W Eisenreich

Summary

Country: Germany

Publications

  1. pmc 13C isotopologue perturbation studies of Listeria monocytogenes carbon metabolism and its modulation by the virulence regulator PrfA
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 103:2040-5. 2006
  2. ncbi request reprint The prediction of isotopic patterns in phenylpropanoids from their precursors and the mechanism of the NIH-shift: basis of the isotopic characteristics of natural aromatic compounds
    Hanns Ludwig Schmidt
    Lehrstuhl für Biologische Chemie der TU München, An der Saatzucht 5, D 85354 Freising, Germany
    Phytochemistry 67:1094-103. 2006
  3. doi request reprint Natural abundance solution 13C NMR studies of a phototropin with photoinduced polarization
    Wolfgang Eisenreich
    Technische Universitat Munchen, Lehrstuhl für Biochemie, Lichtenbergstr 4, 85747 Garching, Germany
    J Am Chem Soc 130:13544-5. 2008
  4. ncbi request reprint Rapid preparation of isotopolog libraries by in vivo transformation of 1)C-glucose. Studies on 6,7-dimethyl-8-ribityllumazine, a biosynthetic precursor of vitamin B2
    Boris Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    J Org Chem 69:5588-94. 2004
  5. pmc Carbon metabolism of enterobacterial human pathogens growing in epithelial colorectal adenocarcinoma (Caco-2) cells
    Andreas Götz
    Lehrstuhl fur Mikrobiologie, Biozentrum der Universität Würzburg, Wurzburg, Germany
    PLoS ONE 5:e10586. 2010
  6. pmc Characterization of rubber particles and rubber chain elongation in Taraxacum koksaghyz
    Thomas Schmidt
    Fraunhofer Institut für Molekularbiologie und Angewandte Ökologie, Forckenbeckstr, 6, 52074 Aachen, Germany
    BMC Biochem 11:11. 2010
  7. pmc Riboflavin synthase of Schizosaccharomyces pombe. Protein dynamics revealed by 19F NMR protein perturbation experiments
    Markus Fischer
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichten bergstr, 4, D 85747 Garching, Germany
    BMC Biochem 4:18. 2003
  8. pmc Studies of the intermediary metabolism in cultured cells of the insect Spodoptera frugiperda using 13C- or 15N-labelled tracers
    Petra Adam
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    BMC Biochem 6:24. 2005
  9. pmc Isotopolog perturbation techniques for metabolic networks: metabolic recycling of nutritional glucose in Drosophila melanogaster
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 101:6764-9. 2004
  10. ncbi request reprint Deoxyxylulose phosphate pathway to terpenoids
    W Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747, Garching, Germany
    Trends Plant Sci 6:78-84. 2001

Collaborators

Detail Information

Publications90

  1. pmc 13C isotopologue perturbation studies of Listeria monocytogenes carbon metabolism and its modulation by the virulence regulator PrfA
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 103:2040-5. 2006
    ..Bioinformatical steady-state network analyses and flux distribution predictions confirmed the experimental data and predicted metabolite fluxes through the enzymes of the pathways under study...
  2. ncbi request reprint The prediction of isotopic patterns in phenylpropanoids from their precursors and the mechanism of the NIH-shift: basis of the isotopic characteristics of natural aromatic compounds
    Hanns Ludwig Schmidt
    Lehrstuhl für Biologische Chemie der TU München, An der Saatzucht 5, D 85354 Freising, Germany
    Phytochemistry 67:1094-103. 2006
    ....
  3. doi request reprint Natural abundance solution 13C NMR studies of a phototropin with photoinduced polarization
    Wolfgang Eisenreich
    Technische Universitat Munchen, Lehrstuhl für Biochemie, Lichtenbergstr 4, 85747 Garching, Germany
    J Am Chem Soc 130:13544-5. 2008
    ..This demonstrates the potential of photo-CIDNP in unraveling reactive intermediates in protein function...
  4. ncbi request reprint Rapid preparation of isotopolog libraries by in vivo transformation of 1)C-glucose. Studies on 6,7-dimethyl-8-ribityllumazine, a biosynthetic precursor of vitamin B2
    Boris Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    J Org Chem 69:5588-94. 2004
    ..The isotope-labeled samples enabled a comprehensive NMR analysis of 6,7-dimethyl-8-ribityllumazine. Isotopolog libraries of a wide variety of microbial metabolites can be produced by the same experimental approach...
  5. pmc Carbon metabolism of enterobacterial human pathogens growing in epithelial colorectal adenocarcinoma (Caco-2) cells
    Andreas Götz
    Lehrstuhl fur Mikrobiologie, Biozentrum der Universität Würzburg, Wurzburg, Germany
    PLoS ONE 5:e10586. 2010
    ..Surprisingly, the metabolism of the host cells, as judged by the efficiency of (13)C-incorporation into host cell amino acids, was not significantly affected by the infection with either of these intracellular pathogens...
  6. pmc Characterization of rubber particles and rubber chain elongation in Taraxacum koksaghyz
    Thomas Schmidt
    Fraunhofer Institut für Molekularbiologie und Angewandte Ökologie, Forckenbeckstr, 6, 52074 Aachen, Germany
    BMC Biochem 11:11. 2010
    ..However, there is very little molecular data available for either the rubber polymer itself or its biosynthesis in T. koksaghyz...
  7. pmc Riboflavin synthase of Schizosaccharomyces pombe. Protein dynamics revealed by 19F NMR protein perturbation experiments
    Markus Fischer
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichten bergstr, 4, D 85747 Garching, Germany
    BMC Biochem 4:18. 2003
    ..Riboflavin synthase is therefore a potential target for the development of antiinfective drugs...
  8. pmc Studies of the intermediary metabolism in cultured cells of the insect Spodoptera frugiperda using 13C- or 15N-labelled tracers
    Petra Adam
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    BMC Biochem 6:24. 2005
    ..For this purpose, Spodoptera frugiperda cells were grown in a complex medium containing [U-13C6]glucose. In a second experiment, cultures of S. frugiperda were grown in the presence of 15N-phenylalanine...
  9. pmc Isotopolog perturbation techniques for metabolic networks: metabolic recycling of nutritional glucose in Drosophila melanogaster
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 101:6764-9. 2004
    ..The perturbation method described can be adapted to a wide variety of experimental systems and isotope-labeled precursors...
  10. ncbi request reprint Deoxyxylulose phosphate pathway to terpenoids
    W Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747, Garching, Germany
    Trends Plant Sci 6:78-84. 2001
    ..Information on this pathway could provide the basis for the development of new antibiotics, herbicides and antimalarials...
  11. ncbi request reprint 13C Isotopologue editing of FMN bound to phototropin domains
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Germany
    FEBS J 274:5876-90. 2007
    ..13)C Chemical shifts of FMN are shown to be differently modulated by complexation with the LOV domains under study, indicating slight differences in the binding interactions of FMN and the apoproteins...
  12. ncbi request reprint Biosynthesis of zeaxanthin via mevalonate in Paracoccus species strain PTA-3335. A product-based retrobiosynthetic study
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Federal Republic of Germany
    J Org Chem 67:871-5. 2002
    ..The data showed that the isoprenoid precursors of zeaxanthin were biosynthesized via the mevalonate pathway. The microorganism was found to utilize glucose mainly via the Entner-Doudoroff pathway...
  13. ncbi request reprint 13C-, 15N- and 31P-NMR studies of oxidized and reduced low molecular mass thioredoxin reductase and some mutant proteins
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, 85747 Garching, Germany
    Eur J Biochem 271:1437-52. 2004
    ..This strongly indicates that the former enzymes are in the FO conformation and the other two are in the FR conformation. The data are discussed briefly in the context of published NMR data obtained with a variety of flavoproteins...
  14. ncbi request reprint Biosynthesis of a neo-epi-verrucosane diterpene in the liverwort Fossombronia alaskana. A retrobiosynthetic NMR study
    W Eisenreich
    Institut fur Organische Chemie und Biochemie, Technische Universitat Munchen, D 85747 Garching, Germany
    J Biol Chem 274:36312-20. 1999
    ..The experimental data can be integrated into a detailed biosynthetic scheme involving a 1,5-hydride shift. The postulated involvement of the 1,5-hydride shift was confirmed by an incorporation experiment with [6,6-(2)H(2)]glucose...
  15. ncbi request reprint Biosynthesis of isoprenoids via the non-mevalonate pathway
    W Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, 85747 Garching, Germany
    Cell Mol Life Sci 61:1401-26. 2004
    ..Detailed knowledge about the mechanisms of this novel route may benefit the development of novel antibiotics, antimalarials and herbicides...
  16. ncbi request reprint Advances of high-resolution NMR techniques in the structural and metabolic analysis of plant biochemistry
    Wolfgang Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Phytochemistry 68:2799-815. 2007
    ..This review summarizes some of the recent advances of high-resolution NMR spectroscopy in the field of plant sciences...
  17. pmc Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate
    S Herz
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 97:2486-90. 2000
    ..This compound does not serve as substrate for the formation of carotenoids by isolated chromoplasts and is assumed to be an in vitro product without metabolic relevance...
  18. ncbi request reprint Biosynthesis of terpenoids: efficient multistep biotransformation procedures affording isotope-labeled 2C-methyl-D-erythritol 4-phosphate using recombinant 2C-methyl-D-erythritol 4-phosphate synthase
    S Hecht
    , , Lichtenbergstrasse 4, D-85747 Garching, Germany
    J Org Chem 66:7770-5. 2001
    ..The overall yield based on the respective isotope-labeled starting material is approximately 50%...
  19. ncbi request reprint Biosynthesis of terpenoids. 2C-Methyl-D-erythritol 2,4-cyclodiphosphate synthase (IspF) from Plasmodium falciparum
    F Rohdich
    Institut fur Organische Chemie und Biochemie, Lehrstuhl III, Technische Universitat Munchen, Garching, Germany
    Eur J Biochem 268:3190-7. 2001
    ..The enzyme is a potential target for antimalarial drugs directed at the nonmevalonate pathway of isoprenoid biosynthesis...
  20. pmc Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol
    H Luttgen
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 97:1062-7. 2000
    ..The sequence of E. coli YchB protein is similar to that of the protein predicted by the tomato cDNA pTOM41 (30% identity), which had been implicated in the conversion of chloroplasts to chromoplasts...
  21. pmc A pentacyclic reaction intermediate of riboflavin synthase
    B Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 98:7224-9. 2001
    ..Enzyme-catalyzed fragmentation of this compound under formation of riboflavin can occur easily by a sequence of two elimination reactions...
  22. pmc Studies on the nonmevalonate pathway to terpenes: the role of the GcpE (IspG) protein
    S Hecht
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 98:14837-42. 2001
    ..Hypothetical mechanisms involving conserved cysteine residues are proposed for the enzymatic conversion of 2C-methyl-D-erythritol 2,4-cyclodiphosphate into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate catalyzed by the GcpE protein...
  23. ncbi request reprint Biosynthesis of pteridines. NMR studies on the reaction mechanisms of GTP cyclohydrolase I, pyruvoyltetrahydropterin synthase, and sepiapterin reductase
    A Bracher
    Institut fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Federal Republic of Germany
    J Biol Chem 273:28132-41. 1998
    ..On the other hand, the reaction catalyzed by sepiapterin reductase does not involve any detectable incorporation of solvent protons into tetrahydrobiopterin...
  24. pmc Biosynthesis of terpenoids: 4-diphosphocytidyl-2C-methyl-D-erythritol synthase of Arabidopsis thaliana
    F Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 97:6451-6. 2000
    ..The Michaelis constants for 4-diphosphocytidyl-2C-methyl-d-erythritol and CTP were 500 microM and 114 microM, respectively...
  25. ncbi request reprint Histidine 179 mutants of GTP cyclohydrolase I catalyze the formation of 2-amino-5-formylamino-6-ribofuranosylamino-4(3H)-pyrimidinone triphosphate
    A Bracher
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Biol Chem 274:16727-35. 1999
    ..The data support the conclusion that the formylamino pyrimidine derivative is an intermediate in the overall reaction catalyzed by GTP cyclohydrolase I...
  26. pmc Biosynthesis of terpenoids: 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase from tomato
    F Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 97:8251-6. 2000
    ..Divalent metal ions, preferably Mg(2+), are required for activity. Neither the tomato enzyme nor the E. coli ortholog catalyzes the phosphorylation of isopentenyl monophosphate...
  27. ncbi request reprint Biosynthesis of terpenoids: 1-deoxy-D-xylulose-5-phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase
    T Radykewicz
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747, Garching, Germany
    FEBS Lett 465:157-60. 2000
    ..Stereospecific transfer of H(Si) from C-4 of the cofactor identifies the Dxr protein of E. coli as a class B dehydrogenase...
  28. ncbi request reprint Rearrangement reactions in the biosynthesis of molybdopterin--an NMR study with multiply 13C/15N labelled precursors
    C Rieder
    Institut fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Germany
    Eur J Biochem 255:24-36. 1998
    ..Carbon atom C1' of compound Z is derived from carbon atom C8 of a guanine derivative. The remodeling of the carbon skeleton of the pentose and purine moieties proceed via intramolecular rearrangement reactions...
  29. ncbi request reprint Anti-malarial drug targets: screening for inhibitors of 2C-methyl-D-erythritol 4-phosphate synthase (IspC protein) in Mediterranean plants
    J Kaiser
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Phytomedicine 14:242-9. 2007
    ..Using photometric and NMR spectroscopic assays, we screened extracts of Mediterranean plants for inhibitors of the enzyme. Strongest inhibitory activity was found in leaf extracts of Cercis siliquastrum...
  30. ncbi request reprint The non-mevalonate pathway of isoprenoids: genes, enzymes and intermediates
    F Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Curr Opin Chem Biol 5:535-40. 2001
    ..The genes specifying these enzymes have been cloned from bacteria, plants and protozoa. Their expression in recombinant bacterial hosts has opened the way to the identification of several novel pathway intermediates...
  31. ncbi request reprint Biosynthesis of riboflavin: studies on the mechanism of GTP cyclohydrolase II
    H Ritz
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Biol Chem 276:22273-7. 2001
    ..The enzyme reaction is cooperative with a Hill coefficient of 1.3. Inhibition by pyrophosphate is competitive. Inhibition by orthophosphate is partially uncompetitive at low concentration and competitive at concentrations above 6 mm...
  32. pmc Cytidine 5'-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol
    F Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 96:11758-63. 1999
    ..A gene from Arabidopsis thaliana with similarity to ygbP carries a putative plastid import sequence, which is well in line with the assumed localization of the deoxyxylulose pathway in the plastid compartment of plants...
  33. ncbi request reprint Isoprenoid biosynthetic pathways as anti-infective drug targets
    F Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, 85747 Garching, Germany
    Biochem Soc Trans 33:785-91. 2005
    ..The results provide the basis for the development of novel anti-infective drugs...
  34. pmc Retrobiosynthetic nuclear magnetic resonance analysis of amino acid biosynthesis and intermediary metabolism. Metabolic flux in developing maize kernels
    E Glawischnig
    , , Lichtenbergstrasse 4, 85747 Garching, Germany
    Plant Physiol 125:1178-86. 2001
    ..Exogenous acetate served as an efficient precursor of sitosterol, as well as of amino acids of the aspartate and glutamate family; in comparison, metabolites formed in the plastidic compartments showed low acetate incorporation...
  35. ncbi request reprint Structures and reaction mechanisms of riboflavin synthases of eubacterial and archaeal origin
    M Fischer
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Biochem Soc Trans 33:780-4. 2005
    ..6,7-Dimethyl-8-ribityllumazine synthase and the archaeal riboflavin synthase appear to have diverged early in the evolution of Archaea from a common ancestor...
  36. ncbi request reprint Biosynthesis of 5-hydroxybenzimidazolylcobamid (factor III) in Methanobacterium thermoautotrophicum
    W Eisenreich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Federal Republic of Germany
    J Biol Chem 266:23840-9. 1991
    ....
  37. ncbi request reprint Analysis of a chemical plant defense mechanism in grasses
    M Frey
    Institut fur Genetik, Technische Universitat Munchen, Lichtenbergstrasse 4, 85747 Garching, Germany
    Science 277:696-9. 1997
    ..Bx2 through Bx5 encode cytochrome P450-dependent monooxygenases that catalyze four consecutive hydroxylations and one ring expansion to form the highly oxidized DIBOA...
  38. ncbi request reprint Synthesis and analysis of thio-, thiono-, and dithio-derivatives of whiskey lactone
    H G Schmarr
    Lehrstuhl fur Allgemeine Lebensmitteltechnologie, Technische Universitat Munchen, Am Forum 2, D 85350 Freising Weihenstephan, Germany
    J Agric Food Chem 49:5923-8. 2001
    ..GC-olfactometry revealed a sweet coconut-like odor for the cis-thio- and pleasant mushroom-like flavors for the cis-thiono- and trans-dithio-derivatives of whiskey lactone...
  39. pmc Aerobic benzoyl-coenzyme A (CoA) catabolic pathway in Azoarcus evansii: conversion of ring cleavage product by 3,4-dehydroadipyl-CoA semialdehyde dehydrogenase
    Johannes Gescher
    Mikrobiologie, Institut fur Biologie II, Universitat Freiburg, Schanzlestrasse 1, D 79104 Freiburg, Germany
    J Bacteriol 188:2919-27. 2006
    ..The further metabolism is thought to lead to 3-oxoadipyl-CoA, the intermediate at which the conventional and the unorthodox pathways merge...
  40. ncbi request reprint Nonphosphate inhibitors of IspE protein, a kinase in the non-mevalonate pathway for isoprenoid biosynthesis and a potential target for antimalarial therapy
    Anna K H Hirsch
    Laboratorium fur Organische Chemie, ETH Zurich, Honggerberg, HCI, 8093 Zurich, Switzerland
    ChemMedChem 2:806-10. 2007
  41. ncbi request reprint Structure of 2C-methyl-d-erythritol-2,4-cyclodiphosphate synthase involved in mevalonate-independent biosynthesis of isoprenoids
    Stefan Steinbacher
    Abteilung für Strukturforschung, Max Planck Institut fur Biochemie, Am Klopferspitz 18a, Martinsried, D 82152, Germany
    J Mol Biol 316:79-88. 2002
    ..The protein forms homotrimers that tightly bind one zinc ion per subunit at the active site, which helps to position the substrate for direct attack of the 2-phosphate group on the beta-phosphate...
  42. ncbi request reprint Stereochemical studies on the making and unmaking of isopentenyl diphosphate in different biological systems
    Ralf Laupitz
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching
    Chem Biodivers 1:1367-76. 2004
    ....
  43. ncbi request reprint Nonmevalonate terpene biosynthesis enzymes as antiinfective drug targets: substrate synthesis and high-throughput screening methods
    Victoria Illarionova
    Lehrstuhl fur Organische Chemie und Biochemie, Department Chemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Org Chem 71:8824-34. 2006
    ..The preparation of 4-diphosphosphocytidyl-2C-methyl-D-erythritol 2-phosphate in multigram quantities is described for the first time...
  44. ncbi request reprint Isoprenoid biosynthesis in plants - 2C-methyl-D-erythritol-4-phosphate synthase (IspC protein) of Arabidopsis thaliana
    Felix Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Germany
    FEBS J 273:4446-58. 2006
    ..The pH optimum is 8.0. NADH can substitute for NADPH, albeit at a low rate (14% as compared to NADPH). The enzyme catalyzes the reverse reaction at a rate of 2.1 micromol x min(-1) x mg(-1)...
  45. ncbi request reprint Biosynthetic precursors of the lipase inhibitor lipstatin
    Christoph A Schuhr
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Federal Republic of Germany
    J Org Chem 67:2257-62. 2002
    ..The leucine moiety of [(13)C-formyl,(15)N]-N-formylleucine (10) was diverted to lipstatin under loss of the (13)C-labeled formyl residue...
  46. ncbi request reprint The crystal structure of a plant 2C-methyl-D-erythritol 4-phosphate cytidylyltransferase exhibits a distinct quaternary structure compared to bacterial homologues and a possible role in feedback regulation for cytidine monophosphate
    Mads Gabrielsen
    Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, University of Dundee, UK
    FEBS J 273:1065-73. 2006
    ....
  47. ncbi request reprint The carotenase AtCCD1 from Arabidopsis thaliana is a dioxygenase
    Holger Schmidt
    Foundation for Biomolecular Food Technology, Technische Universitat Munchen, Lise Meitner Strasse 34, D 84354 Freising, Germany
    J Biol Chem 281:9845-51. 2006
    ..The results unambiguously demonstrate a dioxygenase mechanism for the carotenase AtCCD1 from A. thaliana...
  48. ncbi request reprint Fluorescent inhibitors for IspF, an enzyme in the non-mevalonate pathway for isoprenoid biosynthesis and a potential target for antimalarial therapy
    Christine M Crane
    Laboratorium fur Organische Chemie, ETH Honggerberg, HCI, 8093 Zurich, Switzerland
    Angew Chem Int Ed Engl 45:1069-74. 2006
  49. ncbi request reprint Ligand binding properties of the N-terminal domain of riboflavin synthase from Escherichia coli
    Chan Yong Lee
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, D 85747 Garching, Germany
    J Biochem Mol Biol 40:239-46. 2007
    ....
  50. ncbi request reprint A high-throughput screening platform for inhibitors of the riboflavin biosynthesis pathway
    Johannes Kaiser
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, D 85748 München, Germany
    Anal Biochem 365:52-61. 2007
    ..The assays can be monitored photometrically and have been shown to be robust, as indicated by Z factors 0.87. A (13)C NMR assay for hit verification of 3,4-dihydroxy-2-butanone 4-phosphate synthase inhibitors is also reported...
  51. doi request reprint 2,5-diamino-6-ribitylamino-4(3H)-pyrimidinone 5'-phosphate synthases of fungi and archaea
    Werner Römisch-Margl
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Germany
    FEBS J 275:4403-14. 2008
    ..These results are in agreement with the known three-dimensional structure of the M. jannaschii enzyme...
  52. doi request reprint Inhibitors of the kinase IspE: structure-activity relationships and co-crystal structure analysis
    Anna K H Hirsch
    Laboratorium fur Organische Chemie, ETH Zurich, HCI, CH 8093, Zurich, Switzerland
    Org Biomol Chem 6:2719-30. 2008
    ..This structure provides useful insights for future structure-based developments of inhibitors for the parasite enzymes...
  53. doi request reprint Biosynthesis of isoprenoids: studies on the mechanism of 2C-methyl-D-erythritol-4-phosphate synthase
    Susan Lauw
    Center for Integrated Protein Research, Lehrstuhl für Biochemie, Department Chemie, Technische Universitat Munchen, Garching, Germany
    FEBS J 275:4060-73. 2008
    ....
  54. doi request reprint Structure of lumazine protein, an optical transponder of luminescent bacteria
    Lorenz Chatwell
    Lehrstuhl fur Biologische Chemie, Technische Universitat Munchen, D 85350 Freising Weihenstephan, Germany
    J Mol Biol 382:44-55. 2008
    ..Riboflavin is bound to a shallow cavity in the N-terminal domain of lumazine protein, whereas the C-terminal domain lacks a ligand...
  55. pmc Characterization of Aquifex aeolicus 4-diphosphocytidyl-2C-methyl-d-erythritol kinase - ligand recognition in a template for antimicrobial drug discovery
    Tanja Sgraja
    Division of Biological Chemistry and Drug Discovery, University of Dundee, UK
    FEBS J 275:2779-94. 2008
    ....
  56. ncbi request reprint Synthesis and characterization of cytidine derivatives that inhibit the kinase IspE of the non-mevalonate pathway for isoprenoid biosynthesis
    Christine M Crane
    Laboratorium fur Organische Chemie, ETH Zurich, HCI, CH 8093 Zurich, Switzerland
    ChemMedChem 3:91-101. 2008
    ..aeolicus IspE directs the OH group of a tyrosine residue into a pocket in the active site. In the E. coli enzyme, on the other hand, this pocket is lined by phenylalanine and has a more pronounced hydrophobic character...
  57. pmc Studies on the nonmevalonate terpene biosynthetic pathway: metabolic role of IspH (LytB) protein
    Felix Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 99:1158-63. 2002
    ..coli strain engineered for the expression of the ispH (lytB) gene in addition to recombinant xylB and ispCDEFG genes...
  58. ncbi request reprint Lumazine proteins from photobacteria: localization of the single ligand binding site to the N-terminal domain
    Boris Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Biol Chem 388:1313-23. 2007
    ..These data show that the N-terminal domain is the unique site for ligand binding in lumazine protein...
  59. ncbi request reprint Evolution of vitamin B2 biosynthesis: structural and functional similarity between pyrimidine deaminases of eubacterial and plant origin
    Markus Fischer
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, Garching D 85747, Germany
    J Biol Chem 279:36299-308. 2004
    ..These data show that the riboflavin biosynthesis in plants proceeds by the same reaction steps as in eubacteria, whereas fungi use a different pathway...
  60. ncbi request reprint Biosynthesis of the chromogen hermidin from Mercurialis annua L
    Elena Ostrozhenkova
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Phytochemistry 68:2816-24. 2007
    ..This experimental concept appears ripe for application to a wide variety of problems in plant physiology...
  61. pmc Insights into the autotrophic CO2 fixation pathway of the archaeon Ignicoccus hospitalis: comprehensive analysis of the central carbon metabolism
    Ulrike Jahn
    Lehrstuhl Mikrobiologie und Archaeenzentrum, Universitat Regensburg, Universitatsstrasse 31, D 93053 Regensburg, Germany
    J Bacteriol 189:4108-19. 2007
    ..This comprehensive analysis of the central carbon metabolism of I. hospitalis revealed further evidence for the unexpected and unexplored diversity of metabolic pathways within the (hyperthermophilic) archaea...
  62. ncbi request reprint Random isotopolog libraries for protein perturbation studies. 13C NMR studies on lumazine protein of Photobacterium leiognathi
    Boris Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    J Org Chem 70:9947-54. 2005
    ..Chemical shift modulation of the side chain and chromophore carbon atoms due to protein/ligand interaction is discussed on the basis of the sequence similarity between lumazine protein and riboflavin synthase...
  63. ncbi request reprint Biosynthesis of tetrahydrofolate. Stereochemistry of dihydroneopterin aldolase
    Victoria Illarionova
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Biol Chem 277:28841-7. 2002
    ..The product was analyzed by multinuclear NMR spectroscopy. The data show that the carbinol group of enzymatically formed 6-hydroxymethyl-dihydropterin contained 2H predominantly in the pro-S position...
  64. ncbi request reprint Crystal structure of an archaeal pentameric riboflavin synthase in complex with a substrate analog inhibitor: stereochemical implications
    Arne Ramsperger
    Max Planck Institut fur Biochemie, Abteilung für Strukturforschung, Martinsried, Germany
    J Biol Chem 281:1224-32. 2006
    ..The pentacyclic intermediates of trimeric and pentameric riboflavin synthases are diastereomers...
  65. ncbi request reprint Biosynthesis of riboflavin in archaea studies on the mechanism of 3,4-dihydroxy-2-butanone-4-phosphate synthase of Methanococcus jannaschii
    Markus Fischer
    Institut fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Biol Chem 277:41410-6. 2002
    ..A cluster of charged amino acid residues comprising arginine 25, glutamates 26 and 28, and aspartates 21 and 30 is essential for catalytic activity. Histidine 164 and glutamate 185 were also shown to be essential for catalytic activity...
  66. ncbi request reprint Biochemical characterization of Bacillus subtilis type II isopentenyl diphosphate isomerase, and phylogenetic distribution of isoprenoid biosynthesis pathways
    Ralf Laupitz
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Garching, Germany
    Eur J Biochem 271:2658-69. 2004
    ..Type II isomerase is essential in some important human pathogens including Staphylococcus aureus and Enterococcus faecalis where it may represent a novel target for anti-infective therapy...
  67. ncbi request reprint Studies on the reaction mechanism of riboflavin synthase: X-ray crystal structure of a complex with 6-carboxyethyl-7-oxo-8-ribityllumazine
    Stefan Gerhardt
    Max Planck Institut fur Biochemie, Abteilung Strukturforschung, Am Klopferspitz 18a, D 82152 Martinsried, Germany
    Structure 10:1371-81. 2002
    ..The model suggests that the substrate molecule at the C-terminal domain donates a four-carbon unit to the substrate molecule bound at the N-terminal domain of an adjacent subunit in the oligomer...
  68. ncbi request reprint Rapid one-pot synthesis of riboflavin isotopomers
    Werner Romisch
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    J Org Chem 67:8890-4. 2002
    ..The overall yields of riboflavin based on isotope-labeled glucose are 35-50%...
  69. pmc The deoxyxylulose phosphate pathway of isoprenoid biosynthesis: studies on the mechanisms of the reactions catalyzed by IspG and IspH protein
    Felix Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 100:1586-91. 2003
    ..The striking similarities of IspG and IspH protein are discussed, and plausible mechanistic schemes are proposed for the two reactions...
  70. ncbi request reprint Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by beta-lyase-catalyzed cleavage of cysteine conjugates
    Hidehiko Wakabayashi
    Lehrstuhl fur Allgemeine Lebensmitteltechnologie, Technische Universitat Munchen, Am Forum 2, D 85350 Freising Weihenstephan, Germany
    J Agric Food Chem 52:110-6. 2004
    ..Various yeasts produced 3-mercaptohexanol starting from 1 as well as from 5. The reactions proceeded without preferential formation of one of the enantiomers...
  71. ncbi request reprint Structural basis of fosmidomycin action revealed by the complex with 2-C-methyl-D-erythritol 4-phosphate synthase (IspC). Implications for the catalytic mechanism and anti-malaria drug development
    Stefan Steinbacher
    Max Planck Institut fur Biochemie, Abteilung für Strukturforschung, Am Klopferspitz 18a, D 82152 Martinsried, Germany
    J Biol Chem 278:18401-7. 2003
    ..Both sites are connected by a spacer of three methylene groups. The substrate molecule, 1-d-deoxyxylulose 5-phosphate, can be superimposed onto fosmidomycin, explaining the stereochemical course of the reaction...
  72. ncbi request reprint A possible primordial peptide cycle
    Claudia Huber
    Department for Organic Chemistry and Biochemistry, Technische Universitat Munchen, Lichtenbergstrabetae 4, D 85747 Garching, Germany
    Science 301:938-40. 2003
    ..The (Fe,Ni)S-dependent urea hydrolysis could have been the evolutionary precursor of the nickelenzyme urease. The results support the theory of a chemoautotrophic origin of life with a CO-driven, (Fe,Ni)S-dependent primordial metabolism...
  73. pmc Biosynthesis of isoprenoids: crystal structure of 4-diphosphocytidyl-2C-methyl-D-erythritol kinase
    Linda Miallau
    Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, University of Dundee, Dundee DD1 5EH, United Kingdom
    Proc Natl Acad Sci U S A 100:9173-8. 2003
    ..Our model therefore provides an accurate template to facilitate the structure-based design of broad-spectrum antimicrobial agents...
  74. ncbi request reprint Functional genomics by NMR spectroscopy. Phenylacetate catabolism in Escherichia coli
    Wael Ismail
    Mikrobiologie, Institut fur Biologie II, Universitat Freiburg, Germany
    Eur J Biochem 270:3047-54. 2003
    ..The subsequent beta-oxidation-type degradation of the resulting CoA dicarboxylate via beta-ketoadipyl-CoA to succinyl-CoA and acetyl-CoA appears to be catalyzed by the PaaJ, PaaF and PaaH proteins...
  75. ncbi request reprint Phenylalanine-independent biosynthesis of 1,3,5,8-tetrahydroxyxanthone. A retrobiosynthetic NMR study with root cultures of Swertia chirata
    Chang Zeng Wang
    Biozentrum Pharmazie, Universitat Halle, Halle Saale, Germany
    Eur J Biochem 270:2950-8. 2003
    ..The starter unit, 3-hydroxybenzoyl-CoA, is obtained from an early shikimate pathway intermediate. Phenylalanine, cinnamic acid and benzoic acid were ruled out as intermediates...
  76. ncbi request reprint Crystal structure of the type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase from Bacillus subtilis
    Stefan Steinbacher
    Abteilung für Strukturforschung, Max Planck Institut fur Biochemie, Am Klopferspitz 18a, D 82152 Martinsried, Germany
    J Mol Biol 329:973-82. 2003
    ..Regions harboring strictly conserved residues that are implicated in substrate binding or catalysis remain largely disordered even in the presence of FMN...
  77. ncbi request reprint Biosynthesis of isoprenoids: a bifunctional IspDF enzyme from Campylobacter jejuni
    Mads Gabrielsen
    Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, University of Dundee, UK
    Eur J Biochem 271:3028-35. 2004
    ..These bifunctional proteins are potential drug targets in several human pathogens (e.g. Helicobacter pylori, C. jejuni and Treponema pallidum)...
  78. ncbi request reprint Biosynthesis of isoprenoids. purification and properties of IspG protein from Escherichia coli
    Ferdinand Zepeck
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Org Chem 70:9168-74. 2005
    ....
  79. ncbi request reprint Biosynthesis of terpenes. Preparation of (E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate, an intermediate of the deoxyxylulose phosphate pathway
    Sabine Amslinger
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Federal Republic of Germany
    J Org Chem 67:4590-4. 2002
    ..The compound was shown to be identical with the product of IspG protein, which serves as an intermediate in the nonmevalonate terpene biosynthetic pathway...
  80. pmc Biosynthesis of terpenes: studies on 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase
    Petra Adam
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    Proc Natl Acad Sci U S A 99:12108-13. 2002
    ..The low intrinsic catalytic activities of wild-type E. coli cell extract and isolated chromoplasts of red pepper (Capsicum annuum) are enhanced by the addition of purified recombinant IspH protein...
  81. ncbi request reprint Biosynthesis of vitamin B2: diastereomeric reaction intermediates of archaeal and non-archaeal riboflavin synthases
    Boris Illarionov
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Biol Chem 280:28541-6. 2005
    ..All available data indicate that the respective pentacyclic intermediates of the M. jannaschii and E. coli enzymes are diastereomers...
  82. ncbi request reprint Aerobic benzoyl-CoA catabolic pathway in Azoarcus evansii: studies on the non-oxygenolytic ring cleavage enzyme
    Johannes Gescher
    Institut fur Biologie II, Mikrobiologie, Fakultat fur Biologie, Universitat Freiburg, Schanzlestrasse 1, D 79104 Freiburg, Germany
    Mol Microbiol 56:1586-600. 2005
    ..The complex reaction is part of a widely distributed new principle of aerobic aromatic metabolism in which all intermediates are coenzyme A thioesters and the actual ring-cleavage reaction does not require molecular oxygen...
  83. ncbi request reprint Metabolic flux analysis in complex isotopolog space. Recycling of glucose in tobacco plants
    Christian Ettenhuber
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Phytochemistry 66:323-35. 2005
    ....
  84. ncbi request reprint The identification of isoprenoids that bind in the intersubunit cavity of Escherichia coli 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase by complementary biophysical methods
    Lauris E Kemp
    Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, University of Dundee, Dundee DD1 5EH, Scotland
    Acta Crystallogr D Biol Crystallogr 61:45-52. 2005
    ..The observation that MECP synthase binds three metabolites that are produced by enzymes two, three and four stages downstream in isoprenoid biosynthesis suggests that feedback regulation of the non-mevalonate pathway is possible...
  85. ncbi request reprint IspH protein of Escherichia coli: studies on iron-sulfur cluster implementation and catalysis
    Tobias Grawert
    Contribution from the Lehrstuhl für Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstrasse 4, D 85747 Garching, Germany
    J Am Chem Soc 126:12847-55. 2004
    ..Replacement of any of the conserved cysteine residues reduced the catalytic activity by a factor of more than 70 000...
  86. ncbi request reprint Hexameric assembly of the bifunctional methylerythritol 2,4-cyclodiphosphate synthase and protein-protein associations in the deoxy-xylulose-dependent pathway of isoprenoid precursor biosynthesis
    Mads Gabrielsen
    Division of Biological Chemistry and Molecular Microbiology, School of Life Sciences, University of Dundee, Dow Street, Dundee DD1 5EH, United Kingdom
    J Biol Chem 279:52753-61. 2004
    ..We propose that complex formation of the three enzymes at the core of the DOXP pathway can produce an assembly localizing 18 catalytic centers for the early stages of isoprenoid biosynthesis...
  87. ncbi request reprint New enzymes involved in aerobic benzoate metabolism in Azoarcus evansii
    Annette Zaar
    Institut fur Biologie II, Mikrobiologie, Universitat Freiburg, Schänzlestr 1, D 79104 Freiburg, Germany
    Mol Microbiol 54:223-38. 2004
    ..The benzoyl-CoA oxygenase system has very low similarity to known (di)oxygenase systems and is the first member of a new enzyme family...
  88. ncbi request reprint Evolution of vitamin B2 biosynthesis. A novel class of riboflavin synthase in Archaea
    Markus Fischer
    Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    J Mol Biol 343:267-78. 2004
    ..Some Archaea have eubacterial type riboflavin synthases which may have been acquired by lateral gene transfer...
  89. ncbi request reprint Perspectives in anti-infective drug design. The late steps in the biosynthesis of the universal terpenoid precursors, isopentenyl diphosphate and dimethylallyl diphosphate
    Felix Rohdich
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747 Garching, Germany
    Bioorg Chem 32:292-308. 2004
    ..A hitherto unknown family of IPP isomerases using FMN as coenzyme has been discovered recently in Archaea and certain eubacteria...
  90. ncbi request reprint RNA DNA discrimination by the antitermination protein NusB
    Rene Mühlberger
    Lehrstuhl fur Organische Chemie und Biochemie, Technische Universitat Munchen, Lichtenbergstr 4, D 85747, Garching, Germany
    J Mol Biol 327:973-83. 2003
    ..The impact of structural modification of the boxA motif on the affinity for NusB protein as observed by 1H15N heterocorrelation was analysed by a generic algorithm...