ChemBioChem

Cover image for Vol. 15 Issue 9

June 16, 2014

Volume 15, Issue 9

Pages 1213–1351

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: DNA-Scaffolded Multivalent Ligands to Modulate Cell Function (ChemBioChem 9/2014) (page 1213)

      Prof. Dr. Zhiqing Zhang, Dr. Mark A. Eckert, Dr. M. Monsur Ali, Linan Liu, Dr. Dong-Ku Kang, Elizabeth Chang, Dr. Egest J. Pone, Prof. Dr. Leonard S. Sender, Prof. Dr. David A. Fruman and Prof. Dr. Weian Zhao

      Version of Record online: 11 JUN 2014 | DOI: 10.1002/cbic.201490028

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      The cover picture shows the concept of using DNA-scaffolded multivalent ligands to modulate cell signaling and function, as reported by W. Zhao, et al. on p. 1268 ff. The multivalent ligand is made of a polymeric DNA scaffold that was synthesized by rolling circle amplification; biorecognition ligands (i.e., antibodies) are attached to this. This multivalent DNA material approach represents a new chemical biology tool for interrogating cell receptor signaling and functions and, potentially, for manipulating such functions for the development of therapeutics.

    2. You have free access to this content
      Inside Cover: Designed Di-Heme Binding Helical Transmembrane Protein (ChemBioChem 9/2014) (page 1214)

      Mukesh Mahajan and Prof. Dr. Surajit Bhattacharjya

      Version of Record online: 11 JUN 2014 | DOI: 10.1002/cbic.201490029

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      The inside cover picture shows a rationally designed heme-binding transmembrane protein (HETPRO) in a lipid bilayer. HETPRO assumes an anti-parallel dimeric helical structure in the apo form. On p. 1257 ff., S. Bhattacharjya and M. Mahajan show how, with heme, HETPRO assembles into a four-helix bundle with peroxidase activity that is a model system for electron transfer across lipid bilayers.

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
  3. Corrigendum

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Corrigendum: Designed Di-Heme Binding Helical Transmembrane Protein (page 1221)

      Mukesh Mahajan and Prof. Dr. Surajit Bhattacharjya

      Version of Record online: 11 JUN 2014 | DOI: 10.1002/cbic.201400082

      This article corrects:

      Designed Di-Heme Binding Helical Transmembrane Protein

      Vol. 15, Issue 9, 1257–1262, Version of Record online: 14 MAY 2014

  4. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
  5. Minireviews

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    1. Amorfrutins: A Promising Class of Natural Products that Are Beneficial to Health (pages 1231–1238)

      Dr. Sascha Sauer

      Version of Record online: 4 JUN 2014 | DOI: 10.1002/cbic.201402124

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      Loving the fruit: Amorfrutins form a largely unexplored class of health-beneficial natural products derived from the edible roots of liquorice and other plants. These isoprenoid 2-hydroxybenzoic acid derivatives showed great potential for treating type 2 diabetes and other complex diseases. Amorfrutins offer exciting opportunities for the prevention and medication of common diseases.

    2. The Multivalent Effect in Glycosidase Inhibition: A New, Rapidly Emerging Topic in Glycoscience (pages 1239–1251)

      Prof. Dr. Philippe Compain and Dr. Anne Bodlenner

      Version of Record online: 7 MAY 2014 | DOI: 10.1002/cbic.201402026

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      A bunch of keys, one lock: The multivalent effect in glycosidase inhibition is a new, rapidly emerging area with exciting potential and scope. This review presents a description of the different types of neoglycoclusters and their evaluation as glycosidase inhibitors. The first promising therapeutic applications are discussed, as well as the mechanisms underlying the observed inhibitory multivalent effect.

  6. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    1. A New Chemical Probe for Phosphatidylinositol Kinase Activity (pages 1253–1256)

      Dr. Allison R. Sherratt, Neda Nasheri, Dr. Craig S. McKay, Shifawn O'Hara, Ashley Hunt, Dr. Zhibin Ning, Prof. Daniel Figeys, Prof. Natalie K. Goto and Prof. John Paul Pezacki

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/cbic.201402155

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      Active PIKs: Phosphatidylinositol kinases (PIKs) are key enzymatic regulators of membrane phospholipids and environments that control many aspects of cellular function, from signal transduction to secretion. We developed a photoreactive “clickable” probe, PIK-BPyne, to assess activity of PIKs in native biological systems and demonstrated its ability to monitor hepatitis C virus-induced changes in PIK-IIIβ activity.

    2. Designed Di-Heme Binding Helical Transmembrane Protein (pages 1257–1262)

      Mukesh Mahajan and Prof. Dr. Surajit Bhattacharjya

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/cbic.201402142

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      The designed transmembrane helical protein HETPRO—optimized in a guided fashion for transmembrane orientation, defined 3D structure, and functions—binds two molecules of heme and catalyzes peroxidase activity. Heme binding induces tetramerization. The protein has potential for the development of a functional membrane protein mimic for electron transport and photosystems.

    3. Facile Synthesis of Native and Protease-Resistant Ubiquitylated Peptides (pages 1263–1267)

      Caroline E. Weller, Wei Huang and Prof. Dr. Champak Chatterjee

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/cbic.201402135

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      Dual-duty ubiquitylation: A temporary ligation auxiliary, 2-(aminooxy)ethanethiol, was employed to site-specifically attach ubiquitin and SUMO-3 to Lys side-chain ε-amines. After reduction, the ligation products were viable substrates for the ubiquitin C-terminal hydrolase UCH-L3 and the SUMO-specific protease SENP1. Retention of the ligation auxiliary in the ubiquitylated peptides led to UCH-L3-resistant analogues.

    4. DNA-Scaffolded Multivalent Ligands to Modulate Cell Function (pages 1268–1273)

      Prof. Dr. Zhiqing Zhang, Dr. Mark A. Eckert, Dr. M. Monsur Ali, Linan Liu, Dr. Dong-Ku Kang, Elizabeth Chang, Dr. Egest J. Pone, Prof. Dr. Leonard S. Sender, Prof. Dr. David A. Fruman and Prof. Dr. Weian Zhao

      Version of Record online: 6 MAY 2014 | DOI: 10.1002/cbic.201402100

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      On a roll: DNA molecules synthesized by rolling-circle amplification can serve as simple polymeric scaffolds to interrogate and modulate cell-receptor functions. We have demonstrated that our multivalent ligand can induce apoptosis of cancer cells more effectively than its monovalent counterpart; this represents a new approach for the development of therapeutics.

    5. Biosynthetic Code for Divergolide Assembly in a Bacterial Mangrove Endophyte (pages 1274–1279)

      Dr. Zhongli Xu, Martin Baunach, Dr. Ling Ding, Huiyun Peng, Jakob Franke and Prof. Dr. Christian Hertweck

      Version of Record online: 27 MAY 2014 | DOI: 10.1002/cbic.201402071

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      Digging into divergolide diversity: The molecular basis for the biosynthesis of the divergolides, structurally diverse ansamycins from a mangrove endophyte, was elucidated. Analysis of the assembly line and the full structural elucidation of four new divergolide congeners led to a revised biosynthetic model, which illustrates the formation of four different types of ansamycin chromophores from a single polyketide precursor.

    6. Two-Face, Two-Turn α-Helix Mimetics Based on a Cross-Acridine Scaffold: Analogues of the Bim BH3 Domain (pages 1280–1285)

      Xiangqian Li, Ziqian Wang, Prof. Yingang Feng, Ting Song, Pengchen Su, Chengbin Chen, Gaobo Chai, Ying Yang and Prof. Zhichao Zhang

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/cbic.201402040

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      Building site: A cross-acridine scaffold was designed to project functional groups with spatial and angular geometries that accurately mimic the i, i+3, i+5, and i+7 side chains on a two-turn, two-face section of an α-helix. The binding mode of the most potent compound, 3 d, to Mcl-1 was confirmed by 1H,15N HSQC NMR.

    7. Improving the Stability and Catalyst Lifetime of the Halogenase RebH By Directed Evolution (pages 1286–1289)

      Dr. Catherine B. Poor, Mary C. Andorfer and Prof. Jared C. Lewis

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/cbic.201300780

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      Evolving halos: We have used directed evolution to engineer an RebH halogenase variant with a Topt more than 5 °C higher than that of wild-type RebH, and a second variant with a Tm 18 °C higher. These enzymes provided significantly improved conversion for halogenation of tryptophan and several non-natural substrates.

    8. Yeast Homologous Recombination Cloning Leading to the Novel Peptides Ambactin and Xenolindicin (pages 1290–1294)

      Olivia Schimming, Florian Fleischhacker, Friederike I. Nollmann and Prof. Dr. Helge B. Bode

      Version of Record online: 9 MAY 2014 | DOI: 10.1002/cbic.201402065

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      Yeast does it: We cloned biosynthesis gene clusters from Photorhabdus and Xenorhabdus by using yeast's ability to assemble overlapping DNA fragments into functional plasmids. This “overlap extension PCR-yeast homologous recombination” (ExRec) method followed by overexpression of the gene cluster in E. coli yielded new natural compounds.

  7. Full Papers

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. Corrigendum
    5. News
    6. Minireviews
    7. Communications
    8. Full Papers
    1. Key Residues in Octyl-Tridecaptin A1 Analogues Linked to Stable Secondary Structures in the Membrane (pages 1295–1299)

      Stephen A. Cochrane, Dr. Brandon Findlay, Dr. John C. Vederas and Dr. Elaref S. Ratemi

      Version of Record online: 9 MAY 2014 | DOI: 10.1002/cbic.201402024

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      Just tri it! Analysis of tridecaptin A1 and its octyl analogue have identified key residues responsible for the formation of a stable secondary structure in a model membrane environment. A combination of alanine scanning and CD spectroscopy showed that modification of these residues prevented formation of the secondary structure and abolished antimicrobial activity.

    2. Identification of a Novel Inhibition Site in Translocase MraY Based upon the Site of Interaction with Lysis Protein E from Bacteriophage ϕX174 (pages 1300–1308)

      Dr. Maria T. Rodolis, Agnes Mihalyi, Amy O'Reilly, Justinas Slikas, Dr. David I. Roper, Prof. Robert E. W. Hancock and Prof. Timothy D. H. Bugg

      Version of Record online: 4 JUN 2014 | DOI: 10.1002/cbic.201402064

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      Site of natural interest: An interaction site is identified between the Arg-Trp-x-x-Trp motif in bacteriophage ϕX174 protein E and Phe288 and Glu287 of translocase MraY, based on synthetic peptide structure–activity data and mutant MraY enzymes.

    3. Synthesis, Photophysical Properties and Incorporation of a Highly Emissive and Environment-Sensitive Uridine Analogue Based on the Lucifer Chromophore (pages 1309–1316)

      Arun A. Tanpure and Dr. Seergazhi G. Srivatsan

      Version of Record online: 23 MAY 2014 | DOI: 10.1002/cbic.201402052

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      Green fluorescent nucleoside: A highly emissive uridine analogue containing the Lucifer chromophore at the 5-position of uracil was incorporated into oligonucleotides. It retains appreciable fluorescence and is sensitive to the neighbouring base environment, both its adjacent bases and its partner on the complementary strand in duplexes.

    4. Fluorescent Visualization of Src by Using Dasatinib-BODIPY (pages 1317–1324)

      Dr. Michael L. Vetter, Dr. Zijuan Zhang, Dr. Shuai Liu, Dr. Jinhua Wang, HaeYeon Cho, Dr. Jianming Zhang, Prof. Wei Zhang, Prof. Nathanael S. Gray and Prof. Priscilla L. Yang

      Version of Record online: 14 MAY 2014 | DOI: 10.1002/cbic.201402010

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      Light it up! Bifunctional molecules that couple a kinase inhibitor to a cell-permeable fluorophore can be an alternative to immunofluorescence and genetically encoded reporters. Here, we show that a dasatinib-BODIPY conjugate retains inhibitory activity against target kinases and can be used at sub-inhibitory concentrations to detect Src-expressing cells by flow cytometry and to monitor Src localization and dynamics by live-cell fluorescence microscopy.

    5. Investigation of Binding-Site Homology between Mushroom and Bacterial Tyrosinases by Using Aurones as Effectors (pages 1325–1333)

      Dr. Romain Haudecoeur, Aurélie Gouron, Dr. Carole Dubois, Dr. Hélène Jamet, Mark Lightbody, Dr. Renaud Hardré, Prof. Anne Milet, Dr. Elisabetta Bergantino, Prof. Luigi Bubacco, Dr. Catherine Belle, Dr. Marius Réglier and Prof. Ahcène Boumendjel

      Version of Record online: 21 MAY 2014 | DOI: 10.1002/cbic.201402003

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      A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

    6. Biosynthesis of Colabomycin E, a New Manumycin-Family Metabolite, Involves an Unusual Chain-Length Factor (pages 1334–1345)

      Dr. Kateřina Petříčková, Dr. Stanislav Pospíšil, Dr. Marek Kuzma, Dr. Tereza Tylová, Dr. Michal Jágr, Petr Tomek, Dr. Alica Chroňáková, Eva Brabcová, Dr. Ladislav Anděra, Dr. Václav Krištůfek and Dr. Miroslav Petříček

      Version of Record online: 18 MAY 2014 | DOI: 10.1002/cbic.201400068

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      Working on the chain: A gene cluster encoding for the antibiotic colabomycin E was isolated and characterized from a strain selected by genetic screening. A PKS involved in the formation of one carbon chain was identified. Recombination with a homologous enzyme indicated a new class of short-chain chain-length factors involved in the synthesis of tri- or tetraketides.

    7. Intracellular Light-Activation of Riboswitch Activity (pages 1346–1351)

      Steven Walsh, Laura Gardner, Dr. Alexander Deiters and Dr. Gavin J. Williams

      Version of Record online: 26 MAY 2014 | DOI: 10.1002/cbic.201400024

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      Light switches: The combination of a cell-permeable, photocaged ligand and a theophylline riboswitch provided a simple and efficient strategy to control gene expression within bacterial cells by using light. This approach can be used to regulate artificial genetic circuits.

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