Biosynthetic Routes to the Building Blocks of Isoprenoids
Prof.Dr. Michel Rohmer
- [email protected]
- +33-390241346 | Fax: +33-390241345
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorDr. Myriam Seemann
- [email protected]
- +33-390241349 | Fax: +33-390241346
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorDr. Catherine Grosdemange-Billiard
- [email protected]
- +33-390241349 | Fax: +33-390241346
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorProf.Dr. Michel Rohmer
- [email protected]
- +33-390241346 | Fax: +33-390241345
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorDr. Myriam Seemann
- [email protected]
- +33-390241349 | Fax: +33-390241346
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorDr. Catherine Grosdemange-Billiard
- [email protected]
- +33-390241349 | Fax: +33-390241346
Université Louis Pasteur/CNRS, Institut Le Bel, 4 rue Blaise Pascal, Strasbourg Cedex, France, 67070
Search for more papers by this authorAbstract
- Introduction: Recognition of the Isoprene Unit and Isoprenoids
- Historical Outline
- The Classical Mevalonate Pathway
- The Recently Discovered Methylerythritol Phosphate Pathway
- Labeling Experiments: Discovery and Elucidation of the MEP Pathway
- Origin of the Carbon Skeleton of Isoprene Units
- Identification of Deoxyxylulose and Methylerythritol Derivatives as the First C5 Isoprenoid Precursors
- Enzymology and Genetics
- 1-Deoxy-D-xylulose 5-phosphate Synthase
- 1-Deoxy-D-xylulose 5-phosphate Isomero-reductase
- From Methylerythritol Phosphate to Methylerythritol Cyclodiphosphate
- On the Origin of the Hydrogen Atoms in Isoprene Units: Indications on Further Steps
- Distribution of the MEP Pathway and Evolutionary Impacts
- Outlook and Perspectives
References
- Adam, K. P., Zapp, J. (1998) Biosynthesis of the isoprene units of chamomile sesquiterpenes, Phytochemistry 48, 953–959.
- Adam, K. P., Thiel, R., Zapp, J., Becker, H. (1998) Involvement of the mevalonic acid pathway and the glyceraldehyde-pyruvate pathway in terpenoid biosynthesis of the liverworts Ricciocarpos natans and Conocephalum conicum, Arch. Biochem. Biophys. 354, 181–187.
- Adam, K. P., Thiel, R., Zapp, J. (1999) Incorporation of 1-[1-13C]deoxy-D-xylulose in chamomile sesquiterpenes, Arch. Biochem. Biophys.. 369, 127–132.
- Araki, N., Kusumi, K., Masamoto, K., Niwa, Y., Iba, K. (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, 19–24.
- Arigoni, D., Sagner, S., Latzel, C., Eisenreich, W., Bacher, A., Zenk, M. H. (1997) Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement, Proc. Natl. Acad. Sci. USA 94, 10600–10605.
- Arigoni, D., Eisenreich, W., Latzel, C., Sagner, S., Radykewicz, T., Zenk, M. H., Bacher, A. (1999a) Dimethylallyl diphosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biosynthesis from 1-deoxyxylulose in higher plants, Proc. Natl. Acad. Sci. USA 96, 1309–1314.
- Arigoni, D., Giner, J. L., Sagner, S., Wungsintaweekul, J., Zenk, M. H., Kis, K., Bacher, A., Eisenreich, W. (1999b) Stereochemical course of the reduction in the formation of 2-C-methylerythritol from the terpene precursor 1-deoxyxylulose in higher plants, J. Chem. Soc., Chem. Commun. 1127–1128.
- Bach, T. J. (1995) Some new aspects of isoprenoid biosynthesis in plants – A review, Lipids 30, 191–202.
- Bach, T. J., Lichtenthaler, H. K. (1987) in: Ecology and Metabolism of Plant Lipids ( G. Fuller, W. D. Nes, Eds), American Chemical Society Symposium Series, vol. 325, pp. 109–139. Washington, DC: American Chemical Society.
- Bach, T. J., Motel, A., Weber, T. (1990) Some properties of enzymes involved in the biosynthesis of 3-hydroxy-3-methylglutaryl-CoA in plants, Rec. Adv. Phytochem. 24, 1–82.
- Banthorpe, D. V., Charlwood, B. V., Francis, M. J. (1972) The biosynthesis of monoterpenes, Chem. Rev. 72, 115–155.
- Belmant, C., Espinosa, E., Poupot, R., Peyrat, M. A., Guiraud, M., Poquet, Y., Bonneville, M., Fournié, J. J. (1999) Formyl-1-butyl pyrophosphate, a novel mycobacterial metabolite-activating human γδ T cells, J. Biol. Chem. 274, 32079–32084.
- Bloch, K. (1992) Sterol molecule: structure, biosynthesis and function, Steroids 57, 378–383.
- Bloch, K., Rittenberg, D. (1942) On the utilisation of acetic acid for cholesterol formation, J. Biol. Chem. 143, 625–636.
-
Bochar, D. A.,
Friesen, J. A.,
Stauffacher, C. V.,
Rodwell, V. W.
(1999)
Biosynthesis of mevalonic acid from acetyl-CoA, in: Comprehensive Natural Product Chemistry, Isoprenoids Including Carotenoids and Steroids ( D.E. Cane, Ed.), vol. 2, pp. 15–44. Oxford: Pergamon.
10.1016/B978-0-08-091283-7.00035-7 Google Scholar
- Boucher, Y., Doolittle, W. F. (2000) The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways, Mol. Microbiol. 37, 703–716.
- Bouvet, D., O'Hagan, D. (1999) The synthesis of 1-fluoro- and 1,1-difluoro-analogues of 1-deoxyxylulose, Tetrahedron Lett. 55, 10481–10486.
- Bouvier, F., d'Harlingue, A., Suire, C., Backhaus, R. A., Camara, B. (1998) Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits, Plant Physiol. 117, 1423–1431.
- Broers, S. T. J. (1994) I. Über die frühen Stufen der Biosynthese von Isoprenoiden in Escherichia coli. II. Beitrag zur Aufklärung des Biosynthese von Vitamin B12 in Propionibacterium shermanii, Ph.D. Thesis Nb 10978, Eidgenössische Technische Hochschule, Zürich, Switzerland.
- Cane, D. E., Du, S. C., Robinson, J. K., Hsiung, Y. J., Spenser, I. D. (1999) Biosynthesis of vitamin B6: enzymatic conversion of 1-deoxy-D-xylulose 5-phosphate to pyridoxol phosphate, J. Am. Chem. Soc. 121, 7722–7723.
- Charon, L., Pale-Grosdemange, C., Rohmer, M. (1999) On the reduction steps in the mevalonate-independent 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in the bacterium Zymomonas mobilis, Tetrahedron Lett. 40, 7231–7234.
- Charon, L., Hoeffler, J. F., Pale-Grosdemange, C., Lois, L. M., Campos, N., Boronat, A., Rohmer, M. (2000) Deuterium-labelled isotopomers of 2-C-methyl-D-erythritol as tools for the elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis, Biochem. J. 346, 737–742.
- Connolly, J. D., Hill, R. A. (1992) Dictionary of Terpenoids, New York: Chapman & Hall.
- Contin, A., van der Heijden, R., Lefeber, A. W. M., Verpoorte, R. (1998) The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture, FEBS Lett. 434, 413–416.
- Cvejic, J. H., Rohmer, M. (2000) 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.
- David, S., Estramareix, B., Fischer, J. C., Thérisod, M. (1981) 1-Deoxy-D-threo-2-pentulose: the precursor of the five-carbon chain of the thiazole of thiamine, J. Am. Chem. Soc. 103, 7341–7342.
- Disch, A., Hemmerlin, A., Bach, T., Rohmer, M. (1998a) Mevalonate-derived isopentenyl diphosphate is the precursor of ubiquinone prenyl side-chain in tobacco BY-2 cells, Biochem. J. 331, 615–621.
- Disch, A., Schwender, J., Müller, C., Lichtenthaler, H. K., Rohmer, M. (1998b) Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathway for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714, Biochem. J. 333, 381–388.
- Duvold, T., Bravo, J. M., Pale-Grosdemange, C., Rohmer, M. (1997a) Biosynthesis of 2-C-methyl-D-erythritol, a putative C5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis, Tetrahedron Lett. 38, 4769–4772.
- Duvold, T., Cali, P., Bravo, J. M., Rohmer, M. (1997b) 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, 6181–6184.
- Eichinger, D., Bacher, A., Zenk, M. H., Eisenreich, W. (1999) Analysis of metabolic pathways via quantitative prediction of isotope labeling patterns: a retrobiosynthetic 13C NMR study on the monoterpene loganin, Phytochemistry 51, 223–236.
- Eisenreich, W., Menhard, B., Hylands, P. J., Zenk, M. H., Bacher, A. (1996) Studies on the biosynthesis of taxol: the taxane skeleton is not of mevalonoid origin, Proc. Natl. Acad. Sci. USA 93, 6431–6436.
- Eisenreich, W., Sagner, S., Zenk, M., Bacher, A. (1997) Monoterpenoid essential oils are not of mevalonoid origin, Tetrahedron Lett. 3, 3889–3892.
- Eisenreich, W., Schwarz, M., Cartayrade, A., Arigoni, D., Zenk, M. H., Bacher, A. (1998) The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms, Chem. Biol. 5, R221–R233.
- Fellermeier, M. A., Maier, U. H., Sagner, S., Bacher, A., Zenk, M. H. (1998) (-)-2C-Methyl-D-erythrono-1,4-lactone is formed after application of the terpenoid precursor 1-deoxy-D-xylulose, FEBS Lett. 437, 278–280.
- Fellermeier, M., Kis, K., Sagner, S., Maier, U., Bacher, A., Zenk, M. (1999) Cell-free conversion of 1-deoxy-D-xylulose and 2-C-methylerythritol 4-phosphate into β-carotene in higher plants and its inhibition by fosmidomycin, Tetrahedron Lett. 40, 2743–2746.
- Flesch, G., Rohmer, M. (1988) Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeleton. Formation of isoprenic units from two distinct acetate pools and a novel type of carbon/carbon linkage between a triterpene and D-ribose, Eur. J. Biochem. 175, 405–411.
- Follens, A., Veiga Da Cunha, M., Merckx, R., Van Schaftingen, E., Van Eldere, J. (1999) acs1 of Haemophilus influenzae type a capsulation locus region II encodes a bifunctional ribulose 5-phosphate reductase-CDP-ribitol pyrophosphorylase, J. Bacteriol. 181, 2001–2007.
- Fowler, D. J., Hamilton, J. T. G., Humphrey, A. J., O'Hagan, D. (1999) Plant terpene biosynthesis. The biosynthesis of linalyl acetate in Mentha citrata, Tetrahedron Lett. 40, 3803–3806.
- Giner, J. L., Jaun, B. (1998) Biosynthesis of isoprenoids in Escherichia coli: retention of the methyl H-atoms of 1-deoxy-D-xylulose, Tetrahedron Lett. 39, 8021–8022.
- Giner, J. L., Jaun, B., Arigoni, D. (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. 1857–1858.
- Hahn, F. M., Hurburt, A. P., Poulter, C. D. (1999) Escherichia coli open reading frame 696 is idi, a nonessential gene encoding isopentenyl diphosphate isomerase, J. Bacteriol. 181, 4499–4504.
- Harker, M., Bramley, P. M. (1999) Expression of prokaryotic 1-deoxyxylulose-5-phosphatase in Escherichia coli increases carotenoid and ubiquinone biosynthesis, FEBS Lett. 448, 115–119.
- Hayashi, T., Asai, T., Sankawa, U. (1999) Mevalonate-independent biosynthesis of bicyclic and tetracyclic diterpenes of Scoparia dulcis L., Tetrahedron Lett. 40, 8239–8243.
- Herz, S., Wungsintaweekul, J., Schuhr, C. A., Hecht, S., Lüttgen, H., Sagner, S., Fellermeier, M., Eisenreich, W., Zenk, M. H., Bacher, A., Rohdich, F. (2000) Biosynthesis of terpenoids: YgbP protein converts 4-diphosphocytidyl)-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol to 2,4-cyclodiphosphate, Proc. Natl. Acad. Sci. USA 97, 2486–2490.
- Hoeksema, H., Baczynskyj, L. (1976) A new metabolite from Streptomyces hygroscopicus. II. Identification as 1-deoxy-D-threo-pentulose, J. Antibiot. 29, 688–690.
- Horbach, S., Sahm, H., Welle, R. (1993) Isoprenoid biosynthesis in bacteria: two different pathways? FEMS Microbiol. Lett. 111, 135–140.
- Jomaa, H., Feurle, J., Lühs, K., Kunzmann, V., Tony, H. P., Herderich, M., Wilhelm, M. (1999a) Vγ9/Vδ2 T cells activation induced by bacterial low molecular mass compounds on the 1-deoxy-D-xylulose 5-phosphate pathway of isoprenoid biosynthesis, FEMS Immunol. Med. Microbiol. 25, 371–378.
- Jomaa, H., Wiesner, J., Sanderbrand, S., Altinciek, B., Weidemeyer, C., Hintz, M., Türbachova, I., Eberl, M., Zeidler, J., Lichtenthaler, H. K., Soldati, D., Beck, E. (1999b) Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs, Science 285, 1573–1576.
- Kennedy, I. A., Hill, R. E., Paulowski, R. M., Sayer, B. G., Spenser, I. D. (1995) Biosynthesis of vitamin B6: origin of pyridoxine by the union of two acyclic precursors, 1-deoxy-D-xylulose and 4-hydroxy-L-threonine, J. Am. Chem. Soc. 117, 1661–1662.
- Knöss, W., Reuter, B., Zapp, J. (1997) Biosynthesis of the labdane triterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway, Biochem. J. 326, 449–454.
- Kreuz, K., Kleinig, H. (1981) On the compartmentation of isopentenol diphosphate synthesis and utilization in plant cells, Planta 153, 578–581.
- Kreuz, K., Kleinig, H. (1984) Synthesis of prenyl lipids in cells of spinach leaf; compartmentation of enzymes for formation of isopentenyl diphosphate, Eur. J. Biochem. 141, 531–535.
- Kuzuyama, T., Shimizu, T., Takahashi, S., Seto, H. (1998a) Fosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis, Tetrahedron Lett. 39, 7913–7916.
- Kuzuyama, T., Takahashi, S., Watanabe, H., Seto, H. (1998b) Direct formation of 2-C-methyl-D-erythritol 4-phosphate from 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate, Tetrahedron Lett. 39, 4509–4512.
- Kuzuyama, T., Takagi, M., Kaneda, K., Dairi, T., Seto, H. (2000a) Formation of 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol 4-phosphate by 2-C-methyl erythritol 4-phosphate by 2-C-methyl-D-erythritol 4-phosphate cytidyltransferase, a new enzyme in the nonmevalonate pathway, Tetrahedron Lett. 41, 703–706.
- Kuzuyama, T., Takagi, M., Kaneda, K., Watanabe, H., Dairi, T., Seto, H. (2000b) Studies on the nonmevalonate pathway: conversion of 4-(cytidine 50-diphospho)-2-C-methyl-D-erythritol to its 2-phospho derivative by 4-(cytidine 50-diphospho)-2-C-methyl-D-erythritol kinase; Tetrahedron Lett. 41, 2925–2928.
- Kuzuyama, T., Takagi, M., Takahashi, S., Seto, H. (2000c) Cloning and characterization of 1-deoxy-D-xylulose 5-phosphate synthase from Streptomyces sp. strain CL 190, which uses both the mevalonate and nonmevalonate pathways for isopentenyl diphosphate biosynthesis, J. Bacteriol. 182, 891–897.
- Lange, B. M., Croteau, R. (1999) Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: cloning and heterologous expression of 1-deoxy-D-xylulose-5-phosphate reductoisomerase in peppermint, Arch. Biochem. Biophys. 365, 170–174.
- Lange, B. M., Wildung, M. R., McCaskill, D., Croteau, R. (1998) A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway, Proc. Natl. Acad. Sci. USA 95, 2100–2104.
- Lichtenthaler, H. K. (1999) The 1-deoxy-D-xylulose 5-phosphate pathway of isoprenoid biosynthesis in plants, Annu. Rev. Plant Physiol. Plant Mol. Biol. 50, 47–65.
- Lois, L. M., Campos, N., Rosa Putra, S., Danielsen, K., Rohmer, M. (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, 2105–2110.
- Lois, L. M., Rodriguez-Concepcion, M., Gallego, F., Campos, N., Boronat, A. (2000) Carotenoid biosynthesis during tomato fruit development: regulatory role of 1-deoxy-D-xylulose 5-phosphate synthase, Plant J. 22, 1–11.
- Lüttgen, H., Rohdich, F., Herz, S., Wungsintaweekul, J., Hecht, S., Schuhr, C. A., Fellermeier, M., Sagner, S., Zenk, M. H., Bacher, A., Eisenreich, W. (2000) Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol, Proc. Natl. Acad. Sci. USA 97, 1062–1067.
- Maier, W., Schneider, B., Strack, D. (1998) Biosynthesis of sesquiterpenoid cyclohexenone derivatives in mycorrhizal barley roots proceeds via the glyceraldehyde 3-phosphate/pyruvate pathway, Tetrahedron Lett. 39, 521–524.
- Mandel, M. A., Feldmann, K. A., Herrera-Estrella, L., Rocha-Sosa, M., Leon, P. (1996) CLA1, a novel gene required for chloroplast development, is highly conserved in evolution, Plant J. 9, 649–658.
- Matthews, P. D., Wurtzel, E. T. (2000) Metabolic engineering of carotenoid accumulation in Escherichia coli by modulation of the isoprenoid precursor pool with expression of deoxyxylulose synthase, Appl. Microbiol. Biotechnol. 53, 396–400.
-
Millborrow, B. V.,
Lee, H. S.
(1998)
Endogenous biosynthetic precursors of (+)-abscisic acid. VI carotenoids and ABA are formed by the ‘non-mevalonate’ triose-pyruvate pathway in chloroplasts,
Aust. J. Plant Physiol. 25,
507–512.
10.1071/PP98006 Google Scholar
- Miller, B., Heuser, T., Zimmer, W. (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, 485–490.
- Nabeta, K., Ishikawa, T., Kawae, T., Okuyama, H. (1995a) Biosynthesis of heteroscyphic acid A in cell cultures of Heteroscyphus planus: nonequivalent labelling of C-5 units in diterpene biosynthesis, J. Chem. Soc., Chem Commun. 681–682.
- Nabeta, K., Ishikawa, T., Kawae, T., Okuyama, H. (1995b) Sesqui- and di-terpene biosynthesis from 13C labelled acetate and mevalonate in cultures cells of Heteroscyphus planus, J. Chem. Soc., Perkin Trans. 1, 3111–3115.
- Nabeta, K., Kawae, T., Saitoh, T., Kikuchi, T. (1997) Synthesis of chlorophyll a and β-carotene from 2H- and 13C-labelled mevalonates and 13C-labelled glycine in cultured cells of liverworts Heteroscyphus planus and Lophoclea heterophylla, J. Chem. Soc., Perkin Trans. 1, 261–267.
- Nabeta, K., Saitoh, T., Dachi, K., Komuro, K. (1998) Biosynthesis of phytyl side-chain of chlorophyll a: apparent reutilization of carbon dioxide evolved during acetate assimilation in biosynthesis of chloroplastidic isoprenoid, J. Chem. Soc., Chem. Commun. 671–672.
- Nakanishi, K. (1999) An historical perspective of natural products chemistry, in: Comprehensive Natural Product Chemistry, Isoprenoids Including Carotenoids and Steroids ( D.E. Cane, Ed.), vol. 2, pp. xxi–xxxviii. Oxford: Pergamon Press.
- Ourisson, G., Rohmer, M. (1992) Hopanoids. 2. Biohopanoids: a novel class of bacterial lipids, Acc. Chem. Res. 25, 403–407.
-
Piel, J.,
Donath, J.,
Bandemer, K.,
Boland, W.
(1998)
Mevalonate-independent biosynthesis of terpenoid volatiles in plants: induced and constitutive emission of volatiles,
Angew. Chem. Int. Ed. 37,
2478–2481.
10.1002/(SICI)1521-3773(19981002)37:18<2478::AID-ANIE2478>3.0.CO;2-Q CAS PubMed Web of Science® Google Scholar
- Pandian, S., Saengchan, S., Raman, T. S. (1981) An alternative pathway for the biosynthesis of isoprenoid compounds in bacteria, Biochem. J. 196, 675–681.
- Proteau, P. J. (1998a) Biosynthesis of phytol in the cyanobacterium Synechocystis UTEX 2470: utilization of the non-mevalonate pathway, J. Nat. Prod. 61, 841–843.
- Proteau, P. J. (1998b) Probing the non-mevalonate pathway to phytol in the cyanobacterium Synechocystis sp. UTEX 2470 using deuterium-labeled glucose, Tetrahedron Lett. 39, 9373–9376.
- Proteau, P. J., Woo, Y. H., Williamson, T., Phaosiri, C. (1999) Stereochemistry of the reduction step mediated by recombinant 1-deoxy-D-xylulose 5-phosphate isomeroreductase, Org. Lett. 1, 921–923.
- Qureshi, N., Porter, J. W. (1981) Conversion of acetyl-coenzyme A to isopentenyl pyrophosphate, in: Biosynthesis of Isoprenoid Compounds ( J. W. Porter, S. L. Spurgeon, Eds.), vol. 1, pp. 47–94. New York: John Wiley & Sons.
- Radykewicz, T., Rohdich, F., Wungsintaweekul, J., Herz, S., Kis, K., Eisenreich, W., Bacher, A., Zenk, M. H., Arigoni, D. (2000) Biosynthesis of terpenoids: 1-deoxy-D-xylulose-5-phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase, FEBS Lett. 465, 157–160.
- Rittenberg, D., Schönheimer, R. (1937) Deuterium as indicator in the study of intermediary metabolism. XI. Further studies on the biological uptake of deuterium into organic substances, with special reference to fat and cholesterol formation, J. Biol. Chem. 121, 235–253.
- Rodriguez-Concepcion, M., Campos, N., Lois, L. M., Maldonaldo, C., Hoeffler, J. F., Grosdemange-Billiard, C., Rohmer, M., Boronat, A. (2000) Genetic evidence of branching in the isoprenoid pathway of isopentenyl diphosphate and dimethylallyl diphosphate in Escherichia coli, FEBS Lett. 473, 328–332.
- Rohdich, F., Wungsintaweekul, J., Fellermeier, M., Sagner, S., Herz, S., Kis, K., Eisenreich, W., Bacher, A., Zenk, M. (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, 11758–11763.
- Rohdich, F., Wungsintaweekul, J., Eisenreich, W., Richter, G., Schuhr, C. A., Hecht, S., Zenk, M., Bacher, A. (2000) Biosynthesis of terpenoids: 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase of Arabidopsis thaliana, Proc. Natl. Acad. Sci. USA 97, 6451–6456.
- Rohmer, M. (1993) The biosynthesis of triterpenoids of the hopane series in the Eubacteria: a mine of new enzyme reactions, Pure Appl. Chem. 65, 1293–1298.
-
Rohmer, M.
(1999a)
A mevalonate-independent route to isopentenyl diphosphate, in: Comprehensive Natural Product Chemistry, Isoprenoids Including Carotenoids and Steroids ( D.E. Cane, Ed.), vol. 2, pp. 45–67. Oxford: Pergamon Press.
10.1016/B978-0-08-091283-7.00036-9 Google Scholar
- Rohmer, M. (1999b) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants, Nat. Prod. Rep. 16, 565–574.
- Rohmer, M., Knani, M., Simonin, P., Sutter, B., Sahm, H. (1993) Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate, Biochem. J. 295, 517–524.
- Rohmer, M., Seemann, M., Horbach, S., Bringer-Meyer, S., Sahm, H. (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, 2564–2566.
-
Rosa Putra, S.,
Charon, L.,
Danielsen, K.,
Pale-Grosdemange, C.,
Lois, L. M.,
Campos, N.,
Boronat, A.,
Rohmer, M.
(1998a)
5-Hydroxypentane-2,3-dione (laurencione), a bacterial metabolite of 1-deoxy-D-threo-pentulose,
Tetrahedron Lett. 39,
6185–6188.
10.1016/S0040-4039(98)01301-X Google Scholar
- Rosa Putra, S., Disch, A., Bravo, J.-M., Rohmer, M. (1998b) Distribution of mevalonate and glyceraldehyde 3-phosphate/pyruvate routes for isoprenoid biosynthesis in some Gram-negative bacteria and mycobacteria, FEMS Microbiol. Lett. 164, 169–175.
- Rosa Putra, S., Lois, L. M., Campos, N., Boronat, A., Rohmer, M. (1998c) Incorporation of [2,3-13C2]- and [2,4-13C2]-D-1-deoxyxylulose into ubiquinone of Escherichia coli via the mevalonate-independent pathway or isoprenoid biosynthesis, Tetrahedron Lett. 39, 23–26.
- Ruzicka, L. (1959) History of the isoprene rule: Faraday lecture, Proc. Chem. Soc. 341–360.
- Ruzicka, L., Eschenmoser, A., Heusser, H. (1953) The isoprene rule and biogenesis of terpenic compounds, Experientia 9, 357–396.
- Sagner, S., Eisenreich, W., Fellermeier, M., Latzel, C., Bacher, A., Zenk, M. (1998) Biosynthesis of 2-C-methyl-D-erythritol in plants by rearrangement of the terpenoid precursor 1-deoxy-D-xylulose 5-phosphate, Tetrahedron Lett. 39, 2091–2094.
- Schwarz, M. K. (1994) Terpen-Biosynthese in Ginkgo biloba: eine überraschende Geschichte, Ph.D. Thesis Nb 10951, Eidgenössische Technische Hochschule, Zürich, Switzerland.
-
Schwarz, M.,
Arigoni, D.
(1999)
Ginkgolide biosynthesis, in: Comprehensive Natural Product Chemistry, Isoprenoids Including Carotenoids and Steroids ( D.E. Cane, Ed.), vol. 2, pp. 367–400. Oxford: Pergamon Press.
10.1016/B978-0-08-091283-7.00043-6 Google Scholar
-
Schwender, J.,
Seemann, M.,
Lichtenthaler, H. K.,
Rohmer, M.
(1996)
Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate pathway,
Biochem. J. 306,
73–80.
10.1042/bj3160073 Google Scholar
- Schwender, J., Zeidler, J., Gröner, R., Müller, C., Focke, M., Braun, S., Lichtenthaler, F. W., Lichtenthaler, H. K. (1997) Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae, FEBS Lett. 414, 129–134.
- Schwender, J., Müller, C., Zeidler, J., Lichtenthaler, H. K. (1999) Cloning and heterologous expression of a cDNA encoding 1-deoxy-xylulose-5-phosphate reductoisomerase of Arabidopsis thaliana, FEBS Lett. 455, 140–144.
- Seto, H., Watanabe, Furihata, K. (1996) Simultaneous operation of the mevalonate and non-mevalonate pathways in the biosynthesis of isopentenyl diphosphate in Streptomyces aeriouvifer, Tetrahedron Lett. 37, 7979–7982.
- Seto, H., Orihara, N., Furihata, K. (1998) Studies on the biosynthesis of terpenoids produced by actinomycetes. Part. 4. Formation of BE-40644 by the mevalonate and nonmevalonate pathways, Tetrahedron Lett. 39, 9497–9500.
- Shigi, Y. (1989) Inhibition of bacterial isoprenoid biosynthesis by fosmidomycin, a phosphonic acid-containing antibiotic, J. Antimicrob. Chemother. 24, 131–145.
- Skeggs, H. R., Wright, L. D., Cresson, E. L., MacRae, G. D. E., Hoffman, C. H., Wolff, D. E., Folkers, K. (1956) Discovery of a new acetate-replacing factor, J. Bacteriol. 72, 519–524.
- Skoczylas, E., Swiezewska, E., Chojnacki, T., Tanaka, Y. (1994) Long-chain rubber-like polyisoprenoid alcohols in leaves of Lumnitzera racemosa, Plant Physiol. Biochem. 32, 825–829.
- Sprenger, G. A., Schörken, Wiegert, T., Grolle, S., de Graaf, A., Taylor, S. V., Begley, T. P., Bringer-Meyer, S., Sahm, H. (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, 12857–12862.
- Spurgeon, S. L., Porter, J. W. (1981) Introduction, in: Biosynthesis of Isoprenoid Compounds ( J. W. Porter, S. L. Spurgeon, Eds.), vol. 1, pp. 1–46. New York: John Wiley & Sons.
- Stanjek, V., Piel, J., Boland, W. (1999) Biosynthesis of furanocoumarins: mevalonate-independent prenylation of umbeliferone in Apium graveolens (Apiaceae), Phytochemistry 50, 1141–1145.
- Takagi, M., Kuzuyama, T., Kaneda, K., Watanabe, H., Dairi, T., Seto, H. (2000) Studies on the nonmevalonate pathway: formation of 2-C-methyl-D-eythritol 2,4-cyclodiphosphate from 2-phospho-4-(cytidine 50-diphospho)-2-C-methyl-D-erythritol, Tetrahedron Lett. 41, 3395–3398.
- Takahashi, S., Kuzuyama, T., Watanabe, H., Seto, H. (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, 9879–9884.
- Thiel, R., Adam, K. P., Zapp, J., Becker, H. (1997) Isopentenyl diphosphate biosynthesis in liverworts, Pharm. Pharmacol. Lett. 7, 103–105.
- Treharne, K. J., Mercer, E. I., Goodwin, T. W. (1966) Incorporation of [14C]carbon dioxide and [2-14C]mevalonic acid into terpenoids from higher plants during chloroplast development, Biochem. J. 99, 239–245.
-
Wallach, O.
(1887)
Zur Kenntnis der Terpene und ätherischen Öle,
Liebigs Ann. Chem. 239,
1–54.
10.1002/jlac.18872390102 Google Scholar
- Walter, M. H., Fester, T., Strack, D. (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, 571–578.
- Wright, L. D., Emlen, L., Skeggs, H. R., MacRae, G. D. E., Hoffman, C. H., Wolf, D. E., Folkers, K. (1956) Isolation of a new acetate-replacing factor, J. Am. Chem. Soc. 78, 5273–5275.
- Yokota, A., Sasajima, K. I. (1984) Formation of 1-deoxy-D-threo-pentulose and 1-deoxy-L-threopentulose by cell-free extracts of microorganisms, Agric. Biol. Chem. 48, 149–158.
- Yokota, A., Sasajima, K. I. (1986) Formation of 1-deoxy-ketoses by pyruvate dehydrogenase and acetoin dehydrogenase, Agric. Biol. Chem. 50, 2517–2524.
-
Zeidler, J. G.,
Lichtenthaler, H. K.,
May, H. U.,
Lichtenthaler, F. W.
(1997)
Is isoprene emitted by plants synthesized via the novel isopentenyl pyrophosphate pathway? Z. Naturforsch. 52c,
15–23.
10.1515/znc-1997-1-204 Google Scholar
-
Zeidler, J.,
Schwender, J.,
Müller, C.,
Wiesner, J.,
Weidemeyer, C.,
Beck, E.,
Jomaa, H.,
Lichtenthaler, H. K.
(1998)
Inhibition of the non-mevalonate 1-deoxy-D-xylulose 5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin,
Z. Naturforsch. 53c,
980–936.
10.1515/znc-1998-11-1208 Google Scholar
- Zhou, D., White, R. H. (1991) Early steps of isoprenoid biosynthesis in Escherichia coli, Biochem. J. 273, 627–634.
- Zhou, W. X., Nes, W. D. (2000) Stereochemistry of hydrogen introduction at C-25 in ergosterol synthesized by the non-mevalonate pathway, Tetrahedron Lett. 41, 2791–2795.
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