EC |
4.2.3.174 |
Accepted name: |
(2E,6E)-hedycaryol synthase |
Reaction: |
(2E,6E)-farnesyl diphosphate + H2O = (2E,6E)-hedycaryol + diphosphate |
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For diagram of biosynthesis of ent-germacrene sesquiterpenoids, click here |
Glossary: |
(2E,6E)-hedycaryol = (1E,4E,7S)-germacra-1(10),4-dien-11-ol |
Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (2E,6E)-hedycaryol-forming] |
Comments: |
Isolated from the plant Camellia brevistyla. See also EC 4.2.3.187, (2Z,6E)-hedycaryol synthase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Hattan, J., Shindo, K., Ito, T., Shibuya, Y., Watanabe, A., Tagaki, C., Ohno, F., Sasaki, T., Ishii, J., Kondo, A. and Misawa, N. Identification of a novel hedycaryol synthase gene isolated from Camellia brevistyla flowers and floral scent of Camellia cultivars. Planta 243 (2016) 959–972. [DOI] [PMID: 26744017] |
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[EC 4.2.3.174 created 2017] |
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EC |
4.2.3.187 |
Accepted name: |
(2Z,6E)-hedycaryol synthase |
Reaction: |
(2E,6E)-farnesyl diphosphate + H2O = (2Z,6E)-hedycaryol + diphosphate |
|
For diagram of biosynthesis of ent-germacrene sesquiterpenoids, click here |
Glossary: |
(2Z,6E)-hedycaryol = (1E,4Z,7S)-germacra-1(10),4-dien-11-ol |
Other name(s): |
HcS |
Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (2Z,6E)-hedycaryol-forming] |
Comments: |
Isolated from the bacterium Kitasatospora setae. The stereochemistry suggests the farnesyl diphosphate rearranges to nerolidyl diphosphate or an equivalent intermediate before cyclization. See also EC 4.2.3.174 (2E,6E)-hedycaryol synthase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Baer, P., Rabe, P., Citron, C.A., de Oliveira Mann, C.C., Kaufmann, N., Groll, M. and Dickschat, J.S. Hedycaryol synthase in complex with nerolidol reveals terpene cyclase mechanism. ChemBioChem 15 (2014) 213–216. [DOI] [PMID: 24399794] |
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[EC 4.2.3.187 created 2017] |
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EC |
4.2.3.204 |
Accepted name: |
valerianol synthase |
Reaction: |
(2E,6E)-farnesyl diphosphate + H2O = valerianol + diphosphate |
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For diagram of eremophilane and spirovetivane sesquiterpenoid biosynthesis, click here |
Glossary: |
valerianol = 2-[(2R,8R,8aS)-8,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-2-yl]-propan-2-ol |
Other name(s): |
ChTPS1 (gene name); CsiTPS8 (gene name) |
Systematic name: |
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (valerianol-forming) |
Comments: |
The enzyme was characterized from the trees Camellia hiemalis and Camellia sinensis (black tea). The enzyme from Camellia hiemalis produces (2Z,6E)-hedycaryol as a minor product. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Hattan, J.I., Shindo, K., Sasaki, T., Ohno, F., Tokuda, H., Ishikawa, K. and Misawa, N. Identification of novel sesquiterpene synthase genes that mediate the biosynthesis of valerianol, which was an unknown ingredient of tea. Sci. Rep. 8:12474 (2018). [PMID: 30127518] |
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[EC 4.2.3.204 created 2019] |
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