Loading Pathway...
Error: Pathway image not found.
Hide
Pathway Description
Epoxysqualene Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2017-02-23
Last Updated: 2025-01-29
Epoxysqualene biosynthesis is a pathway that begins in the chloroplast and finishes on the cytosolic side of the endoplasmic reticulum (coloured dark green in the image) by which isopentenyl diphosphate becomes 2,3-epoxisqualene, an intermediate in the synthesis of the cell membrane sterol precursor cycloartenol . First, isopentenyl diphosphate isomerase catalyzes the reversible synthesis of dimethylallyl diphosphate from isopentenyl diphosphate. This enzyme requires FAD, NAD(P)H, and a divalent cation (e.g. magnesium) as cofactors. Second, geranylpyrophosphate uses magnesium ion as a cofactor to convert dimethylallyl diphosphate into geranyl diphosphate. Third, (2E,6E)-farnesyl diphosphate synthase catalyzes the conversion of geranyl diphosphate into farnesyl diphosphate. Farnesyl diphosphate then must be transported out of the chloroplast and into the cytosol via a predicted farnesyl diphosphate transporter. Fourth, squalene synthase uses a magnesium or manganese ion as a cofactor to catalyze the conversion of two farnesyl diphosphates into squalene. Fifth, squalene monooxygenase uses FAD as a cofactor to catalyze the conversion of squalene into 2,3-epoxisqualene.
References
Epoxysqualene Biosynthesis References
Cunillera N, Arro M, Delourme D, Karst F, Boronat A, Ferrer A: Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes. J Biol Chem. 1996 Mar 29;271(13):7774-80.
Pubmed: 8631820
Rasbery JM, Shan H, LeClair RJ, Norman M, Matsuda SP, Bartel B: Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development. J Biol Chem. 2007 Jun 8;282(23):17002-13. doi: 10.1074/jbc.M611831200. Epub 2007 Apr 10.
Pubmed: 17426032
Campbell M, Hahn FM, Poulter CD, Leustek T: Analysis of the isopentenyl diphosphate isomerase gene family from Arabidopsis thaliana. Plant Mol Biol. 1998 Jan;36(2):323-8. doi: 10.1023/a:1005935516274.
Pubmed: 9484444
Sato S, Kotani H, Nakamura Y, Kaneko T, Asamizu E, Fukami M, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. I. Sequence features of the 1.6 Mb regions covered by twenty physically assigned P1 clones. DNA Res. 1997 Jun 30;4(3):215-30. doi: 10.1093/dnares/4.3.215.
Pubmed: 9330910
Cheng CY, Krishnakumar V, Chan AP, Thibaud-Nissen F, Schobel S, Town CD: Araport11: a complete reannotation of the Arabidopsis thaliana reference genome. Plant J. 2017 Feb;89(4):789-804. doi: 10.1111/tpj.13415. Epub 2017 Feb 10.
Pubmed: 27862469
Bouvier F, Suire C, d'Harlingue A, Backhaus RA, Camara B: Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells. Plant J. 2000 Oct;24(2):241-52.
Pubmed: 11069698
Jun L, Saiki R, Tatsumi K, Nakagawa T, Kawamukai M: Identification and subcellular localization of two solanesyl diphosphate synthases from Arabidopsis thaliana. Plant Cell Physiol. 2004 Dec;45(12):1882-8. doi: 10.1093/pcp/pch211.
Pubmed: 15653808
Lin X, Kaul S, Rounsley S, Shea TP, Benito MI, Town CD, Fujii CY, Mason T, Bowman CL, Barnstead M, Feldblyum TV, Buell CR, Ketchum KA, Lee J, Ronning CM, Koo HL, Moffat KS, Cronin LA, Shen M, Pai G, Van Aken S, Umayam L, Tallon LJ, Gill JE, Adams MD, Carrera AJ, Creasy TH, Goodman HM, Somerville CR, Copenhaver GP, Preuss D, Nierman WC, White O, Eisen JA, Salzberg SL, Fraser CM, Venter JC: Sequence and analysis of chromosome 2 of the plant Arabidopsis thaliana. Nature. 1999 Dec 16;402(6763):761-8. doi: 10.1038/45471.
Pubmed: 10617197
Cunillera N, Boronat A, Ferrer A: The Arabidopsis thaliana FPS1 gene generates a novel mRNA that encodes a mitochondrial farnesyl-diphosphate synthase isoform. J Biol Chem. 1997 Jun 13;272(24):15381-8. doi: 10.1074/jbc.272.24.15381.
Pubmed: 9182568
Asamizu E, Sato S, Kaneko T, Nakamura Y, Kotani H, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. VIII. Sequence features of the regions of 1,081,958 bp covered by seventeen physically assigned P1 and TAC clones. DNA Res. 1998 Dec 31;5(6):379-91. doi: 10.1093/dnares/5.6.379.
Pubmed: 10048488
Nakashima T, Inoue T, Oka A, Nishino T, Osumi T, Hata S: Cloning, expression, and characterization of cDNAs encoding Arabidopsis thaliana squalene synthase. Proc Natl Acad Sci U S A. 1995 Mar 14;92(6):2328-32. doi: 10.1073/pnas.92.6.2328.
Pubmed: 7892265
Kribii R, Arro M, Del Arco A, Gonzalez V, Balcells L, Delourme D, Ferrer A, Karst F, Boronat A: Cloning and characterization of the Arabidopsis thaliana SQS1 gene encoding squalene synthase--involvement of the C-terminal region of the enzyme in the channeling of squalene through the sterol pathway. Eur J Biochem. 1997 Oct 1;249(1):61-9. doi: 10.1111/j.1432-1033.1997.00061.x.
Pubmed: 9363754
Mayer K, Schuller C, Wambutt R, Murphy G, Volckaert G, Pohl T, Dusterhoft A, Stiekema W, Entian KD, Terryn N, Harris B, Ansorge W, Brandt P, Grivell L, Rieger M, Weichselgartner M, de Simone V, Obermaier B, Mache R, Muller M, Kreis M, Delseny M, Puigdomenech P, Watson M, Schmidtheini T, Reichert B, Portatelle D, Perez-Alonso M, Boutry M, Bancroft I, Vos P, Hoheisel J, Zimmermann W, Wedler H, Ridley P, Langham SA, McCullagh B, Bilham L, Robben J, Van der Schueren J, Grymonprez B, Chuang YJ, Vandenbussche F, Braeken M, Weltjens I, Voet M, Bastiaens I, Aert R, Defoor E, Weitzenegger T, Bothe G, Ramsperger U, Hilbert H, Braun M, Holzer E, Brandt A, Peters S, van Staveren M, Dirske W, Mooijman P, Klein Lankhorst R, Rose M, Hauf J, Kotter P, Berneiser S, Hempel S, Feldpausch M, Lamberth S, Van den Daele H, De Keyser A, Buysshaert C, Gielen J, Villarroel R, De Clercq R, Van Montagu M, Rogers J, Cronin A, Quail M, Bray-Allen S, Clark L, Doggett J, Hall S, Kay M, Lennard N, McLay K, Mayes R, Pettett A, Rajandream MA, Lyne M, Benes V, Rechmann S, Borkova D, Blocker H, Scharfe M, Grimm M, Lohnert TH, Dose S, de Haan M, Maarse A, Schafer M, Muller-Auer S, Gabel C, Fuchs M, Fartmann B, Granderath K, Dauner D, Herzl A, Neumann S, Argiriou A, Vitale D, Liguori R, Piravandi E, Massenet O, Quigley F, Clabauld G, Mundlein A, Felber R, Schnabl S, Hiller R, Schmidt W, Lecharny A, Aubourg S, Chefdor F, Cooke R, Berger C, Montfort A, Casacuberta E, Gibbons T, Weber N, Vandenbol M, Bargues M, Terol J, Torres A, Perez-Perez A, Purnelle B, Bent E, Johnson S, Tacon D, Jesse T, Heijnen L, Schwarz S, Scholler P, Heber S, Francs P, Bielke C, Frishman D, Haase D, Lemcke K, Mewes HW, Stocker S, Zaccaria P, Bevan M, Wilson RK, de la Bastide M, Habermann K, Parnell L, Dedhia N, Gnoj L, Schutz K, Huang E, Spiegel L, Sehkon M, Murray J, Sheet P, Cordes M, Abu-Threideh J, Stoneking T, Kalicki J, Graves T, Harmon G, Edwards J, Latreille P, Courtney L, Cloud J, Abbott A, Scott K, Johnson D, Minx P, Bentley D, Fulton B, Miller N, Greco T, Kemp K, Kramer J, Fulton L, Mardis E, Dante M, Pepin K, Hillier L, Nelson J, Spieth J, Ryan E, Andrews S, Geisel C, Layman D, Du H, Ali J, Berghoff A, Jones K, Drone K, Cotton M, Joshu C, Antonoiu B, Zidanic M, Strong C, Sun H, Lamar B, Yordan C, Ma P, Zhong J, Preston R, Vil D, Shekher M, Matero A, Shah R, Swaby IK, O'Shaughnessy A, Rodriguez M, Hoffmann J, Till S, Granat S, Shohdy N, Hasegawa A, Hameed A, Lodhi M, Johnson A, Chen E, Marra M, Martienssen R, McCombie WR: Sequence and analysis of chromosome 4 of the plant Arabidopsis thaliana. Nature. 1999 Dec 16;402(6763):769-77. doi: 10.1038/47134.
Pubmed: 10617198
Kato A, Suzuki M, Kuwahara A, Ooe H, Higano-Inaba K, Komeda Y: Isolation and analysis of cDNA within a 300 kb Arabidopsis thaliana genomic region located around the 100 map unit of chromosome 1. Gene. 1999 Nov 1;239(2):309-16. doi: 10.1016/s0378-1119(99)00403-5.
Pubmed: 10548732
Theologis A, Ecker JR, Palm CJ, Federspiel NA, Kaul S, White O, Alonso J, Altafi H, Araujo R, Bowman CL, Brooks SY, Buehler E, Chan A, Chao Q, Chen H, Cheuk RF, Chin CW, Chung MK, Conn L, Conway AB, Conway AR, Creasy TH, Dewar K, Dunn P, Etgu P, Feldblyum TV, Feng J, Fong B, Fujii CY, Gill JE, Goldsmith AD, Haas B, Hansen NF, Hughes B, Huizar L, Hunter JL, Jenkins J, Johnson-Hopson C, Khan S, Khaykin E, Kim CJ, Koo HL, Kremenetskaia I, Kurtz DB, Kwan A, Lam B, Langin-Hooper S, Lee A, Lee JM, Lenz CA, Li JH, Li Y, Lin X, Liu SX, Liu ZA, Luros JS, Maiti R, Marziali A, Militscher J, Miranda M, Nguyen M, Nierman WC, Osborne BI, Pai G, Peterson J, Pham PK, Rizzo M, Rooney T, Rowley D, Sakano H, Salzberg SL, Schwartz JR, Shinn P, Southwick AM, Sun H, Tallon LJ, Tambunga G, Toriumi MJ, Town CD, Utterback T, Van Aken S, Vaysberg M, Vysotskaia VS, Walker M, Wu D, Yu G, Fraser CM, Venter JC, Davis RW: Sequence and analysis of chromosome 1 of the plant Arabidopsis thaliana. Nature. 2000 Dec 14;408(6814):816-20. doi: 10.1038/35048500.
Pubmed: 11130712
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