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HORT640 - Metabolic Plant Physiology
References, geranyl diphosphate
Aharoni A, Giri AP, Verstappen FW, Bertea CM, Sevenier R, Sun Z, Jongsma MA, Schwab W, Bouwmeester HJ. Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16: 3110-3131 (2004).
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Bohlmann J, Martin D, Oldham NJ, Gershenzon J. Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase. Arch. Biochem. Biophys. 375: 261-269 (2000).
Bohlmann J, Phillips M, Ramachandiran V, Katoh S, Croteau R. cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis). Arch. Biochem. Biophys. 368: 232-243 (1999).
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, Suire C, D'Harlingue A, Backhaus RA, Camara B. Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells. Plant J. 24: 241-252 (2000).
Bouwmeester HJ, Gershenzon J, Konings MC, Croteau R. Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration of enzyme activities and their changes with development. Plant Physiol. 117: 901-912 (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).
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).
Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Plant Physiol. 135: 1956-1966 (2004).
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).
Collakova E, DellaPenna D. Isolation and functional analysis of homogentisate phytyltransferase from Synechocystis sp. PCC 6803 and Arabidopsis. Plant Physiol. 127: 1113-1124 (2001).
Davidovich-Rikanati R, Lewinsohn E, Bar E, Iijima Y, Pichersky E, Sitrit Y. Overexpression of the lemon basil alpha-zingiberene synthase gene (ZIS) increases both mono- and sesquiterpene contents in tomato fruit. Plant J. 56: 228-238 (2008).
Dudareva N, Martin D, Kish CM, Kolosova N, Gorenstein N, Faldt J, Miller B, Bohlmann J. (E)-beta-ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: function and expression of three terpene synthase genes of a new terpene synthase subfamily. Plant Cell 15: 1227-1241 (2003).
Edwards PA, Ericsson J. Sterols and isoprenoids: signaling molecules derived from the cholesterol biosynthetic pathway. Annu. Rev. Biochem. 68: 157-185 (1999).
Engels B, Dahm P, Jennewein S. Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production. Metab. Eng. 10: 201-206 (2008).
Fellermeier M, Eisenreich W, Bacher A, Zenk MH. Biosynthesis of cannabinoids. Incorporation experiments with 13C-labeled glucoses. Eur. J. Biochem. 268: 1596-1604 (2001).
Fraser PD, Schuch W, Bramley PM. Phytoene synthase from tomato (Lycopersicon esculentum) chloroplasts--partial purification and biochemical properties. Planta 211: 361-369 (2000).
Fujisawa M, Watanabe M, Choi SK, Teramoto M, Ohyama K, Misawa N. Enrichment of carotenoids in flaxseed (Linum usitatissimum) by metabolic engineering with introduction of bacterial phytoene synthase gene crtB. J. Biosci. Bioeng. 105: 636-641 (2008).
Galpaz N, Ronen G, Khalfa Z, Zamir D, Hirschberg J. A chromoplast-specific carotenoid biosynthesis pathway is revealed by cloning of the tomato white-flower locus. Plant Cell 18: 1947-1960 (2006).
Gang DR. Evolution of flavors and scents. Annu. Rev. Plant Biol. 56: 301-325 (2005).
Gerber E, Hemmerlin A, Hartmann M, Heintz D, Hartmann MA, Mutterer J, Rodríguez-Concepcion M, Boronat A, Van Dorsselaer A, Rohmer M, Crowell DN, Bach TJ. The plastidial 2-C-methyl-D-erythritol 4-phosphate pathway provides the isoprenyl moiety for protein geranylgeranylation in tobacco BY-2 cells. Plant Cell 21: 285-300 (2009).
Giannino D, Condello E, Bruno L, Testone G, Tartarini A, Cozza R, Innocenti AM, Bitonti MB, Mariotti D. The gene geranylgeranyl reductase of peach (Prunus persica [L.] Batsch) is regulated during leaf development and responds differentially to distinct stress factors. J. Exp. Bot. 55: 2063-2073 (2004).
GraBes T, Grimm B, Koroleva O, Jahns P. Loss of alpha-tocopherol in tobacco plants with decreased geranylgeranyl reductase activity does not modify photosynthesis in optimal growth conditions but increases sensitivity to high-light stress. Planta 213: 620-628 (2001).
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).
Hefner J, Rubenstein SM, Ketchum RE, Gibson DM, Williams RM, Croteau R. Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5alpha-ol: the first oxygenation step in taxol biosynthesis. Chem. Biol. 3: 479-489 (1996).
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).
Hezari M, Croteau R. Taxol biosynthesis: an update. Planta Med. 63: 291-295 (1997).
Hezari M, Ketchum RE, Gibson DM, Croteau R. Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures. Arch. Biochem. Biophys. 337: 185-190 (1997).
Hirschberg J. Carotenoid biosynthesis in flowering plants. Curr. Opin. Plant Biol. 4: 210-218 (2001).
Hoelscher DJ, Williams DC, Wildung MR, Croteau R. A cDNA clone for 3-carene synthase from Salvia stenophylla( small star, filled ). Phytochemistry 62: 1081-1086 (2003).
Hsiao YY, Jeng MF, Tsai WC, Chuang YC, Li CY, Wu TS, Kuoh CS, Chen WH, Chen HH. A novel homodimeric geranyl diphosphate synthase from the orchid Phalaenopsis bellina lacking a DD(X)2-4D motif. Plant J. 55: 719-733 (2008).
Hsiao YY, Tsai WC, Kuoh CS, Huang TH, Wang HC, Wu TS, Leu YL, Chen WH, Chen HH. Comparison of transcripts in Phalaenopsis bellina and Phalaenopsis equestris (Orchidaceae) flowers to deduce monoterpene biosynthesis pathway. BMC Plant Biol. 6: 14 (2006).
Huang KX, Huang QL, Wildung MR, Croteau R, Scott AI. Overproduction, in Escherichia coli, of soluble taxadiene synthase, a key enzyme in the Taxol biosynthetic pathway. Protein Expr. Purif. 13: 90-96 (1998).
Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, Lewinsohn E, Pichersky E. The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol. 136: 3724-3736 (2004).
Iijima Y, Gang DR, Fridman E, Lewinsohn E, Pichersky E. Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiol. 134: 370-379 (2004).
Koepp AE, Hezari M, Zajicek J, Vogel BS, LaFever RE, Lewis NG, Croteau R. Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the committed step of taxol biosynthesis in Pacific yew. J. Biol. Chem. 270: 8686-8690 (1995).
Komatsu M, Tsuda M, Omura S, Oikawa H, Ikeda H. Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol. Proc. Natl. Acad. Sci. U.S.A. 105: 7422-7427 (2008).
Kovacs K, Zhang L, Linforth RS, Whittaker B, Hayes CJ, Fray RG. Redirection of carotenoid metabolism for the efficient production of taxadiene [taxa-4(5),11(12)-diene] in transgenic tomato fruit. Transgenic Res. 16: 121-126 (2007).
Kremer A, Westrich L, Li SM. A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization. Microbiology 153: 3409-3416 (2007).
Kuhn U, Rottenberger S, Biesenthal T, Wolf A, Schebeske G, Ciccioli P, Kesselmeier J. Strong correlation between isoprene emission and gross photosynthetic capacity during leaf phenology of the tropical tree species Hymenaea courbaril with fundamental changes in volatile organic compounds emission composition during early leaf development. Plant Cell Environ. 27: 1469-1485 (2004).
Lee PC, Petri R, Mijts BN, Watts KT, Schmidt-Dannert C. Directed evolution of Escherichia coli farnesyl diphosphate synthase (IspA) reveals novel structural determinants of chain length specificity. Metab. Eng. 7: 18-26 (2005).
Lin X, Hezari M, Koepp AE, Floss HG, Croteau R. Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in Pacific yew. Biochemistry 35: 2968-2977 (1996).
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).
Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY. Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression. Plant Physiol. 130: 477-486 (2002).
Lucker J, El Tamer MK, Schwab W, Verstappen FW, van der Plas LH, Bouwmeester HJ, Verhoeven HA. Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases. Eur. J. Biochem. 269: 3160-3171 (2002).
Miller B, Oschinski C, Zimmer W. First isolation of an isoprene synthase gene from poplar and successful expression of the gene in Escherichia coli. Planta 213: 483-487 (2001).
Muhlenweg A, Melzer M, Li SM, Heide L. 4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound prenyltransferase. Planta 205: 407-413 (1998).
Munoz-Bertomeu J, Ros R, Arrillaga I, Segura J. Expression of spearmint limonene synthase in transgenic spike lavender results in an altered monoterpene composition in developing leaves. Metab. Eng. 10: 166-177 (2008).
Nagegowda DA, Gutensohn M, Wilkerson CG, Dudareva N. Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers. Plant J. 55: 224-239 (2008).
Nakagiri T, Lee JB, Hayashi T. cDNA cloning, functional expression and characterization of ent-copalyl diphosphate synthase from Scoparia dulcis L.. Plant Sci. 169: 760-767 (2005).
Nogues I, Brilli F, Loreto F. Dimethylallyl diphosphate and geranyl diphosphate pools of plant species characterized by different isoprenoid emissions. Plant Physiol. 141: 721-730 (2006).
Nualkaew N, De-Eknamkul W, Kutchan TM, Zenk MH. Membrane-bound geranylgeranyl diphosphate phosphatases: purification and characterization from Croton stellatopilosus leaves. Phytochemistry 67: 1613-1620 (2006).
Ohara K, Ujihara T, Endo T, Sato F, Yazaki K. Limonene production in tobacco with Perilla limonene synthase cDNA. J. Exp. Bot. 54: 2635-2642 (2003).
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, Ohara K, Yazaki K, Nozaki K, Uchida N, Kawamukai M, Nojiri H, Yamane H. The AtPPT1 gene encoding 4-hydroxybenzoate polyprenyl diphosphate transferase in ubiquinone biosynthesis is required for embryo development in Arabidopsis thaliana. Plant Mol. Biol. 55: 567-577 (2004).
Okada K, Saito T, Nakagawa T, Kawamukai M, Kamiya Y. Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis. Plant Physiol. 122: 1045-1056 (2000).
Pateraki I, Kanellis AK. Isolation and functional analysis of two Cistus creticus cDNAs encoding geranylgeranyl diphosphate synthase. Phytochemistry 69: 1641-1652 (2008).
Pechous SW, Whitaker BD. Cloning and functional expression of an (E, E)-alpha-farnesene synthase cDNA from peel tissue of apple fruit. Planta 219: 84-94 (2004).
Prisic S, Peters RJ. Synergistic substrate inhibition of ent-copalyl diphosphate synthase: a potential feed-forward inhibition mechanism limiting gibberellin metabolism. Plant Physiol. 144: 445-454 (2007).
Ravanello MP, Ke D, Alvarez J, Huang B, Shewmaker CK. Coordinate expression of multiple bacterial carotenoid genes in canola leading to altered carotenoid production. Metab. Eng. 5: 255-263 (2003).
Ro DK, Bohlmann J. Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry 67: 1572-1578 (2006).
Saelices L, Youssar L, Holdermann I, Al-Babili S, Avalos J. Identification of the gene responsible for torulene cleavage in the Neurospora carotenoid pathway. Mol. Genet. Genomics 278: 527-537 (2007).
Schmidt A, Gershenzon J. Cloning and characterization of isoprenyl diphosphate synthases with farnesyl diphosphate and geranylgeranyl diphosphate synthase activity from Norway spruce (Picea abies) and their relation to induced oleoresin formation. Phytochemistry 68: 2649-2659 (2007).
Suire C, Bouvier F, Backhaus RA, Begu D, Bonneu M, Camara B. Cellular localization of isoprenoid biosynthetic enzymes in Marchantia polymorpha. Uncovering a new role of oil bodies. Plant Physiol. 124: 971-978 (2000).
Tanaka R, Oster U, Kruse E, Rudiger W, Grimm B. Reduced activity of geranylgeranyl reductase leads to loss of chlorophyll and tocopherol and to partially geranylgeranylated chlorophyll in transgenic tobacco plants expressing antisense RNA for geranylgeranyl reductase. Plant Physiol. 120: 695-704 (1999).
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).
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Valentin HE, Lincoln K, Moshiri F, Jensen PK, Qi Q, Venkatesh TV, Karunanandaa B, Baszis SR, Norris SR, Savidge B, Gruys KJ, Last RL. The Arabidopsis vitamin E pathway gene5-1 mutant reveals a critical role for phytol kinase in seed tocopherol biosynthesis. Plant Cell 18: 212-224 (2006).
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Wildung MR, Croteau R. A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. J. Biol. Chem. 271: 9201-9204 (1996).
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Xu M, Hillwig ML, Prisic S, Coates RM, Peters RJ. Functional identification of rice syn-copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products. Plant J. 39: 309-318 (2004).
Number of references = 82
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