ChemBioChem

Cover image for Vol. 13 Issue 9

June 18, 2012

Volume 13, Issue 9

Pages 1217–1375

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Cover Picture: Peptoid–Peptide Hybrid Ligands Targeting the Polo Box Domain of Polo-Like Kinase 1 (ChemBioChem 9/2012) (page 1217)

      Dr. Fa Liu, Dr. Jung-Eun Park, Dr. Wen-Jian Qian, Dr. Dan Lim, Andrej Scharow, Prof. Thorsten Berg, Prof. Michael B. Yaffe, Dr. Kyung S. Lee and Dr. Terrence R. Burke Jr.

      Article first published online: 13 JUN 2012 | DOI: 10.1002/cbic.201290033

      Thumbnail image of graphical abstract

      The cover picture shows the binding of a PLHSpT derivative, 6 q, to the polo-like kinase 1 (Plk1) polo-box domain (PBD), thereby uncovering a new hydrophobic channel (magnified upper right), which is absent in the unliganded protein (magnified lower left). On p. 1291 ff., K. S. Lee, T. R. Burke, Jr., et al. explain how, as a consequence of the additional interaction with the channel, the peptide binds to the Plk1 PBD with a binding affinity more than two orders of magnitude higher. The background image of a stained cell nucleus depicts how this binding results in interference with Plk1 (red dots)-dependent bipolar spindle formation (green), and this ultimately leads to mitotic block and apoptotic cell death in cultured cancer cells. (Background image taken from Nat. Chem. Biol. 2011, 7, 595–601 with permission. Copyright Nature Publishing Group 2011.)

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
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    1. Inside Cover: Visible Light-Driven NADH Regeneration Sensitized by Proflavine for Biocatalysis (ChemBioChem 9/2012) (page 1218)

      Dong Heon Nam and Prof. Chan Beum Park

      Article first published online: 13 JUN 2012 | DOI: 10.1002/cbic.201290034

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      The inside cover picture shows a successful coupling of photochemical NAD(P)H regeneration with redox enzymatic synthesis by using proflavine as a light-harvesting molecule. Proflavine exhibited a high capacity to drive the reduction of NAD(P)+ into NAD(P)H, and the photoregenerated NAD(P)H was enzymatically active to be oxidized by oxidoreductases. For further details, see the paper by C. B. Park and D. H. Nam on p. 1278 ff.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
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    1. Graphical Abstract: ChemBioChem 9/2012 (pages 1219–1226)

      Article first published online: 13 JUN 2012 | DOI: 10.1002/cbic.201290035

  4. News

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

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
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    1. Organometallic Compounds: An Opportunity for Chemical Biology? (pages 1232–1252)

      Dr. Malay Patra and Prof. Dr. Gilles Gasser

      Article first published online: 22 MAY 2012 | DOI: 10.1002/cbic.201200159

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      Flexible metals: This review summarises recent advances in the use of organometallic compounds in the field of chemical biology, a research area that we are defining as “organometallic chemical biology”.

  6. Highlights

    1. Top of page
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    4. Graphical Abstract
    5. News
    6. Review
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    8. Communications
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    1. Chemical Biology Techniques Unlock the Secrets of Casein Kinase 2 Regulation by Phosphorylation and Glycosylation (pages 1253–1255)

      Karolina Pavic and Dr. Maja Köhn

      Article first published online: 3 MAY 2012 | DOI: 10.1002/cbic.201200235

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      The key to understanding: The application of expressed protein ligation and protein microarrays enabled an unparalleled insight into the complex interaction of phosphorylation and glycosylation on casein kinase 2 and its biological outcome.

    2. Resveratrol and Health: The Starting Point (pages 1256–1259)

      Dr. Lucia Biasutto, Dr. Andrea Mattarei and Dr. Mario Zoratti

      Article first published online: 13 MAY 2012 | DOI: 10.1002/cbic.201200193

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      Cascade of youth? Resveratrol, the celebrated phytoalexin of red wine, was known to activate AMPK indirectly, but how this happened was unclear. In a paper recently published in Cell, S.-J. Park, J. H. Chung and co-workers identify the signalling cascade, which begins with the inhibition of phosphodiesterases, in particular PDE4. But questions remain, even while new perspectives open up.

  7. Communications

    1. Top of page
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    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
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    8. Communications
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    1. The Catalytic Redox Activity of Prion Protein–CuII is Controlled by Metal Exchange with the ZnII–Thiolate Clusters of Zn7Metallothionein-3 (pages 1261–1265)

      Dr. Gabriele Meloni, Andrea Crameri, Günter Fritz, Dr. Paul Davies, Prof. David R. Brown, Prof. Peter M. H. Kroneck and Prof. Milan Vašák

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200198

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      Silencing prion: Copper-catalyzed transformations of prion protein (PrP) lead to the production of reactive oxygen species (ROS), PrP oxidation, and cleavage and aggregation in transmissible spongiphorm encephalopathies. Zn7MT-3 efficiently targets CuII bound in different coordination modes to PrP–CuII. By an unusual redox-dependent metal-swap reaction, MT-3 modulates the catalytic redox properties of PrP–CuII.

    2. Structural and Mechanistic Basis of the Interaction between a Pharmacological Chaperone and Human Phenylalanine Hydroxylase (pages 1266–1269)

      Renzo Torreblanca, Erandi Lira-Navarrete, Prof. Javier Sancho and Dr. Ramon Hurtado-Guerrero

      Article first published online: 30 APR 2012 | DOI: 10.1002/cbic.201200188

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      Not without a chaperone: Pharmacological chaperones are designed to bind and ideally stabilise their target protein. Here, we elucidate the molecular mechanism of a potential pharmacological chaperone to treat phenylketonuria. The crystal structure of human phenylalanine hydroxylase with compound IV may help in the rational design of more efficient compounds to treat this disease.

    3. Dehalogenation of an Anthropogenic Compound by an Engineered Variant of the Mouse Cytokine Macrophage Migration Inhibitory Factor (pages 1270–1273)

      Anna A. Wasiel, Bert-Jan Baas, Ellen Zandvoort, Prof. Dr. Wim J. Quax and Dr. Gerrit J. Poelarends

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200153

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      An unconventional dehalogenase: An engineered variant (I64V/V106L) of the mouse cytokine macrophage migration inhibitory factor (MIF) promiscuously catalyzes the hydrolytic dehalogenation of the xenobiotic organohalogen trans-3-chloroacrylic acid to acetaldehyde. Although the dehalogenase activity of this MIF variant is quite low, it achieves an ∼109-fold rate enhancement, matching those of conventional enzymes acting on their natural substrates.

    4. Enhancement of the Promiscuous Aldolase and Dehydration Activities of 4-Oxalocrotonate Tautomerase by Protein Engineering (pages 1274–1277)

      Ellen Zandvoort, Dr. Edzard M. Geertsema, Prof. Dr. Wim J. Quax and Dr. Gerrit J. Poelarends

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200225

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      Double play: The enzyme 4-oxalocrotonate tautomerase (4-OT) catalyzes not only the initial cross-coupling of acetaldehyde and benzaldehyde to yield 3-hydroxy-3-phenylpropanal, but also the subsequent dehydration of this aldol compound to yield cinnamaldehyde as the final product. Mechanism-inspired engineering provided an active site mutant (F50A) with strongly enhanced aldol condensation activity.

    5. Visible Light-Driven NADH Regeneration Sensitized by Proflavine for Biocatalysis (pages 1278–1282)

      Dong Heon Nam and Prof. Chan Beum Park

      Article first published online: 3 MAY 2012 | DOI: 10.1002/cbic.201200115

      Thumbnail image of graphical abstract

      Harvest time: Proflavine drives the reduction of NAD+ in the presence of a Rh-based electron mediator. Photoregenerated NADH was enzymatically active for oxidation by NADH-dependent L-glutamate dehydrogenase for the synthesis of L-glutamate. This work suggests that proflavine has the potential to become an efficient light-harvesting component in biocatalytic photosynthesis driven by solar energy.

    6. You have full text access to this OnlineOpen article
      Bioconjugation of Green Fluorescent Protein via an Unexpectedly Stable Cyclic Sulfonium Intermediate (pages 1283–1285)

      Ramiz Nathani, Paul Moody, Dr. Mark E. B. Smith, Dr. Richard J. Fitzmaurice and Prof. Stephen Caddick

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cbic.201200231

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      Smooth converter: Bioconjugation of superfolder GFP involving the formation of an unusually stable, and unprecedented, cyclic sulfonium species is described. This sulfonium can undergo smooth reaction with a range of nucleophiles to give sulfur-, selenium- and azide-modified GFP derivatives in high conversions.

    7. DNA Microarray Expression Analysis of Baicalin-Induced Differentiation of C17.2 Neural Stem Cells (pages 1286–1290)

      Dr. Ming Li, Sze-Ting Choi, Prof. Kam-Sze Tsang, Prof. Pang-Chui Shaw and Prof. Kwok-Fai Lau

      Article first published online: 3 MAY 2012 | DOI: 10.1002/cbic.201200145

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      Identifying baicalin-regulated genes for neuronal differentiation: Baicalin is a potent neuronal-differentiation-inducing compound. This study explored the gene expression regulated through baicalin-induced differentiation of C17.2 neural stem cells by using a DNA microarray followed by qPCR validation. The expression of 15 genes was significantly regulated among the 58 differentially expressed genes important for nervous system development and function.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. Peptoid–Peptide Hybrid Ligands Targeting the Polo Box Domain of Polo-Like Kinase 1 (pages 1291–1296)

      Dr. Fa Liu, Dr. Jung-Eun Park, Dr. Wen-Jian Qian, Dr. Dan Lim, Andrej Scharow, Prof. Thorsten Berg, Prof. Michael B. Yaffe, Dr. Kyung S. Lee and Dr. Terrence R. Burke Jr.

      Article first published online: 8 MAY 2012 | DOI: 10.1002/cbic.201200206

      Thumbnail image of graphical abstract

      Putting the hole in the polo: Replacing the amino terminal Pro residue of the Plk1 polo box domain (PBD)-binding pentamer peptide, PLHSpT, with a library of N-alkyl-Gly “peptoids” gave low-nanomolar affinity peptide–peptoid hybrids. An X-ray crystal structure of one PBD-bound hybrid showed that a long-chain alkylphenyl group created a hydrophobic channel (right) that was not present in the PLHSpT-bound complex (yellow circle, left).

    2. Dimerization Determines Substrate Specificity of a Bacterial Prenyltransferase (pages 1297–1303)

      David Peterhoff, Dr. Hermann Zellner, Dr. Harald Guldan, Dr. Rainer Merkl, Prof. Dr. Reinhard Sterner and Dr. Patrick Babinger

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200127

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      Working together: Many enzymes are active only when assembled as multimeric complexes, whereas a few are active both as monomers and multimers—but with different substrate specificity. We identified the dimer interface of a bacterial heptaprenylglyceryl phosphate synthase and showed that oligomer formation is crucial for binding the long-chain substrate.

      Corrected by:

      Corrigendum: Corrigendum: Dimerization Determines Substrate Specificity of a Bacterial Prenyltransferase

      Vol. 13, Issue 12, 1710, Article first published online: 3 AUG 2012

    3. DNA Interaction of the CcrM DNA Methyltransferase: A Mutational and Modeling Study (pages 1304–1311)

      Razvan F. Albu, Prof. Dr. Martin Zacharias, Dr. Tomasz P. Jurkowski and Prof. Dr. Albert Jeltsch

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cbic.201200082

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      DNA recognition by the CcrM DNA methyltransferase was studied by protein modeling and site-directed mutagenesis of 20 amino acid residues. Four residues in two loops of the protein were identified to be important for DNA recognition by CcrM, which occurs in a very cooperative process.

    4. You have full text access to this OnlineOpen article
      The Complex of Cytochrome f and Plastocyanin from Nostoc sp. PCC 7119 is Highly Dynamic (pages 1312–1318)

      Sandra Scanu, Johannes Förster, Dr. Michela G. Finiguerra, Maryam Hashemi Shabestari, Dr. Martina Huber and Prof. Dr. Marcellus Ubbink

      Article first published online: 22 MAY 2012 | DOI: 10.1002/cbic.201200073

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      Brief encounter: Cytochrome f and plastocyanin are redox partners in photosynthesis. Paramagnetic NMR spectroscopy was applied to characterize this complex from the cyanobacterium Nostoc sp. PCC 7119. The results show that the complex cannot be described by a single well-defined state, thus indicating that the interaction is highly dynamic.

    5. Papain-Specific Activating Esters in Aqueous Dipeptide Synthesis (pages 1319–1326)

      Roseri J. A. C. de Beer, Barbara Zarzycka, Michiel Mariman, Helene I. V. Amatdjais-Groenen, Marc J. Mulders, Dr. Peter J. L. M. Quaedflieg, Dr. Floris L. van Delft, Dr. Sander B. Nabuurs and Prof. Floris P. J. T. Rutjes

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200017

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      A set of new activating esters was evaluated in an enzymatic, papain-catalyzed approach to synthesizing dipeptides under aqueous conditions. In particular, benzyl and dimethylaminophenyl esters yielded the corresponding dipeptides in several instances in high yields and with relatively small levels of hydrolysis. These results were also interpreted by computational docking analysis.

    6. You have full text access to this OnlineOpen article
      Cellular Uptakes, Biostabilities and Anti-miR-210 Activities of Chiral Arginine-PNAs in Leukaemic K562 Cells (pages 1327–1337)

      Dr. Alex Manicardi, Dr. Enrica Fabbri, Dr. Tullia Tedeschi, Prof. Stefano Sforza, Dr. Nicoletta Bianchi, Dr. Eleonora Brognara, Prof. Roberto Gambari, Prof. Rosangela Marchelli and Prof. Roberto Corradini

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cbic.201100745

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      Chiral PNAs containing backbone arginine residues have been shown to display good anti-miR activities against miR-210, thus affecting cellular differentiation because they display strong RNA-binding properties, good cellular permeation and resistance to peptidases. We show that the stereochemistry, type of modification and distribution of modified monomers affect the overall anti-miR properties.

    7. NEIL1 Binding to DNA Containing 2′-Fluorothymidine Glycol Stereoisomers and the Effect of Editing (pages 1338–1348)

      Dr. Kazumitsu Onizuka, Jongchan Yeo, Prof. Dr. Sheila S. David and Prof. Dr. Peter A. Beal

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cbic.201200139

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      DNA repair and RNA editing: Oligodeoxynucleotides containing 2′-fluorothymidine glycol with either ribo or arabino configuration were synthesized and their binding with the unedited and edited forms of hNEIL1 along with Endo III were investigated. For both forms of hNEIL1, the binding affinities were similar, unlike the significant difference in glycosylase activity between the two forms of NEIL1.

    8. Species-Specific Activity of Glycolipid Ligands for Invariant NKT Cells (pages 1349–1356)

      Dr. Emma M. Dangerfield, Janice M. H. Cheng, Deborah A. Knight, Dr. Robert Weinkove, Prof. P. Rod Dunbar, A/Prof. Ian F. Hermans, Dr. Mattie S. M. Timmer and Dr. Bridget L. Stocker

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cbic.201200095

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      Two 4-deoxy analogues of α-GalCer were synthesised and their species-specific activities investigated. Here, we show that the 4-hydroxyl of α-GalCer is critical for the activation of human, but not murine, iNKT cells. This species-specific activity is due to a lack of human iNKT cell recognition, rather than insufficient CD1d presentation.

    9. STD NMR Study of the Interactions between Antibody 2G12 and Synthetic Oligomannosides that Mimic Selected Branches of gp120 Glycans (pages 1357–1365)

      Dr. Pedro M. Enríquez-Navas, Fabrizio Chiodo, Dr. Marco Marradi, Dr. Jesús Angulo and Prof. Dr. Soledad Penadés

      Article first published online: 24 MAY 2012 | DOI: 10.1002/cbic.201200119

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      Sweet gp120 arms: Molecular recognition of synthetic linear tri- and tetramannosides by the anti-HIV-1 antibody 2G12 was studied by NMR spectroscopy. These sugar ligands mimic the arms of two higher branched oligomannosides that contain structural motifs from natural gp120 glycans. Their binding epitopes and affinities for 2G12 were determined and compared to previous studies.

    10. Recognition by Nonaromatic and Stereochemical Subunit-Containing Polyamides of the Four Watson–Crick Base Pairs in the DNA Minor Groove (pages 1366–1374)

      Hong-Fei Zhang, Prof. Yan-Ling Wu, Shi-Kun Jiang, Prof. Pu Wang, Prof. Hiroshi Sugiyama, Xing-Lai Chen, Prof. Wen Zhang, Yan-Juan Ji and Chuan-Xin Guo

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cbic.201200137

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      Groovy recognition: A chiral nonaromatic five-membered cyclic subunit, (1R,3R)-3-aminocyclopentane carboxylic acid, serves as a DNA thymine-specific recognition element when incorporated into polyamides, in minor-groove sequence-specific recognition events. The results broaden our understanding and will help in the design of novel polyamides that include T-recognition preference.

  9. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Review
    7. Highlights
    8. Communications
    9. Full Papers
    10. Preview
    1. You have free access to this content
      Preview: ChemBioChem 10/2012 (page 1375)

      Article first published online: 13 JUN 2012 | DOI: 10.1002/cbic.201290037

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