MetaCyc Chimeric Pathway: superpathway of linalool biosynthesis
Traceable author statement to experimental supportInferred from experiment

Enzyme View:

Pathway diagram: superpathway of linalool biosynthesis

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: BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisLinalool Biosynthesis
BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisMonoterpenoids BiosynthesisLinalool Biosynthesis
Generation of Precursor Metabolites and Energy

Some taxa known to possess parts of the pathway include : Clarkia breweri, Lavandula angustifolia, Solanum lycopersicum

Expected Taxonomic Range: Fungi, Magnoliophyta

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.

General Background

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

This superpathway describes the production of the two linalool enantiomers (3R)-linalool and (3S)-linalool, which does not necessarily occur in the same organism.

The C10 monoterpene geranyl diphosphate (GPP) is synthesized from the C5 compounds isopentenyl diphosphate and dimethylallyl diphosphate by the action of EC, dimethylallyltranstransferase [Ogura98].

(3S)-linalool is produced in a single step from geranyl diphosphate by the monomeric enzyme EC, S-linalool synthase (LIS), which was discovered in the plant Clarkia breweri [Pichersky95]. LIS activity is detected only in floral tissues of the plant.

(3R)-linalool is produced in a single step from geranyl diphosphate by EC, R-linalool synthase, which was discovered in Mentha x piperita citrata (bergamot mint) [Crowell02].

Subpathways: (3R)-linalool biosynthesis, (3S)-linalool biosynthesis

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

Crowell02: Crowell AL, Williams DC, Davis EM, Wildung MR, Croteau R (2002). "Molecular cloning and characterization of a new linalool synthase." Arch Biochem Biophys 405(1);112-21. PMID: 12176064

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

Ogura98: Ogura K, Koyama T (1998). "Enzymatic Aspects of Isoprenoid Chain Elongation." Chem Rev 98(4);1263-1276. PMID: 11848932

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

Raguso99: Raguso (1999). "A day in the life of a linalool molecule." Plant Species Biology, 14, 95-120.

vanSchie07: van Schie CC, Haring MA, Schuurink RC (2007). "Tomato linalool synthase is induced in trichomes by jasmonic acid." Plant Mol Biol 64(3);251-63. PMID: 17440821

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

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

Barnard81: Barnard GF, Popjak G (1981). "Human liver prenyltransferase and its characterization." Biochim Biophys Acta 661(1);87-99. PMID: 7295734

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

Chen93c: 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

Chooi10: Chooi YH, Cacho R, Tang Y (2010). "Identification of the viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum." Chem Biol 17(5);483-94. PMID: 20534346

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

Daum98: Daum G, Lees ND, Bard M, Dickson R (1998). "Biochemistry, cell biology and molecular biology of lipids of Saccharomyces cerevisiae." Yeast 1998;14(16);1471-510. PMID: 9885152

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

Eberhardt75: Eberhardt NL, Rilling HC (1975). "Prenyltransferase from Saccharomyces cerevisiae. Purification to homogeneity and molecular properties." J Biol Chem 1975;250(3);863-6. PMID: 234442

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

Gilg09: Gilg AB, Tittiger C, Blomquist GJ (2009). "Unique animal prenyltransferase with monoterpene synthase activity." Naturwissenschaften 96(6);731-5. PMID: 19277597

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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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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