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

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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]

2-C-Methyl-D-erythritol-2,4-cyclodiphosphate
Skeletal formula of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate
Ball-and-stick model of the 2-C-methyl-D-erythritol-2,4-cyclodiphosphate molecule
Names
IUPAC name
(6R,7S)-2,4-Dihydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5-trioxa-2λ5,4λ5-diphosphacyclooctan-7-ol
Identifiers
151435-51-7 YesY
3D model (Jmol) Interactive image
MeSH 2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate
PubChem 68
Properties
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).
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Infobox references

References[edit]

  1. ^ 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. doi:10.1073/pnas.040554697. PMC 15955Freely accessible. PMID 10694574. 
  2. ^ 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. PMC 1134649Freely accessible. PMID 8240308. 
  3. ^ 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 409939Freely accessible. PMID 15123794. 
  4. ^ 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.