2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate

2-C-Methyl-d-erythritol-2,4-cyclodiphosphate
Names


Systematic IUPAC name (6S,7R)-2,4,7-Trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ⁵,4λ⁵-trioxadiphosphocane-2,4-dione
Identifiers
CAS Number	151435-51-7^Y
3D model (JSmol)	Interactive image
MeSH	2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate
PubChem CID	68
CompTox Dashboard (EPA)	DTXSID10931210 DTXSID60610886, DTXSID10931210
SMILES C[C@]1([C@H](COP(=O)(OP(=O)(O1)O)O)O)CO
Properties
Chemical formula	C₅H₁₂O₉P₂
Molar mass	278.09 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

2-C-Methyl-d-erythritol-2,4-cyclopyrophosphate (MEcPP) (also 2-C-Methyl-d-erythritol-2,4-cyclodiphosphate) is an intermediate in the MEP pathway (non-mevalonate) of isoprenoid precursor biosynthesis.^[1] MEcPP is produced by MEcPP synthase (IspF) and is a substrate for HMB-PP synthase (IspG).

Under conditions of oxidative stress, MEcPP accumulates in certain bacteria.^[2] MEcPP releases histone-like proteins from DNA, triggering nucleoid decondensation in Chlamydia trachomatis during the process of terminal differentiation.^[3] Abiotic stresses to plants, including wounding and excessive high-light exposure, lead to an increase in MEcPP accumulation in chloroplasts. Transported from the chloroplast to the plant cell nucleus, MEcPP engages in retrograde signalling that leads to the specific induction of nuclear-encoded stress-response genes.^[4]

References

^ Herz S, Wungsintaweekul J, Schuhr CA, Hecht S, Lüttgen H, Sagner S, Fellermeier M, Eisenreich W, Zenk MH, Bacher A, Rohdich F (2000). "Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate". Proc. Natl. Acad. Sci. USA. 97 (6): 2486–90. Bibcode:2000PNAS...97.2486H. doi:10.1073/pnas.040554697. PMC 15955. PMID 10694574.
^ Ostrovsky D, Shashkov A, Sviridov A (1993). "Bacterial oxidative-stress substance is 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate". Biochem J. 295 (3): 901–2. doi:10.1042/bj2950901. PMC 1134649. PMID 8240308.
^ Grieshaber NA, Fischer ER, Mead DJ, Dooley CA, Hackstadt T (2004). "Chlamydial histone-DNA interactions are disrupted by a metabolite in the methylerythritol phosphate pathway of isoprenoid biosynthesis". Proc. Natl. Acad. Sci. USA. 101 (19): 7451–6. doi:10.1073/pnas.0400754101. PMC 409939. PMID 15123794.
^ Xiao Y, Savchenko T, Baidoo EE, Chehab WE, Hayden DM, Tolstikov V, Corwin JA, Kliebenstein DJ, Keasling JD, Dehesh K (2012). "Retrograde signaling by the plastidial metabolite MEcPP regulates expression of nuclear stress-response genes". Cell. 149 (7): 1525–35. doi:10.1016/j.cell.2012.04.038. PMID 22726439.

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

Lanosterol
14-demethyllanosterol
4alpha-Methylzymosterol
Zymosterone
Zymosterol

From Cholesterol
to Steroid hormones

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

This page was last edited on 26 April 2023, at 13:48

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References