EC
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1.14.13.207
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Transferred entry: | ipsdienol synthase. Now EC 1.14.14.31, ipsdienol synthase
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[EC 1.14.13.207 created 2015, deleted 2016] |
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EC |
1.14.14.31 |
Accepted name: |
ipsdienol synthase |
Reaction: |
myrcene + [reduced NADPH—hemoprotein reductase] + O2 = (R)-ipsdienol + [oxidized NADPH—hemoprotein reductase] + H2O |
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For diagram of acyclic monoterpenoid biosynthesis, click here |
Glossary: |
myrcene = 7-methyl-3-methyleneocta-1,6-diene
ipsdienol = 2-methyl-6-methyleneocta-2,7-dien-4-ol |
Other name(s): |
myrcene hydroxylase; CYP9T2; CYP9T3 |
Systematic name: |
myrcene,NADPH—hemoprotein reductase:O2 oxidoreductase (hydroxylating) |
Comments: |
A cytochrome P-450 heme-thiolate protein. Involved in the insect aggregation pheromone production. Isolated from the pine engraver beetle, Ips pini. A small amount of (S)-ipsdienol is also formed. In vitro it also hydroxylated (+)- and (–)-α-pinene, 3-carene, and (+)-limonene, but not α-phellandrene, (–)-β-pinene, γ-terpinene, or terpinolene. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Sandstrom, P., Welch, W.H., Blomquist, G.J. and Tittiger, C. Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol. Insect Biochem. Mol. Biol. 36 (2006) 835–845. [DOI] [PMID: 17046597] |
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Song, M., Kim, A.C., Gorzalski, A.J., MacLean, M., Young, S., Ginzel, M.D., Blomquist, G.J. and Tittiger, C. Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations. Insect Biochem. Mol. Biol. 43 (2013) 336–343. [DOI] [PMID: 23376633] |
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[EC 1.14.14.31 created 2015 as EC 1.14.13.207, transferred 2016 to EC 1.14.14.31] |
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EC |
4.2.3.107 |
Accepted name: |
(+)-car-3-ene synthase |
Reaction: |
geranyl diphosphate = (+)-car-3-ene + diphosphate |
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For diagram of monoterpenoid biosynthesis, click here |
Glossary: |
(+)-car-3-ene = (1S,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene |
Other name(s): |
3-carene cyclase; 3-carene synthase; 3CAR; (+)-3-carene synthase |
Systematic name: |
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming] |
Comments: |
The enzyme reacts with (3S)-linalyl diphosphate twice as rapidly as geranyl diphosphate, but 25 times as rapidly as (3R)-linalyl diphosphate. It is assumed that (3S)-linalyl diphosphate is normally formed as an enzyme bound intermediate in the reaction. In the reaction the 5-pro-R hydrogen of geranyl diphosphate is eliminated during cyclopropane ring formation [1,2]. In Picea abies (Norway spruce) and Picea sitchensis (Sitka spruce) terpinolene is also formed [4,6]. See EC 4.2.3.113 terpinolene synthase. (+)-Car-3-ene is associated with resistance of Picea sitchensis (Sitka spruce) to white pine weevil [6]. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Savage, T.J. and Croteau, R. Biosynthesis of monoterpenes: regio- and stereochemistry of (+)-3-carene biosynthesis. Arch. Biochem. Biophys. 305 (1993) 581–587. [DOI] [PMID: 8373196] |
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Savage, T.J., Ichii, H., Hume, S.D., Little, D.B. and Croteau, R. Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents. Arch. Biochem. Biophys. 320 (1995) 257–265. [DOI] [PMID: 7625832] |
3. |
Savage, T.J., Hatch, M.W. and Croteau, R. Monoterpene synthases of Pinus contorta and related conifers. A new class of terpenoid cyclase. J. Biol. Chem. 269 (1994) 4012–4020. [PMID: 8307957] |
4. |
Faldt, J., Martin, D., Miller, B., Rawat, S. and Bohlmann, J. 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 (2003) 119–133. [PMID: 12602896] |
5. |
Hamberger, B., Hall, D., Yuen, M., Oddy, C., Hamberger, B., Keeling, C.I., Ritland, C., Ritland, K. and Bohlmann, J. Targeted isolation, sequence assembly and characterization of two white spruce (Picea glauca) BAC clones for terpenoid synthase and cytochrome P450 genes involved in conifer defence reveal insights into a conifer genome. BMC Plant Biol. 9:106 (2009). [DOI] [PMID: 19656416] |
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Hall, D.E., Robert, J.A., Keeling, C.I., Domanski, D., Quesada, A.L., Jancsik, S., Kuzyk, M.A., Hamberger, B., Borchers, C.H. and Bohlmann, J. An integrated genomic, proteomic and biochemical analysis of (+)-3-carene biosynthesis in Sitka spruce (Picea sitchensis) genotypes that are resistant or susceptible to white pine weevil. Plant J. 65 (2011) 936–948. [DOI] [PMID: 21323772] |
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[EC 4.2.3.107 created 2012] |
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EC |
4.2.3.113 |
Accepted name: |
terpinolene synthase |
Reaction: |
geranyl diphosphate = terpinolene + diphosphate |
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For diagram of menthane monoterpenoid biosynthesis, click here |
Glossary: |
terpinolene = 1-methyl-4-(propan-2-ylidene)cyclohexene |
Other name(s): |
ag9; PmeTPS2; LaLIMS_RR |
Systematic name: |
geranyl-diphosphate diphosphate-lyase (cyclizing, terpinolene-forming) |
Comments: |
Requires Mg2+. Mn2+ is less effective and product ratio changes. Forms traces of other monoterpenoids.
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Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Croteau, R. and Satterwhite, D.M. Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage. J. Biol. Chem. 264 (1989) 15309–15315. [PMID: 2768265] |
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Bohlmann, J., Phillips, M., Ramachandiran, V., Katoh, S. and Croteau, R. 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 (1999) 232–243. [DOI] [PMID: 10441373] |
3. |
Faldt, J., Martin, D., Miller, B., Rawat, S. and Bohlmann, J. 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 (2003) 119–133. [PMID: 12602896] |
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Huber, D.P.W., Philippe, R.N., Godard, K.-A., Sturrock, R.N. and Bohlmann, J. Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii. Phytochemistry 66 (2005) 1427–1439. [DOI] [PMID: 15921711] |
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Landmann, C., Fink, B., Festner, M., Dregus, M., Engel, K.H. and Schwab, W. Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia). Arch. Biochem. Biophys. 465 (2007) 417–429. [DOI] [PMID: 17662687] |
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[EC 4.2.3.113 created 2012] |
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