| EC |
4.2.3.73 |
| Accepted name: |
valencene synthase |
| Reaction: |
(2E,6E)-farnesyl diphosphate = (+)-valencene + diphosphate |
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For diagram of eremophilane and spirovetivane sesquiterpenoid biosynthesis, click here |
| Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (valencene-forming) |
| Comments: |
The recombinant enzyme from Vitis vinifera gave 49.5% (+)-valencene and 35.5% (-)-7-epi-α-selinene. Initial cyclization gives (+)-germacrene A in an enzyme bound form which is not released to the medium. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Lucker, J., Bowen, P. and Bohlmann, J. Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (-)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries. Phytochemistry 65 (2004) 2649–2659. [DOI] [PMID: 15464152] |
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| [EC 4.2.3.73 created 2011] |
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| EC |
4.2.3.86 |
| Accepted name: |
7-epi-α-selinene synthase |
| Reaction: |
(2E,6E)-farnesyl diphosphate = 7-epi-α-selinene + diphosphate |
|
For diagram of eudesmol and selinene biosynthesis, click here |
| Glossary: |
7-epi-α-selinene = (2S,4aR,8aR)-4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene |
| Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (7-epi-α-selinene-forming) |
| Comments: |
The recombinant enzyme from Vitis vinifera forms 49.5% (+)-valencene (cf. EC 4.2.3.73, valencene synthase) and 35.5% (-)-7-epi-α-selinene. Initial cyclization gives (+)-germacrene A in an enzyme bound form which is not released to the medium. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Lucker, J., Bowen, P. and Bohlmann, J. Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (-)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries. Phytochemistry 65 (2004) 2649–2659. [DOI] [PMID: 15464152] |
| 2. |
Martin, D.M., Toub, O., Chiang, A., Lo, B.C., Ohse, S., Lund, S.T. and Bohlmann, J. The bouquet of grapevine (Vitis vinifera L. cv. Cabernet Sauvignon) flowers arises from the biosynthesis of sesquiterpene volatiles in pollen grains. Proc. Natl. Acad. Sci. USA 106 (2009) 7245–7250. [DOI] [PMID: 19359488] |
|
| [EC 4.2.3.86 created 2011] |
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| EC |
4.2.3.90 |
| Accepted name: |
5-epi-α-selinene synthase |
| Reaction: |
(2E,6E)-farnesyl diphosphate = 5-epi-α-selinene + diphosphate |
|
For diagram of eudesmol and selinene biosynthesis, click here |
| Glossary: |
5-epi-α-selinene = 5β-eudesma-3,11-diene = (2R,4aR,8aS)-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(prop-1-en-2-yl)naphthalene
[= 8a-epi-α-selinene which uses naththalene numbering not eudesmane] |
| Other name(s): |
8a-epi-α-selinene synthase; NP1 |
| Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, 5-epi-α-selinene-forming) |
| Comments: |
Requires Mg2+. The enzyme forms 5-epi-α-selinene possibly via germecrene A or a 1,6-hydride shift mechanism. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Agger, S.A., Lopez-Gallego, F., Hoye, T.R. and Schmidt-Dannert, C. Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120. J. Bacteriol. 190 (2008) 6084–6096. [DOI] [PMID: 18658271] |
|
| [EC 4.2.3.90 created 2011] |
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| EC |
4.2.3.198 |
| Accepted name: |
α-selinene synthase |
| Reaction: |
(2E,6E)-farnesyl diphosphate = α-selinene + diphosphate |
|
For diagram of eudesmol and selinene biosynthesis, click here |
| Glossary: |
α-selinene = (2R,4aR,8aS)-4,8a-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
β-selinene = (4aR,7R,8aS)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)decahydronaphthalene
aromadendrene = (1aR,4aR,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidenedecahydro-1H-cyclopropa[e]azulene
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| Other name(s): |
LfTPS2 (gene name) |
| Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, α-selinene-forming) |
| Comments: |
The enzyme from the plant Ocimum basilicum (sweet basil) also produces β-selinene while that from Liquidambar formosana (Formosan sweet gum) also produces traces of aromadendrene. |
| Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
| References: |
| 1. |
Iijima, Y., Davidovich-Rikanati, R., Fridman, E., Gang, D.R., Bar, E., Lewinsohn, E. and Pichersky, E. 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 (2004) 3724–3736. [DOI] [PMID: 15516500] |
| 2. |
Chuang, L., Wen, C.H., Lee, Y.R., Lin, Y.L., Hsu, L.R., Wang, S.Y. and Chu, F.H. Identification, functional characterization, and seasonal expression patterns of five sesquiterpene synthases in Liquidambar formosana. J Nat Prod 81 (2018) 1162–1172. [PMID: 29746128] |
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| [EC 4.2.3.198 created 2018] |
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