D-Erythritol

D-arab/no-Hexos-2-ulose phenylosotriazole or (1 fl)-1-(2-phenyl-2H-1,2,3-triazol-4-yl))-D-erythritol or 2-phenyl-4-(D-arab/no-1,2,3,4-tetrahydroxybutyl)-2H-1,2,3-triazole... 

D-glyceraldehyde-3-phosphate, pyruvate (G3P) l-deoxy-D-xylulose-5-phosphate (DXP) 2C-methyl-D-erythritol-4-phosphate (MEP) 4-diphosph-2C-methyl-D-erythritol (CDP-ME) 4-diphosphocytidyl-2C-methyl-D-erythritol-2-phophate (CDP-MEP)... 

C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-cPP) l-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate (HMBPP)... 

There are two distinct pathways for biosynthesis of the IPP and DMAPP the mevalonate (MVA) pathway and the DXP pathway (Figure 12.3). The MVA pathway functions primarily in eukaryotes, while the DXP pathway is typically present in prokaryotes and the plastids of plants [90,91]. The first reaction in the DXP pathway is the condensation of pyruvate and D-glyceraldehyde-3-phosphate (G3P) to form DXP, which is catalyzed by DXP synthase encoded by the gene dxs [92]. In the second step, DXP is reduced to 2-C-methyl-D-erythritol-4-phosphate (MEP) by DXP reductoisomerase, which is encoded by the gene dxr (ispC) in E. coli. An array of other enzymes encoded by is pi), ispE, ispF, ispG, and ispH act in subsequent sequential reactions, leading to the conversion of MEP to IPP and DMAPP, which are interconverted by the enzyme encoded by idi [93-97],... 

Luttgen, H., Rohdich, F., Herz, S. et al. (2000) Biosynthesis of terpenoids YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Proceedings of the National Academy of Sciences of the United States of America, 97, 1062-1067. 

Figure 9.4 Monoterpene biosynthesis in peppermint oil gland secretory cells. The enzymes involved in this pathway are (1) 1-deoxy-D-xylulose 5-phosphate synthase, (2) 2-C-methyl-D-erythritol 4-phosphate reductoisomerase, (3) 2-C-methyl-D-erythritol 4-phosphate cytidyltransferase, (4) 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol kinase, (5) 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, (6) isopentenyl diphosphate isomerase, (7) geranyl diphosphate synthase, (8)...

It had been suggested that the second step of the mevalonate-independent pathway involved an intramolecular rearrangement and subsequent reduction of DXP to yield 2-C-methyl-D-erythritol 4-phosphate (Fig. 9.6A).29-3 Seto and co-workers reported the isolation, by using a mutant complementation approach, and characterization of such a reductoisomerase gene from E. coli)2 Based on likely... 

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. 

SAGNER, S., EISENREICH, W., FELLERMEIER, M LATZEL, C., BACHER, A., ZENK, M.H., Biosynthesis of 2-C-methyl-D-erythritol in plants by rearrangement of the terpenoid precursor, 1-deoxy-D-xylulose 5-phosphate, Tetrahedron Lett., 1998, 39, 2091-2094. 

TAKAHASHI, S., KUZUYAMA, T WATANABE H., SETO, H., A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway, Proc. Natl. Acad. Sci. USA, 1998, 95, 9879-9884. 

KUZUYAMA, T., TAKAGI, M., KANEDA, K, WATANABE, H, DAIRI, T., SETO, H., Studies on the nonmevalonate pathway conversion of 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol to its 2-phospho derivative by 4-(cytidine 5 -diphospho)-2-C-methyl-D-erythritol kinase, Tetrahedron Lett., 2000, 41, 2925-2928. 

The CPPase substrate DMAPP (15) is formed from isopentenyl pyrophosphate (IPP) (14) via the IPP isomerase reaction. It had been assumed that IPP was generated only via mevalonic acid (12) (Fig. 2), but Rohmer discovered another route, 2-C-methyl-D-erythritol 4-phosphate (13) (MEP) pathway (Fig. 2) [22, 23]. A key step in the MEP pathway is the reaction catalyzed by 1-deoxy-D-xylulose 5-phosphate synthase (DXS), which combines hydroxyethyl thiamine pyrophosphate (hydroxyethyl TPP) generated from pyruvic acid (17) and TPP with glyceral-dehyde 3-phosphate (18) to yield 1-deoxy-D-xylulose 5-phosphate (19) containing five carbons. The mevalonate pathway operates in the cytosol of plants and animals, whereas the MEP pathway is present in the plastid of plants or in eubacteria [24-27]. 

Fig. 2 Two possible biosynthetic pathways to pyrethrolone. The [l-13C]D-glucose-derived 13C labels that occur in the mevalonic acid and 2-C-methyl-D-erythritol 4-phosphate (13) pathways are colored in red and green, respectively. The phosphate moiety is indicated as P ...

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... 

It has been established" that the leaves of Liriodendron tulipifera convert 1-deoxy-D-xylulose (285) into 2-C-methyl-D-erythritol (286) via a skeletal rearrangement (see Scheme 90) reminiscent of the formation of terpene precursors from 1-deoxy-D-xylulose 4-phosphate. An esterase-catalysed regioselective 6-deacylation of... 

Gerber E, Hemmerlin A, Hartmann M, Heintz D, Hartmann MA, Mutterer J, Rodriguez-Concepcion M, Boronat A, Van Dorsselaer A, Rohmer M, CroweU DN, Bach TJ (2009) The plastidial 2-C-methyl-D-erythritol 4-phosphate pathway provides the isoprenyl moiety for protein geranylgeranylation in tobacco BY-2 ceUs. Plant Cell 21 285-300... 

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