Loading Pathway...
Error: Pathway image not found.
Hide
Pathway Description
Phylloquinol Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2017-02-23
Last Updated: 2025-02-08
Phylloquinol biosynthesis is a pathway that occurs in the cytoplast by which geranylgeranyl diphosphate and 2-carboxy-1,4-naphthoquinol becomes phylloquinol, a naphtoquinone designated as vitamin K1 (along with phylloquinone) which posttranslatonally modifies precursors for blood coagualation. The three reactions of the subpathway to synthesize phytyl diphosphate from geranylgeranyl diphosphate are catalyzed by the same enzyme, geranylgeranyl dehydrogenase. This enzyme converts geranylgeranyl diphosphate into dihydrogeranylgeranyl diphosphate, dihydrogeranylgeranyl diphosphate into tetrahydrogeranylgeranyl diphosphate, and tetrahydrogeranylgeranyl diphosphate into phytyl diphosphate. The single reaction of the subpathway to synthesize 2-carboxy-1,4-naphthoquinone from 2-carboxy-1,4-naphthoquinol is catalyzed by 2-carboxy-1,4-naphthoquinol reductase. Next, the chloroplast-membrane-associated enzyme 2-carboxy-1,4-naphthoquinone phytyltransferase (coloured dark green in the image) converts phytyl diphosphate and 2-carboxy-1,4-naphthoquinone into demethylphylloquinone. Then, demethylphylloquinone dehydrogenase uses FAD as a cofactor to convert demethylphylloquinone into demethylphylloquinol. Lastly, demethylphylloquinol methyltransferase converts demethylphylloquinol into phylloquinol.
References
Phylloquinol Biosynthesis References
Keller Y, Bouvier F, d'Harlingue A, Camara B: Metabolic compartmentation of plastid prenyllipid biosynthesis--evidence for the involvement of a multifunctional geranylgeranyl reductase. Eur J Biochem. 1998 Jan 15;251(1-2):413-7.
Pubmed: 9492312
Shimada H, Ohno R, Shibata M, Ikegami I, Onai K, Ohto MA, Takamiya K: Inactivation and deficiency of core proteins of photosystems I and II caused by genetical phylloquinone and plastoquinone deficiency but retained lamellar structure in a T-DNA mutant of Arabidopsis. Plant J. 2005 Feb;41(4):627-37. doi: 10.1111/j.1365-313X.2004.02326.x.
Pubmed: 15686525
Fatihi A, Latimer S, Schmollinger S, Block A, Dussault PH, Vermaas WF, Merchant SS, Basset GJ: A Dedicated Type II NADPH Dehydrogenase Performs the Penultimate Step in the Biosynthesis of Vitamin K1 in Synechocystis and Arabidopsis. Plant Cell. 2015 Jun;27(6):1730-41. doi: 10.1105/tpc.15.00103. Epub 2015 May 28.
Pubmed: 26023160
Keller Y, Bouvier F, d'Harlingue A, Camara B: Metabolic compartmentation of plastid prenyllipid biosynthesis--evidence for the involvement of a multifunctional geranylgeranyl reductase. Eur J Biochem. 1998 Jan 15;251(1-2):413-7. doi: 10.1046/j.1432-1327.1998.2510413.x.
Pubmed: 9492312
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
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
Tabata S, Kaneko T, Nakamura Y, Kotani H, Kato T, Asamizu E, Miyajima N, Sasamoto S, Kimura T, Hosouchi T, Kawashima K, Kohara M, Matsumoto M, Matsuno A, Muraki A, Nakayama S, Nakazaki N, Naruo K, Okumura S, Shinpo S, Takeuchi C, Wada T, Watanabe A, Yamada M, Yasuda M, Sato S, de la Bastide M, Huang E, Spiegel L, Gnoj L, O'Shaughnessy A, Preston R, Habermann K, Murray J, Johnson D, Rohlfing T, Nelson J, Stoneking T, Pepin K, Spieth J, Sekhon M, Armstrong J, Becker M, Belter E, Cordum H, Cordes M, Courtney L, Courtney W, Dante M, Du H, Edwards J, Fryman J, Haakensen B, Lamar E, Latreille P, Leonard S, Meyer R, Mulvaney E, Ozersky P, Riley A, Strowmatt C, Wagner-McPherson C, Wollam A, Yoakum M, Bell M, Dedhia N, Parnell L, Shah R, Rodriguez M, See LH, Vil D, Baker J, Kirchoff K, Toth K, King L, Bahret A, Miller B, Marra M, Martienssen R, McCombie WR, Wilson RK, Murphy G, Bancroft I, Volckaert G, Wambutt R, Dusterhoft A, Stiekema W, Pohl T, Entian KD, Terryn N, Hartley N, Bent E, Johnson S, Langham SA, McCullagh B, Robben J, Grymonprez B, Zimmermann W, Ramsperger U, Wedler H, Balke K, Wedler E, Peters S, van Staveren M, Dirkse W, Mooijman P, Lankhorst RK, Weitzenegger T, Bothe G, Rose M, Hauf J, Berneiser S, Hempel S, Feldpausch M, Lamberth S, Villarroel R, Gielen J, Ardiles W, Bents O, Lemcke K, Kolesov G, Mayer K, Rudd S, Schoof H, Schueller C, Zaccaria P, Mewes HW, Bevan M, Fransz P: Sequence and analysis of chromosome 5 of the plant Arabidopsis thaliana. Nature. 2000 Dec 14;408(6814):823-6. doi: 10.1038/35048507.
Pubmed: 11130714
Seki M, Narusaka M, Kamiya A, Ishida J, Satou M, Sakurai T, Nakajima M, Enju A, Akiyama K, Oono Y, Muramatsu M, Hayashizaki Y, Kawai J, Carninci P, Itoh M, Ishii Y, Arakawa T, Shibata K, Shinagawa A, Shinozaki K: Functional annotation of a full-length Arabidopsis cDNA collection. Science. 2002 Apr 5;296(5565):141-5. doi: 10.1126/science.1071006. Epub 2002 Mar 21.
Pubmed: 11910074
Iida K, Fukami-Kobayashi K, Toyoda A, Sakaki Y, Kobayashi M, Seki M, Shinozaki K: Analysis of multiple occurrences of alternative splicing events in Arabidopsis thaliana using novel sequenced full-length cDNAs. DNA Res. 2009 Jun;16(3):155-64. doi: 10.1093/dnares/dsp009. Epub 2009 May 7.
Pubmed: 19423640
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
Downloads
Settings