ChemBioChem

Cover image for ChemBioChem

June 14, 2011

Volume 12, Issue 9

Pages 1285–1435

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireview
    7. Highlight
    8. Full Papers
    9. Communications
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    1. Cover Picture: Dissecting the Role of Single Regions of an IAPP Mimic and IAPP in Inhibition of Aβ40 Amyloid Formation and Cytotoxicity (ChemBioChem 9/2011) (page 1285)

      Erika Andreetto, Dr. Li-Mei Yan, Dr. Andrea Caporale and Prof. Aphrodite Kapurniotu

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201190036

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      The cover picture shows the effects of individual regions of IAPP-GI, a nonamyloidogenic mimic of the type 2 diabetes islet amyloid polypeptide (IAPP), on amyloid formation of the Alzheimer's disease amyloid β-peptide (Aβ). IAPP-GI has previously been found to bind Aβ with high affinity and to block its cytotoxic amyloidogenesis. Moreover, the Aβ-IAPP cross-amyloid interaction suppresses cytotoxic self-association by both polypeptides and might be a molecular link between the two diseases. Here the 37-residue IAPP-GI was dissected into shorter segments including the two hot-spot regions of the Aβ-IAPP(IAPP-GI) interaction interface IAPP(8–18) (pink) and IAPP(22–28)-GI (green) and the N- or C-terminal regions IAPP(1–7) (light blue) and IAPP(30–37) (dark blue). Only IAPP-GI and IAPP(1–28)-GI inhibited Aβ cytotoxic self-assembly and amyloidogenesis whereas all other segments even the ones containing hot-spot regions, such as IAPP(8–28)-GI, were unable to inhibit uncovering thus important molecular determinants of the IAPP-GI(IAPP) mediated inhibition of Aβ self-assembly. For more details, see the paper by A. Kapurniotu et al. on p. 1313 ff.

  2. Graphical Abstract

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    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireview
    7. Highlight
    8. Full Papers
    9. Communications
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  3. Corrigenda

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    4. Corrigenda
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    1. You have free access to this content
      Corrigendum: Caught in the Act: Visualization of SNARE-Mediated Fusion Events in Molecular Detail (page 1293)

      Herre Jelger Risselada, Carsten Kutzner and Prof. Helmut Grubmüller

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201190038

      This article corrects:

      Caught in the Act: Visualization of SNARE-Mediated Fusion Events in Molecular Detail

      Vol. 12, Issue 7, 1049–1055, Version of Record online: 23 MAR 2011

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      Corrigendum: Carbohydrate–Protein Interactions: A 3D View by NMR (page 1293)

      Dr. Virginia Roldós, Prof. Dr. F. Javier Cañada and Prof. Dr. Jesús Jiménez-Barbero

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201190041

      This article corrects:

      Carbohydrate–Protein Interactions: A 3D View by NMR

      Vol. 12, Issue 7, 990–1005, Version of Record online: 15 APR 2011

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      Corrigendum: Mechanism of Action of the Cytotoxic Macrolides Amphidinolide X and J (page 1293)

      Chiara Trigili, Benet Pera, Dr. Marion Barbazanges, Prof. Dr. Janine Cossy, Dr. Christophe Meyer, Dr. Oriol Pineda, Dr. Carles Rodríguez-Escrich, Prof. Fèlix Urpí, Prof. Dr. Jaume Vilarrasa, Dr. J. Fernando Díaz and Dr. Isabel Barasoain

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201190042

      This article corrects:

      Mechanism of Action of the Cytotoxic Macrolides Amphidinolide X and J

      Vol. 12, Issue 7, 1027–1030, Version of Record online: 15 APR 2011

  4. News

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    4. Corrigenda
    5. News
    6. Minireview
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    9. Communications
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  5. Minireview

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    1. Switching Modulation for Protein Labeling with Activatable Fluorescent Probes (pages 1299–1308)

      Dr. Kalyan K. Sadhu, Dr. Shin Mizukami, Dr. Yuichiro Hori and Prof. Dr. Kazuya Kikuchi

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/cbic.201100137

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      Fluorogenic protein-labeling techniques have been successfully used in live-cell imaging. Fluorescence derived from specific labeling can monitor the localization of proteins. Newly developed chemical techniques have addressed such specific incorporation of probes in the physiological environment. We conclude that some recent promising switching techniques should provide further molecular functional exploitation in vivo.

  6. Highlight

    1. Top of page
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    3. Graphical Abstract
    4. Corrigenda
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    1. Protein Modification by Strain-Promoted Alkyne–Azide Cycloaddition (pages 1309–1312)

      Dr. Jan C. M. van Hest and Dr. Floris L. van Delft

      Version of Record online: 10 MAY 2011 | DOI: 10.1002/cbic.201100206

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      Taking the strain: Strain-promoted cycloadditions between alkynes and azides have facilitated mild and bioorthogonal protein modification. Azides can be introduced into a protein by a variety of chemical, enzymatic or genetic techniques. Now genetic encoding of a cyclooctyne offers new opportunities for protein modification and the study of proteins in their native habitat.

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireview
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    8. Full Papers
    9. Communications
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    1. Dissecting the Role of Single Regions of an IAPP Mimic and IAPP in Inhibition of Aβ40 Amyloid Formation and Cytotoxicity (pages 1313–1322)

      Erika Andreetto, Dr. Li-Mei Yan, Dr. Andrea Caporale and Prof. Aphrodite Kapurniotu

      Version of Record online: 31 MAY 2011 | DOI: 10.1002/cbic.201100192

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      Block buster: We have previously found that the interaction of the type 2 diabetes islet amyloid polypeptide (IAPP) and its nonamyloidogenic mimic IAPP-GI with the Alzheimer's disease β-amyloid peptide (Aβ) blocks Aβ aggregation and cytotoxicity. Here we uncover the role of individual IAPP-GI and IAPP regions in the inhibitory function on Aβ40 amyloidogenesis and cytotoxicity and suggest a molecular basis for this effect.

    2. Discovery of a Small Peptide from Combinatorial Libraries That Can Activate the Plant Immune System by a Jasmonic Acid Signaling Pathway (pages 1323–1329)

      Prof. Masahiro Miyashita, Masashi Oda, Yuji Ono, Eriko Komoda and Prof. Hisashi Miyagawa

      Version of Record online: 12 MAY 2011 | DOI: 10.1002/cbic.201000694

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      A combinatorial random hexapeptide library was screened for peptides that can activate the plant immune system, by monitoring H2O2 generation. We discovered a novel small peptide (YGIHTH-amide) that triggered several plant defense responses, such as phytoalexin biosynthesis, in tobacco cells.

    3. Role of Disulfide Bridges in Archaeal Family-B DNA Polymerases (pages 1330–1336)

      Dr. Tom Killelea and Prof. Bernard A. Connolly

      Version of Record online: 20 MAY 2011 | DOI: 10.1002/cbic.201100145

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      Some like it hot: The family-B DNA polymerases from the Thermococcales are extensively used in PCR. They usually contain two disulfide bridges (see figure), the role of which in thermostability has been probed with site directed mutagenesis. The disulfides play a role in stability but even deletion of both does not compromise PCR performance. This opens the way to single cysteine variants, amenable to useful chemical modification.

    4. C5-DNA Methyltransferase Inhibitors: From Screening to Effects on Zebrafish Embryo Development (pages 1337–1345)

      Alexandre Ceccaldi, Arumugam Rajavelu, Christine Champion, Dr. Christine Rampon, Dr. Renata Jurkowska, Gytis Jankevicius, Catherine Sénamaud-Beaufort, Dr. Loïc Ponger, Dr. Nathalie Gagey, Hana Dali Ali, Dr. Jörg Tost, Prof. Sophie Vriz, Dr. Sindu Ros, Dr. Daniel Dauzonne, Prof. Albert Jeltsch, Dr. Dominique Guianvarc'h and Dr. Paola B. Arimondo

      Version of Record online: 1 JUN 2011 | DOI: 10.1002/cbic.201100130

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      Screen shots: A set of flavones and flavanones is described as a new family of nanomolar DNA methyltransferase inhibitors. Structure–activity relationships, enzymatic competition and docking studies (see figure) have provided insights on their mode of action. Two inhibitors effected zebrafish development in a similar fashion to the reference drug, 5-azacytidine.

    5. An Efficient Route to Selective Bio-oxidation Catalysts: an Iterative Approach Comprising Modeling, Diversification, and Screening, Based on CYP102A1 (pages 1346–1351)

      Alexander Seifert, Mihaela Antonovici, Prof. Dr. Bernhard Hauer and Prof. Dr. Jürgen Pleiss

      Version of Record online: 17 MAY 2011 | DOI: 10.1002/cbic.201100067

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      Successive rounds of modeling (MD simulations of enzyme–substrate complexes to identify hotspots for selectivity), diversification (design of minimal library) and screening of a minimal library is shown to be an efficient approach to shift and maximize regioselectivity of CYP102A1, and thus to generate the valuable oxidation product perillyl alcohol from cheap and readily available limonene.

    6. Lucifensin, a Novel Insect Defensin of Medicinal Maggots: Synthesis and Structural Study (pages 1352–1361)

      Dr. Václav Čeřovský, Dr. Jiřina Slaninová, Dr. Vladimír Fučík, Lenka Monincová, Dr. Lucie Bednárová, Dr. Petr Maloň and Dr. Jitka Štokrová

      Version of Record online: 10 MAY 2011 | DOI: 10.1002/cbic.201100066

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      Lucifensin is the key antimicrobial peptide of the green bottle fly larvae Lucilia sericata. This defensin protects the larvae when they are exposed to the infectious environment of a wound during maggot therapy and it also contributes as a disinfectant and healing factor. Three disulfide bridges keep this 40-amino-acid peptide in the specific conformation required for its antimicrobial activity.

    7. Biomineralization in Diatoms: The Role of Silacidins (pages 1362–1366)

      Patrick Richthammer, Mandy Börmel, Prof. Dr. Eike Brunner and Prof. Karl-Heinz van Pée

      Version of Record online: 10 MAY 2011 | DOI: 10.1002/cbic.201000775

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      Hardware applications: Biosilica from the diatom Thalassiosira pseudonana is a composite material containing proteins (silaffins, silacidins) and long-chain polyamines. These organic constituents are important players in silica biomineralization. The concentration of silacidins associated with the silica cell wall increases at low silicic acid levels. Their influence on silica precipitation strictly depends on the phosphorylation of serine.

    8. Site-Specific Labeling of Proteins by Using Biotin Protein Ligase Conjugated with Fluorophores (pages 1367–1375)

      Prof. Shinji Sueda, Sawako Yoneda and Hideki Hayashi

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/cbic.201000738

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      Protein labeling in living cells: We describe a fluorescent protein-labeling method that uses a unique biotinylation mechanism from the archaeon Sulfolobus tokodaii. A membrane protein fused to the biotin acceptor sequence (BCCP) was labeled by using biotin protein ligase (BPL) conjugated with fluorophores, both outside and inside the cell.

    9. Genetic Safeguard against Mycotoxin Cyclopiazonic Acid Production in Aspergillus oryzae (pages 1376–1382)

      Dr. Naoki Kato, Dr. Masafumi Tokuoka, Yasutomo Shinohara, Dr. Makoto Kawatani, Dr. Masakazu Uramoto, Dr. Yasuyo Seshime, Prof. Dr. Isao Fujii, Prof. Dr. Katsuhiko Kitamoto, Dr. Tadashi Takahashi, Dr. Shunji Takahashi, Dr. Yasuji Koyama and Dr. Hiroyuki Osada

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/cbic.201000672

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      The end product of a more ancient four-step cyclopiazonic acid pathway existing in the domesticated fungus A. oryzae is less toxic than that of the prevalent three-step pathway in the wild fungus A. flavus. The detoxifying properties of cpaH, which have been lost in the A. flavus pathway, reflect the relationship of the two species.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireview
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    9. Communications
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    1. Site-Selective Traceless Staudinger Ligation for Glycoprotein Synthesis Reveals Scope and Limitations (pages 1383–1386)

      Dr. Gonçalo J. L. Bernardes, Dr. Lars Linderoth, Dr. Katie J. Doores, Dr. Omar Boutureira and Prof. Benjamin G. Davis

      Version of Record online: 19 MAY 2011 | DOI: 10.1002/cbic.201100125

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      Making it traceless: A traceless Staudinger reaction between a specifically functionalized sugar phosphine and an azide-tagged protein allows the construction of well-defined reverse N-linked glycoproteins (see scheme). This reaction was applied to different azidoprotein substrates and its potentials and limitations are outlined.

    2. Colorimetric SNP Genotyping Based on Allele-Specific PCR by Using a Thiol-Labeled Primer (pages 1387–1390)

      Ye Lim Jung, Cheulhee Jung, Dr. Harshala Parab, Dr. Dae-Yeon Cho and Prof. Hyun Gyu Park

      Version of Record online: 6 MAY 2011 | DOI: 10.1002/cbic.201100098

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      Red gold/blue gold: A highly convenient colorimetric method for the identification of single-nucleotide polymorphism was developed by utilizing gold nanoparticles and an allele-specific polymerase chain reaction. Its diagnostic capability was successfully demonstrated by correctly identifying various mutations in the BRCA1 gene.

    3. Engineering Biofilms for Biocatalysis (pages 1391–1395)

      Dr. Andreas N. Tsoligkas, Michael Winn, Dr. James Bowen, Dr. Tim W. Overton, Dr. Mark J. H. Simmons and Dr. Rebecca J. M. Goss

      Version of Record online: 23 MAY 2011 | DOI: 10.1002/cbic.201100200

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      Biofilm, friend not foe: Single species biofilms can be engineered to form robust biocatalysts with greater catalytic activity and significantly improved catalytic longevity than purified and immobilised enzymes. We report the engineering, structural analysis and biocatalytic capability of a biofilm that can mediate the conversion of serine and haloindoles to halotryptophans (see scheme).

    4. Ascorbate as an Alternative to Thiol Additives in Native Chemical Ligation (pages 1396–1400)

      Heike Rohde, Josephine Schmalisch, Ziv Harpaz, Franziska Diezmann and Prof. Dr. Oliver Seitz

      Version of Record online: 6 MAY 2011 | DOI: 10.1002/cbic.201100179

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      Vitamin C for peptide ligation: Phosphine and thiol additives maintain reducing environments and increase the reactivities of peptide thioesters in native chemical ligation. Thiol additives such as thiophenol also act as radical scavengers that inhibit phosphine-induced desulfurization of cysteine. This role can be assumed by the odourless, nontoxic, highly water-soluble and inexpensive ascorbate, which can replace the usually added thiols.

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      Abyssomicin Biosynthesis: Formation of an Unusual Polyketide, Antibiotic-Feeding Studies and Genetic Analysis (pages 1401–1410)

      Elvira M. Gottardi, Joanna M. Krawczyk, Hanna von Suchodoletz, Simone Schadt, Agnes Mühlenweg, Gabriel C. Uguru, Dr. Stefan Pelzer, Prof. Dr. Hans-Peter Fiedler, Prof. Dr. Mervyn J. Bibb, Dr. James E. M. Stach and Prof. Roderich D. Süssmuth

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201100172

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      Small wonder: Atrop-abyssomicin C is a small, yet complex spirotetronate (see scheme) that is active against Gram-positive bacteria, such as MRSA. Feeding studies and genetic manipulation of its producer, Verrucosispora maris AB-18-032, for the first time give insight into its biosynthesis and demonstrate how closely related the members of this important class of molecules are.

    6. Identification and Characterization of the Althiomycin Biosynthetic Gene Cluster in Myxococcus xanthus DK897 (pages 1411–1416)

      Niña Socorro Cortina, Ole Revermann, Dr. Daniel Krug and Prof. Dr. Rolf Müller

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/cbic.201100154

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      Althiomycin biosynthetic gene cluster: The potent broad-spectrum antibiotic althiomycin is a product of a nonribosomal peptide/polyketide assembly line. The biosynthetic gene cluster from the natural producer Myxococcus xanthus DK897 was identified and characterized.

    7. Insights into the Mechanistic Role of the [Fe4S4] Cubane in the A-Cluster {[Fe4S4]-(SR)-[NipNid]} of Acetyl-Coenzyme A Synthase (pages 1417–1421)

      Yi Liu, Dr. Feng Wang, Prof. Pingwei Li and Prof. Xiangshi Tan

      Version of Record online: 27 MAY 2011 | DOI: 10.1002/cbic.201100101

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      Cubane revolution: We have constructed various mutants to probe the role of [Fe4S4] cubane. The results show that [Fe4S4] cubane, which is bridged to a [NipNid] center via Cys509 cysteinate in the A-cluster of acetyl-coenzyme A synthase (see figure), modulates the redox properties of the catalytic metal Nip and stabilizes the low valence of Nip through the {[Fe4S4][BOND](SR)[BOND]Nip} “conjugation system”.

    8. Identification of Novel Quadruplex Ligands from Small Molecule Libraries by FRET-Based High-Throughput Screening (pages 1422–1426)

      Armin Benz, Dr. Vijay Singh, Prof. Dr. Thomas U. Mayer and Prof. Dr. Jörg S. Hartig

      Version of Record online: 26 MAY 2011 | DOI: 10.1002/cbic.201100094

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      Quadruple alliance: By performing a screen for binders of the human telomeric repeat sequence with small molecule libraries, the principle of which is outlined in the scheme, we have identified novel compounds that stabilise the G quadruplex structure. Some of these could be suitable leads for further optimisation as potent and selective quadruplex ligands.

    9. Peptidic Partial Bisubstrates as Inhibitors of the Protein Arginine N-Methyltransferases (pages 1427–1432)

      Peter 't Hart, Dr. Ted M. Lakowski, Dylan Thomas, Dr. Adam Frankel and Dr. Nathaniel I. Martin

      Version of Record online: 10 MAY 2011 | DOI: 10.1002/cbic.201100074

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      Double player: Protein arginine N-methyltransferases (PRMTs) employ a general SN2-like bisubstrate reaction mechanism with the cofactor S-adenosyl-L-methionine (AdoMet) to methylate L-arginine residues in target proteins. In this study, new peptidic partial bisubstrate analogues, bearing a minimal AdoMet fragment (highlighted in yellow) were prepared and evaluated as PRMT inhibitors.

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireview
    7. Highlight
    8. Full Papers
    9. Communications
    10. Preview
    1. You have free access to this content
      Preview: ChemBioChem 10/2011 (page 1435)

      Version of Record online: 9 JUN 2011 | DOI: 10.1002/cbic.201190040

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