ChemBioChem

Cover image for Vol. 8 Issue 1

January 2, 2007

Volume 8, Issue 1

Pages 1–150

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. Cover Picture: A Gene Cluster Encoding Rhizoxin Biosynthesis in “Burkholderia rhizoxina”, the Bacterial Endosymbiont of the Fungus Rhizopus microsporus (ChemBioChem 1/2007) (page 1)

      Laila P. Partida-Martinez and Christian Hertweck

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200690039

      The cover picture shows a confocal scanning micrograph of bacterial endosymbionts (Burkholderia rhizoxina) residing in the mycelium of the plant-pathogenic fungus Rhizopus microsporus, stained with a fluorescent dye. This symbiosis is a unique example in which a fungus harbors bacteria for the production of a virulence factor, the potent antimitotic macrolide rhizoxin. The entire 82 kb gene cluster that encodes rhizoxin biosynthesis has been located, cloned, and sequenced, and its identity has been confirmed by a targeted gene inactivation in the genome of the cultured endosymbionts. Analyses of the gene cluster revealed that rhizoxin polyketide assembly involves a giant trans-AT PKS-NRPS thiotemplate system with some unusual features. The elucidation of rhizoxin biosynthesis sheds more light on an unparalleled phytopathogenic symbiosis and sets the basis for engineering new derivatives of the potential antitumor drug. Further details can be found in the article by C. Hertweck et al. on p. 41 ff.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
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      Withstanding the Test of Time (pages 3–7)

      Peter Gölitz, Lobat Doostdar and Lisa Abel

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200600468

  3. Graphical Abstract

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

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. The Role of Internal Water Molecules in the Structure and Function of the Rhodopsin Family of G Protein-Coupled Receptors (pages 19–24)

      Leonardo Pardo, Xavier Deupi, Nicole Dölker, María Luz López-Rodríguez and Mercedes Campillo

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200600429

      Thumbnail image of graphical abstract

      Not so watered down. In this review, we summarize the role of water molecules embedded in the transmembrane bundle of G protein-coupled receptors in stabilizing intra- and interhelical interactions, and their use for building computer-generated homology models.

  5. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. A Molecular Probe for the Detection of Homopurine Sequences (pages 25–27)

      Ivan Trkulja, Sarah M. Biner, Simon M. Langenegger and Robert Häner

      Version of Record online: 23 NOV 2006 | DOI: 10.1002/cbic.200600378

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      The highly selective detection of homopurine target strands with a triplex-forming molecular probe is described. The binding of a clamp-type oligonucleotide containing two terminally attached pyrene molecules to the target sequence is easily monitored through excimer formation. The oligonucleotide probe allows the efficient discrimination of single nucleotide mismatches because of the high mismatch sensitivity of the triplex formation.

    2. Predicting the Nature and Timing of Epimerisation on a Modular Polyketide Synthase (pages 28–31)

      Antonio Starcevic, Marcel Jaspars, John Cullum, Daslav Hranueli and Paul F. Long

      Version of Record online: 29 NOV 2006 | DOI: 10.1002/cbic.200600399

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      When and where? Modular polyketide synthases catalyse the Claisen condensation of simple organic acids with inversion of configuration to give a 2R methyl centre. However, according to Celmer's rules, the ultimate stereochemical configuration of many polyketides requires epimerisation to the 2S isomer. It has been generally believed that the epimerisation is performed by the ketosynthase domains. We challenge this traditional thinking and propose bifunctionality of the ketoreductase domains.

    3. Functional Immobilization of the Small GTPase Rab6A on DNA–Gold Nanoparticles by Using a Site-Specifically Attached Poly(ethylene glycol) Linker and Thiol Place-Exchange Reaction (pages 32–36)

      Christian F. W. Becker, Yoann Marsac, Pompi Hazarika, Jens Moser, Roger S. Goody and Christof M. Niemeyer

      Version of Record online: 23 NOV 2006 | DOI: 10.1002/cbic.200600422

      Thumbnail image of graphical abstract

      PEG'ed to gold. An approach for the functional immobilization of proteins via a thiol-modified PEG linker on gold nanoparticles is described. A place-exchange reaction of thiolated oligonucleotides with PEG-modified proteins leads to stable protein–nanoparticle conjugates.

    4. Efficient Enzymatic Glycosylation of Peptides and Oligosaccharides from GalNAc and UTP (pages 37–40)

      Vanessa Bourgeaux, Martine Cadène, Friedrich Piller and Véronique Piller

      Version of Record online: 17 NOV 2006 | DOI: 10.1002/cbic.200600369

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      One-pot synthesis: A system has been developed to glycosylate peptides, proteins, and oligosaccharides more efficiently than conventional procedures. With the simple precursors GalNAc, UTP, and creatine-P, four enzymes are employed in one pot to regenerate UDP-GalNAc which is used for the transfer of GalNAc to specific acceptor substrates.

    5. A Gene Cluster Encoding Rhizoxin Biosynthesis in “Burkholderia rhizoxina”, the Bacterial Endosymbiont of the Fungus Rhizopus microsporus (pages 41–45)

      Laila P. Partida-Martinez and Christian Hertweck

      Version of Record online: 8 DEC 2006 | DOI: 10.1002/cbic.200600393

      Thumbnail image of graphical abstract

      Cloning, sequencing and gene analysis of the rhi gene locus in the genome of the rhizoxin-producing bacterial endosymbiont “Burkholderia rhizoxina” of the rice-pathogenic fungus Rhizopus microsporus provides the first insight into the giant trans-AT NRPS–PKS thiotemplate assembly line for the potent antimitotic macrolide.

    6. Synthesis of [1,2-13C2,15N]-L-Homoserine and Its Incorporation by the PKS-NRPS System of Fusarium moniliforme into the Mycotoxin Fusarin C (pages 46–50)

      David O. Rees, Nick Bushby, Russell J. Cox, John R. Harding, Thomas J. Simpson and Christine L. Willis

      Version of Record online: 23 NOV 2006 | DOI: 10.1002/cbic.200600404

      Thumbnail image of graphical abstract

      Fungal PKS/NRPS: [1,2-13C2,15N]-L-Homoserine has been prepared from [13C2,15N]-glycine in good yield. Incubation studies with cultures of the fungus Fusarium moniliforme confirm its intact incorporation into the pyrrolidinone ring of fusarin C.

    7. Developments in the Characterisation of the Catalytic Triad of α-Chymotrypsin: Effect of the Protonation State of Asp102 on the 1H NMR Signals of His57 (pages 51–54)

      Gilles Bruylants, Christina Redfield and Kristin Bartik

      Version of Record online: 23 NOV 2006 | DOI: 10.1002/cbic.200600433

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      Protonated or not?1H NMR spectra of α-chymotrypsin were recorded as a function of pH (from top to bottom pH 8.6, 5.1 and 4.2). Slow exchange is observed for the NH protons of His57 between two environments due to different protonation states of Asp102.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. Functional Cell-Surface Display of a Lipase-Specific Chaperone (pages 55–60)

      Susanne Wilhelm, Frank Rosenau, Stefan Becker, Sebastian Buest, Sascha Hausmann, Harald Kolmar and Karl-Erich Jaeger

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200600203

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      Lifs like these. Several bacterial lipases of biotechnological importance need specific chaperones, termed lipase specific foldases (Lifs), to fold into an enzymatically active conformation. Here, the functional cell-surface display of the Lif protein from Pseudomonas aeruginosa is demonstrated (see figure). This foldase autodisplay system could enable the study of protein–protein interactions and allow the ultrahigh-throughput screening of large libraries of foldase variants.

    2. Microtiter Plate-Based Screening for the Optimization of DNA–Protein Conjugate Synthesis by Means of Expressed Protein Ligation (pages 61–67)

      Marina Lovrinovic and Christof M. Niemeyer

      Version of Record online: 23 NOV 2006 | DOI: 10.1002/cbic.200600303

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      Making the most of your reaction: A facile microtiter plate-based screening assay has been applied to the quantitative monitoring of various experimental parameters of EPL-based DNA–protein conjugate synthesis (see scheme). As a consequence, the ligation of a model protein-thioester with the oligonucleotide has been improved to near quantitative yields.

    3. Bifunctional Ligands that Target Cells Displaying the αvβ3 Integrin (pages 68–82)

      Robert M. Owen, Coby B. Carlson, Jinwang Xu, Patricia Mowery, Elisabetta Fasella and Laura L. Kiessling

      Version of Record online: 8 DEC 2006 | DOI: 10.1002/cbic.200600339

      Thumbnail image of graphical abstract

      Targeting cancer: We have synthesized an RDG-based peptidomimetic that binds selectively to the integrin αvβ3, which is displayed on cancer cells. The integrin ligand can be elaborated to generate conjugates for imaging, delivering chemotherapeutics, or recruiting an immune response. When the ligand is attached to an antigenic carbohydrate, (α-Gal), the resulting small molecule selectively recruits endogenous anti-Gal antibodies to the target cells.

    4. Generation of New Landomycins with Altered Saccharide Patterns through Over-expression of the Glycosyltransferase Gene lanGT3 in the Biosynthetic Gene Cluster of Landomycin A in Streptomyces cyanogenus S-136 (pages 83–88)

      Lili Zhu, Andriy Luzhetskyy, Martha Luzhetska, Cynthia Mattingly, Val Adams, Andreas Bechthold and Jürgen Rohr

      Version of Record online: 1 DEC 2006 | DOI: 10.1002/cbic.200600360

      Thumbnail image of graphical abstract

      The Las: Two new landomycin analogues with unprecedented saccharide moieties were generated by changing the biosynthetic flux of the assembly of the landomycin saccharide chain. This was achieved by over-expression of the glycosyltransferases gene, lanGT3, in the landomycin producer, Streptomyces cyanogenus S-136.

    5. Caged Capsaicins: New Tools for the Examination of TRPV1 Channels in Somatosensory Neurons (pages 89–97)

      Daniel Gilbert, Katharina Funk, Brigitte Dekowski, Ralf Lechler, Sandro Keller, Frank Möhrlen, Stephan Frings and Volker Hagen

      Version of Record online: 8 DEC 2006 | DOI: 10.1002/cbic.200600437

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      Light flashes and chili peppers. Extra- and intracellular concentration jumps of the vanilloid capsaicin can be achieved by photolysis of the newly developed α-carboxy-4,5-dimethoxy-2-nitrobenzyl- and {7-[bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl-caged capsaicins. These phototriggers are powerful tools for the kinetic analysis of capsaicin receptor channels (TRPV1) and for study of the asymmetry of capsaicin action on these channels.

    6. Selective Labeling of Proteins by Using Protein Farnesyltransferase (pages 98–105)

      Benjamin P. Duckworth, Zhiyuan Zhang, Ayako Hosokawa and Mark D. Distefano

      Version of Record online: 29 NOV 2006 | DOI: 10.1002/cbic.200600340

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      Many methods exist to label proteins, but few offer the selectivity that is often required. This paper presents a new in vitro protein-labeling strategy that offers selectivity. An enzyme is used to label a target protein with an alkyne-containing molecule, which is then treated with an azide-containing fluorophore.

    7. Learning from Directed Evolution: Further Lessons from Theoretical Investigations into Cooperative Mutations in Lipase Enantioselectivity (pages 106–112)

      Manfred T. Reetz, Michael Puls, José Daniel Carballeira, Andreas Vogel, Karl-Erich Jaeger, Thorsten Eggert, Walter Thiel, Marco Bocola and Nikolaj Otte

      Version of Record online: 29 NOV 2006 | DOI: 10.1002/cbic.200600359

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      A little theory helps: By using molecular-dynamics simulations, the source of enhanced enantioselectivity of a lipase mutant (see figure) that catalyzes the hydrolysis of a chiral ester has been traced to a relay mechanism. Two of the six mutations are instrumental, and this double mutant is even more enantioselective than previous mutants.

    8. Novel Bcl-2 Inhibitors: Discovery and Mechanism Study of Small Organic Apoptosis-Inducing Agents (pages 113–121)

      Zhichao Zhang, Liji Jin, Xuhong Qian, Meijiao Wei, Yuanyuan Wang, Jing Wang, Yuanyuan Yang, Qin Xu, Yongting Xu and Fengyu Liu

      Version of Record online: 1 DEC 2006 | DOI: 10.1002/cbic.200600305

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      Setting the right target. A novel strategy to rapidly obtain protein-targeted apoptosis inducers as antitumor leads instead of conventional DNA-targeted ones has been established. By effective screening, followed by the discovery of a molecular target, and by combining the information obtained from virtual-modification experiments, a series of novel Bcl-2 inhibitors was obtained. These inhibitors represent favorable leads for the development of more agents with improved affinity for the Bcl-2 protein, and provided a valuable starting point for the development of an acceptable antitumor treatment.

    9. A Resonance Energy Transfer Immunoassay Based on a Thiol-Reactive Ruthenium Donor Dye and a Longwave-Emitting Acceptor (pages 122–128)

      Jochen Weh, Axel Duerkop and Otto S. Wolfbeis

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200600316

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      A thiol-reactive ruthenium metal–ligand complex is used as the donor dye in a sensitive luminescence energy transfer (LET) immunoassay. The thiol label allows for improved reproducibility of labelling positions on proteins, because the number of reactive thiol groups of proteins is usually small, and helps to retain the biofuntionality of labelled proteins.

    10. Tetrabromocinnamic Acid (TBCA) and Related Compounds Represent a New Class of Specific Protein Kinase CK2 Inhibitors (pages 129–139)

      Mario A. Pagano, Giorgia Poletto, Giovanni Di Maira, Giorgio Cozza, Maria Ruzzene, Stefania Sarno, Jenny Bain, Matthew Elliott, Stefano Moro, Giuseppe Zagotto, Flavio Meggio and Lorenzo A. Pinna

      Version of Record online: 29 NOV 2006 | DOI: 10.1002/cbic.200600293

      Thumbnail image of graphical abstract

      Examining the cellular functions of CK2 and counteracting its pathogenic potentials: Even small monocyclic molecules such as the tetrabromophenyl acrylates (shown) can behave as powerful and selective ATP-mimetic inhibitors of the prosurvival activity of protein kinase CK2, provided that they possess both apolar and polar crucial elements to interact effectively with the unique features of its catalytic site.

  7. Conference Report

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. Chemical Biology: Directing Biosynthesis (pages 141–143)

      Antony N. Appleyard

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200600494

  8. Book Reviews

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

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. Minireview
    6. Communications
    7. Full Papers
    8. Conference Report
    9. Book Reviews
    10. Preview
    1. Preview: ChemBioChem 2/2007 (page 150)

      Version of Record online: 15 DEC 2006 | DOI: 10.1002/cbic.200690040

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