ChemBioChem

Cover image for Vol. 13 Issue 4

March 5, 2012

Volume 13, Issue 4

Pages 489–603

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: An Adaptable Luminescence Resonance Energy Transfer Assay for Measuring and Screening Protein–Protein Interactions and their Inhibition. (ChemBioChem 4/2012) (page 489)

      Engin Yapici, Dr. D. Rajasekhar Reddy and Prof. Dr. Lawrence W. Miller

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/cbic.201290008

      Thumbnail image of graphical abstract

      The cover picture shows the interaction of a green fluorescent protein (GFP) fusion (blue) with an Escherichia coli dihydrofolate reductase (eDHFR) fusion protein (red). Selective, noncovalent labeling of eDHFR with a trimethoprim (TMP)–terbium complex conjugate enables time-resolved, background-free detection of the long-lifetime (∼ms), terbium-to-GFP luminescence resonance energy transfer (LRET) signal, which indicates fusion protein interaction. On p. 553 ff, L. W. Miller et al. describe highly sensitive (signal-to-background ratio >100), LRET-based detection and accurate quantification of interactions between FK506 binding protein 12 (fused to GFP) and the rapamycin-binding domain of mTOR (fused to eDHFR) in impure bacterial lysates. TMP/eDHFR labeling can be easily adapted to develop high-throughput screening assays and complementary, quantitative counter screens for measuring interactions between a wide variety of protein targets that may not be amenable to purification.

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Inside Cover: Identification of a Novel Protein Synthesis Inhibitor Active against Gram-Positive Bacteria (ChemBioChem 4/2012) (page 490)

      Nora R. Eibergen, Dr. Isak Im, Nisha Y. Patel and Prof. Paul J. Hergenrother

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/cbic.201290009

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      The inside cover picture shows the inhibition of ribosomal protein synthesis in Staphylococcus aureus by the benzothiazolium salt, ABTZ-1. This antibacterial, which inhibits the growth of multidrug-resistant Gram-positive bacteria, prevents the incorporation of radiolabeled methionine into S. aureus protein. Strains resistant to ABTZ-1 also display cross-resistance to fusidic acid and streptogramins. For more information on the discovery and characterization of ABTZ-1 by P. J. Hergenrother et al., see p. 574 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
  4. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Corrigendum: Redundant Pathways of Sunscreen Biosynthesis in a Cyanobacterium (page 497)

      Dr. Edward Spence, Dr. Walter C. Dunlap, Prof. J. Malcolm Shick and Dr. Paul F. Long

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/cbic.201200076

      This article corrects:

      Redundant Pathways of Sunscreen Biosynthesis in a Cyanobacterium1

      Vol. 13, Issue 4, 531–533, Version of Record online: 25 JAN 2012

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
  6. Highlights

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
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    1. A FlAsH Reporter for Protein-Dimerization Triggers (pages 505–507)

      Dr. Thorsten Stafforst

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/cbic.201100787

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      A FlAsH of potential: The specific binding of the biarsenical probe to the tetracysteine motif has matured as a tool for cell biology studies. Combining two such binders in one probe generates a useful reporter of protein dimerization events. The current state of art and the perspective for future developments are highlighted.

    2. “Clicking” on the Lights To Reveal Bacterial Social Networking (pages 508–510)

      Kenneth D. Clevenger and Prof. Walter Fast

      Version of Record online: 19 JAN 2012 | DOI: 10.1002/cbic.201100767

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      Send to know: A recent publication by Garner, Janda and co-workers develops a novel, extensible, fluorescent, dendrimeric probe for detecting AI-2 receptors, now enabling the imaging of quorum-sensing receptors in a wide variety of bacteria without the use of reporter genes.

    3. Photocaged DNA Provides New Levels of Transcription Control (pages 511–513)

      Luke M. Ceo and Prof. John T. Koh

      Version of Record online: 23 JAN 2012 | DOI: 10.1002/cbic.201100683

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      Spot lit: Photocaged nucleic acids have been used to regulate gene expression through the action of light. Whereas most methods target mRNAs, DNA decoys have recently been used to target DNA transcription by targeting specific DNA-transcription-factor interactions. This has allowed researchers to “turn-off” transcription through the action of light on caged nucleic acids for the first time.

  7. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Design of Photocontrolled RNA-Binding Peptidomimetics (pages 515–519)

      Dr. Robert J. Mart, Piotr Wysoczański, Dr. Sabine Kneissl, Dr. Antonio Ricci, Dr. Andrea Brancale and Prof. Dr. Rudolf K. Allemann

      Version of Record online: 2 FEB 2012 | DOI: 10.1002/cbic.201100800

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      Positively constrained: The first examples of photocontrolled RNA binding peptides are described. The large number of positively charged sides chains in the Rev response element (RRE) of an HIV type I targeting α-helix imposes constraints on the choice of azobenzene-derived crosslinker.

    2. A Single Active Site Mutation Inverts Stereoselectivity of 16-Hydroxylation of Testosterone Catalyzed by Engineered Cytochrome P450 BM3 (pages 520–523)

      Harini Venkataraman, Stephanie B. A. de Beer, Laura A. H. van Bergen, Nick van Essen, Dr. Daan P. Geerke, Prof. Dr. Nico P. E. Vermeulen and Dr. Jan N. M. Commandeur

      Version of Record online: 24 JAN 2012 | DOI: 10.1002/cbic.201100750

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      Inversion of stereoselectivity: screening of a minimal mutant library revealed a cytochrome P450 BM3 variant M01 A82W S72I capable of producing 16 α-OH-testosterone. Remarkably, a single active site mutation S72I in M01 A82W inverted the stereoselectivity of hydroxylation from 16 β to 16 α. Introduction of S72I mutation in another 16 β-OH-selective variant M11 V87I, also resulted in similar inversion of stereoselectivity.

    3. Glycosylation Assists Binding of HIV Protein gp120 to Human CD4 Receptor (pages 524–527)

      Dr. Dennis Wilhelm, Dipl.-Chem. Henning N. Behnken and Prof. Dr. Bernd Meyer

      Version of Record online: 20 JAN 2012 | DOI: 10.1002/cbic.201100740

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      The role of glycosylation of proteins on its binding affinity is not well understood. Even a monosaccharide (magenta) placed at a glycosylation site can significantly enhance binding of peptides to their receptor. If glycosylated, an HIV protein binds stronger and faster to its primary receptors on human cells.

    4. Stereospecific Formation of a Ternary Complex of (S)-α,β-Fluoromethylene-dATP with DNA Pol β (pages 528–530)

      Brian T. Chamberlain, Dr. Vinod K. Batra, Dr. William A. Beard, Anastasia P. Kadina, David D. Shock, Dr. Boris A. Kashemirov, Dr. Charles E. McKenna, Dr. Myron F. Goodman and Dr. Samuel H. Wilson

      Version of Record online: 7 FEB 2012 | DOI: 10.1002/cbic.201100738

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      The influence of water: Crystallization of (R/S)-α,β-CHF-dATP with the preorganized pol β-DNA complex shows that (S)-α,β-CHF-dATP is preferentially bound to the active site with the C[BOND]F fluorine proximal to a structural water bound to Asp276.

    5. Redundant Pathways of Sunscreen Biosynthesis in a Cyanobacterium (pages 531–533)

      Dr. Edward Spence, Dr. Walter C. Dunlap, Prof. J. Malcolm Shick and Dr. Paul F. Long

      Version of Record online: 25 JAN 2012 | DOI: 10.1002/cbic.201100737

      Thumbnail image of graphical abstract

      Route of the sun block: According to empirical evidence, sun-screening mycosporine-like amino acids (MAAs) in Eukarya originate from the shikimic acid pathway, whereas in cyanobacteria, biosynthesis of the MAA shinorine reportedly occurs through the pentose phosphate pathway. However, gene deletion shows that the cyanobacterium Anabaena variabilis ATCC 29143 does not biosynthesise shinorine exclusively by this route.

    6. In-Cell Solid-State NMR as a Tool to Study Proteins in Large Complexes (pages 534–537)

      Dr. Sina Reckel, Dr. Jakob J. Lopez, Dr. Frank Löhr, Prof. Dr. Clemens Glaubitz and Prof. Dr. Volker Dötsch

      Version of Record online: 1 FEB 2012 | DOI: 10.1002/cbic.201100721

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      A major limitation of solution NMR is molecular tumbling, which is often too slow for detection. Here we demonstrate that solid-state NMR spectroscopy in combination with flash freezing of cells can be used to detect proteins in the cellular environment and provides information on backbone chemical shifts.

    7. Identification of Hydrophobic Tags for the Degradation of Stabilized Proteins (pages 538–541)

      Dr. Hyun Seop Tae, Dr. Thomas B. Sundberg, Dr. Taavi K. Neklesa, Devin J. Noblin, Dr. Jeffrey L. Gustafson, Dr. Anke G. Roth, Kanak Raina and Prof. Craig M. Crews

      Version of Record online: 23 JAN 2012 | DOI: 10.1002/cbic.201100793

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      New HyTs are a knockout: We previously reported that labeling HaloTag proteins with low molecular weight hydrophobic tags (HyTs) leads to targeted degradation of HaloTag fusion proteins. In this report, we employed a chemical approach to extend this hydrophobic tagging methodology to highly stabilized proteins by synthesizing and evaluating a library of HyTs, which led to the identification of HyT36.

    8. Synthesis of Cyclic Peptides and Cyclic Proteins via Ligation of Peptide Hydrazides (pages 542–546)

      Ji-Shen Zheng, Shan Tang, Ye Guo, Hao-Nan Chang and Prof. Dr. Lei Liu

      Version of Record online: 2 FEB 2012 | DOI: 10.1002/cbic.201100580

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      Intramolecular ligation of peptide hydrazides is reported to occur readily, causing the lactamization of fully unprotected peptides in an epimerization-free manner. This method relies on the routine procedures of Fmoc solid-phase peptide synthesis. It can be used to prepare cyclic peptides and cyclic proteins under simpler, mild conditions at lower costs.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Characterization of a Single Gene Cluster Responsible for Methylpendolmycin and Pendolmycin Biosynthesis in the Deep Sea Bacterium Marinactinospora thermotolerans (pages 547–552)

      Dr. Junying Ma, Dianguang Zuo, Dr. Yongxiang Song, Dr. Bo Wang, Dr. Hongbo Huang, Yueliang Yao, Prof. Wenjun Li, Prof. Si Zhang, Prof. Changsheng Zhang and Prof. Jianhua Ju

      Version of Record online: 23 FEB 2012 | DOI: 10.1002/cbic.201100700

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      Indolactam alkaloids: A single gene cluster responsible for biosynthesis of methylpendolmycin and pendolmycin has been characterized. Bioinformatics analysis and gene inactivation, coupled with metabolite characterization, reveal that MpnB (a nonribosomal peptide synthetase), MpnC (a cytochrome P450), and MpnD (a prenyltransferase) are sufficient to catalyze the biosynthesis of the two antibiotics from L-Ile (or L-Val), L-Trp, and methionine.

    2. An Adaptable Luminescence Resonance Energy Transfer Assay for Measuring and Screening Protein–Protein Interactions and their Inhibition. (pages 553–558)

      Engin Yapici, Dr. D. Rajasekhar Reddy and Prof. Dr. Lawrence W. Miller

      Version of Record online: 23 JAN 2012 | DOI: 10.1002/cbic.201100710

      Thumbnail image of graphical abstract

      Assay of a lifetime: Noncovalent binding of a trimethoprim-linked Tb3+ complex (TMP-Tb) to E. coli dihydrofolate reductase (eDHFR) enables a highly sensitive, luminescent resonance energy transfer (LRET) assay to detect and measure protein–protein interactions and their inhibition.

    3. Versatile Effects of Aurone Structure on Mushroom Tyrosinase Activity (pages 559–565)

      Carole Dubois, Romain Haudecoeur, Dr. Maylis Orio, Dr. Catherine Belle, Dr. Constance Bochot, Prof. Ahcène Boumendjel, Dr. Renaud Hardré, Dr. Hélène Jamet and Dr. Marius Réglier

      Version of Record online: 3 FEB 2012 | DOI: 10.1002/cbic.201100716

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      Inhibitor development: We have highlighted the extraordinary versatile effects of the aurone structure on mushroom Ty activity. Depending on the position of the OH group on the B-ring, aurones can behave either as substrates or as activator. We also synthesized and evaluated a compound combining an aurone moiety with HOPNO, an efficient inhibitor for mushroom Ty (Kiu=1.62 μM and Kic=1.27 μM).

    4. An Enzyme Catalyzing O-Prenylation of the Glucose Moiety of Fusicoccin A, a Diterpene Glucoside Produced by the Fungus Phomopsis amygdali (pages 566–573)

      Dr. Motoyoshi Noike, Chengwei Liu, Dr. Yusuke Ono, Dr. Yoshimitsu Hamano, Dr. Tomonobu Toyomasu, Prof. Dr. Takeshi Sassa, Prof. Dr. Nobuo Kato and Prof. Dr. Tohru Dairi

      Version of Record online: 27 JAN 2012 | DOI: 10.1002/cbic.201100725

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      A novel sugar prenyltansferase, PAPT, from the fungus Phomopsis amygdali has been cloned and characterized. This enzyme transfers dimethylallyl diphosphate to the 6′-hydroxy group of the glucose moiety of fusicoccin (FC) A, a diterpene glucoside. To the best of our knowledge, this is the first enzyme to catalyze prenylation of a hydroxyl group in a glucose moiety.

    5. Identification of a Novel Protein Synthesis Inhibitor Active against Gram-Positive Bacteria (pages 574–583)

      Nora R. Eibergen, Dr. Isak Im, Nisha Y. Patel and Prof. Paul J. Hergenrother

      Version of Record online: 24 FEB 2012 | DOI: 10.1002/cbic.201100727

      Thumbnail image of graphical abstract

      Structurally novel antibacterial compounds are needed to fight rapidly emerging antibiotic-resistant infections. A whole-cell screen for novel antibacterial chemotypes has revealed ABTZ-1, an inhibitor of protein synthesis with potent activity against multidrug-resistant Gram-positive bacterial strains.

    6. Antagonism of microRNA Function in Zebrafish Embryos by Using Locked Nucleic Acid Enzymes (LNAzymes) (pages 584–589)

      Hemant Suryawanshi, Mukesh Kumar Lalwani, Soundhar Ramasamy, Rajiv Rana, Dr. Vinod Scaria, Dr. Sridhar Sivasubbu and Dr. Souvik Maiti

      Version of Record online: 7 FEB 2012 | DOI: 10.1002/cbic.201100789

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      In vivo miRNA assassination: We designed and employed a strategy with locked nucleic acid enzyme (LNAzyme) for in vivo knockdown of microRNA (miRNA) in zebrafish embryos. We demonstrate that LNAzyme can efficiently knockdown miRNAs with minimal toxicity to the zebrafish embryos.

    7. Pyrene-Modified Unlocked Nucleic Acids: Synthesis, Thermodynamic Studies, and Fluorescent Properties (pages 590–601)

      Dr. Kasper K. Karlsen, Dr. Anna Pasternak, Dr. Troels B. Jensen and Prof. Dr. Jesper Wengel

      Version of Record online: 7 FEB 2012 | DOI: 10.1002/cbic.201100689

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      We have combined the fluorescent properties of pyrene with the acyclic UNA (unlocked nucleic acid) scaffold to produce novel fluorescent oligonucleotides with high mismatch discriminative power and the ability to detect DNA targets in homogeneous fluorescence assays. These probes therefore show great promise in the field of nucleic acid diagnostics.

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Preview: ChemBioChem 5/2012 (page 603)

      Version of Record online: 29 FEB 2012 | DOI: 10.1002/cbic.201290012

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