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MetaCyc Pathway: fenchol biosynthesis II

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 Monoterpenoids Biosynthesis

Some taxa known to possess this pathway include ? : Ocimum basilicum

Expected Taxonomic Range: Lamiales

Summary:
Fenchol or 1,3,3-trimethyl-2-norbornanol is a terpene and an isomer of borneol. The naturally occurring enantiopure (1R)-endo-(+)-fenchol is used extensively in perfumery. The have been isolated from the fruits and leaves of Foeniculum vulgare. It is used in the fragrances of soaps, shampoos, and other toiletries and detergents [Bhatia08]. Given the commercial importance of this compound, it has been under intensive research. Several studies have established the mechanism by which the geranyl diphosphate (GPP), the precursor is converted into (-)-endo-fenchol. They are reviewed in the following papers: [Croteau80] and [Satterwhite85]. The stereochemistry of the enzymatic conversion of geranyl diphosphate to (-)-endo-fenchol has been elucidated [Croteau88]. No free intermediate is formed during the cyclization of geranyl diphosphate [Croteau80b].

In this pathway, the biosynthesis of (-)-endo-fenchol in Ocimum basilicum is shown and the mechanistic behavior of fenchol cyclase was shown to be similar to other known monoterpene cyclases. The fenchol biosynthesis II pathway is distinct from fenchol biosynthesis I as the enzyme catalyzing (-)-endo-fenchol is multifunctional and synthesizes three known monoterpenes: (-)-α-pinene, (4S)-limonene and an unknown monoterpene [Iijima04a]. The fenchol biosynthesis II pathway also does not lead to the formation of the fenchol derivatives: α-fenchene, β-fenchene, α-fenchocamphorone and β-fenchocamphorone.

Credits:
Created 01-Mar-2010 by Pujar A , Boyce Thompson Institute
Revised 18-Dec-2011 by Weerasinghe D , SRI International


References

Bhatia08: Bhatia SP, McGinty D, Letizia CS, Api AM (2008). "Fragrance material review on fenchyl alcohol." Food Chem Toxicol 46 Suppl 11;S157-9. PMID: 18640185

Croteau80: Croteau R, Felton M, Ronald RC (1980). "Biosynthesis of monoterpenes: conversion of the acyclic precursors geranyl pyrophosphate and neryl pyrophosphate to the rearranged monoterpenes fenchol and fenchone by a soluble enzyme preparation from fennel (Foeniculum vulgare)." Arch Biochem Biophys 200(2);524-33. PMID: 7436420

Croteau80b: Croteau R, Felton M, Ronald RC (1980). "Biosynthesis of monoterpenes: preliminary characterization of i-endo-fenchol synthetase from fennel (Foeniculum vulgare) and evidence that no free intermediate is involved in the cyclization of geranyl pyrophosphate to the rearranged product." Arch Biochem Biophys 200(2);534-46. PMID: 7436421

Croteau88: Croteau R, Satterwhite DM, Wheeler CJ, Felton NM (1988). "Biosynthesis of monoterpenes. Stereochemistry of the enzymatic cyclization of geranyl pyrophosphate to (-)-endo-fenchol." J Biol Chem 263(30);15449-53. PMID: 3170591

Iijima04a: Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, Lewinsohn E, Pichersky E (2004). "The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil." Plant Physiol 136(3);3724-36. PMID: 15516500

Satterwhite85: Satterwhite DM, Wheeler CJ, Croteau R (1985). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol." J Biol Chem 260(26);13901-8. PMID: 4055764

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

Alonso92: Alonso WR, Rajaonarivony JI, Gershenzon J, Croteau R (1992). "Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita) and spearmint (Mentha spicata)." J Biol Chem 267(11);7582-7. PMID: 1559995

Bohlmann00: Bohlmann J, Martin D, Oldham NJ, Gershenzon J (2000). "Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase." Arch Biochem Biophys 375(2);261-9. PMID: 10700382

Bohlmann97: Bohlmann J, Steele CL, Croteau R (1997). "Monoterpene synthases from grand fir (Abies grandis). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase." J Biol Chem 272(35);21784-92. PMID: 9268308

Bohlmann99: Bohlmann J, Phillips M, Ramachandiran V, Katoh S, Croteau R (1999). "cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)." Arch Biochem Biophys 368(2);232-43. PMID: 10441373

Chen04c: Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D (2004). "Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole." Plant Physiol 135(4);1956-66. PMID: 15299125

Colby93: Colby SM, Alonso WR, Katahira EJ, McGarvey DJ, Croteau R (1993). "4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase." J Biol Chem 268(31);23016-24. PMID: 8226816

Croteau89: Croteau R, Miyazaki JH, Wheeler CJ (1989). "Monoterpene biosynthesis: mechanistic evaluation of the geranyl pyrophosphate:(-)-endo-fenchol cyclase from fennel (Foeniculum vulgare)." Arch Biochem Biophys 269(2);507-16. PMID: 2919880

Duetz03: Duetz WA, Bouwmeester H, van Beilen JB, Witholt B (2003). "Biotransformation of limonene by bacteria, fungi, yeasts, and plants." Appl Microbiol Biotechnol 61(4);269-77. PMID: 12743755

Faldt03a: Faldt J, Martin D, Miller B, Rawat S, Bohlmann J (2003). "Traumatic resin defense in Norway spruce (Picea abies): methyl jasmonate-induced terpene synthase gene expression, and cDNA cloning and functional characterization of (+)-3-carene synthase." Plant Mol Biol 51(1);119-33. PMID: 12602896

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Martin04: Martin DM, Faldt J, Bohlmann J (2004). "Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily." Plant Physiol 135(4);1908-27. PMID: 15310829

Steele98: Steele CL, Crock J, Bohlmann J, Croteau R (1998). "Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase." J Biol Chem 273(4);2078-89. PMID: 9442047


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, BIOCYC13B.