ChemBioChem

Cover image for Vol. 12 Issue 16

November 4, 2011

Volume 12, Issue 16

Pages 2377–2519

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Cover Picture: A Synthetic Mirror Image of Kalata B1 Reveals that Cyclotide Activity Is Independent of a Protein Receptor (ChemBioChem 16/2011) (page 2377)

      Dr. Lillian Sando, Dr. Sónia Troeira Henriques , Fiona Foley, Dr. Shane M. Simonsen, Dr. Norelle L. Daly, Dr. Kristopher N. Hall, Dr. Kirk R. Gustafson, Prof. Marie-Isabel Aguilar and Prof. David J. Craik

      Version of Record online: 26 OCT 2011 | DOI: 10.1002/cbic.201190074

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      The cover picture shows mirror image forms of the cyclotide kalata B1, a 29-residue peptide with a cyclic backbone and a cystine knot. The native peptide is isolated from the African plant Oldenlandia affinis, which is used in an indigenous medicinal tea to accelerate labour, but has a range of other activities, including anti-HIV activity. The synthetic mirror image form, made from D-amino acids, was assembled by solid-phase peptide synthesis and used to demonstrate that membrane binding, rather than a chiral receptor, is implicated in cyclotide bioactivity. For more information, see the paper by D. J. Craik et al. on p. 2456 ff. (Cover art designed by David Wilson, University of Queensland.)

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Inside Cover: Identification of Anchor Points for Chemical Modification of a Small Cysteine-Rich Protein by Using a Cysteine Scan (ChemBioChem 16/2011) (page 2378)

      Tine N. Vinther, Ulla Ribel, Dr. Thomas Åskov Pedersen, Dr. Thomas B. Kjeldsen, Prof. Dr. Knud J. Jensen and Dr. František Hubálek

      Version of Record online: 26 OCT 2011 | DOI: 10.1002/cbic.201190075

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      The inside cover picture shows the cysteine scanning mutagenesis of insulin in yeast resulting in expression of post-translationally modified insulin analogues. On p. 2448 ff, F. Hubálek et al. show how selective reduction and subsequent alkylation of the introduced cysteine residues allow for chemoselective modification of insulin, as illustrated by a PEGylated insulin variant.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
  4. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
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      Corrigendum: A Reversible Protection Strategy To Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach (page 2386)

      Dr. Santosh K. Mahto, Cecil J. Howard, John C. Shimko and Prof. Jennifer J. Ottesen

      Version of Record online: 26 OCT 2011 | DOI: 10.1002/cbic.201190077

      This article corrects:

      A Reversible Protection Strategy To Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach

      Vol. 12, Issue 16, 2488–2494, Version of Record online: 12 SEP 2011

  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
  6. Essay

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Making Proteins with Unnatural Amino Acids: The First Engineered Aminoacyl-tRNA Synthetase Revisited (pages 2395–2398)

      Prof. Dr. Peter Kast

      Version of Record online: 26 SEP 2011 | DOI: 10.1002/cbic.201100533

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      Relaxed specificity: 20 years ago, the first “rationally” reengineered phenylalanyl-tRNA synthetase provided a gateway for the biosynthetic incorporation of unnatural amino acids into proteins. The synthetase design relied neither on structural information nor directed evolution, but rather on a simple steric model. A recently published crystal structure prompts a look back at this historic strategy for producing proteins containing non-standard residues.

  7. Highlight

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Condensin Engages Chromatin (pages 2399–2401)

      Boryana Petrova and Dr. Christian H. Haering

      Version of Record online: 23 SEP 2011 | DOI: 10.1002/cbic.201100531

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      How are condensin complexes, the major organizers of mitotic chromosomes, targeted to their DNA substrate? Recent discoveries suggest that a remarkable interplay between recruitment factors and kinase-regulated direct interactions with histone proteins enable condensin to structure chromatin fibers.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
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    1. Identification and Characterization of the Linalool/Nerolidol Synthase from Streptomyces clavuligerus (pages 2403–2407)

      Dr. Chiaki Nakano, Hyo-Kyoung Kim and Prof. Yasuo Ohnishi

      Version of Record online: 12 SEP 2011 | DOI: 10.1002/cbic.201100501

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      No cyclization: To produce the parent skeletons of diverse terpenoids, linear isoprenyl diphosphate precursors are usually cyclized by terpenoid cyclases. However, some terpenoid synthases produce acyclic terpenoids from the linear substrates. The linalool/nerolidol synthase reported here is the first example of a bacterial acyclic terpenoid synthase that shows significant homology to bacterial terpenoid cyclases.

    2. An Additional Dehydratase-Like Activity is Required for Lankacidin Antibiotic Biosynthesis (pages 2408–2412)

      Dr. Jeroen S. Dickschat , Dr. Olivia Vergnolle , Dr. Hui Hong, Dr. Stephen Garner, Susanna R. Bidgood, Hannah C. Dooley, Prof. Zixin Deng, Prof. Peter F. Leadlay and Prof. Yuhui Sun

      Version of Record online: 27 SEP 2011 | DOI: 10.1002/cbic.201100474

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      Lankacidin biosynthesis is processed by an unusual NRPS/PKS. A previously unrecognised dehydratase domain was shown in knockout experiments to act together with the discrete dehydratase LkcB in lankacidin biosynthesis and may control the switch from the iterative to the modular mode of operation that is implied in this system.

    3. Semisynthesis of Prenylated Rab GTPases by Click Ligation (pages 2413–2417)

      Long Yi, Mostafa Abootorabi and Dr. Yao-Wen Wu

      Version of Record online: 29 SEP 2011 | DOI: 10.1002/cbic.201100466

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      Click on the link: Tandem expressed protein ligation (EPL) and click reaction provide access to functional geranylgeranylated Rab GTPases (see scheme). The reactions are quantitative and highly efficient. This ligation strategy could open up a new avenue for lipidated protein production and provide pure post-translationally modified lipidated proteins for various biological studies.

    4. In Situ RBL Receptor Visualization and Its Mediated Anticancer Activity for Solasodine Rhamnosides (pages 2418–2420)

      Dr. Yanyan Wang, Dr. Jian Gao, Dr. Guofeng Gu, Gang Li, Changzhi Cui, Dr. Bin Sun and Prof. Dr. Hongxiang Lou

      Version of Record online: 26 SEP 2011 | DOI: 10.1002/cbic.201100551

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      Made visible: In situ visualization of the RBL receptor on cancer cell line surfaces was developed by using biotinylated rhamnose and chacotriose bound to quantum dots. The RBL receptor showed different expression patterns on various cell lines. Also, solasodine rhamnosides were found to kill cancer cells more effectively (see graphic). The finding of the RBL receptor-mediated anticancer activity could help the design of chemotherapy agents.

    5. Direct Investigation of the Aspergillus GDP-Mannose Transporter by STD NMR Spectroscopy (pages 2421–2425)

      Andrea Maggioni, Julian Meier, Prof. Françoise Routier, Dr. Thomas Haselhorst and Dr. Joe Tiralongo

      Version of Record online: 23 SEP 2011 | DOI: 10.1002/cbic.201100483

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      The direct analysis of the Aspergillus GDP-Man transporter (GMT) by competition STD NMR spectroscopy revealed that GDP binds tighter to the GMT than GMP and GDP-Man, with Man the weakest binding ligand. Our data permits the relative affinity of individual ligand moieties that bind the Aspergillus GMT to be summarized as follows: GDP≥ GMP≃GDP-Man≫Man

    6. Simultaneous “One Pot” Expressed Protein Ligation and CuI-Catalyzed Azide/Alkyne Cycloaddition for Protein Immobilization (pages 2426–2430)

      Max Steinhagen, Dr. Kai Holland-Nell, Prof. Dr. Morten Meldal and Prof. Dr. Annette G. Beck-Sickinger

      Version of Record online: 8 SEP 2011 | DOI: 10.1002/cbic.201100434

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      One-pot recipe: Usually protein modification, purification and immobilization are performed in distinct steps. Here, a simultaneous one-step immobilization of proteins by combining expressed protein ligation and CuI-catalyzed azide/alkyne [3+2] cycloaddition is presented (see scheme). The native protein structure was retained and the proteins could be characterized by fluorescence microscopy and enzymatic activity.

    7. Correlated Optical and Electrical Single-Molecule Measurements Reveal Conformational Diffusion from Ligand Binding to Channel Gating in the Nicotinic Acetylcholine Receptor (pages 2431–2434)

      Dr. Ralf Schmauder , Dr. Davor Kosanic, Dr. Ruud Hovius and Prof. Horst Vogel

      Version of Record online: 14 SEP 2011 | DOI: 10.1002/cbic.201100302

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      Towards channel opening: The time delay between binding of a fluorescent agonist and the subsequent gating event was evaluated directly from optical and electrical single-event traces measured on an individual receptor. The distribution of such time delays was best fitted by a 3/2 power-law, indicating that conformational diffusion was the channel-activation mechanism.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Peptide-Controlled Access to the Interior Surface of Empty Virus Nanoparticles (pages 2435–2440)

      Dr. Frank Sainsbury , Dr. Keith Saunders, Alaa A. A. Aljabali, Prof. David J. Evans and Prof. George P. Lomonossoff

      Version of Record online: 27 SEP 2011 | DOI: 10.1002/cbic.201100482

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      Empty virus nanoparticles have potentially many uses in nanotechnology and medicine. Certain capsid-protein peptides were found to govern access of diffusing metal ions to the interior of such particles. Enzymatic or genetic manipulation of this peptide can be used to determine the pattern of metal deposition.

    2. Cell Targeting with Hybrid Qβ Virus-Like Particles Displaying Epidermal Growth Factor (pages 2441–2447)

      Dr. Jonathan K. Pokorski, Marisa L. Hovlid and Prof. M. G. Finn

      Version of Record online: 29 SEP 2011 | DOI: 10.1002/cbic.201100469

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      A means to many ends: EGF can be displayed on the surface of the bacteriophage Qβ through genetic manipulation of the capsid protein. Viral nanoparticles that display EGF retain their ability to bind to and activate the EGF receptor. These methods provide a convenient way to encode receptor-targeting functionality into a protein nanoparticle.

    3. Identification of Anchor Points for Chemical Modification of a Small Cysteine-Rich Protein by Using a Cysteine Scan (pages 2448–2455)

      Tine N. Vinther, Ulla Ribel, Dr. Thomas Åskov Pedersen, Dr. Thomas B. Kjeldsen, Prof. Dr. Knud J. Jensen and Dr. František Hubálek

      Version of Record online: 8 SEP 2011 | DOI: 10.1002/cbic.201100464

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      Cysteine galore: Cysteine scanning was performed on insulin, a protein containing three disulfides. Several analogues with an extra cysteine were expressed to provide Cys7 insulin analogues for the first time. This allowed chemical modification of insulin at hitherto inaccessible positions as a new route to biopharmaceutically relevant insulins.

    4. A Synthetic Mirror Image of Kalata B1 Reveals that Cyclotide Activity Is Independent of a Protein Receptor (pages 2456–2462)

      Dr. Lillian Sando, Dr. Sónia Troeira Henriques , Fiona Foley, Dr. Shane M. Simonsen, Dr. Norelle L. Daly, Dr. Kristopher N. Hall, Dr. Kirk R. Gustafson, Prof. Marie-Isabel Aguilar and Prof. David J. Craik

      Version of Record online: 16 SEP 2011 | DOI: 10.1002/cbic.201100450

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      D activated: Positive results from hemolysis assays with the all-D isomer imply that the activity of cyclotide kalata B1 is primarily modulated by the lipid-bilayer environment and the self-assembly of cyclotides on the lipid membrane rather than depending on the recognition of chiral receptors.

    5. Metabolically Stable Cellular Adhesion to Inert Surfaces (pages 2463–2470)

      Prof. Morten Meldal , Dr. Boqian Wu, Dr. Frederik Diness, Dr. Roice Michael and Grith Hagel 

      Version of Record online: 16 SEP 2011 | DOI: 10.1002/cbic.201100382

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      Novel adhesion peptides for the growth of cell monolayers on inert surfaces were identified by screening D-amino acid split-mix combinatorial libraries. Peptide adhesion was superior to that of poly D-lysine and allowed a monolayer of nonadhesive HEK293 cells to be established on the surface of PEG-based polymer beads for on-bead cellular screening.

    6. Fluorescence of 1,2-Diaminoanthraquinone and its Nitric Oxide Reaction Product within Macrophage Cells (pages 2471–2477)

      María J. Marín, Dr. Paul Thomas, Víctor Fabregat, Prof. Santiago V. Luis, Prof. David A. Russell and Dr. Francisco Galindo

      Version of Record online: 27 SEP 2011 | DOI: 10.1002/cbic.201100371

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      Confirming the intracellular formation of a triazole derivative: Both confocal fluorescence microscopy images and spectroscopic information obtained from macrophage cells were extensively studied to confirm the intracellular formation of the triazole derivative of 1,2-diaminoanthraquinone (DAA-TZ) when the NO probe DAA reacts with NO in the presence of oxygen.

    7. Identification and Characterisation of a Calcium Carbonate-Binding Protein, Blue Mussel Shell Protein (BMSP), from the Nacreous Layer (pages 2478–2487)

      Dr. Michio Suzuki, Ai Iwashima, Dr. Naoaki Tsutsui, Dr. Tsuyoshi Ohira, Dr. Toshihiro Kogure and Prof. Hiromichi Nagasawa

      Version of Record online: 20 SEP 2011 | DOI: 10.1002/cbic.201100317

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      Common proteins in nacre: We have identified and characterised a protein (BMSP) from the blue mussel, Mytilus galloprovincialis. BMSP is similar to Pif, which plays a role in nacre formation in the Japanese pearl oyster. Both proteins contain a signal peptide (pink), VWA domains (blue) and a Peritrophin A-type chitin-binding domain (yellow), suggesting a common mechanism for nacre formation in these molluscs.

    8. A Reversible Protection Strategy To Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach (pages 2488–2494)

      Dr. Santosh K. Mahto, Cecil J. Howard, John C. Shimko and Prof. Jennifer J. Ottesen

      Version of Record online: 12 SEP 2011 | DOI: 10.1002/cbic.201100472

      Thumbnail image of graphical abstract

      Branching? Out! The 3,4-diaminobenzoic acid linker (Dbz) is susceptible to mis-acylation, which leads to branched and acetylated products during Fmoc-SPPS of peptide thioesters. Reversible allyloxycarbonyl protection eliminates these side products and improves yields, particularly for Gly-rich and synthetically challenging sequences. A protected Dbz(Alloc) base resin is compatible with common native chemical ligation termini.

    9. Delineation of the Core Aggregation Sequences of TDP-43 C-Terminal Fragment (pages 2495–2501)

      Akash Saini and Dr. Virander Singh Chauhan

      Version of Record online: 8 SEP 2011 | DOI: 10.1002/cbic.201100427

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      Who′s responsible? The C-terminal cleavage products of TDP-43 are thought to be important for aggregation of the protein, and thus for diseases like amyotrophic lateral sclerosis. Using synthetic peptides, we identified two sequences within the TDP-43 C-terminal fragment that could be responsible for its aggregation. This could help in the design of peptide-based aggregation inhibitors.

    10. Enhancing the Thermal Robustness of an Enzyme by Directed Evolution: Least Favorable Starting Points and Inferior Mutants Can Map Superior Evolutionary Pathways (pages 2502–2510)

      Dr. Yosephine Gumulya and Prof. Dr. Manfred T. Reetz

      Version of Record online: 13 SEP 2011 | DOI: 10.1002/cbic.201100412

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      When the best is not best: When applying directed evolution to optimizing the catalytic properties of an enzyme, non-improved or even inferior variants in a mutant library can be the best templates for further mutagenesis. Neutral drift or a type of quasi-species might be involved in this unusual observation. Here, we have applied this technique to the epoxide hydrolase from Aspergillus niger (ANEH, see figure).

    11. Novel Allene Oxide Synthase Products Formed via Favorskii-Type Rearrangement: Mechanistic Implications for 12-Oxo-10,15-phytodienoic Acid Biosynthesis (pages 2511–2517)

      Prof. Alexander N. Grechkin, Natalia V. Lantsova, Dr. Yana Y. Toporkova, Svetlana S. Gorina, Dr. Faina K. Mukhitova and Boulat I. Khairutdinov

      Version of Record online: 16 SEP 2011 | DOI: 10.1002/cbic.201100346

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      Novel oxylipins, such as 1, have been detected as products of the incubation of allene oxide synthases with linolenic acid (S)-hydroperoxides. These dicarboxylic acids are formed via cyclopropanones by Favorskii-type rearrangements. The data demonstrate the coexistence of cyclopropanones with 18:3-allene oxides. Cyclopropanone is either a byproduct or a precursor of 12-oxo-PDA.

  10. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. Advances in Enzymology and Related Areas of Molecular Biology Vol. 77. Edited by Eric J. Toone. (page 2518)

      Hiroshi Yoneyama

      Version of Record online: 26 AUG 2011 | DOI: 10.1002/cbic.201100480

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      Wiley Hoboken 2011, XIII+418 pp., hardcover $ 125.00.—ISBN 978-0-470-63835-4

  11. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. Corrigendum
    6. News
    7. Essay
    8. Highlight
    9. Communications
    10. Full Papers
    11. Book Review
    12. Preview
    1. You have free access to this content
      Preview: ChemBioChem 17/2011 (page 2519)

      Version of Record online: 26 OCT 2011 | DOI: 10.1002/cbic.201190079

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