ChemBioChem

Cover image for ChemBioChem

May 9, 2003

Volume 4, Issue 5

Pages 357–454

    1. Cover Picture: Semisynthesis and Characterization of the First Analogues of Pro-Neuropeptide Y (ChemBioChem 5/2003) (page 357)

      Regula von Eggelkraut-Gottanka, Zuzana Machova, Eric Grouzmann and Annette G. Beck-Sickinger

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200390063

    2. Aspartic Proteases Involved in Alzheimer's Disease (pages 366–378)

      Boris Schmidt

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200532

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      Enigmatic proteases: α-,β- and γ-secretases are the three executioners of amyloid precursor protein processing (see figure). They are widely believed to cause Alzheimer's disease. Progress has been made in selective inhibition, regardless of the lack of availability of structural information. Four distinctly different structural moieties have been developed and the first candidates are in clinical trials.

    3. Signaling Effects of Demethylasterriquinone B1, a Selective Insulin Receptor Modulator (pages 379–385)

      Nicholas J. G. Webster, Kaapjoo Park and Michael C. Pirrung

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200468

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      Sweet success: The effects of synthetic demethylasterriquinone B1, an orally active natural product that lowers blood glucose levels, on gene expression and second messenger signaling as compared to the effects of insulin were studied by using DNA microarrays (see figure). The results suggest that demethylasterriquinone B1 is a selective insulin receptor modulator.

    4. Indolocarbazole Glycosides in Inactive Conformations (pages 386–395)

      Michaël Facompré, Carolina Carrasco, Hervé Vezin, John D. Chisholm, Joshua C. Yoburn, David L. Van Vranken and Christian Bailly

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200478

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      Getting in shape: The capacity of indolocarbazole glycosides to target DNA and topoisomerase I depends on the conformation of the sugar moiety. Methylation of the NH indole group (1[RIGHTWARDS ARROW]2) drives a major conformational change that abolishes activity against the enzyme and restricts the access of the drug to DNA, thereby reducing cytotoxicity.

    5. Monitoring the Cellular Surface Display of Recombinant Proteins by Cysteine Labeling and Flow Cytometry (pages 396–405)

      Joachim Jose and Steffen Handel

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200530

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      Making a mark: A general method is described that allows monitoring of the surface display of recombinant proteins in Escherichia coli without having to use specific antibodies or enzymatic reactions. The method is based on cysteine-specific labeling through Michael addition to the double bond of maleimide and its derivatives (see scheme; R=variable group). An artificially introduced cysteine residue as well as natural cysteine residues occurring in recombinant proteins can be used for labeling.

    6. Large-Scale In Vivo Synthesis of the Carbohydrate Moieties of Gangliosides GM1 and GM2 by Metabolically Engineered Escherichia coli (pages 406–412)

      Tatiana Antoine, Bernard Priem, Alain Heyraud, Lionel Greffe, Michel Gilbert, Warren W. Wakarchuk, Joseph S. Lam and Eric Samain

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200540

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      A bacterial factory: A microbiological process for synthesis of the carbohydrate portion of gangliosides GM1 and GM2 (see scheme) is described. Lactose and sialic acid are used as exogenous precursors by metabolically engineered Escherichia coli strains that overexpress the genes for the appropriate glycosyltransferases and sugar-nucleotide synthases.

    7. Comparison of the Chemical Properties of Iron and Cobalt Porphyrins and Corrins (pages 413–424)

      Kasper P. Jensen and Ulf Ryde

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200449

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      A complex task for a ring: Density functional calculations have been used to compare the geometric, electronic and functional properties of iron and cobalt porphyrins and corrins by using models of the type shown in the picture. The corrin ring stabilises low-spin cobalt systems and gives strong Co[BOND]C bonds, whereas iron centres give low reorganisation energies.

    8. Semisynthesis and Characterization of the First Analogues of Pro-Neuropeptide Y (pages 425–433)

      Regula von Eggelkraut-Gottanka, Zuzana Machova, Eric Grouzmann and Annette G. Beck-Sickinger

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200546

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      Putting the pieces together: The first full-length analogues of prohormone neuropeptide Y (proNPY 1–69) have been synthesized by expressed protein ligation. Recombinant thioester fragments (proNPY 1–40/1–54) were ligated to the corresponding synthetic peptides, each bearing an Nterminal cysteine residue. Chemical modifications (with carboxyfluorescein, biotin) were site-specifically introduced into the protein sequence. Monoclonal antibodies (YNPY02, YCPON01) recognized the proNPY substrates and revealed a linear binding epitope for YCPON01.

    9. [7-(Dialkylamino)coumarin-4-yl]methyl-Caged Compounds as Ultrafast and Effective Long-Wavelength Phototriggers of 8Bromo-Substituted Cyclic Nucleotides (pages 434–442)

      Volker Hagen, Stephan Frings, Burkhard Wiesner, Siegrun Helm, U. Benjamin Kaupp and Jürgen Bendig

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200300561

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      Light-induced activation of biomolecules: Synthetic cyclic nucleotides whose biological activity is controlled by UV light have been developed and shown to exhibit remarkable advantageous properties, such as resistance to hydrolysis, significant solubility in aqueous buffer solutions, and rapid photocleavage under long-wavelength excitation (see figure). The compounds serve as excellent intracellular sources of 8-bromoadenosine 3′,5′-cyclic monophosphate and 8bromoguanosine 3′,5′-cyclic monophosphate. The novel cage compounds were succesfully applied in studies of cyclic-nucleotide-gated ion channels and will extend the repertoire of tools available for investigation of spatial- and time-dependent aspects of cyclic-nucleotide-dependent cellular processes.

    10. Application of the Nucleotidylyltransferase Ep toward the Chemoenzymatic Synthesis of dTDP-Desosamine Analogues (pages 443–446)

      Jiqing Jiang, Christoph Albermann and Jon S. Thorson

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200200566

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      Sweet transfer: The macrolide sugar β-D-desosamine (1) is a key contributor to the anti-infective properties of many macrolide antibiotics, and methods to alter this substituent may lead to macrolide variants with enhanced properties. The application of a nucleotidylyltransferase (Ep) toward the synthesis of analogues of the precursor dTDP-desosamine is demonstrated and the substrate specificity of this important class of enzyme and its integral participation in natural product 'glycorandomization' is commented on.

    11. Preview: ChemBioChem 5/2003 (page 454)

      Version of Record online: 5 MAY 2003 | DOI: 10.1002/cbic.200390070

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