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4-Diphosphocytidyl-2-C-methylerythritol

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(Redirected from CDP-ME)
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
KEGG
MeSH 4-diphosphocytidyl-2-C-methylerythritol
UNII
  • 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
  • CC(CO)(C(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O)O)O
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).

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]

Biochemical role

[edit]

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]

ATP + CDP-ME
 
 
 
 
Rightward reaction arrow
 
 
 
ADP +
 
2D representation of the chemical structure of 4-Diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate.
CDP-MEP

References

[edit]
  1. ↑ Richard SB, Bowman ME, Kwiatkowski W, Kang I, Chow C, Lillo AM, Cane DE, Noel JP (2001). "Structure of 4-diphosphocytidyl-2-C- methylerythritol synthetase involved in mevalonate- independent isoprenoid biosynthesis". Nature Structural & Molecular Biology. 8 (7): 641–8. doi:10.1038/89691. PMID 11427897. S2CID 8494543.
  2. 1 2 Lüttgen H, Rohdich F, Herz S, Wungsintaweekul J, Hecht S, Schuhr CA, Fellermeier M, Sagner S, Zenk MH, Bacher A, Eisenreich W (2000). "Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-d-erythritol". Proc. Natl. Acad. Sci. U.S.A. 97 (3): 1062–7. Bibcode:2000PNAS...97.1062L. doi:10.1073/pnas.97.3.1062. PMC 15522. PMID 10655484.
  3. ↑ Kuzuyama T, Takagi M, Kaneda K, Watanabe H, Dairi T, Seto H (2000). "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. 41 (16): 2925–2928. doi:10.1016/S0040-4039(00)00295-1.
  4. ↑ W. Eisenreich; A. Bacher; D. Arigoni; F. Rohdich (2004). "Review Biosynthesis of isoprenoids via the non-mevalonate pathway". Cellular and Molecular Life Sciences. 61 (12): 1401–1426. doi:10.1007/s00018-004-3381-z. PMC 11138651. PMID 15197467. S2CID 24558920.
  5. ↑ Hunter, WN (2007). "The Non-mevalonate Pathway of Isoprenoid Precursor Biosynthesis". Journal of Biological Chemistry. 282 (30): 21573–21577. doi:10.1074/jbc.R700005200. PMID 17442674.
  6. ↑ Rohmer M; Rohmer, Michel (1999). "The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants". Nat Prod Rep. 16 (5): 565–574. doi:10.1039/a709175c. PMID 10584331.
  7. ↑ Vranová, Eva; Coman, Diana; Gruissem, Wilhelm (2013-04-29). "Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis". Annual Review of Plant Biology. 64 (1): 665–700. Bibcode:2013AnRPB..64..665V. doi:10.1146/annurev-arplant-050312-120116. ISSN 1543-5008. PMID 23451776.
  8. ↑ Rohdich F, Wungsintaweekul J, Fellermeier M, et al. (1999). "Cytidine 5'-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol". Proc. Natl. Acad. Sci. USA. 96 (21): 11758–63. Bibcode:1999PNAS...9611758R. doi:10.1073/pnas.96.21.11758. PMC 18359. PMID 10518523.
  9. ↑ Rohdich F, Wungsintaweekul J, Eisenreich W, Richter G, Schuhr CA, Hecht S, Zenk MH, Bacher A (June 2000). "Biosynthesis of terpenoids: 4-diphosphocytidyl-2C-methyl-D-erythritol synthase of Arabidopsis thaliana". Proceedings of the National Academy of Sciences of the United States of America. 97 (12): 6451–6. Bibcode:2000PNAS...97.6451R. doi:10.1073/pnas.97.12.6451. PMC 18623. PMID 10841550.
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