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Pure Appl. Chem., 2003, Vol. 75, No. 2-3, pp. 393-405

http://dx.doi.org/10.1351/pac200375020393

The deoxyxylulose phosphate pathway of isoprenoid biosynthesis. Discovery and function of the ispDEFGH genes and their cognate enzymes

F. Rohdich, Stefan Hecht, Adelbert Bacher and Wolfgang Eisenreich

Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstraße 4, D-85747 Garching, Germany

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  • Gräwert Tobias, Groll Michael, Rohdich Felix, Bacher Adelbert, Eisenreich Wolfgang: Biochemistry of the non-mevalonate isoprenoid pathway. Experienlia 2011, 68, 3797. <http://dx.doi.org/10.1007/s00018-011-0753-z>
  • Gräwert Tobias, Span Ingrid, Bacher Adelbert, Groll Michael: Reduktive Dehydroxylierung von Allylalkoholen durch IspH-Protein. Angew Chem 2010, 122, 8984. <http://dx.doi.org/10.1002/ange.201000833>
  • Gräwert Tobias, Span Ingrid, Bacher Adelbert, Groll Michael: Reductive Dehydroxylation of Allyl Alcohols by IspH Protein. Angew Chem Int Ed 2010, 49, 8802. <http://dx.doi.org/10.1002/anie.201000833>
  • Sitthithaworn Worapan, Wungsintaweekul Juraithip, Sirisuntipong Tanawan, Charoonratana Tossaton, Ebizuka Yutaka, De-Eknamkul Wanchai: Cloning and expression of 1-deoxy-d-xylulose 5-phosphate synthase cDNA from Croton stellatopilosus and expression of 2C-methyl-d-erythritol 4-phosphate synthase and geranylgeranyl diphosphate synthase, key enzymes of plaunotol biosynthesis. J  Plant Physiol 2010, 167, 292. <http://dx.doi.org/10.1016/j.jplph.2009.09.001>
  • Hirsch Anna K. H., Diederich François, Antonietti Markus, Börner Hans G.: Bioconjugates to specifically render inhibitors water-soluble. Soft Matt 2010, 6, 88. <http://dx.doi.org/10.1039/b915928b>
  • Grawert T., Span I., Eisenreich W., Rohdich F., Eppinger J., Bacher A., Groll M.: Probing the reaction mechanism of IspH protein by x-ray structure analysis. Proceedings of the National Academy of Sciences 2010, 107, 1077. <http://dx.doi.org/10.1073/pnas.0913045107>
  • Xiao Youli, Liu Pinghua: Synthesis of [1-13C] and stereo-specifically [1-2H] labeled fluorinated substrate analogues of IspH enzyme in the deoxyxylulose phosphate pathway. Tetrahetron Lett 2009, 50, 309. <http://dx.doi.org/10.1016/j.tetlet.2008.10.151>
  • Xiao Youli, Chu Lisa, Sanakis Yiannis, Liu Pinghua: Revisiting the IspH Catalytic System in the Deoxyxylulose Phosphate Pathway: Achieving High Activity. J Am Chem Soc 2009, 131, 9931. <http://dx.doi.org/10.1021/ja903778d>
  • Xiao Youli, Liu Pinghua: IspH Protein of the Deoxyxylulose Phosphate Pathway: Mechanistic Studies with C1-Deuterium-Labeled Substrate and Fluorinated Analogue. Angew Chem 2008, 120, 9868. <http://dx.doi.org/10.1002/ange.200803452>
  • Xiao Youli, Liu Pinghua: IspH Protein of the Deoxyxylulose Phosphate Pathway: Mechanistic Studies with C1-Deuterium-Labeled Substrate and Fluorinated Analogue. Angew Chem Int Ed 2008, 47, 9722. <http://dx.doi.org/10.1002/anie.200803452>
  • Crane Christine M., Hirsch Anna K. H., Alphey Magnus S., Sgraja Tanja, Lauw Susan, Illarionova Victoria, Rohdich Felix, Eisenreich Wolfgang, Hunter William N., Bacher Adelbert: Synthesis and Characterization of Cytidine Derivatives that Inhibit the Kinase IspE of the Non-Mevalonate Pathway for Isoprenoid Biosynthesis. ChemMedChem 2008, 3, 91. <http://dx.doi.org/10.1002/cmdc.200700208>
  • Hirsch Anna K. H., Alphey Magnus S., Lauw Susan, Seet Michael, Barandun Luzi, Eisenreich Wolfgang, Rohdich Felix, Hunter William N., Bacher Adelbert, Diederich François: Inhibitors of the kinase IspE: structure–activity relationships and co-crystal structure analysis. Org Biomol Chem 2008, 6, 2719. <http://dx.doi.org/10.1039/b804375b>
  • Davidovich-Rikanati Rachel, Lewinsohn Efraim, Bar Einat, Iijima Yoko, Pichersky Eran, Sitrit Yaron: Overexpression of the lemon basil α-zingiberene synthase gene increases both mono- and sesquiterpene contents in tomato fruit. Plant J 2008, 56, 228. <http://dx.doi.org/10.1111/j.1365-313X.2008.03599.x>
  • Hirsch Anna K. H., Fischer Felix R., Diederich François: Molekulare Erkennung von Phosphaten in der Strukturbiologie. Angew Chem 2007, 119, 342. <http://dx.doi.org/10.1002/ange.200603420>
  • Hirsch Anna K. H., Fischer Felix R., Diederich François: Phosphate Recognition in Structural Biology. Angew Chem Int Ed 2007, 46, 338. <http://dx.doi.org/10.1002/anie.200603420>
  • Hirsch Anna K. H., Lauw Susan, Gersbach Philipp, Schweizer W. Bernd, Rohdich Felix, Eisenreich Wolfgang, Bacher Adelbert, Diederich François: Nonphosphate Inhibitors of IspE Protein, a Kinase in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy. ChemMedChem 2007, 2, 806. <http://dx.doi.org/10.1002/cmdc.200700014>
  • Baumgartner Corinne, Eberle Christian, Diederich François, Lauw Susan, Rohdich Felix, Eisenreich Wolfgang, Bacher Adelbert: Structure-Based Design and Synthesis of the First Weak Non-Phosphate Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway of Isoprenoid Biosynthesis. HCA 2007, 90, 1043. <http://dx.doi.org/10.1002/hlca.200790105>
  • Crane Christine M., Kaiser Johannes, Ramsden Nicola L., Lauw Susan, Rohdich Felix, Eisenreich Wolfgang, Hunter William N., Bacher Adelbert, Diederich François: Fluoreszierende Inhibitoren von IspF, einem Enzym im “Nicht-Mevalonat-Biosyntheseweg” der Isoprenoide und möglichen Ziel einer Antimalariatherapie. Angew Chem 2006, 118, 1082. <http://dx.doi.org/10.1002/ange.200503003>
  • Crane Christine M., Kaiser Johannes, Ramsden Nicola L., Lauw Susan, Rohdich Felix, Eisenreich Wolfgang, Hunter William N., Bacher Adelbert, Diederich François: Fluorescent Inhibitors for IspF, an Enzyme in the Non-Mevalonate Pathway for Isoprenoid Biosynthesis and a Potential Target for Antimalarial Therapy. Angew Chem Int Ed 2006, 45, 1069. <http://dx.doi.org/10.1002/anie.200503003>
  • Rodríguez-Concepción Manuel: Early Steps in Isoprenoid Biosynthesis: Multilevel Regulation of the Supply of Common Precursors in Plant Cells. Phytochem Rev 2006, 5, 1. <http://dx.doi.org/10.1007/s11101-005-3130-4>
  • Besumbes Oscar, Campos Narciso, Boronat Albert, Rodríguez-Concepción Manuel, Carretero-Paulet Lorenzo, Cairó Albert, Botella-Pavía Patricia: Enhanced flux through the methylerythritol 4-phosphate pathway in Arabidopsis plants overexpressing deoxyxylulose 5-phosphate reductoisomerase. Plant Mol Biol 2006, 62, 683. <http://dx.doi.org/10.1007/s11103-006-9051-9>
  • Chang Michelle C Y, Keasling Jay D: Production of isoprenoid pharmaceuticals by engineered microbes. Nat Chem Biol 2006, 2, 674. <http://dx.doi.org/10.1038/nchembio836>
  • Kao Chai-lin, Kittleman William, Zhang Hua, Seto Haruo, Liu Hung-wen: Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates. Org Lett 2005, 7, 5677. <http://dx.doi.org/10.1021/ol0524050>
  • Laupitz Ralf, Hecht Stefan, Amslinger Sabine, Zepeck Ferdinand, Kaiser Johannes, Richter Gerald, Schramek Nicholas, Steinbacher Stefan, Huber Robert, Arigoni Duilio: Biochemical characterization of Bacillus subtilis type II isopentenyl diphosphate isomerase, and phylogenetic distribution of isoprenoid biosynthesis pathways : B. subtilis type II IPP isomerase. Eur J Biochem 2004, 271, 2658. <http://dx.doi.org/10.1111/j.1432-1033.2004.04194.x>
  • Gabrielsen Mads, Rohdich Felix, Eisenreich Wolfgang, Gräwert Tobias, Hecht Stefan, Bacher Adelbert, Hunter William N.: Biosynthesis of isoprenoids : A bifunctional IspDF enzyme from Campylobacter jejuni. Eur J Biochem 2004, 271, 3028. <http://dx.doi.org/10.1111/j.1432-1033.2004.04234.x>
  • Yin Xihou, Proteau Philip J: Characterization of native and histidine-tagged deoxyxylulose 5-phosphate reductoisomerase from the cyanobacterium Synechocystis sp. PCC6803. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 2003, 1652, 75. <http://dx.doi.org/10.1016/j.bbapap.2003.08.005>