1-Deoxyxylulose 5-phosphate pathway, terpenoid

Dewick, P.M. (2001) The mevalonate and deoxyxylulose phosphate pathways terpenoids and steroids. In P.M. Dewick (ed.). Medicinal Natural Products A Biosynthetic Approach, 2nd edn. John WUey Sons Ltd., Chichester, pp. 167-289. 

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. 

EISENREICH, W., ROHDICH, F., BACHER, A., Deoxyxylulose phosphate pathway to terpenoids, Trends Plant Sci., 2001,6, 78-84. 

S ATP + 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol <1> (<1> involved in terpenoid biosynthesis via deoxyxylulose phosphate pathway... 

In the 1970s the biosynthesis of cannabinoids was investigated with radiolabeling experiments. 14C-labeled mevalonate and malonate were shown to be incorporated into tetrahydrocannabinolic acid and cannabichromenic acid at very low rates (< 0.02%). Until 1990 the precursors of all terpenoids, isopentenyl diphosphate and dimethyl-allyl diphosphate were believed to be biosynthesized via the mevalonate pathway. Subsequent studies, however, proved that many plant terpenoids are biosynthesized via the recently discovered deoxyxylulose phosphate pathway (Eisenreich et al., 1998 Rohmer, 1999). It was shown that the Cio-terpenoid moiety of cannabinoids is biosynthesized entirely or predominantly (>98%) via this pathway (Fellermeister et al., 2001). The phenolic moiety is generated by a polyketide-type reaction sequence. 

For convenience, the major oils listed are divided into two groups. Those which contain principally chemicals which are aromatic in nature and which are derived by the shikimate pathway are given in Table 4.1 below. Those oils which are composed predominantly of terpenoid compounds are listed in Table 5.1 on page 177, since they are derived via the deoxyxylulose phosphate pathway. It must be appreciated that many oils may contain aromatic and terpenoid components, but usually one group predominates. The oil yields, and the exact composition of any sample of oil will be variable, depending on the particular plant material used in its preparation. The quality of an oil and its commercial value is dependent on the proportion of the various components. 

Eisenreich, W., Schwarz, M., Cartayrade, A., Arigoni, D., Zenk, M.H., and Bacher, A. (1998). The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms. Chem Biol 5 R221-R233. 

Marine macroalgae produce a wide variety of intriguing and diverse isoprenoid structures derived from C5 isoprene units, and many reports have been published on the ecological roles of these metabolites. Marine terpenoids are frequently found with halogenated functionalities and one or more rings, which can have important implications for their biological activities. Isoprenoid metabolites are derived via the classical mevalonate pathway or the more recently discovered deoxyxylulose phosphate pathway. Isoprenoids are... 

McCASKILL, D., CROTEAU, R., Isopentenyl diphosphate is the terminal product of the deoxyxylulose 5-phosphate pathway for terpenoid biosynthesis in plants, Tetrahedron Lett., 1999,40,653-656. 

FROM ACETATE TO ME VALONATE AND DEOXYXYLULOSE PHOSPHATE BIOSYNTHETIC PATHWAYS AN INTRODUCTION TO TERPENOIDS... 

Biosynthetically, all terpenoids are traced back to a common synthon of biochemically active isoprene unit found in the forms of pyrophosphate esters either as dimeth-ylallyl diphosphate (DMAPP) or isopentenyl diphosphate (IPP) (Fig. 5.1). In turn, DMAPP and IPP are derived by two distinct biosynthetic pathways, the mevalonate pathway (MVA pathway) and the mevalonate-independent pathway or pathway of deoxyxylulose phosphate (DXP pathway), which are considered to be the major natural synthetic routes for the synthesis of terpenoids (Fig. 5.2). 

The terpenoid precursor isopentenyl diphosphate, formerly called isopentenyl pyrophosphate and abbreviated IPP, is biosynthesized by two different pathways depending on the organism and the structure of the final product. In animals and higher plants, sesquiterpenoids and triterpenoids arise primarily from the mevalonate pathway, whereas monoterpenoids, diterpenoids, and tetraterpenoids are biosynthesized by the 1-deoxyxylulose 5-phosphate (DXP) pathway. In bacteria,... 

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