ChemBioChem

Cover image for Vol. 10 Issue 2

January 26, 2009

Volume 10, Issue 2

Pages 189–382

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireviews
    7. Highlight
    8. Communications
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    10. Book Reviews
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    1. Cover Picture: Evidence that Thienamycin Biosynthesis Proceeds via C-5 Epimerization: ThnE Catalyzes the Formation of (2S,5S)-trans-Carboxymethylproline (ChemBioChem 2/2009) (page 189)

      Refaat B. Hamed, Edward T. Batchelar, Jasmin Mecinović, Timothy D. W. Claridge and Christopher J. Schofield

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990000

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      The cover picture shows a view from a crystal structure of a carboxymethylproline synthase with the malonyl-CoA-derived enolate and pyroline-5-carboxylate modelled into the active site. Carboxymethylproline synthases (e.g. CarB and ThnE from Pectobacterium carotovorum and Streptomyces cattleya, respectively) catalyse the formation of carboxymethylproline intermediates in the biosynthesis of the clinically important carbapenem subfamily of β-lactam antibiotics. Epimerization reactions enable diversification in the biosynthetic pathways leading to all subfamilies of bicyclic β-lactam antibiotics: penicillins/cephalosporins, carbapenems and clavams. For more information, see the article by C. J. Schofield et al. on p. 246 ff.

  2. Graphical Abstract

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    1. Graphical Abstract: ChemBioChem 2/2009 (pages 191–199)

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990001

  3. Corrigenda

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    3. Graphical Abstract
    4. Corrigenda
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    8. Communications
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    10. Book Reviews
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    1. You have free access to this content
      Biological Implications of the Ribosome's Stunning Stereochemistry (page 198)

      Ella Zimmerman and Ada Yonath

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990002

      This article corrects:

      Biological Implications of the Ribosome's Stunning Stereochemistry

      Vol. 10, Issue 1, 63–72, Article first published online: 16 DEC 2008

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      Extremely Tight Binding of a Ruthenium Complex to Glycogen Synthase Kinase 3 (page 198)

      G. Ekin Atilla-Gokcumen, Nicholas Pagano, Craig Streu, Jasna Maksimoska, Panagis Filippakopoulos, Stefan Knapp and Eric Meggers

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990005

      This article corrects:

      Extremely Tight Binding of a Ruthenium Complex to Glycogen Synthase Kinase 3

      Vol. 9, Issue 18, 2933–2936, Article first published online: 26 NOV 2008

  4. News

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    1. Spotlights on our sister journals: ChemBioChem 2/2009 (pages 202–203)

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990003

  5. Minireviews

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    1. Quorum Sensing and Quorum Quenching: The Yin and Yang of Bacterial Communication (pages 205–216)

      Stéphane Uroz, Yves Dessaux and Phil Oger

      Article first published online: 12 DEC 2008 | DOI: 10.1002/cbic.200800521

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      Safety in numbers. N-Acyl homoserine lactone (AHL) signalling molecules can be degraded or modified through various ways, including: 1) lactone hydrolysis, 2) amidohydrolysis, 3) reduction of the keto group present on the C3 position, and 4) oxidation or reduction of the acyl chain. All of these reactions lead to a possible perturbation or quenching of the function(s) regulated by quorum sensing.

    2. Fine Tuning the N-Terminal Residue Excision with Methionine Analogues (pages 217–220)

      Birgit Wiltschi, Lars Merkel and Nediljko Budisa

      Article first published online: 9 DEC 2008 | DOI: 10.1002/cbic.200800605

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      The amino acid composition of the N terminus of a protein determines whether the first methionine residue is excised or not. Its replacement by a chemically distinct noncanonical analogue by an expanded genetic code affects the overall efficiency of this process. Recent advances have provided novel insight into the N-terminal residue excision rules; this certainly will enrich the repertoire of chemical protein engineering.

  6. Highlight

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    1. Strigolactones: The First Members of a New Family of “Shoot Branching Hormones” in Plants? (pages 221–223)

      Doreen Schachtschabel and Wilhelm Boland

      Article first published online: 12 DEC 2008 | DOI: 10.1002/cbic.200800727

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      Hey, bud! Strigolactones are a new class of plant hormones that control shoot branching. These apocarotenoids are endogenous, acting as rhizosphere signals that modulate shoot outgrowth, mycorrhizal symbiosis, and parasitic weed interactions.

  7. Communications

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    1. From Kinase to Cyclase: An Unusual Example of Catalytic Promiscuity Modulated by Metal Switching (pages 225–229)

      Israel Sánchez-Moreno, Laura Iturrate, Rocio Martín-Hoyos, María Luisa Jimeno, Montaña Mena, Agatha Bastida and Eduardo García-Junceda

      Article first published online: 4 DEC 2008 | DOI: 10.1002/cbic.200800573

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      Evolution of new enzyme functions: We describe the promiscuous behaviour of the dihydroxyacetone (DHA) kinase from Citrobacter freundii strain CECT 4626. In addition to the transfer of the γ-phosphate of adenosine-5′-triphosphate (ATP) to DHA, this ATP-dependent DHAK is able to catalyse the cyclization of FAD to yield riboflavin 4′,5′-cyclic phosphate (4′,5′-cFMN). This catalytic promiscuity is modulated by the divalent cation that forms the complex with the phosphorylated substrate.

    2. Design of Cell-Surface-Retained Polymers for Artificial Ligand Display (pages 230–233)

      Ryosuke Kamitani, Kenichi Niikura, Takaharu Okajima, Yasutaka Matsuo and Kuniharu Ijiro

      Article first published online: 17 DEC 2008 | DOI: 10.1002/cbic.200800621

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      We propose a cell-surface modification method based on the use of synthetic polymers that can be retained on the cell surface without rapid internalization. Secondary amine-displaying cationic polymers act as an effective scaffold for the display of artificial ligands, thus affording a new technique for the control of cell adhesion events through the specific recognition of these ligands.

    3. Exploring Kinase Cosubstrate Promiscuity: Monitoring Kinase Activity through Dansylation (pages 234–237)

      Keith D. Green and Mary Kay H. Pflum

      Article first published online: 23 DEC 2008 | DOI: 10.1002/cbic.200800393

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      FRET-based kinase assay: Based on cosubstrate promiscuity, the kinase-catalyzed dansylation reaction enables efficient detection of kinase activity and inhibition in vitro and in cell lysates. Importantly, these studies substantiate ATP cosubstrate promiscuity as a functional property of kinases.

    4. Identification of a Toxic Peptide through Bidirectional Expression of Small RNAs (pages 238–241)

      Wendy W. K. Mok, Naveen K. Navani, Courtney Barker, Bobbijo L. Sawchyn, Jimmy Gu, Ranjana Pathania, Rebecca D. Zhu, Eric D. Brown and Yingfu Li

      Article first published online: 17 DEC 2008 | DOI: 10.1002/cbic.200800591

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      Identifying lethal sRNA genes: We established a novel screening strategy that integrates the use of an RNA expression system to search uncharacterized small RNAs and their antisense counterparts for lethal phenotype.

    5. A Fluorescent Probe for the 70 S-Ribosomal GTPase-Associated Center (pages 242–245)

      Sebastian Schoof, Sascha Baumann, Bernhard Ellinger and Hans-Dieter Arndt

      Article first published online: 12 DEC 2008 | DOI: 10.1002/cbic.200800642

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      A ribosomal beacon: The thiopeptide antibiotic thiostrepton was transformed into a fluorescent probe for the 70 S ribosomal GTPase center. Comparative affinity determinations in the pM range were achieved for thiopeptide natural products and novel semisynthetic thiostrepton antibiotics. Initial antibacterial studies of the thiostrepton derivatives against methicillin-susceptible and methicillin-resistant S. aureus (MSSA and MRSA) cell cultures are reported.

    6. Evidence that Thienamycin Biosynthesis Proceeds via C-5 Epimerization: ThnE Catalyzes the Formation of (2S,5S)-trans-Carboxymethylproline (pages 246–250)

      Refaat B. Hamed, Edward T. Batchelar, Jasmin Mecinović, Timothy D. W. Claridge and Christopher J. Schofield

      Article first published online: 17 DEC 2008 | DOI: 10.1002/cbic.200800652

      Thumbnail image of graphical abstract

      Unusual antibiotic biosynthesis enzymes: The observation that formation of trans-carboxymethylproline (t-CMP) and 6-methyl-t-CMP is catalyzed by ThnE from Streptomyces cattleya using glutamate semi-aldehyde and malonyl- or methylmalonyl-CoA implies the need for a C-5 epimerization step in the biosynthesis of thienamycin and reveals the possibility that a methyl group at C-6 might be introduced at an early stage.

  8. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireviews
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
    11. Preview
    1. Reversible Control of Exo- and Endo-Budding Transitions in a Photosensitive Lipid Membrane (pages 251–256)

      Ken-ichi Ishii, Tsutomu Hamada, Masaomi Hatakeyama, Ryoko Sugimoto, Takeshi Nagasaki and Masahiro Takagi

      Article first published online: 8 JAN 2009 | DOI: 10.1002/cbic.200800482

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      Photomanipulation of vesicle shapes: We were able to control lipid membrane morphology between budding toward the centre of the liposome (endo-bud) and budding out of the liposome (exo-bud) through the use of a photoresponsive amphiphilic molecule containing an azobenzene unit. Because the shape transitions agreed with the morphological changes caused by osmotic pressure, the mechanism of these photoinduced transformations is interpreted in terms of changes in membrane surface area.

    2. Stable Long-Term Intracellular Labelling with Fluorescently Tagged Cationic Magnetoliposomes (pages 257–267)

      Stefaan J. H. Soenen, Dries Vercauteren, Kevin Braeckmans, Wim Noppe, Stefaan De Smedt and Marcel De Cuyper

      Article first published online: 12 DEC 2008 | DOI: 10.1002/cbic.200800510

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      Under your skin: Magnetoliposomes offer unique features for cell labelling, because the simple modification of the phospholipid bilayer surrounding the iron oxide core allows the generation of (doubly) fluorescently tagged cationic magnetoliposomes; this results in an efficiently internalised and nonexocytosed label. Upon cellular internalisation, the phospholipid coating provides a very stable shield for the iron oxide core and allows extremely long nanoparticle retention.

    3. The Molecular Basis of Inhibition of Golgi α-Mannosidase II by Mannostatin A (pages 268–277)

      Douglas A. Kuntz , Wei Zhong , Jun Guo, David R. Rose and Geert-Jan Boons

      Article first published online: 19 DEC 2008 | DOI: 10.1002/cbic.200800538

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      Zinc in pocket: The thiomethyl containing mannostatin A (MsnA) is a potent inhibitor of Golgi α-mannosidase II (GMII). Removal of the thiomethyl group led to a ∼7000-fold increase in Ki. X-ray crystallography of GMII–MsnA and analogues illustrated the importance of a main-chain carbonyl–thio interaction, as well as aromatic–methyl interactions (see figure).

    4. Inactivation of the Ketoreductase gilU Gene of the Gilvocarcin Biosynthetic Gene Cluster Yields New Analogues with Partly Improved Biological Activity (pages 278–286)

      Tao Liu, Madan K. Kharel, Lili Zhu, Samuel A. Bright, Cynthia Mattingly, Val R. Adams and Jürgen Rohr

      Article first published online: 9 DEC 2008 | DOI: 10.1002/cbic.200800348

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      Four new gilvocarcin-type analogues, partly with novel saccharide moieties and increased antitumor activity, were generated through the inactivation of gilU, which is a gene encoding an unusual ketoreductase involved in the formation of the sugar moiety of gilvocarcin V.

    5. Identification of Physiological and Toxic Conformations in Aβ42 Aggregates (pages 287–295)

      Yuichi Masuda, Satoko Uemura, Ryutaro Ohashi, Azusa Nakanishi, K. Takegoshi, Takahiko Shimizu, Takuji Shirasawa and Kazuhiro Irie

      Article first published online: 29 DEC 2008 | DOI: 10.1002/cbic.200800411

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      Pathogenesis of AD: The 42-residue amyloid β-protein (Aβ42) that causes Alzheimer's disease (AD) exists in two conformational states: a physiological one with a turn at positions 25 and 26 as a major component and a toxic one with a turn at positions 22 and 23 as a minor component. The interplay between Tyr10 and Met35 in the toxic conformer might promote radical production and oligomerization of Aβ42.

    6. Elucidation of Oxygenation Steps during Oviedomycin Biosynthesis and Generation of Derivatives with Increased Antitumor Activity (pages 296–303)

      Felipe Lombó, Mohamed S. Abdelfattah, Alfredo F. Braña, José A. Salas, Jürgen Rohr and Carmen Méndez

      Article first published online: 5 NOV 2008 | DOI: 10.1002/cbic.200800425

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      Eight different angucyclinones have been produced in Streptomyces albus by combining three oxygenase genes together with the polyketide synthase and cyclases genes from the oviedomycin biosynthetic gene cluster from Streptomyces antibioticus ATCC 11891. Three of these angucyclinones show higher antitumor activity than oviedomycin (1).

    7. Biosynthetic Gene Cluster of Cetoniacytone A, an Unusual Aminocyclitol from the Endosymbiotic Bacterium Actinomyces sp. Lu 9419 (pages 304–314)

      Xiumei Wu, Patricia M. Flatt, Hui Xu and Taifo Mahmud

      Article first published online: 19 DEC 2008 | DOI: 10.1002/cbic.200800527

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      Beetle endosymbiont biosynthesis: A gene cluster responsible for the biosynthesis of the antitumor agent cetoniacytone was identified in the endosymbiotic bacterium isolated from the intestines of the rose chafer beetle (Cetonia aurata). Functional analysis of the cluster revealed a new member of the vicinal oxygen chelate (VOC) superfamily with a new catalytic function.

    8. Shaping the Polypropionate Biosynthesis in the Solar-Powered Mollusc Elysia viridis (pages 315–322)

      Adele Cutignano, Guido Cimino, Guido Villani and Angelo Fontana

      Article first published online: 29 DEC 2008 | DOI: 10.1002/cbic.200800531

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      Sunscreen for molluscs: Polypropionate biosynthesis in the sacoglossan Elysia viridis proceeds through condensation of eight C3 units to give unstable pyronyl-decatetraenone 10. Cyclisation of this intermediate generates a network of light-sensitive molecules; levels of these molecules are apparently regulated by epoxidation/deepoxidation of the key compound elysione (6).

    9. In vitro Synthesis of New Cyclodepsipeptides of the PF1022-Type: Probing the α-D-Hydroxy Acid Tolerance of PF1022 Synthetase (pages 323–328)

      Jane Müller, Sven C. Feifel, Timo Schmiederer, Rainer Zocher and Roderich D. Süssmuth

      Article first published online: 12 DEC 2008 | DOI: 10.1002/cbic.200800539

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      Cyclodepsipeptides made easy: The in vitro synthesis of new PF1022 derivatives, such as 1, demonstrates that PF1022-NRPS has remarkably broad substrate specificity; this makes the system an ideal target for combinatorial biosynthesis, which could lead to new products with improved biological activity.

    10. The Influence of Ligand Valency on Aggregation Mechanisms for Inhibiting Bacterial Toxins (pages 329–337)

      Cristina Sisu, Andrew J. Baron, Hilbert M. Branderhorst, Simon D. Connell, Carel A. G. M. Weijers, Renko de Vries, Edward D. Hayes, Aliaksei V. Pukin, Michel Gilbert, Roland J. Pieters, Han Zuilhof, Gerben M. Visser and W. Bruce Turnbull

      Article first published online: 25 NOV 2008 | DOI: 10.1002/cbic.200800550

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      Mastering multivalency: Multivalency is widely exploited for increasing the activity of inhibitors against multimeric proteins. Here we show that the valency of the inhibitor also has a dramatic effect on the kinetics of aggregation and the stability of intermediate protein complexes.

    11. Enzymatic Synthesis of Enantiopure α- and β-Amino Acids by Phenylalanine Aminomutase-Catalysed Amination of Cinnamic Acid Derivatives (pages 338–344)

      Bian Wu, Wiktor Szymanski, Piet Wietzes, Stefaan de Wildeman, Gerrit J. Poelarends, Ben L. Feringa and Dick B. Janssen

      Article first published online: 2 JAN 2009 | DOI: 10.1002/cbic.200800568

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      A novel enzymatic method for obtaining enantiopure aromatic β-amino acids by using a one-step ammonia addition reaction catalysed by phenylalanine aminomutase is described. The 5-methylene-3,5-dihydroimidazol-4-one group of the enzyme is essential for this reaction. Several non-natural aromatic β-amino acids can be prepared by this route, and the enzymatic mechanism is discussed.

    12. Combinatorial Mutasynthesis of Scrambled Beauvericins, Cyclooligomer Depsipeptide Cell Migration Inhibitors from Beauveria bassiana (pages 345–354)

      Yuquan Xu, E. M. Kithsiri Wijeratne, Patricia Espinosa-Artiles, A. A. Leslie Gunatilaka and István Molnár

      Article first published online: 22 DEC 2008 | DOI: 10.1002/cbic.200800570

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      Scrambled depsipeptides: We demonstrate a novel variant mutasynthesis technique. Combinatorial simultaneous feeding of precursor analogues to a Beauveria bassiana strain with a targeted knockout in the newly identified ketoisovalerate reductase gene yields unnatural beauvericins with altered cell migration inhibitory activities.

    13. New Pacidamycin Antibiotics Through Precursor-Directed Biosynthesis (pages 355–360)

      Sabine Grüschow, Emma J. Rackham, Benjamin Elkins, Philip L. A. Newill, Lionel M. Hill and Rebecca J. M. Goss

      Article first published online: 17 DEC 2008 | DOI: 10.1002/cbic.200800575

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      Probing the pacidamycin pathway: Pacidamycins, mureidomycins and napsamycins are structurally related uridyl peptide antibiotics that target translocase I. By using precursor-directed biosynthesis, eleven new pacidamycin derivatives with altered C termini were produced. The ability to generate bromo- and chloropacidamycins opens up the possibility of generating further analogues through chemical cross-coupling.

    14. Iodothyronamines are Oxidatively Deaminated to Iodothyroacetic Acids in vivo (pages 361–365)

      Warren J. L. Wood, Travis Geraci, Aaron Nilsen, Andrea E. DeBarber and Thomas S. Scanlan

      Article first published online: 22 DEC 2008 | DOI: 10.1002/cbic.200800607

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      Thyroid hormone metabolism. In this investigation, 3-iodothyronamine (T1AM) and 3,3′,5-triiodothyronamine (T3AM) were metabolized to 3-iodothyroacetic acid (TA1) and 3,3′,5-triiodothyroacetic acid (Triac), respectively, in both cell and tissue extracts. TA1 was found to be present in trace quantities in human serum, and was present in substantial levels in serum from T1AM treated rats. This metabolism may be the source of the corresponding endogenous Triac and TA1.

    15. Investigations into Viomycin Biosynthesis by Using Heterologous Production in Streptomyces lividans (pages 366–376)

      John J. Barkei, Brian M. Kevany, Elizabeth A. Felnagle and Michael G. Thomas

      Article first published online: 22 DEC 2008 | DOI: 10.1002/cbic.200800646

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      Deciphering viomycin biosynthesis: Streptomyces lividans 1326 was shown to be a competent host for the heterologous production of viomycin. Using metabolic engineering of the viomycin biosynthetic gene cluster in Escherichia coli prior to its introduction into S. lividans 1326 provided a means for deciphering viomycin biosynthesis and producing viomycin derivatives.

  9. Book Reviews

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  10. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. Corrigenda
    5. News
    6. Minireviews
    7. Highlight
    8. Communications
    9. Full Papers
    10. Book Reviews
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    1. You have free access to this content
      Preview: ChemBioChem 3/2009 (page 382)

      Article first published online: 15 JAN 2009 | DOI: 10.1002/cbic.200990004

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