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{{DISPLAYTITLE:2-''C''-Methyl-<small>D</small>-erythritol-2,4-cyclopyrophosphate}} |
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{{DISPLAYTITLE: 2-C-Methyl-<small>D</small>-erythritol-2,4-cyclopyrophosphate}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 360752150 |
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| verifiedrevid = 424935328 |
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|Name=2-''C''-Methyl-<small>D</small>-erythritol-2,4-cyclopyrophosphate |
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| Name=2-''C''-Methyl-{{sm|d}}-erythritol-2,4-cyclodiphosphate |
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|ImageFile=2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate.png |
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| ImageFile=2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate.png |
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|ImageSize=200px |
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| ImageSize=200px |
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| ImageAlt = Skeletal formula of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate |
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|IUPACName=(6''R'',7''S'')-2,4-Dihydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5-trioxa-2λ5,4λ5-diphosphacyclooctan-7-ol |
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| ImageFile1 = 2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate-3D-balls.png |
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|OtherNames= |
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| ImageSize1 = 150 |
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| ImageAlt1 = Ball-and-stick model of the 2-C-methyl-D-erythritol-2,4-cyclodiphosphate molecule |
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| SystematicName=(6''S'',7''R'')-2,4,7-Trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ<sup>5</sup>,4λ<sup>5</sup>-trioxadiphosphocane-2,4-dione |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=151435-51-7 |
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| CASNo=151435-51-7 |
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| PubChem=68 |
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| PubChem=68 |
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| SMILES=C1((COP(=O)(OP(=O)(O1)O)O)O)CO |
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| SMILES=C1((COP(=O)(OP(=O)(O1)O)O)O)CO |
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| MeSHName=2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate |
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| MeSHName=2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>5</sub>H<sub>12</sub>O<sub>9</sub>P<sub>2</sub> |
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| Formula=C<sub>5</sub>H<sub>12</sub>O<sub>9</sub>P<sub>2</sub> |
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| MolarMass=278.09 g/mol |
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| MolarMass=278.09 g/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''2-''C''-Methyl-{{sm|d}}-erythritol-2,4-cyclopyrophosphate''' ('''MEcPP''') (also ''2-C-Methyl-{{sm|d}}-erythritol-2,4-cyclodiphosphate'') is an intermediate in the ] (non-mevalonate) of ] precursor biosynthesis.<ref>{{Cite journal|title = Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate|vauthors=Herz S, Wungsintaweekul J, Schuhr CA, Hecht S, Lüttgen H, Sagner S, Fellermeier M, Eisenreich W, Zenk MH, Bacher A, Rohdich F|date = 2000|journal = Proc. Natl. Acad. Sci. USA |issue=6 |doi = 10.1073/pnas.040554697|pmid = 10694574|pmc=15955|volume=97|pages=2486–90|bibcode=2000PNAS...97.2486H|doi-access=free}}</ref> MEcPP is produced by ] (IspF) and is a substrate for ] (IspG). |
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'''2-''C''-Methyl-<small>D</small>-erythritol-2,4-cyclopyrophosphate''' (or '''2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate''') is an intermediate in the ]. |
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Under conditions of oxidative stress, MEcPP accumulates in certain bacteria.<ref>{{Cite journal|title = Bacterial oxidative-stress substance is 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate|vauthors=Ostrovsky D, Shashkov A, Sviridov A|date = 1993|journal = Biochem J |volume=295 |issue=3 |pages=901–2|doi = 10.1042/bj2950901|pmid = 8240308|pmc=1134649}}</ref> MEcPP releases histone-like proteins from DNA, triggering ] decondensation in '']'' during the process of terminal differentiation.<ref>{{Cite journal|title = Chlamydial histone-DNA interactions are disrupted by a metabolite in the methylerythritol phosphate pathway of isoprenoid biosynthesis|vauthors=Grieshaber NA, Fischer ER, Mead DJ, Dooley CA, Hackstadt T|date = 2004|journal = Proc. Natl. Acad. Sci. USA |issue=19 |doi = 10.1073/pnas.0400754101|pmid = 15123794|pmc=409939|volume=101|pages=7451–6|doi-access=free}}</ref> Abiotic stresses to plants, including wounding and excessive high-light exposure, lead to an increase in MEcPP accumulation in ]s. Transported from the chloroplast to the plant cell ], MEcPP engages in ] that leads to the specific induction of ] stress-response genes.<ref>{{Cite journal|title = Retrograde signaling by the plastidial metabolite MEcPP regulates expression of nuclear stress-response genes|vauthors=Xiao Y, Savchenko T, Baidoo EE, Chehab WE, Hayden DM, Tolstikov V, Corwin JA, Kliebenstein DJ, Keasling JD, Dehesh K|date = 2012|journal = Cell |volume=149 |issue=7 |pages=1525–35|doi = 10.1016/j.cell.2012.04.038|pmid = 22726439|doi-access = free}}</ref> |
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{{DEFAULTSORT:Methyl-D-erythritol-2,4-cyclopyrophosphate, 2,C-}} |
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==References== |
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{{Reflist}} |
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{{Cholesterol metabolism intermediates}} |
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{{organic-compound-stub}} |
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{{DEFAULTSORT:Methyl-D-erythritol-2,4-cyclopyrophosphate, 2,C-}} |
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] |
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] |