Isoprenoids, biosynthesis

KAJIWARA s, FRASER p D, KONDO K and MISAWA N (1997) Expressiou of an exogenous isopentenyl diphosphate isomerase gene enhances isoprenoid biosynthesis in Escherichia coli Biochem J, 324, 421-6. 

LicHTENTHALER H K (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants , Ann Rev Plant Physiol Plant Mol Biol, 50, 47-65. 

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

Rodriguez-Concepcion, M. and Boronat, A., Elncidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in hacteria and plastids a metabolic milestone achieved throngh genomics. Plant Physiol. 130, 1079, 2002. Rodriguez-Concepcion, M., Early steps in isoprenoid biosynthesis multilevel regulation of the supply of common precursors in plant cells, Phytochem. Rev. 5, 1, 2006. Eisenreich, W., Rohdich, F., and Bacher, A., Deoxyxylulose phosphate pathway to terpenoids, Trends Plant Sci. 6, 78, 2001. 

Sprenger, G.A. et al.. 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, 1997. Lange, B.M. et al., A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway, Proc. Natl. Acad Sci. USA 95, 2100, 1998. Lois, L.M. et al., 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, 1998. 

Lichtenthaler, H.K. et al., The non-mevalonate isoprenoid biosynthesis of plants as a test system for new herbicides and drugs against pathogenic bacteria and the malaria parasite, Z. Naturforsch. C 55, 305, 2000. 

Laule, O. et al.. Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thabana, Pmc. Natl. Acad. Sci. USA 100, 6866, 2003. 

Hsieh, M.H. and Goodman, H.M., The Arabidopsis IspH homolog is involved in the plastid nonmevalonate pathway of isoprenoid biosynthesis, Plant Physiol. 138, 641, 2005. 

Shelton, D.A., Leach, D.N., and Henry, R.J., Isopentenyl pyrophosphate isomerases from Melaleuca altemifolia (Cheel) and their role in isoprenoid biosynthesis, J. Hort. 

Walter, M.H., Fester, T., and Strack, D., 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, 2000. 

Estevez, J.M. et al., l-Deoxy-D-xylulose-5-phosphate synthase, a limiting enzyme for plastidic isoprenoid biosynthesis in plants, J. Biol. Chem. 276, 22901, 2001. 

Lange, B.M., Rujan, T., Martin, W. and Croteau, R. (2000) Isoprenoid biosynthesis the evolution of two ancient and distinct pathways across genomes. Proceedings of the National Academy of Sciences of the United States of America, 97, 13172-13177. 

Disch, A., Schwender, J., Muller, C., Lichtenthaler, H.K., and Rohmer, M., Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyanobacterium Synechocystis PCC 6714, Biochem.., 333, 381, 1998. 

Figure 9.7 Separation and detection of intermediates of the mevalonate-independent pathway of isoprenoid biosynthesis by LC-MS extracted ion chromatograms at (A) m/z 213 (1-deoxy-D-xylulose 5-phosphate), (B) m/z 215 (2-C-methyl-D-erythritol 4-phosphate), (C) m/z 520 (4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol), (D) m/z 600 (2-...

Table 9.2 Incorporation rate of [2-14C]-pyruvate into monoterpenes of isolated peppermint oil gland secretory cells in the presence of fosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase, an enzyme of the mevalonate-independent pathway of isoprenoid biosynthesis.

The peppermint oil gland secretory cell cDNA library has proven to provide a highly enriched source of candidate genes involved in essential oil biosynthesis. A functional genomics approach has successfully been employed to clone genes involved in the mevalonate-independent pathway of isoprenoid biosynthesis and in the peppermint-specific steps producing (-)-menthol and (-)-menthone. The optimization of LC-MS technology to profile phosphoiylated carbohydrates and... 

LANGE, B.M., WILDUNG, M.R., McCASKILL, D., CROTEAU, R., A family of transketolases that directs isoprenoid biosynthesis via a mevalonate-independent pathway, Proc. Natl. Acad. Sci. USA, 1998, 95, 2100-2104. 

LANGE, B.M., KETCHUM, R.E.B., CROTEAU, R., Isoprenoid biosynthesis metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis, Plant Physiol., 2001,127, 305-314. 

ROHMER, M., KNANI, M., SIMONIN, P., SUTTER, B., SAHM, H., Isoprenoid biosynthesis in bacteria a novel pathway for the early steps leading to isopentenyl diphosphate, Biochem. J., 1993,295, 517-524. 

DUVOLD, T., BRAVO, J.-M., PALE-GROSDEMANGE, C., ROHMER, M., Biosynthesis of 2-C-methyl-D-erythritol, a putative C5 intermediate in the mevalonate independent pathway for isoprenoid biosynthesis, Tetrahedron Lett., 1997, 38, 4769-4772. 

ZEIDLER, J., SCHWENDER, J., MULLER, C WIESNER, J., WEIDEMEYER, C., BECK, E., JOMAA, H., LICHTENTHALER, H.K., Inhibition of the non-mevalonate 1-deoxy-D-xylulose 5-phosphate pathway of plant isoprenoid biosynthesis by fosmidomycin, Z. Naturforsch., 1998,53c, 980-986. 

Cvejic JH, Rohmer M (2000) C02 as main carbon source for isoprenoid biosynthesis via the mevalonate-independent methylerythritol 4-phosphate route in the marine diatoms Phaeodactylum tricomutum and Nitzschia ovalis. Phytochemistry 53 21-28 de Nys R, Steinberg PD, Willemsen P, Dworjanyn SA, Gabelish CL, King RJ (1995) Broad-spectrum effects of secondary metabolites from the red alga Delisea pulchra in antifouling assays. Biofouling 8 259-271... 

Lichtenthaler HK, Rohmer M, Schwender J (1997) Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiol Plantarum... 

Wanke M, Skorupinska-Tudek K, Swiezewska E (2001) Isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway. Act... 

Besumbes O, Sauret-Giieto S, Phillips MA, Imperial S, Rodn guez-Concepcion M, Boronat A. (2004) Metabolic engineering of isoprenoid biosynthesis in Arabidopsis for the production of taxadiene, the first committed precursor of taxol. Biotechnol Bioeng 88 168-175. 

Liu Y, Wang H, Ye H-C, Li G-F. (2005) Advances in the plant isoprenoid biosynthesis pathway and its metabolic engineering. J Integr Plant Biol 47 769-782. 

C-methyl-D-erythritol 2,4-cyclodiphosphate synthase catalyses the conversion of 4-diphospho-cytidyl-2-C-methyl-D-erythritol 2-phosphate to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP) (Equation (7)). This reaction is part of the isoprenoid biosynthesis pathway in many plants and bacteria. The structure of the E. coli enzyme bound to Mn, cytosine monophosphate, and 2-C-methyl-D-erythritol 2,4-cyclodiphosphate has been determined. The enzyme in the crystal and probably in solution is trimeric, three monomers are packed in a circular assembly with three-fold symmetry. The active site is at the interface of two adjacent monomers all the ligands bound to the Mn + come from one monomer and a MECDP molecule. The structure of this active site is shown in Figure 29 ... 

---