ChemBioChem

Cover image for Vol. 15 Issue 6

Early View (Online Version of Record published before inclusion in an issue)

Editor: Peter Gölitz

Online ISSN: 1439-7633

Associated Title(s): ChemCatChem, ChemMedChem, ChemPhysChem, ChemSusChem

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  1. 1 - 18
  1. Communications

    1. Synthesis of a Glycopeptide Vaccine Conjugate for Induction of Antibodies Recognizing O-Mannosyl Glycopeptides

      MSc Jin Yu and Dr. Ulrika Westerlind

      Article first published online: 17 APR 2014 | DOI: 10.1002/cbic.201300537

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      Sugars from the brain: The chemical synthesis and immunization of a glycopeptide vaccine construct containing the common O-mannose motif Galβ1-4GlcNAcβ1-2ManαThr was accomplished to generate antibody-based tools for enrichment, detection, and identification of mammalian O-mannosyl glycoproteins and glycopeptides.

  2. Minireviews

    1. Exosomes and Microvesicles: Identification and Targeting By Particle Size and Lipid Chemical Probes

      Noah Kastelowitz and Prof. Dr. Hang Yin

      Article first published online: 16 APR 2014 | DOI: 10.1002/cbic.201400043

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      Targeting extracellular vesicles: Exosomes and microvesicles are submicroscopic vesicles released by cells into the extracellular space that play important signaling roles in normal and pathophysiologic processes. We highlight current methods to detect these vesicles and focus on potential future applications of lipid chemical probes to target these vesicles.

  3. Communications

    1. Structural Basis of Furan–Amino Acid Recognition by a Polyspecific Aminoacyl-tRNA-Synthetase and its Genetic Encoding in Human Cells

      Moritz J. Schmidt, Annemarie Weber, Moritz Pott, Prof. Wolfram Welte and Dr. Daniel Summerer

      Article first published online: 15 APR 2014 | DOI: 10.1002/cbic.201402006

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      Photo opportunity: We report the genetic encoding of a furan-based, photo-crosslinking amino acid in human cells by a mutant pyrrolysyl-tRNA synthetase (PylRS) with broad polyspecificity. Crystal structures of this enzyme reveal the mode of furan amino acid recognition and the basis of polyspecificity, thus providing a promising starting point for engineering PylRS mutants with increased substrate scope.

  4. Full Papers

    1. A New Bifunctional Chelator Enables Facile Biocoupling and Radiolabeling as the Basis for a Bioconjugation Kit

      Dr. Ali Barandov, Dr. Dan Grünstein, Dr. Ivalaya Apostolova, Dr. Ralph Buchert, Michel Roger, Prof. Dr. Winfried Brenner, Prof. Dr. Ulrich Abram and Prof. Dr. Peter H. Seeberger

      Article first published online: 10 APR 2014 | DOI: 10.1002/cbic.201400001

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      Bioconjugation kit: We present a facile biocoupling approach using a new tridendate bifunctional chelator that enables synthesis of glycoconjugates in a single step with high yields and short preparation time. Radiolabeled carbohydrates were achieved in both pre- and postlabeling fashion by using this approach.

  5. Book Reviews

  6. Full Papers

    1. Cellular Scent of Influenza Virus Infection.

      Dr. Alexander A. Aksenov, Christian E. Sandrock, Dr. Weixiang Zhao, Shankar Sankaran, Michael Schivo, Richart Harper, Dr. Carol J. Cardona, Dr. Zheng Xing and Dr. Cristina E. Davis

      Article first published online: 9 APR 2014 | DOI: 10.1002/cbic.201300695

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      A case of sniffles: The composition of volatile organic compounds (VOCs) in human breath changes under disease conditions, including viral infection. The VOC profiles upon infection with three influenza virus strains were assayed in a cell line. Diagnostic devices based on VOC analysis have enormous potential in the clinical setting.

    2. Rational Design, Synthesis and Biological Evaluation of Modular Fluorogenic Substrates with High Affinity and Selectivity for PTP1B

      Dr. Silvano Sanchini, Dr. Francesca Perruccio and Dr. Grazia Piizzi

      Article first published online: 9 APR 2014 | DOI: 10.1002/cbic.201400033

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      Smart probes: The aminocoumarin latent chromophore is released through an enzyme-initiated 1,6-elimination reaction. Optimisation of the stereoelectronic properties and of the binding interactions at the enzyme active site led to substrates with high affinity and promising selectivity.

  7. Communications

    1. Using Singular Value Decomposition to Characterize Protein–Protein Interactions by In-cell NMR Spectroscopy

      Subhabrata Majumder, Christopher M. DeMott, Dr. David S. Burz and Dr. Alexander Shekhtman

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201400030

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      Peering inside a cell: Single-value decomposition (SVD) analysis of in-cell NMR spectra differentiates between specific binding and random events and identifies the principal binding mode between two interacting species. The analysis implicates a set of amino acids involved in specific in-cell protein–protein interactions that differs from previous NMR analyses but is in good agreement with crystallographic data.

  8. Full Papers

    1. A Tryptophan 6-Halogenase and an Amidotransferase Are Involved in Thienodolin Biosynthesis

      Dr. Daniela Milbredt, Dr. Eugenio P. Patallo and Prof. Karl-Heinz van Pée

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201400016

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      The skeleton lives: Thienodolin shows concentration-dependent growth-regulating activity towards rice seedlings. This secondary metabolite has a thienoindole skeleton chlorinated in the 6-position of the indole ring. Here we present insights into the biosynthesis of the alkaloid, including the complete gene cluster and elucidation of two biosynthetic steps.

    2. Baceridin, a Cyclic Hexapeptide from an Epiphytic Bacillus Strain, Inhibits the Proteasome

      Dr. Jutta Niggemann, Dr. Przemyslaw Bozko, Nicole Bruns, Anne Wodtke, Dr. Marc Timo Gieseler, Kevin Thomas, Dr. Christine Jahns, Dr. Manfred Nimtz, Inge Reupke, Prof. Dr. Thomas Brüser, Prof. Georg Auling, Prof. Dr. Nisar Malek and Prof. Dr. Markus Kalesse

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201300778

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      Go your own way: The cyclic hexapeptide baceridin was isolated from the culture medium of a plant-associated Bacillus strain. The configuration could be assigned by chemical degradation and total synthesis. In the course of biological validations baceridin was identified as a proteasome inhibitor that inhibits cell-cycle progression and induces apoptosis in tumor cells by a p53-independent pathway.

    3. Solution-NMR Characterization of Outer-Membrane Protein A from E. coli in Lipid Bilayer Nanodiscs and Detergent Micelles

      Lukas Sušac, Dr. Reto Horst and Prof. Kurt Wüthrich

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201300729

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      NMR studies of OmpA in nanodiscs yielded structural data on this E coli outer membrane protein closely similar to those seen in three different detergent micelles. The result validates the use of detergent micelles for structural studies of β-barrel membrane proteins and supports the conjecture that the conformational dynamics of OmpA observed for the reconstituted protein are related to its physiological function.

    4. Enhancing the Efficiency and Regioselectivity of P450 Oxidation Catalysts by Unnatural Amino Acid Mutagenesis

      Joshua N. Kolev, Jacqueline M. Zaengle, Rajesh Ravikumar and Prof. Rudi Fasan

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201400060

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      Unnatural choice: Incorporating unnatural amino acids at single positions within the active site of a cytochrome P450 significantly changes the regioselectivity (shown) of the enzyme or enhances its catalytic efficiency. This study demonstrates that unnatural amino acid mutagenesis constitutes a promising new strategy for improving P450 oxidation catalysts.

    5. Biochemical Investigations of Two 6-DMATS Enzymes from Streptomyces Reveal New Features of L-Tryptophan Prenyltransferases

      Julia Winkelblech and Prof. Dr. Shu-Ming Li

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201400046

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      They can do more: L-Tryptophan (1 a) and derivatives as well as hydroxynaphthalenes like 2,3-dihydroxynaphthalene (10 a) were accepted by 6-DMATSSa and 6-DMATSSv from Streptomyces strains, in the presence of DMAPP and GPP. C6-prenylated indole derivatives and dihydroxynaphthalenes with prenylation at the unsubstituted ring were identified as enzyme products of 6-DMATSSa.

  9. Communications

    1. Catalytic Molecular Logic Devices by DNAzyme Displacement

      Carl W. Brown III, Dr. Matthew R. Lakin, Dr. Darko Stefanovic and Dr. Steven W. Graves

      Article first published online: 1 APR 2014 | DOI: 10.1002/cbic.201400047

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      Catalytic control: We demonstrate a simple, programmable method for controlling the catalytic activity of DNAzymes using DNA strand displacement reactions. This work broadens the impact of strand displacement logic devices by using the rich range of biochemical reactions catalyzed by DNAzymes as outputs.

    2. A Coumarin-Labeled Vinyl Sulfone as Tripeptidomimetic Activity-Based Probe for Cysteine Cathepsins

      Matthias D. Mertens, Janina Schmitz, Dr. Martin Horn, Norbert Furtmann, Prof. Dr. Jürgen Bajorath, Dr. Michael Mareš and Prof. Dr. Michael Gütschow

      Article first published online: 19 MAR 2014 | DOI: 10.1002/cbic.201300806

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      Tricycle light: A tripeptidomimetic, vinyl sulfone-type activity-based probe containing a rigid coumarin moiety fluorophore was prepared by convergent synthesis. The probe was evaluated as an inactivator of human cathepsins and, as exemplified with cathepsin S, it proved to be suitable for imaging in SDS-PAGE.

    3. Terpendole E and its Derivative Inhibit STLC- and GSK-1-Resistant Eg5

      Yuka Tarui, Takumi Chinen, Dr. Yoko Nagumo, Dr. Takayuki Motoyama, Dr. Toshiaki Hayashi, Dr. Hiroshi Hirota, Dr. Makoto Muroi, Yasuyuki Ishii, Hisae Kondo, Prof. Dr. Hiroyuki Osada and Prof. Dr. Takeo Usui

      Article first published online: 19 MAR 2014 | DOI: 10.1002/cbic.201300808

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      Out of the loop? A new natural Eg5 inhibitor, 11-ketopaspaline, was isolated, and the effects of terpendole E and 11-ketopaspaline on Eg5–microtubule interaction in several Eg5 mutants were investigated. Terpendole E and its analogues might have a binding site and/or inhibitory mechanism than differ from those of L5 loop-binding-type Eg5 inhibitors.

  10. Full Papers

    1. Nanosecond Dynamics of Calmodulin and Ribosome-Bound Nascent Chains Studied by Time-Resolved Fluorescence Anisotropy

      Dr. Paraskevas Lamprou, Daryan Kempe, Dr. Alexandros Katranidis, Prof. Georg Büldt and Prof. Jörg Fitter

      Article first published online: 18 MAR 2014 | DOI: 10.1002/cbic.201400014

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      All wrapped up: Coupling between polypeptide chain elongation and protein folding is a key issue in protein biosynthesis. We present an experimental approach to analyze the structural and dynamic properties of nascent polypeptide chains synthesized by a cell-free expression system with truncated peptides. For calmodulin we identified a pronounced interaction of the nascent chains with the synthesizing ribosome.

  11. Communications

    1. You have full text access to this OnlineOpen article
      A Native Chemical Ligation Handle that Enables the Synthesis of Advanced Activity-Based Probes: Diubiquitin as a Case Study

      Dr. Monique P. C. Mulder, Dr. Farid El Oualid, Jarno ter Beek and Prof. Dr. Huib Ovaa

      Article first published online: 12 MAR 2014 | DOI: 10.1002/cbic.201402012

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      Protease profiling: A new native chemical ligation handle that functions as a masked electrophile and allows the total chemical synthesis of complex activity-based probes (ABPs) has been developed. We show the efficiency of our approach by synthesizing deubiquitylating enzyme (DUB) ABPs based on all seven diubiquitin (diUb) isopeptide topoisomers and examining their ability to capture DUBs selectively with distinct target preference.

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