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

2-C-Methyl-D-erythritol-2,4-cyclodiphosphate (MEcPP) is an intermediate in the MEP pathway (non-mevalonate) of isoprenoid precursor biosynthesis. 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. MEcPP releases histone-like proteins from DNA, triggering nucleoid decondensation in Chlamydia trachomatis during the process of terminal differentiation. 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.

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

Ball-and-stick model of the 2-C-methyl-D-erythritol-2,4-cyclodihosphate 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
CAS Number	151435-51-7 Y
Jmol 3D model	Interactive image
MeSH	2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate
PubChem	68
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
Vapor pressure	{{{value}}}
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