Loading Pathway...
Error: Pathway image not found.
Hide
Pathway Description
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid Biosynthesis
Escherichia coli
Metabolic Pathway
The biosynthesis of isoprenoids starts with a D-glyceraldehyde 3-phosphate interacting with a hydrogen ion through a 1-deoxyxylulose-5-phosphate synthase resulting in a carbon dioxide and 1-Deoxy-D-xylulose. The latter compound then interacts with a hydrogen ion through a NADPH driven 1-deoxy-D-xylulose 5-phosphate reductoisomerase resulting in a NADP and a 2-C-methyl-D-erythritol 4-phosphate. The latter compound then interacts with a cytidine triphosphate and a hydrogen ion through a 4-diphosphocytidyl-2C-methyl-D-erythritol synthase resulting in a pyrophosphate and a 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound is then phosphorylated through an ATP driven
4-diphosphocytidyl-2-C-methylerythritol kinase resulting in a release of an ADP, a hydrogen ion and a 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. The latter compound then interacts with a
2C-methyl-D-erythritol 2,4-cyclodiphosphate synthase resulting in the release of a 2-C-methyl-D-erythritol-2,4-cyclodiphosphate resulting in the release of a cytidine monophosphate and 2-C-methyl-D-erythritol-2,4-cyclodiphosphate. The latter compound then interacts with a reduced flavodoxin through a
1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate synthase resulting in the release of a water molecule, a hydrogen ion, an oxidized flavodoxin and a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate.
The compound 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate can interact with an NADPH,a hydrogen ion through a 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase resulting in a NADP, a water molecule and either a Dimethylallylpyrophosphate or a Isopentenyl pyrophosphate. These two last compounds can be are isomers that can be produced through a isopentenyl diphosphate isomerase.
Dimethylallylpyrophosphate interacts with the isopentenyl pyrophosphate through a geranyl diphosphate synthase / farnesyl diphosphate synthase resulting in a pyrophosphate and a geranyl--PP. The latter compound interacts with a Isopentenyl pyrophosphate through a geranyl diphosphate synthase / farnesyl diphosphate synthase resulting in the release of a pyrophosphate and a farnesyl pyrophosphate. The latter compound interacts with isopentenyl pyrophosphate either through a undecaprenyl diphosphate synthase resulting in a release of a pyrophosphate and a di-trans,octa-cis-undecaprenyl diphosphate or through a octaprenyl diphosphate synthase resulting in a pyrophosphate and an octaprenyl diphosphate
References
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid Biosynthesis References
Charon L, Hoeffler JF, Pale-Grosdemange C, Lois LM, Campos N, Boronat A, Rohmer M: Deuterium-labelled isotopomers of 2-C-methyl-D-erythritol as tools for the elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis. Biochem J. 2000 Mar 15;346 Pt 3:737-42.
Pubmed: 10698701
Feurle J, Espinosa E, Eckstein S, Pont F, Kunzmann V, Fournie JJ, Herderich M, Wilhelm M: Escherichia coli produces phosphoantigens activating human gamma delta T cells. J Biol Chem. 2002 Jan 4;277(1):148-54. doi: 10.1074/jbc.M106443200. Epub 2001 Oct 23.
Pubmed: 11675382
Hecht S, Eisenreich W, Adam P, Amslinger S, Kis K, Bacher A, Arigoni D, Rohdich F: Studies on the nonmevalonate pathway to terpenes: the role of the GcpE (IspG) protein. Proc Natl Acad Sci U S A. 2001 Dec 18;98(26):14837-42. doi: 10.1073/pnas.201399298.
Pubmed: 11752431
Kim SW, Keasling JD: Metabolic engineering of the nonmevalonate isopentenyl diphosphate synthesis pathway in Escherichia coli enhances lycopene production. Biotechnol Bioeng. 2001 Feb 20;72(4):408-15.
Pubmed: 11180061
Luttgen H, Rohdich F, Herz S, Wungsintaweekul J, Hecht S, Schuhr CA, Fellermeier M, Sagner S, Zenk MH, Bacher A, Eisenreich W: Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-diphosphocytidyl-2C-methyl-D-erythritol. Proc Natl Acad Sci U S A. 2000 Feb 1;97(3):1062-7.
Pubmed: 10655484
Schwender J, Seemann M, Lichtenthaler HK, Rohmer M: Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus. Biochem J. 1996 May 15;316 ( Pt 1):73-80.
Pubmed: 8645235
Eisenreich W, Rohdich F, Bacher A: Deoxyxylulose phosphate pathway to terpenoids. Trends Plant Sci. 2001 Feb;6(2):78-84.
Pubmed: 11173292
Eisenreich W, Bacher A, Arigoni D, Rohdich F: Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci. 2004 Jun;61(12):1401-26. doi: 10.1007/s00018-004-3381-z.
Pubmed: 15197467
Highlighted elements will appear in red.
Highlight Compounds
Highlight Proteins
Enter relative concentration values (without units). Elements will be highlighted in a color gradient where red = lowest concentration and green = highest concentration. For the best results, view the pathway in Black and White.
Visualize Compound Data
Visualize Protein Data
Settings