Chemistry:4-Diphosphocytidyl-2-C-methylerythritol
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| IUPAC name
Cytidine 5′-(1-deoxy-2-C-methyl-D-erythritol-1-yl dihydrogen diphosophate)
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| 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 | |
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3D model (JSmol)
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| MeSH | 4-diphosphocytidyl-2-C-methylerythritol |
PubChem CID
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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). | |
| Infobox references | |
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
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]
- REDIRECT Template:Chemical reaction
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]
- REDIRECT Template:Chemical reaction
References
- ↑ "Structure of 4-diphosphocytidyl-2-C- methylerythritol synthetase involved in mevalonate- independent isoprenoid biosynthesis.". Nature Structural & Molecular Biology 8 (7): 641–8. 2001. doi:10.1038/89691. PMID 11427897.
- ↑ 2.0 2.1 "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. 2000. doi:10.1073/pnas.97.3.1062. PMID 10655484. Bibcode: 2000PNAS...97.1062L.
- ↑ "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. 2000. doi:10.1016/S0040-4039(00)00295-1.
- ↑ 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. PMID 15197467.
- ↑ 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.
- ↑ 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.
- ↑ Vranová, Eva; Coman, Diana; Gruissem, Wilhelm (2013-04-29). "Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis" (in en). Annual Review of Plant Biology 64 (1): 665–700. doi:10.1146/annurev-arplant-050312-120116. ISSN 1543-5008. PMID 23451776. Bibcode: 2013AnRPB..64..665V. https://www.annualreviews.org/doi/10.1146/annurev-arplant-050312-120116.
- ↑ "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. 1999. doi:10.1073/pnas.96.21.11758. PMID 10518523. Bibcode: 1999PNAS...9611758R.
- ↑ "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. June 2000. doi:10.1073/pnas.97.12.6451. PMID 10841550. Bibcode: 2000PNAS...97.6451R.
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