Isoprenoids biosynthesis pathways

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 ... 

De novo synthesis of cholesterol is catalyzed by the isoprenoid biosynthesis pathway. This pathway produces a variety of sterol and nonsterol isoprenoids with... 

Boucher, Y., and Doolittle, W.F. (2000). The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways. Mol Microbiol 37 703-716. 

Schuhr C, Radykewicz Sagner S, Latzel C, Zenk MH, Arigoni D, Bacher A, Rohdich F, Eisenreich W. Quantitative assessment of crosstalk between the two isoprenoid biosynthesis pathways by NMR spectroscopy. Phytochem. Rev. 2003 2 3-16. 

Poly(c -l,4-isoprene) belongs to the family of polyisoprenoids, which are the most structurally diverse and abundant natural products known, with more than 23,000 primary and secondary metabolites. This huge family comprises, for example, sterols which display not only structural functions (control of biological membrane fluidity) but also hormonal functions (steroid hormones). Key phyto-hormones, such as abscisic acid, gibberellins and cytokinins, are isoprenoids too. Moreover, isoprenoids are used in protein prenylation, which is a key step in the activation and the localization of metabolic enzymes in many organisms. The first common step of all isoprenoid biosynthesis pathways is the formation of isopentenyl diphosphate (IPP). ... 

Metabolism employs phosphorus compounds in many ways. Phosphate esters are central to information storage, serve as the currency for energy exchange, and contribute to membrane fluidity. They are important intermediates in carbohydrate metabolism, in formation of nucleotides and their assembly into RNA and DNA, and in steroid fabrication and protein lipidation through the isoprenoid biosynthesis pathways. They hold key roles in cell signaling processes, including G-protein... 

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. 

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. 

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. 

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. 

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. 

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

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