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

{{DISPLAYTITLE:2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate}} 2-C-Methyl-d-erythritol-2,4-cyclodiphosphate 2-C-methyl-D-erythritol 2,4-cyclic diphosphate.svg 200px Skeletal formula of 2-C-methyl-D-erythritol-2,4-cyclodiphosphate 2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate-3D-balls.png 150 Ball-and-stick model of the 2-C-methyl-D-erythritol-2,4-cyclodiphosphate molecule (6S,7R)-2,4,7-Trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ5,4λ5-trioxadiphosphocane-2,4-dione correct CAS 143488-44-2 112576 126747 C11453 18425 1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-,5+/m1/s1 SFRQRNJMIIUYDI-UHNVWZDZSA-N CC1(C(COP(=O)(OP(=O)(O1)O)O)O)CO 2-methyl-butan-1,2,3,4-tetraol-2,4-cyclopyrophosphate C5H12O9P2 278.09 g/mol 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. Biosynthesis of terpenoids: YgbB protein converts 4-diphosphocytidyl-2C-methyl-D-erythritol 2-phosphate to 2C-methyl-D-erythritol 2,4-cyclodiphosphate Herz S, Wungsintaweekul J, Schuhr CA, Hecht S, Lüttgen H, Sagner S, Fellermeier M, Eisenreich W, Zenk MH, Bacher A, Rohdich F 2000 Proc. Natl. Acad. Sci. USA 6 10.1073/pnas.040554697 10694574 15955 97 2486–90 2000PNAS...97.2486H free MEcPP is produced by MEcPP synthase (IspF) and is a substrate for HMB-PP synthase (IspG). Biochemical role Non-mevalonate pathway MEcPP is an intermediate in the non-mevalonate pathway for the biosynthesis of the isoprenoid precursors isopentenyl pyrophosphate and dimethylallyl pyrophosphate.W. Eisenreich A. Bacher D. Arigoni F. Rohdich Review Biosynthesis of isoprenoids via the non-mevalonate pathway 2004 Cellular and Molecular Life Sciences 61 12 1401–1426 10.1007/s00018-004-3381-z 15197467 24558920 11138651 Hunter, WN 2007 The Non-mevalonate Pathway of Isoprenoid Precursor Biosynthesis Journal of Biological Chemistry 282 30 21573–21577 10.1074/jbc.R700005200 17442674 free Most gram-negative bacteria, the photosynthetic cyanobacteria and green algae use only this pathway, while higher plants also use the mevalonate pathway.Rohmer M The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants Nat Prod Rep 16 5 565–574 1999 10584331 10.1039/a709175c Rohmer MichelVranová Eva Coman Diana Gruissem Wilhelm 2013-04-29 Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis https://www.annualreviews.org/doi/10.1146/annurev-arplant-050312-120116 Annual Review of Plant Biology en 64 1 665–700 10.1146/annurev-arplant-050312-120116 23451776 2013AnRPB..64..665V 1543-5008 subscription The enzyme 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase, splits 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-MEP) into MEcPP and cytidine monophosphate. 65% 4-Diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate CDP-MEP 2 Q27103069 MEcPP + cytidine monophosphate Next, 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase uses two reduced ferredoxin proteins per molecule of MEcPP to convert it to (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP):Hecht Stefan Eisenreich Wolfgang Adam Petra Amslinger Sabine Kis Klaus Bacher Adelbert Arigoni Duilio Rohdich Felix Studies on the nonmevalonate pathway to terpenes: The role of the GcpE (IspG) protein Proceedings of the National Academy of Sciences 2001 98 26 14837–14842 10.1073/pnas.201399298 free 11752431 64945 Okada Ken Hase Toshiharu Cyanobacterial Non-mevalonate Pathway Journal of Biological Chemistry 2005 280 21 20672–20679 10.1074/jbc.M500865200 free 15792953 60% MEcPP + 2 oxidised ferredoxin H2O Q76285996 HMB-PP + 2 reduced ferredoxin Under conditions of oxidative stress, MEcPP accumulates in certain bacteria. Bacterial oxidative-stress substance is 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate Ostrovsky D, Shashkov A, Sviridov A 1993 Biochem J 295 3 901–2 10.1042/bj2950901 8240308 1134649 MEcPP releases histone-like proteins from DNA, triggering nucleoid decondensation in Chlamydia trachomatis during the process of terminal differentiation. Chlamydial histone-DNA interactions are disrupted by a metabolite in the methylerythritol phosphate pathway of isoprenoid biosynthesis Grieshaber NA, Fischer ER, Mead DJ, Dooley CA, Hackstadt T 2004 Proc. Natl. Acad. Sci. USA 19 10.1073/pnas.0400754101 15123794 409939 101 7451–6 free 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. Retrograde signaling by the plastidial metabolite MEcPP regulates expression of nuclear stress-response genes Xiao Y, Savchenko T, Baidoo EE, Chehab WE, Hayden DM, Tolstikov V, Corwin JA, Kliebenstein DJ, Keasling JD, Dehesh K 2012 Cell 149 7 1525–35 10.1016/j.cell.2012.04.038 22726439 free References Category:Pyrophosphate esters Category:Eight-membered rings Category:Heterocyclic compounds with 1 ring Category:Diols Category:Phosphorus heterocycles Category:Oxygen heterocycles