4-Diphosphocytidyl-2-C-methylerythritol
Chemical compound
From Wikipedia, the free encyclopedia
4-Diphosphocytidyl-2-C-methylerythritol (or CDP-ME) is an intermediate in the MEP pathway (non-mevalonate pathway) of isoprenoid precursor biosynthesis. It is produced by the enzyme 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (IspD) and is a substrate for CDP-ME kinase (IspE).[1][2][3]
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| Names | |
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| IUPAC name
Cytidine 5′-(1-deoxy-2-C-methyl-D-erythritol-1-yl dihydrogen diphosophate) | |
| Preferred IUPAC name
O1-{[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxan-2-yl]methyl} O3-[(2R,3S)-2,3,4-trihydroxy-3-methylbutyl] dihydrogen diphosphate | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| KEGG | |
| MeSH | 4-diphosphocytidyl-2-C-methylerythritol |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C14H25N3O14P2 | |
| Molar mass | 521.31 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biochemical role
CDP-ME is an intermediate in the non-mevalonate pathway for the biosynthesis of the isoprenoid precursors isopentenyl pyrophosphate and dimethylallyl pyrophosphate.[4][5] Most gram-negative bacteria, the photosynthetic cyanobacteria and green algae use only this pathway, while higher plants also use the mevalonate pathway.[6][7]
The enzyme 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase combines 2-C-methylerythritol 4-phosphate and cytidine triphosphate to form CDP-ME, with a pyrophosphate (PPi) fragment as a byproduct:[8][9]
In the next step, the enzyme 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol kinase uses the cofactor, adenosine triphosphate (ATP) to introduce a terminal phosphate group, giving 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-MEP) and adenosine diphosphate (ADP):[2]
