4-Diphosphocytidyl-2-C-methylerythritol

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).

4-Diphosphocytidyl-2-C-methylerythritol
Names
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)
ChEBI
ChemSpider
MeSH 4-diphosphocytidyl-2-C-methylerythritol
  • InChI=1S/C14H25N3O14P2/c1-14(23,6-18)8(19)5-29-33(26,27)31-32(24,25)28-4-7-10(20)11(21)12(30-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21,23H,4-6H2,1H3,(H,24,25)(H,26,27)(H2,15,16,22)/t7-,8-,10-,11-,12-,14+/m1/s1 checkY
    Key: YFAUKWZNPVBCFF-XHIBXCGHSA-N checkY
  • InChI=1/C14H25N3O14P2/c1-14(23,6-18)8(19)5-29-33(26,27)31-32(24,25)28-4-7-10(20)11(21)12(30-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21,23H,4-6H2,1H3,(H,24,25)(H,26,27)(H2,15,16,22)/t7-,8-,10-,11-,12-,14+/m1/s1
    Key: YFAUKWZNPVBCFF-XHIBXCGHBP
  • C[C@](CO)([C@@H](COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O)O)O
  • O=P(OC[C@@H](O)[C@](O)(C)CO)(O)OP(=O)(O)OC[C@H]2O[C@@H](N/1C(=O)/N=C(/N)\C=C\1)[C@H](O)[C@@H]2O
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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Infobox references


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