Elucidation of the Methylerythritol Phosphate Pathway for Isoprenoid Biosynthesis in Bacteria and Plastids. A Metabolic Milestone Achieved through Genomics

Oxford University Press (OUP) - Tập 130 Số 3 - Trang 1079-1089 - 2002
Manuel Rodríguez‐Concepción1, Albert Boronat1
1Departament de Bioquı́mica i Biologia Molecular, Facultat de Quı́mica, Universitat de Barcelona, Martı́ i Franquès 1–7, 08028 Barcelona, Spain

Tóm tắt

Từ khóa


Tài liệu tham khảo

Altincicek, 2001, LytB, a novel gene of the 2-C-methyl-d-erythritol 4-phosphate pathway of isoprenoid biosynthesis in Escherichia coli., FEBS Lett, 499, 37, 10.1016/S0014-5793(01)02516-9

Altincicek, 2001, GcpE is involved in the 2-C-methyl-d-erythritol 4-phosphate pathway of isoprenoid biosynthesis in Escherichia coli., J Bacteriol, 183, 2411, 10.1128/JB.183.8.2411-2416.2001

Altincicek, 2001, Human gamma-delta T cells are activated by intermediates of the 2-C-methyl-d-erythritol 4-phosphate pathway of isoprenoid biosynthesis., J Immunol, 166, 3655, 10.4049/jimmunol.166.6.3655

Araki, 2000, Temperature-sensitive Arabidopsis mutant defective in 1-deoxy-d-xylulose 5-phosphate synthase within the plastid non-mevalonate pathway of isoprenoid biosynthesis., Physiol Plant, 108, 19

Bouvier, 1998, Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits., Plant Physiol, 117, 1423, 10.1104/pp.117.4.1423

Broers, 1994, Über die frühen Stufen der Biosynthese von Isoprenoiden in Escherichia coli. PhD thesis.

Budziszewski, 2001, Arabidopsis genes essential for seedling viability: isolation of insertional mutants and molecular cloning., Genetics, 159, 1765, 10.1093/genetics/159.4.1765

Campos, 2001, Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate: a novel system for genetic analysis of the 2-C-methyl-d-erythritol 4-phosphate pathway., Biochem J, 353, 59, 10.1042/bj3530059

Campos, 2001, Identification of gcpE as a novel gene of the 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis in Escherichia coli., FEBS Lett, 488, 170, 10.1016/S0014-5793(00)02420-0

Carretero-Paulet, 2002, Expression and molecular analysis of the Arabidopsis thaliana DXR gene encoding 1-deoxy-d-xylulose 5-phosphate reductoisomerase, the first committed enzyme of the 2-C-methyl-d-erythritol 4-phosphate pathway., Plant Physiol, 129, 1581, 10.1104/pp.003798

Chahed, 2000, 1-Deoxy-d-xylulose 5-phosphate synthase from periwinkle: cDNA identification and induced gene expression in terpenoid indole alkaloid-producing cells., Plant Physiol Biochem, 38, 559, 10.1016/S0981-9428(00)00781-6

Chappell, 1995, Biochemistry and molecular biology of the isoprenoid biosynthetic pathway in plants., Annu Rev Plant Physiol Plant Mol Biol, 46, 521, 10.1146/annurev.pp.46.060195.002513

Chappell, 2002, The genetics and molecular genetics of terpene and sterol origami., Curr Opin Plant Biol, 5, 151, 10.1016/S1369-5266(02)00241-8

Charon, 2000, Deuterium labeled isotopomers of 2-C-methyl-d-erythritol as tools for the elucidation of the 2-C-methyl-d-erythritol 4-phosphate (MEP) pathway for isoprenoid synthesis., Biochem J, 346, 737, 10.1042/bj3460737

Croteau, 2000, Natural products (secondary metabolites)., Biochemistry and Molecular Biology of Plants., 1250

Cunningham, 2000, Evidence of a role for lytB in the nonmevalonate pathway of isoprenoid biosynthesis., J Bacteriol, 182, 5841, 10.1128/JB.182.20.5841-5848.2000

Duvold, 1997, Incorporation of 2-C-methyl-d-erythritol, a putative isoprenoid precursor in the mevalonate-independent pathway, into ubiquinone and menaquinone of Escherichia coli., Tetrahedron Lett, 38, 6181, 10.1016/S0040-4039(97)01392-0

Eisenreich, 2001, Deoxyxylulose phosphate pathway to terpenoids., Trends Plant Sci, 6, 78, 10.1016/S1360-1385(00)01812-4

Eisenreich, 1998, The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms., Chem Biol, 5, R221, 10.1016/S1074-5521(98)90002-3

Estévez, 2001, 1-Deoxy-d-xylulose-5-phosphate synthase, a limiting enzyme for plastidic isoprenoid biosynthesis in plants., J Biol Chem, 25, 22901, 10.1074/jbc.M100854200

Estévez, 2000, Analysis of the expression of CLA1, a gene that encodes the 1-deoxyxylulose 5-phosphate synthase of the 2-C-methyl-d-erythritol-4-phosphate pathway in Arabidopsis., Plant Physiol, 124, 95, 10.1104/pp.124.1.95

Flesch, 1988, Prokaryotic hopanoids: the biosynthesis of the bacteriohopan skeleton., Eur J Biochem, 175, 405, 10.1111/j.1432-1033.1988.tb14210.x

Fray, 1995, Constitutive expression of a fruit phytoene synthase gene in transgenic tomatoes causes dwarfism by redirecting metabolites from the gibberellin pathway., Plant J, 8, 693, 10.1046/j.1365-313X.1995.08050693.x

Giner, 1998, Biosynthesis of isoprenoids in Escherichia coli: the fate of the 3-H and 4-H atoms of 1-deoxy-d-xylulose., J Chem Soc Chem Commun, 17, 1857, 10.1039/a804461i

Hahn, 1999, Escherichia coli open reading frame 696 is idi, a nonessential gene encoding isopentenyl diphosphate isomerase., J Bacteriol, 181, 4499, 10.1128/JB.181.15.4499-4504.1999

Harker, 1999, Expression of procaryotic 1-deoxy-d-xylulose 5-phosphatases in Escherichia coli increases carotenoid and ubiquinone biosynthesis., FEBS Lett, 448, 115, 10.1016/S0014-5793(99)00360-9

Hecht, 2001, Studies on the nonmevalonate pathway to terpenes: the role of the GcpE (IspG) protein., Proc Natl Acad Sci USA, 26, 14837, 10.1073/pnas.201399298

Herz, 2000, Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-d-erythritol 2-phosphate to 2C-methyl-d-erythritol 2,4-cyclodiphosphate., Proc Natl Acad Sci USA, 97, 2486, 10.1073/pnas.040554697

Hintz, 2001, Identification of (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate as a major activator for human T cells in Escherichia coli., FEBS Lett, 509, 317, 10.1016/S0014-5793(01)03191-X

Jomaa, 1999, Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs., Science, 285, 1573, 10.1126/science.285.5433.1573

Kemp, 2001, Crystallization and preliminary x-ray diffraction studies of recombinant Escherichia coli 4-diphosphocytidyl- 2-C-methyl-d-erythritol synthetase., Acta Crystallogr D Biol Crystallogr, 57, 1189, 10.1107/S0907444901010137

Kemp, 2002, Structure of 2C-methyl-d-erythritol 2,4-cyclodiphosphate synthase: an essential enzyme for isoprenoid biosynthesis and target for antimicrobial drug development., Proc Natl Acad Sci USA, 99, 6591, 10.1073/pnas.102679799

Kuzuyama, 2000, Formation of 4-(cytidine 5′-diphospho)-2-C-methyl-d-erythritol from 2-C-methyl-d-erythritol 4-phosphate by 2-C-methyl-d-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway., Tetrahedron Lett, 41, 703, 10.1016/S0040-4039(99)02143-7

Kuzuyama, 2000, Studies on the nonmevalonate pathway: conversion of 4-(cytidine 5′-diphospho)-2-C-methyl-d-erythritol to its 2-phospho derivative by 4-(cytidine 5′-diphospho)-2-C-methyl-d-erythritol kinase., Tetrahedron Lett, 41, 2925, 10.1016/S0040-4039(00)00295-1

Kuzuyama, 2000, Cloning and characterization of 1-deoxy-d-xylulose 5-phosphate synthase from Streptomyces sp. strain CL190, which uses both the mevalonate and nonmevalonate pathways for isopentenyl diphosphate biosynthesis., J Bacteriol, 182, 891, 10.1128/JB.182.4.891-897.2000

Kuzuyama, 1998, Direct formation of 2-C-methyl-d-erythritol 4-phosphate from 1-deoxy-d-xylulose 5-phosphate by 1-deoxy-d-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate., Tetrahedron Lett, 39, 4509, 10.1016/S0040-4039(98)00802-8

Lange, 1999, Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: isopentenyl monophosphate kinase catalyzes the terminal enzymatic step., Proc Natl Acad Sci USA, 96, 13714, 10.1073/pnas.96.24.13714

Lange, 1999, Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: cloning and heterologous expression of 1-deoxy-d-xylulose 5-phosphate reductoisomerase from peppermint., Arch Biochem Biophys, 365, 170, 10.1006/abbi.1999.1168

Lange, 2001, Isoprenoid biosynthesis: metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis., Plant Physiol, 127, 305, 10.1104/pp.127.1.305

Lange, 1998, A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway., Proc Natl Acad Sci USA, 95, 2100, 10.1073/pnas.95.5.2100

Lichtenthaler, 1999, The 1-deoxy-d-xylulose 5-phosphate pathway of isoprenoid biosynthesis in plants., Annu Rev Plant Physiol Plant Mol Biol, 50, 47, 10.1146/annurev.arplant.50.1.47

Lichtenthaler, 1997, Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants., Physiol Plant, 101, 643, 10.1111/j.1399-3054.1997.tb01049.x

Lois, 1998, Cloning and characterization of a gene from Escherichia coli encoding a transketolase-like enzyme that catalyzes the synthesis of d-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin, and pyridoxol biosynthesis., Proc Natl Acad Sci USA, 95, 2105, 10.1073/pnas.95.5.2105

Lois, 2000, Carotenoid biosynthesis during tomato fruit development: regulatory role of 1-deoxy-d-xylulose 5-phosphate synthase., Plant J, 22, 503, 10.1046/j.1365-313x.2000.00764.x

Lüttgen, 2000, Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2-C-methyl-d-erythritol., Proc Natl Acad Sci USA, 97, 1062, 10.1073/pnas.97.3.1062

Mahmoud, 2001, Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase., Proc Natl Acad Sci USA, 98, 8915, 10.1073/pnas.141237298

Mandel, 1996, CLA1, a novel gene required for chloroplast development, is highly conserved in evolution., Plant J, 9, 649, 10.1046/j.1365-313X.1996.9050649.x

Matthews, 2000, Metabolic engineering of carotenoid accumulation in Escherichia coli by modulation of the isoprenoid precursor pool with expression of deoxyxylulose phosphate synthase., Appl Microbiol Biotechnol, 53, 396, 10.1007/s002530051632

McGarvey, 1995, Terpenoid metabolism., Plant Cell, 7, 1015

Miller, 1999, A Synechococcus leopoliensis SAUG 1402-1 operon harboring the 1-deoxyxylulose 5-phosphate synthase gene and two additional open reading frames is functionally involved in the dimethylallyl diphosphate synthesis., FEBS Lett, 460, 485, 10.1016/S0014-5793(99)01397-6

Miller, 2000, Functional involvement of a deoxy-d-xylulose 5-phosphate reductoisomerase gene harboring locus of Synechococcus leopoliensis in isoprenoid biosynthesis., FEBS Lett, 481, 221, 10.1016/S0014-5793(00)02014-7

Okada, 2002, Antisense and chemical suppression of the nonmevalonate pathway affects ent-kaurene biosynthesis in Arabidopsis., Planta, 215, 339, 10.1007/s00425-002-0762-0

Querol, 2002, Functional analysis of the Arabidopsis thaliana GCPE protein involved in plastid isoprenoid biosynthesis., FEBS Lett, 514, 343, 10.1016/S0014-5793(02)02402-X

Querol, 2001, Essential role of residue H49 for activity of Escherichia coli 1-deoxy-d-xylulose 5-phosphate synthase, the enzyme catalyzing the first step of the 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis., Biochem Biophys Res Commun, 289, 155, 10.1006/bbrc.2001.5957

Reuter, 2002, Crystal structure of 1-deoxy-d-xylulose-5-phosphate reductoisomerase, a crucial enzyme in the non-mevalonate pathway of isoprenoid biosynthesis., J Biol Chem, 277, 5378, 10.1074/jbc.M109500200

Richard, 2001, Structure of 4-diphosphocytidyl-2-C-methylerythritol synthetase involved in mevalonate-independent isoprenoid biosynthesis., Nat Struct Biol, 8, 641, 10.1038/89691

Richard, 2002, Structure and mechanism of 2-C-methyl-d-erythritol 2,4-cyclodiphosphate synthase: an enzyme in the mevalonate-independent isoprenoid biosynthetic pathway., J Biol Chem, 277, 8667, 10.1074/jbc.C100739200

Rodrı́guez-Concepción, 2001, 1-Deoxy-d-xylulose 5-phosphate reductoisomerase and plastid isoprenoid biosynthesis during tomato fruit ripening., Plant J, 27, 213, 10.1046/j.1365-313x.2001.01089.x

Rodrı́guez-Concepción, 2000, Genetic evidence of branching in the isoprenoid pathway for the production of isopentenyl diphosphate and dimethylallyl diphosphate in Escherichia coli., FEBS Lett, 473, 328, 10.1016/S0014-5793(00)01552-0

Rodrı́guez-Concepción, 1999, Arachidonic acid alters tomato HMG expression and fruit growth and induces 3-hydroxy-3-methylglutaryl coenzyme A reductase-independent lycopene accumulation., Plant Physiol, 119, 41, 10.1104/pp.119.1.41

Rohdich, 2002, Studies on the nonmevalonate terpene biosynthetic pathway: metabolic role of IspH (LytB) protein., Proc Natl Acad Sci USA, 99, 1158, 10.1073/pnas.032658999

Rohdich, 2000, Biosynthesis of terpenoids: 4-diphosphocytidyl-2-C-methyl-d-erythritol synthase of Arabidopsis thaliana., Proc Natl Acad Sci USA, 97, 6451, 10.1073/pnas.97.12.6451

Rohdich, 1999, Cytidine 5′-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol., Proc Natl Acad Sci USA, 96, 11758, 10.1073/pnas.96.21.11758

Rohdich, 2000, Biosynthesis of terpenoids: 4-diphosphocytidyl-2-C-methyl-d-erythritol kinase from tomato., Proc Natl Acad Sci USA, 97, 8251, 10.1073/pnas.140209197

Rohmer, 1999, The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants., Nat Prod Rep, 16, 565, 10.1039/a709175c

Rohmer, 1993, Isoprenoid biosynthesis in bacteria: a novel pathway for early steps leading to isopentenyl diphosphate., Biochem J, 295, 517, 10.1042/bj2950517

Rohmer, 1996, Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis., J Am Chem Soc, 118, 2564, 10.1021/ja9538344

Schindler, 1985, Differential inhibition by mevinolin of prenyllipid accumulation in radish seedlings., Z Naturforsch, 40c, 208, 10.1515/znc-1985-3-412

Schwarz, 1994, Terpen Biosynthese in Ginkgo biloba: Eine überraschende Geschichte. PhD thesis.

Schwender, 1999, Cloning and heterologous expression of a cDNA encoding 1-deoxy-d-xylulose 5-phosphate reductoisomerase of Arabidopsis thaliana., FEBS Lett, 455, 140, 10.1016/S0014-5793(99)00849-2

Seemann, 2002, Isoprenoid biosynthesis in Escherichia coli via the methylerythritol phosphate pathway: enzymatic conversion of methylerythritol cyclodiphosphate into a phosphorylated derivative of (E)-2-methylbut-2-ene-1,4-diol., Tetrahedron Lett, 43, 1413, 10.1016/S0040-4039(02)00003-5

Seemann, 2002, Isoprenoid biosynthesis via the methylerythritol phosphate pathway: 2-C-methyl-d-erythritol 2,4-cyclodiphosphate as putative substrate of the gcpE gene product in Escherichia coli., Tetrahedron Lett, 43, 775, 10.1016/S0040-4039(01)02269-9

Sprenger, 1997, Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-d-xylulose 5-phosphate precursor to isoprenoids, thiamin, and pyridoxol., Proc Natl Acad Sci USA, 94, 12857, 10.1073/pnas.94.24.12857

Steinbacher, 2002, Structure of 2-C-methyl-d-erythritol-2,4-cyclodiphosphate synthase involved in mevalonate-independent biosynthesis of isoprenoids., J Mol Biol, 316, 79, 10.1006/jmbi.2001.5341

Takagi, 2000, Studies on the nonmevalonate pathway: formation of 2-C-methyl-d-erythritol 2,4-cyclodiphosphate from 2-phospho-4-(cytidine 5′-diphospho)- 2-C-methyl-d-erythritol., Tetrahedron Lett, 41, 3395, 10.1016/S0040-4039(00)00375-0

Takahashi, 1998, A 1-deoxy-d-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-d-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis., Proc Natl Acad Sci USA, 95, 9879, 10.1073/pnas.95.17.9879

Veau, 2000, Cloning and expression of cDNAs encoding two enzymes of the MEP pathway in Catharanthus roseus., Biochim Biophys Acta, 1517, 159, 10.1016/S0167-4781(00)00240-2

Walter, 2000, Arbuscular mycorrhizal fungi induce the non-mevalonate methylerythritol phosphate pathway of isoprenoid biosynthesis correlated with accumulation of the “yellow pigment” and other apocarotenoids., Plant J, 21, 571, 10.1046/j.1365-313x.2000.00708.x

Wolff, 2002, Isoprenoid biosynthesis via the methylerythritol phosphate pathway. (E)-4-Hydroxy-3-methyl but-2-enyl diphosphate: chemical synthesis and formation from methylerythritol cyclodiphosphate by a cell-free system from Escherichia coli., Tetrahedron Lett, 43, 2555, 10.1016/S0040-4039(02)00293-9

Yajima, 2002, Crystal structure of 1-deoxy-d-xylulose 5-Phosphate reductoisomerase complexed with cofactors: implications of a flexible loop movement upon substrate binding., J Biochem, 131, 313, 10.1093/oxfordjournals.jbchem.a003105

Zeidler, 2000, The non-mevalonate isoprenoid biosynthesis of plants as a test system for drugs against malaria and pathogenic bacteria., Biochem Soc Trans, 28, 796, 10.1042/bst0280796

Zeidler, 1998, Inhibition of the non-mevalonate 1-deoxy-d-xylulose-5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin., Z Naturforsch, 53c, 980, 10.1515/znc-1998-11-1208