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N Use By Plants
Nitrate Assimilation
Ammonia Assimilation
Glu, Gln, Asn, Gly, Ser
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Asp, Ala, GABA
Val, Leu, Ileu, Thr, Lys
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HORT640 - Metabolic Plant Physiology

References, isopentenyl diphosphate

Bajguz A, Asami T. Effects of brassinazole, an inhibitor of brassinosteroid biosynthesis, on light- and dark-grown Chlorella vulgaris. Planta 218: 869-877 (2004).

Bede JC, Musser RO, Felton GW, Korth KL. Caterpillar herbivory and salivary enzymes decrease transcript levels of Medicago truncatula genes encoding early enzymes in terpenoid biosynthesis. Plant Mol. Biol. 60: 519-531 (2006).

Botella-Pavia P, Besumbes O, Phillips MA, Carretero-Paulet L, Boronat A, Rodriguez-Concepcion M. Regulation of carotenoid biosynthesis in plants: evidence for a key role of hydroxymethylbutenyl diphosphate reductase in controlling the supply of plastidial isoprenoid precursors. Plant J. 40: 188-199 (2004).

Bouvier F, d'Harlingue A, Suire C, Backhaus RA, Camara B. Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits. Plant Physiol. 117: 1423-1431 (1998).

Brandle JE, Richman A, Swanson AK, Chapman BP. Leaf ESTs from Stevia rebaudiana: a resource for gene discovery in diterpene synthesis. Plant Mol. Biol. 50: 613-622 (2002).

Brodelius M, Lundgren A, Mercke P, Brodelius PE. Fusion of farnesyldiphosphate synthase and epi-aristolochene synthase, a sesquiterpene cyclase involved in capsidiol biosynthesis in Nicotiana tabacum. Eur. J. Biochem. 269: 3570-3577 (2002).

Bruggemann N, Schnitzler JP. Relationship of isopentenyl diphosphate (IDP) isomerase activity to isoprene emission of oak leaves. Tree Physiol. 22: 1011-1018 (2002).

Brugiere N, Humbert S, Rizzo N, Bohn J, Habben JE. A member of the maize isopentenyl transferase gene family, Zea mays isopentenyl transferase 2 (ZmIPT2), encodes a cytokinin biosynthetic enzyme expressed during kernel development. Cytokinin biosynthesis in maize. Plant Mol. Biol. 67: 215-229 (2008).

Burlat V, Oudin A, Courtois M, Rideau M, St-Pierre B. Co-expression of three MEP pathway genes and geraniol 10-hydroxylase in internal phloem parenchyma of Catharanthus roseus implicates multicellular translocation of intermediates during the biosynthesis of monoterpene indole alkaloids… Plant J. 38: 131-141 (2004).

Campbell M, Hahn FM, Poulter CD, Leustek T. Analysis of the isopentenyl diphosphate isomerase gene family from Arabidopsis thaliana. Plant Mol. Biol. 36: 323-328 (1998).

Campos N, Rodriguez-Concepcion M, Sauret-Gueto S, Gallego F, Lois LM, Boronat A. Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate: a novel system for the genetic analysis of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis. Biochem. J. 353: 59-67 (2001).

Cervantes-Cervantes M, Gallagher CE, Zhu C, Wurtzel ET. Maize cDNAs expressed in endosperm encode functional farnesyl diphosphate synthase with geranylgeranyl diphosphate synthase activity. Plant Physiol. 141: 220-231 (2006).

Clastre M, Bantignies B, Feron G, Soler E, Ambid C. Purification and characterization of geranyl diphosphate synthase from Vitis vinifera L. cv Muscat de Frontignan cell cultures. Plant Physiol. 102: 205-211 (1993).

Cordier H, Karst F, Berges T. Heterologous expression in Saccharomyces cerevisiae of an Arabidopsis thaliana cDNA encoding mevalonate diphosphate decarboxylase. Plant Mol. Biol. 39: 953-967 (1999).

Cunillera N, Boronat A, Ferrer A. Spatial and temporal patterns of GUS expression directed by 5' regions of the Arabidopsis thaliana farnesyl diphosphate synthase genes FPS1 and FPS2. Plant Mol. Biol. 44: 747-758 (2000).

Cutler AJ, Krochko JE. Formation and breakdown of ABA. Trends Plant Sci. 4: 472-478 (1999).

Cvejic JH, Rohmer M. CO2 as main carbon source for isoprenoid biosynthesis via the mevalonate-independent methylerythritol 4-phosphate route in the marine diatoms Phaeodactylum tricornutum and Nitzschia ovalis. Phytochemistry 53: 21-28 (2000).

Disch A, Hemmerlin A, Bach TJ, Rohmer M. Mevalonate-derived isopentenyl diphosphate is the biosynthetic precursor of ubiquinone prenyl side chain in tobacco BY-2 cells. Biochem. J. 331: 615-621 (1998).

Dudareva N, Andersson S, Orlova I, Gatto N, Reichelt M, Rhodes D, Boland W, Gershenzon J. The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. Proc. Natl. Acad. Sci. U.S.A. 102: 933-938 (2005).

Eisenreich W, Rohdich F, Bacher A. Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci. 6: 78-84 (2001).

Engprasert S, Taura F, Shoyama Y. Molecular cloning, expression and characterization of recombinant 1-deoxy-D-xylulose-5-phosphate reductoisomerase from Coleus forskohlii Briq. Plant Sci. 169: 287-294 (2005).

Fellermeier M, Raschke M, Sagner S, Wungsintaweekul J, Schuhr CA, Hecht S, Kis K, Radykewicz T, Adam P, Rohdich F, Eisenreich W, Bacher A, Arigoni D, Zenk MH. Studies on the nonmevalonate pathway of terpene biosynthesis. The role of 2C-methyl-D-erythritol 2,4-cyclodiphosphate in plants. Eur. J. Biochem. 268: 6302-6310 (2001).

Fraser PD, Schuch W, Bramley PM. Phytoene synthase from tomato (Lycopersicon esculentum) chloroplasts--partial purification and biochemical properties. Planta 211: 361-369 (2000).

Gil MJ, Coego A, Mauch-Mani B, Jorda L, Vera P. The Arabidopsis csb3 mutant reveals a regulatory link between salicylic acid-mediated disease resistance and the methyl-erythritol 4-phosphate pathway. Plant J. 44: 155-166 (2005).

Guevara-Garcia A, San Roman C, Arroyo A, Cortes ME, de la Luz Gutierrez-Nava M, Leon P. Characterization of the Arabidopsis clb6 mutant illustrates the importance of posttranscriptional regulation of the methyl-D-erythritol 4-phosphate pathway. Plant Cell 17: 628-643 (2005).

Hahn FM, Hurlburt AP, Poulter CD. Escherichia coli open reading frame 696 is idi, a nonessential gene encoding isopentenyl diphosphate isomerase. J. Bacteriol. 181: 4499-4504 (1999).

Harada H, Yu F, Okamoto S, Kuzuyama T, Utsumi R, Misawa N. Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli. Appl. Microbiol. Biotechnol. 81: 915-925 (2009).

Harker M, Bramley PM. Expression of prokaryotic 1-deoxy-D-xylulose-5-phosphatases in Escherichia coli increases carotenoid and ubiquinone biosynthesis. FEBS Lett. 448: 115-119 (1999).

Hefner J, Ketchum RE, Croteau R. Cloning and functional expression of a cDNA encoding geranylgeranyl diphosphate synthase from Taxus canadensis and assessment of the role of this prenyltransferase in cells induced for taxol production. Arch. Biochem. Biophys. 360: 62-74 (1998).

Hemmi H, Noike M, Nakayama T, Nishino T. An alternative mechanism of product chain-length determination in type III geranylgeranyl diphosphate synthase. Eur. J. Biochem. 270: 2186-2194 (2003).

Hirschberg J. Carotenoid biosynthesis in flowering plants. Curr. Opin. Plant Biol. 4: 210-218 (2001).

Hong SB, Hughes EH, Shanks JV, San KY, Gibson SI. Role of the non-mevalonate pathway in indole alkaloid production by Catharanthus roseus hairy roots. Biotechnol. Prog. 19: 1105-1108 (2003).

Hsieh MH, Goodman HM. Functional evidence for the involvement of Arabidopsis IspF homolog in the nonmevalonate pathway of plastid isoprenoid biosynthesis. Planta 223: 779-784 (2006).

Jones KL, Kim SW, Keasling JD. Low-copy plasmids can perform as well as or better than high-copy plasmids for metabolic engineering of bacteria. Metab. Eng. 2: 328-338 (2000).

Khemvong S, Suvachittanont W. Molecular cloning and expression of a cDNA encoding 1-deoxy-D-xylulose-5-phosphate synthase from oil palm Elaeis guineensis Jacq.. Plant Sci. 169: 571-578 (2005).

Kim IJ, Ryu SB, Kwak YS, Kang H. A novel cDNA from Parthenium argentatum Gray enhances the rubber biosynthetic activity in vitro. J. Exp. Bot. 55: 377-385 (2004).

Kim SW, Keasling JD. Metabolic engineering of the nonmevalonate isopentenyl diphosphate synthesis pathway in Escherichia coli enhances lycopene production. Biotechnol. Bioeng. 72: 408-415 (2001).

Kreuzwieser J, Schnitzler JP, Steinbrecher R. Biosynthesis of organic compounds emitted by plants. Plant Biol. 1: 149-159 (1999).

Kuzuyama T. Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units. Biosci. Biotechnol. Biochem. 66: 1619-1627 (2002).

Lange BM, Croteau R. 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: 170-174 (1999).

Lange BM, Ketchum RE, Croteau RB. Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis. Plant Physiol. 127: 305-314 (2001).

Lange BM, Wildung MR, McCaskill D, Croteau R. A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway. Proc. Natl. Acad. Sci. U.S.A. 95: 2100-2104 (1998).

Lichtenthaler HK. The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 50: 47-65 (1999).

Lichtenthaler HK. Non-mevalonate isoprenoid biosynthesis: enzymes, genes and inhibitors. Biochem. Soc. Trans. 28: 785-789 (2000).

Logan BA, Monson RK, Potosnak MJ. Biochemistry and physiology of foliar isoprene production. Trends Plant Sci. 5: 477-481 (2000).

Lois LM, Campos N, Putra SR, Danielsen K, Rohmer M, Boronat A. 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. U.S.A. 95: 2105-2110 (1998).

Lopes AA, Baldoqui DC, Lopez SN, Kato MJ, Bolzani Vda S, Furlan M. Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae). Phytochemistry 68: 2053-2058 (2007).

Manzano D, Busquets A, Closa M, Hoyerova K, Schaller H, Kaminek M, Arro M, Ferrer A. Overexpression of farnesyl diphosphate synthase in Arabidopsis mitochondria triggers light-dependent lesion formation and alters cytokinin homeostasis. Plant Mol. Biol. 61: 195-213 (2006).

McCaskill D, Croteau R. Some caveats for bioengineering terpenoid metabolism in plants. Trends Biotechnol. 16: 349-355 (1998).

McCaskill D, Croteau R. Strategies for bioengineering the development and metabolism of glandular tissues in plants. Nat. Biotechnol. 17: 31-36 (1999).

McCaskill D, Croteau R. Isopentenyl diphosphate is the terminal product of the deoxyxylulose-5-phosphate pathway for terpenoid biosynthesis in plants. Tetrahedron Lett. 40: 653-656 (1999).

McCaskill D, Croteau R. Monoterpene and sesquiterpene biosynthesis in glandular trichomes of peppermint (Mentha x piperita) rely exclusively on plastid-derived isopentenyl diphosphate. Planta 197: 49-56 (1995).

Milborrow BV. The pathway of biosynthesis of abscisic acid in vascular plants: a review of the present state of knowledge of ABA biosynthesis. J. Exp. Bot. 52: 1145-1164 (2001).

Miller B, Heuser T, Zimmer W. 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: 485-490 (1999).

Munoz-Bertomeu J, Arrillaga I, Ros R, Segura J. Up-regulation of 1-deoxy-D-xylulose-5-phosphate synthase enhances production of essential oils in transgenic spike lavender. Plant Physiol. 142: 890-900 (2006).

Nagata N, Suzuki M, Yoshida S, Muranaka T. Mevalonic acid partially restores chloroplast and etioplast development in Arabidopsis lacking the non-mevalonate pathway. Planta 216: 345-350 (2002).

Ohto C, Ishida C, Nakane H, Muramatsu M, Nishino T, Obata S. A thermophilic cyanobacterium Synechococcus elongatus has three different Class I prenyltransferase genes. Plant Mol. Biol. 40: 307-321 (1999).

Okada A, Shimizu T, Okada K, Kuzuyama T, Koga J, Shibuya N, Nojiri H, Yamane H. Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice. Plant Mol. Biol. 65: 177-187 (2007).

Okada K, Kasahara H, Yamaguchi S, Kawaide H, Kamiya Y, Nojiri H, Yamane H. Genetic evidence for the role of isopentenyl diphosphate isomerases in the mevalonate pathway and plant development in Arabidopsis. Plant Cell Physiol. 49: 604-616 (2008).

Okada K, Kawaide H, Kuzuyama T, Seto H, Curtis IS, Kamiya Y. Antisense and chemical suppression of the nonmevalonate pathway affects ent-kaurene biosynthesis in Arabidopsis. Planta 215: 339-344 (2002).

Owen SM, Penuelas J. Opportunistic emissions of volatile isoprenoids. Trends Plant Sci. 10: 420-426 (2005).

Page JE, Hause G, Raschke M, Gao W, Schmidt J, Zenk MH, Kutchan TM. Functional analysis of the final steps of the 1-deoxy-D-xylulose 5-phosphate (DXP) pathway to isoprenoids in plants using virus-induced gene silencing. Plant Physiol. 134: 1401-1413 (2004).

Pan X, Chen M, Liu Y, Wang Q, Zeng L, Li L, Liao Z. A new isopentenyl diphosphate isomerase gene from Camptotheca acuminata: cloning, characterization and functional expression in Escherichia coli. DNA Seq. 19: 98-105 (2008).

Paseshnichenko VA. A new alternative non-mevalonate pathway for isoprenoid biosynthesis in eubacteria and plants. Biochemistry (Mosc.) 63: 139-148 (1998).

Sapir-Mir M, Mett A, Belausov E, Tal-Meshulam S, Frydman A, Gidoni D, Eyal Y. Peroxisomal localization of Arabidopsis isopentenyl diphosphate isomerases suggests that part of the plant isoprenoid mevalonic acid pathway is compartmentalized to peroxisomes. Plant Physiol. 148: 1219-1228 (2008).

Schwender J, Gemunden C, Lichtenthaler HK. Chlorophyta exclusively use the 1-deoxyxylulose 5-phosphate/2-C-methylerythritol 4-phosphate pathway for the biosynthesis of isoprenoids. Planta 212: 416-423 (2001).

Schwender J, Muller C, Zeidler J, Lichtenthaler HK. Cloning and heterologous expression of a cDNA encoding 1-deoxy-D-xylulose-5-phosphate reductoisomerase of Arabidopsis thaliana. FEBS Lett. 455: 140-144 (1999).

Schwender J, Seemann M, Lichtenthaler HK, Rohmer M. Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus. Biochem. J. 316: 73-80 (1996).

Schwender J, Zeidler J, Groner R, Muller C, Focke M, Braun S, Lichtenthaler FW, Lichtenthaler HK. Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett. 414: 129-134 (1997).

Sprenger GA, Schorken U, Wiegert T, Grolle S, de Graaf AA, Taylor SV, Begley TP, Bringer-Meyer S, Sahm H. 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. U.S.A. 94: 12857-12862 (1997).

Takahashi S, Kuzuyama T, Watanabe H, Seto H. 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. U.S.A. 95: 9879-9884 (1998).

Tholl D, Kish CM, Orlova I, Sherman D, Gershenzon J, Pichersky E, Dudareva N. Formation of monoterpenes in Antirrhinum majus and Clarkia breweri flowers involves heterodimeric geranyl diphosphate synthases. Plant Cell 16: 977-992 (2004).

Thulasiram HV, Poulter CD. Farnesyl diphosphate synthase: the art of compromise between substrate selectivity and stereoselectivity. J. Am. Chem. Soc. 128: 15819-15823 (2006).

Vallabhaneni R, Wurtzel ET. Timing and biosynthetic potential for carotenoid accumulation in genetically diverse germplasm of maize. Plant Physiol. 150: 562-572 (2009).

Walter MH, Hans J, Strack D. Two distantly related genes encoding 1-deoxy-d-xylulose 5-phosphate synthases: differential regulation in shoots and apocarotenoid-accumulating mycorrhizal roots. Plant J. 31: 243-254 (2002).

Wolfertz M, Sharkey TD, Boland W, Kuhnemann F, Yeh S, Weise SE. Biochemical regulation of isoprene emission. Plant Cell Environ. 26: 1357-1364 (2003).

Wolff M, Seemann M, Bui BTS, Frapart Y, Tritsch D, Estrabot AG, Rodriguez-Concepcion M, Boronat A, Marquet A, Rohmer M. Isoprenoid biosynthesis via the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate reductase (LytB/IspH) from Escherichia coli is a [4Fe-4S] protein. FEBS Lett. 541: 115-120 (2003).

Zahiri HS, Yoon SH, Keasling JD, Lee SH, Won Kim S, Yoon SC, Shin YC. Coenzyme Q10 production in recombinant Escherichia coli strains engineered with a heterologous decaprenyl diphosphate synthase gene and foreign mevalonate pathway. Metab. Eng. 8: 406-416 (2006).

Zeidler J, Lichtenthaler HK. Biosynthesis of 2-methyl-3-buten-2-ol emitted from needles of Pinus ponderosa via the non-mevalonate DOXP/MEP pathway of isoprenoid formation. Planta 213: 323-326 (2001).

Zhong JJ, Yue CJ. Plant cells: secondary metabolite heterogeneity and its manipulation. Adv. Biochem. Eng. Biotechnol. 100: 53-88 (2005).

Number of references = 80

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David Rhodes
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