This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
|Superclasses:||Biosynthesis → Secondary Metabolites Biosynthesis → Terpenoids Biosynthesis → Linalool Biosynthesis|
|Biosynthesis → Secondary Metabolites Biosynthesis → Terpenoids Biosynthesis → Monoterpenoids Biosynthesis → Linalool Biosynthesis|
|Generation of Precursor Metabolites and Energy|
Note: This is a chimeric pathway, comprising reactions from multiple organisms, and typically will not occur in its entirety in a single organism. The taxa listed here are likely to catalyze only subsets of the reactions depicted in this pathway.
Linalool is an acyclic monoterpene alcohol with a pleasant fragrance associated with a diverse array of plant [Raguso99]. It is a primary compound in floral scent research. Both (3R)-linalool and (3S)-linalool enantiomeric forms occur in nature.
Linalool is involved as an attractant in plant interactions with pollinators, herbivores and parasitoids [Raguso99]. It has also been shown to be induced by artificial wounding and by jasmonic acid [vanSchie07]. The de novo synthesis of linalool has been demonstrated in floral tissues [vanSchie07], barks and roots [Raguso99]. Fungi, junipers, dicots and monocots emit linalool along with other monoterpenoids [Raguso99].
Even though fungi typically do not produce monoterpenes, the de novo synthesis of linalool was demonstrate in the wine yeast strain, S. cerevisiae M522, in the absence of grape derived precursors [Carrau05].
Recently, it has been demonstrated that linalool is a potent precursor for an advanced biofuel. It can be chemically converted to 1-methyl-cyclopent-2-enol and isobutylene. Dehydration of the alcohol gives rise to methylcyclopentadiene dimers which can be converted into a high density fuel [Meylemans11].
About this Pathway
The C10 monoterpene geranyl diphosphate (GPP) is synthesized from the C5 compounds isopentenyl diphosphate and dimethylallyl diphosphate by the action of EC 220.127.116.11, dimethylallyltranstransferase [Ogura98].
(3S)-linalool is produced in a single step from geranyl diphosphate by the monomeric enzyme EC 18.104.22.168, S-linalool synthase (LIS), which was discovered in the plant Clarkia breweri [Pichersky95]. LIS activity is detected only in floral tissues of the plant.
Created 03-Sep-2007 by Pujar A, Cornell University
Reviewed 07-Jun-2012 by Foerster H, Boyce Thompson Institute
Revised 22-Aug-2012 by Weerasinghe D, SRI International
Reviewed 14-Jan-2013 by Weerasinghe D, SRI International
Revised 28-Jul-2015 by Caspi R, SRI International
Carrau05: Carrau FM, Medina K, Boido E, Farina L, Gaggero C, Dellacassa E, Versini G, Henschke PA (2005). "De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts." FEMS Microbiol Lett 243(1);107-15. PMID: 15668008
Guo94: Guo W, Hosoi R, Sakata K, Watanabe N, Yagi A, Ina K, Luo S (1994). "(S)-linalyl, 2-phenylethyl, and benzyl disaccharide glycosides isolated as aroma precursors from oolong tea leaves." Biosci Biotechnol Biochem 58(8);1532-4. PMID: 7522061
Meylemans11: Meylemans HA, Quintana RL, Goldsmith BR, Harvey BG (2011). "Solvent-free conversion of linalool to methylcyclopentadiene dimers: a route to renewable high-density fuels." ChemSusChem 4(4);465-9. PMID: 21488169
Pichersky95: Pichersky E, Lewinsohn E, Croteau R (1995). "Purification and characterization of S-linalool synthase, an enzyme involved in the production of floral scent in Clarkia breweri." Arch Biochem Biophys 316(2);803-7. PMID: 7864636
Anderson89a: Anderson MS, Yarger JG, Burck CL, Poulter CD (1989). "Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae." J Biol Chem 1989;264(32);19176-84. PMID: 2681213
Bouvier00: Bouvier F, Suire C, d'Harlingue A, Backhaus RA, Camara B (2000). "Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells." Plant J 24(2);241-52. PMID: 11069698
Burke02: Burke C, Croteau R (2002). "Interaction with the small subunit of geranyl diphosphate synthase modifies the chain length specificity of geranylgeranyl diphosphate synthase to produce geranyl diphosphate." J Biol Chem 277(5);3141-9. PMID: 11733504
Burke04: Burke C, Klettke K, Croteau R (2004). "Heteromeric geranyl diphosphate synthase from mint: construction of a functional fusion protein and inhibition by bisphosphonate substrate analogs." Arch Biochem Biophys 422(1);52-60. PMID: 14725857
Burke99: Burke CC, Wildung MR, Croteau R (1999). "Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer." Proc Natl Acad Sci U S A 96(23);13062-7. PMID: 10557273
Chen93: Chen A, Poulter CD (1993). "Purification and characterization of farnesyl diphosphate/geranylgeranyl diphosphate synthase. A thermostable bifunctional enzyme from Methanobacterium thermoautotrophicum." J Biol Chem 268(15);11002-7. PMID: 8388380
Chooi12: Chooi YH, Fang J, Li Y, Wu K, Wang P, Tang Y (2012). "Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferases." J Am Chem Soc 134(22);9428-37. PMID: 22590971
Delourme94: Delourme D, Lacroute F, Karst F (1994). "Cloning of an Arabidopsis thaliana cDNA coding for farnesyl diphosphate synthase by functional complementation in yeast." Plant Mol Biol 26(6);1867-73. PMID: 7858223
Dogbo87: Dogbo, O., Camara, B. (1987). "Purification of isopentenyl pyrophosphate isomerase and geranylgeranyl pyrophosphate synthase from Capsicum chromoplasts by affinity chromatography." Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 920(2):140-148.
Dudareva96: Dudareva N, Cseke L, Blanc VM, Pichersky E (1996). "Evolution of floral scent in Clarkia: novel patterns of S-linalool synthase gene expression in the C. breweri flower." Plant Cell 8(7);1137-48. PMID: 8768373
Fujisaki86: Fujisaki S, Nishino T, Katsuki H (1986). "Isoprenoid synthesis in Escherichia coli. Separation and partial purification of four enzymes involved in the synthesis." J Biochem (Tokyo) 1986;99(5);1327-37. PMID: 3519603
Fujisaki89: Fujisaki S, Nishino T, Katsuki H, Hara H, Nishimura Y, Hirota Y (1989). "Isolation and characterization of an Escherichia coli mutant having temperature-sensitive farnesyl diphosphate synthase." J Bacteriol 1989;171(10);5654-8. PMID: 2676985
Gilg05: Gilg AB, Bearfield JC, Tittiger C, Welch WH, Blomquist GJ (2005). "Isolation and functional expression of an animal geranyl diphosphate synthase and its role in bark beetle pheromone biosynthesis." Proc Natl Acad Sci U S A 102(28);9760-5. PMID: 15983375
Hosfield04: Hosfield DJ, Zhang Y, Dougan DR, Broun A, Tari LW, Swanson RV, Finn J (2004). "Structural basis for bisphosphonate-mediated inhibition of isoprenoid biosynthesis." J Biol Chem 279(10);8526-9. PMID: 14672944
Jia99: Jia JW, Crock J, Lu S, Croteau R, Chen XY (1999). "(3R)-Linalool synthase from Artemisia annua L.: cDNA isolation, characterization, and wound induction." Arch Biochem Biophys 372(1);143-9. PMID: 10562427
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