorganic molecules on the surface of these ∼55 nm nanoparticles.

    6. Surface Modification of Tobacco Mosaic Virus with “Click” Chemistry (pages 519–523)

      Michael A. Bruckman, Gagandeep Kaur, L. Andrew Lee, Fang Xie, Jennifer Sepulveda, Rebecca Breitenkamp, Xiongfei Zhang, Maisie Joralemon, Thomas P. Russell, Todd Emrick and Qian Wang

      Version of Record online: 21 JAN 2008 | DOI: 10.1002/cbic.200700559

      Thumbnail image of graphical abstract

      Click conjugation of tobacco mosaic virus: As a prototype of “click” chemistry, the CuI catalyzed azide-alkyne cycloaddition reaction in combination with diazonium-coupling proved to be an efficient, versatile, and benign method to conjugate a wide range of compounds to phenolic groups of protein tyrosines. In particular, plant virus tobacco mosaic virus was chosen as a multivalent protein scaffold to demonstrate this bioconjugation strategy.

    7. Rapid Identification of a Protein Binding Partner for the Marine Natural Product Kahalalide F by Using Reverse Chemical Proteomics (pages 524–530)

      Andrew M. Piggott and Peter Karuso

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/cbic.200700608

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      Capable chemists: Chemists are playing an ever more important role in biology through the application of small molecules to biological systems. In this paper, we combine affinity chromatography and phage display (reverse chemical proteomics), to isolate a cellular receptor for the new anticancer drug and marine natural product, kahalalide F. The results challenge biologists to uncover the significance of the interaction between the drug and its target protein.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Minireview
    6. Communications
    7. Full Papers
    8. Book Reviews
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    1. How Metal Ions Affect Amyloid Formation: Cu2+- and Zn2+-Sensitive Peptides (pages 531–536)

      Kevin Pagel, Tomomi Seri, Hans von Berlepsch, Jan Griebel, Reinhard Kirmse, Christoph Böttcher and Beate Koksch

      Version of Record online: 29 JAN 2008 | DOI: 10.1002/cbic.200700656

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      Cu2+or Zn2+? A set of coiled-coil based model peptides that predictably react in the presence of transition metal ions is presented. The position of the coordinating His residue (see picture) as well as the nature of the metal ion dictate conformation and aggregate morphology. As a result, amyloid formation could either be inhibited or accelerated by the addition of Cu2+ or Zn2+.

    2. Exchange Rate Constants of Invisible Protons in Proteins Determined by NMR Spectroscopy (pages 537–542)

      Takuya Segawa, Fatiha Kateb, Luminita Duma, Geoffrey Bodenhausen and Philippe Pelupessy

      Version of Record online: 5 FEB 2008 | DOI: 10.1002/cbic.200700600

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      Heteronuclear NMR spectroscopy has been used to measure the exchange rate constants of labile protons in the side chains of lysine and arginine residues in ubiquitin at pH 7.45. The capability to measure exchange rate constants and activation energies for individual sites at a physiologically relevant pH should allow one to obtain deeper insight into interactions between proteins (folded or unfolded) and to map out the contact interfaces in complexes made up of proteins and other macromolecules.

      Corrected by:

      Corrigendum: Exchange Rate Constants of Invisible Protons in Proteins Determined by NMR Spectroscopy

      Vol. 10, Issue 5, 782, Version of Record online: 17 MAR 2009

    3. Cellular Origin of Dysiherbaine, an Excitatory Amino Acid Derived from a Marine Sponge (pages 543–551)

      Ryuichi Sakai, Kazufumi Yoshida, Atsuko Kimura, Kanae Koike, Mitsuru Jimbo, Kazuhiko Koike, Atsushi Kobiyama and Hisao Kamiya

      Version of Record online: 31 JAN 2008 | DOI: 10.1002/cbic.200700498

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      Pinpointing responsibility: The marine-sponge toxin dysiherbaine was shown by immunohistochemical methods to be localized in the cells of the endosymbiotic cyanobacteria Synechosystis harbored in the host sponge Lendenfeldia chondrodes (see light micrograph of cells). Chemical analysis indicated the presence of two chemotypes of the cyanobacterium, only one of which appears to produce the toxin.

    4. A Robust Protein Host for Anchoring Chelating Ligands and Organocatalysts (pages 552–564)

      Manfred T. Reetz, Martin Rentzsch, Andreas Pletsch, Andreas Taglieber, Frank Hollmann, Régis J. G. Mondière, Norbert Dickmann, Birte Höcker, Simona Cerrone, Michaela C. Haeger and Reinhard Sterner

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/cbic.200700413

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      Robust hybrid catalysts: A platform for directed evolution of hybrid catalysts has been optimized and miniaturized by using a thermostable enzyme, tHisF (see figure) from Thermotoga maritima. A tHisF mutant with a strategically placed cysteine was identified and subjected to bioconjugation by introducing a variety of ligands for metal ligation, a ligand/metal moiety, and several organocatalysts such as flavin and thiazolium entities.

    5. Light-Driven Biocatalytic Oxidation and Reduction Reactions: Scope and Limitations (pages 565–572)

      Andreas Taglieber, Frank Schulz, Frank Hollmann, Monika Rusek and Manfred T. Reetz

      Version of Record online: 20 FEB 2008 | DOI: 10.1002/cbic.200700435

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      Nicotinamide-(in)dependent oxidoreductases. Ways to circumvent the limitations of the PAMO-P3 enzyme system were explored by using EDTA as a sacrificial reductant. We have broadened the light-driven regeneration approach to the class of flavin-dependent reductases. By using the Old Yellow Enzyme homologue YqjM as a model system (see figure), a significantly higher catalytic turnover for the enzyme catalyst was achieved; we assign this to a higher accessibility of the flavin prosthetic group, as well as to the absence of oxidative uncoupling.

    6. Analysis of Organo–Silica Interactions during Valve Formation in Synchronously Growing Cells of the Diatom Navicula pelliculosa (pages 573–584)

      Alejandro Heredia, Han J. van der Strate, Ivonne Delgadillo, Vladimir A. Basiuk and Engel G. Vrieling

      Version of Record online: 21 FEB 2008 | DOI: 10.1002/cbic.200700313

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      Time-resolved analysis of valve formation in the diatom Navicula pelliculosa enabled characterization of the dynamics of the chemical bonds by ATR-FTIR spectroscopy. The variations in FTIR band intensity represented specific interactions between organic and inorganic molecules in the course of the major silicification event, during which stretching of Si[BOND]O bonds was predominantly noticed. The experimentally obtained frequencies of the major bonds corresponded to those obtained by MM+ and PM3 FTIR simulations.

    7. Authentic Heterologous Expression of the Tenellin Iterative Polyketide Synthase Nonribosomal Peptide Synthetase Requires Coexpression with an Enoyl Reductase (pages 585–594)

      Laura M. Halo, James W. Marshall, Ahmed A. Yakasai, Zhongshu Song, Craig P. Butts, Matthew P. Crump, Mary Heneghan, Andrew M. Bailey, Thomas J. Simpson, Colin. M. Lazarus and Russell J. Cox

      Version of Record online: 12 FEB 2008 | DOI: 10.1002/cbic.200700390

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      Total synthesis fungal style: When the ∼12 kb tenellin synthetase gene (tenS) alone was expressed in Aspergillus oryzae, at least three novel tetramic acids were synthesised, illustrating the diversity of synthetic routes available to the polyketide synthase (PKS). However, when tenS was expressed with orf3, which encodes a PKS enoyl reductase component, a single compound, pretenellin A, was produced. The tenellin synthetase gene encodes a putative C-terminal reductase domain, but this appears to catalyse a Dieckmann cyclisation (DKC) during the synthesis of pretenellin A, rather than a reduction.

    8. Azotobacter vinelandii Metal Storage Protein: “Classical” Inorganic Chemistry Involved in Mo/W Uptake and Release Processes (pages 595–602)

      Jörg Schemberg, Klaus Schneider, Dirk Fenske and Achim Müller

      Version of Record online: 13 FEB 2008 | DOI: 10.1002/cbic.200700446

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      The Mo storage protein is the only known non-iron storage protein; it differs fundamentally from all other described Mo-containing proteins and even all metalloproteins and, last but not least, combines the fields of protein biochemistry and polyoxometalate cluster chemistry. The Mo storage protein can bind up to 115 Mo or W atoms in the form of metal–oxygen clusters. A detailed study on the release of Mo from the Mo storage protein revealed a pH-dependent, three-step process.

    9. Assembly and Heterologous Expression of the Coumermycin A1 Gene Cluster and Production of New Derivatives by Genetic Engineering (pages 603–612)

      Manuel Wolpert, Lutz Heide, Bernd Kammerer and Bertolt Gust

      Version of Record online: 20 FEB 2008 | DOI: 10.1002/cbic.200700483

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      New hybrid antibiotics: The entire coumermycin A1 gene cluster has been reconstituted from two overlapping cosmid inserts into one single clone by the exclusive use of λ RED recombination technology. Heterologous expression in Streptomyces coelicolor M512 and modification of the assembled gene cluster led to the formation of coumermycin A1 and also of new derivatives, which were further tested for antibacterial activities.

    10. Direct Evidence for ArO[BOND]S Bond Cleavage upon Inactivation of Pseudomonas aeruginosa Arylsulfatase by Aryl Sulfamates (pages 613–623)

      Pavla Bojarová, Emma Denehy, Ian Walker, Karen Loft, David P. De Souza, L. W. Lawrence Woo, Barry V. L. Potter, Malcolm J. McConville and Spencer J. Williams

      Version of Record online: 20 FEB 2008 | DOI: 10.1002/cbic.200700579

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      A dead-end street: Brønsted analysis of the time-dependent inactivation of P. aeruginosa sulfatase by aryl sulfamates identified the cleavage of the ArO[BOND]S bond as the first irreversible chemical step. A variable inactivation stoichiometry (see figure) suggests that multiple sulfamoylation events occur. These data provide new insight into the inactivation of human estrone sulfatase in the treatment of hormone-dependent breast cancer.

    11. Glycosylated Derivatives of Steffimycin: Insights into the Role of the Sugar Moieties for the Biological Activity (pages 624–633)

      Carlos Olano, Mohamed S. Abdelfattah, Sonia Gullón, Alfredo F. Braña, Jürgen Rohr, Carmen Méndez and José A. Salas

      Version of Record online: 25 JAN 2008 | DOI: 10.1002/cbic.200700610

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      Combinatorial biosynthesis: Twelve steffimycin derivatives, each possessing an altered glycosylation pattern, have been generated by combinatorial biosynthesis. Analysis of their biological activities against three human tumor cell lines revealed that two of them (see structures) show improved antitumor activities. Some insights into the structure–activity relationships of the new steffimycin derivatives are presented.

    12. A Novel Sensor Platform Based on Aptamer-Conjugated Polypyrrole Nanotubes for Label-Free Electrochemical Protein Detection (pages 634–641)

      Hyeonseok Yoon, June-Hyung Kim, Nahum Lee, Byung-Gee Kim and Jyongsik Jang

      Version of Record online: 5 FEB 2008 | DOI: 10.1002/cbic.200700660

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      Direct detection: Conducting polymer nanotubes with tailored chemical functionalities were fabricated and readily integrated into a field-effect transistor sensor device. The sensor response was controlled by tuning the chemical functionality of the nanotubes; this demonstrates the possibility of using the nanotubes as smart signal transducers.

  7. Book Reviews

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    3. Graphical Abstract
    4. News
    5. Minireview
    6. Communications
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    8. Book Reviews
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    1. Molecules and Medicine. By E. J. Corey, Barbara Czakó, and László Kürti. (pages 643–644)

      Hilmar Weinmann and Eckhard Ottow

      Version of Record online: 21 FEB 2008 | DOI: 10.1002/cbic.200700785

  8. Preview

    1. Top of page
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    4. News
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    6. Communications
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    1. Preview: ChemBioChem 5/2008 (page 650)

      Version of Record online: 21 FEB 2008 | DOI: 10.1002/cbic.200890012

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