EC |
4.2.3.8 |
Accepted name: |
casbene synthase |
Reaction: |
geranylgeranyl diphosphate = casbene + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Other name(s): |
casbene synthetase; geranylgeranyl-diphosphate diphosphate-lyase (cyclizing) |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase (cyclizing, casbene-forming) |
Comments: |
The enzyme from castor bean (Ricinus communis) produces the antifungal diterpene casbene. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 69106-45-2 |
References: |
1. |
Moesta, P. and West, C.A. Casbene synthetase: regulation of phytoalexin biosynthesis in Ricinus communis L. seedlings. Purification of casbene synthetase and regulation of its biosynthesis during elicitation. Arch. Biochem. Biophys. 238 (1985) 325–333. [DOI] [PMID: 3985625] |
2. |
Mau, C.J. and West, C.A. Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants. Proc. Natl. Acad. Sci. USA 91 (1994) 8497–8501. [DOI] [PMID: 8078910] |
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[EC 4.2.3.8 created 1989 as EC 4.6.1.7, transferred 2000 to EC 4.2.3.8, modified 2024] |
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EC |
4.2.3.148 |
Accepted name: |
cembrene C synthase |
Reaction: |
geranylgeranyl diphosphate = cembrene C + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Glossary: |
cembrene C = (1E,5E,9E)-1,5,9-trimethyl-12-(propan-2-ylidene)cyclotetradeca-1,5,9-triene |
Other name(s): |
DtcycA (gene name) |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase (cembrene-C-forming) |
Comments: |
Requires Mg2+. Isolated from the bacterium Streptomyces sp. SANK 60404. This bifunctional enzyme also produces (R)-nephthenol. See EC 4.2.3.149, nephthenol synthase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Meguro, A., Tomita, T., Nishiyama, M. and Kuzuyama, T. Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. ChemBioChem 14 (2013) 316–321. [DOI] [PMID: 23386483] |
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[EC 4.2.3.148 created 2014] |
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EC |
4.2.3.149 |
Accepted name: |
nephthenol synthase |
Reaction: |
geranylgeranyl diphosphate + H2O = (R)-nephthenol + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Glossary: |
(R)-nephthenol = 2-[(1R,3E,7E,11E)-4,8,12-trimethyltetradeca-3,7,11-trien-1-yl]propan-2-ol |
Other name(s): |
DtcycA (gene name); DtcycB (gene name) |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase [(R)-nephthenol-forming] |
Comments: |
Requires Mg2+. Two isozymes with this activity were isolated from the bacterium Streptomyces sp. SANK 60404. The enzyme encoded by the DtcycA gene also produces cembrene C (see EC 4.2.3.148, cembrene C synthase), while the enzyme encoded by the DtcycB gene also produces (R)-cembrene A and (1S,4E,8E,12E)-2,2,5,9,13-pentamethylcyclopentadeca-4,8,12-trien-1-ol (see EC 4.2.3.150, cembrene A synthase, and EC 4.2.3.151, pentamethylcyclopentadecatrienol synthase). |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Meguro, A., Tomita, T., Nishiyama, M. and Kuzuyama, T. Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. ChemBioChem 14 (2013) 316–321. [DOI] [PMID: 23386483] |
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[EC 4.2.3.149 created 2014] |
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EC |
4.2.3.150 |
Accepted name: |
cembrene A synthase |
Reaction: |
geranylgeranyl diphosphate = (R)-cembrene A + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Glossary: |
cembrene A = (1E,5E,9E,12R)-1,5,9-trimethyl-12-(propan-2-en-2-yl)cyclotetradeca-1,5,9-triene |
Other name(s): |
DtcycB (gene name) |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase [(R)-cembrene-A-forming] |
Comments: |
Requires Mg2+. Isolated from the bacterium Streptomyces sp. SANK 60404. This trifunctional enzyme, which contains a [4Fe-4S] cluster, also produces (R)-nephthenol and (1S,4E,8E,12E)-2,2,5,9,13-pentamethylcyclopentadeca-4,8,12-trien-1-ol. See EC 4.2.3.149, nephthenol synthase and EC 4.2.3.151, pentamethylcyclopentadecatrienol synthase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Meguro, A., Tomita, T., Nishiyama, M. and Kuzuyama, T. Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. ChemBioChem 14 (2013) 316–321. [DOI] [PMID: 23386483] |
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[EC 4.2.3.150 created 2014] |
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EC |
4.2.3.151 |
Accepted name: |
pentamethylcyclopentadecatrienol synthase |
Reaction: |
geranylgeranyl diphosphate + H2O = (1S,4E,8E,12E)-2,2,5,9,13-pentamethylcyclopentadeca-4,8,12-trien-1-ol + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Other name(s): |
DtcycB (gene name) |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase [(1S,4E,8E,12E)-2,2,5,9,13-pentamethylcyclopentadeca-4,8,12-trien-1-ol-forming] |
Comments: |
Requires Mg2+. Isolated from the bacterium Streptomyces sp. SANK 60404. This trifunctional enzyme, which contains a [4Fe-4S] cluster, also produces (R)-nephthenol and (R)-cembrene A. See EC 4.2.3.150, cembrene A synthase and EC 4.2.3.149, nephthenol synthase. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Meguro, A., Tomita, T., Nishiyama, M. and Kuzuyama, T. Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. ChemBioChem 14 (2013) 316–321. [DOI] [PMID: 23386483] |
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[EC 4.2.3.151 created 2014] |
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EC |
4.2.3.200 |
Accepted name: |
β-pinacene synthase |
Reaction: |
geranylgeranyl diphosphate = β-pinacene + diphosphate |
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For diagram of cembrene and related diterpenoids, click here |
Glossary: |
β-pinacene = 4,8,12-trimethyl-1-(propan-2-yl)cyclotetradeca-1,3,7,11-tetraene |
Other name(s): |
PcS |
Systematic name: |
geranylgeranyl-diphosphate diphosphate-lyase (cyclizing, β-pinacene-forming) |
Comments: |
Isolated from the slime mould Dictyostelium discoideum. The 1-proR hydrogen atom of geranylgeranyl diphosphate is lost in the reaction. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Rinkel, J., Rabe, P., Chen, X., Kollner, T.G., Chen, F. and Dickschat, J.S. Mechanisms of the diterpene cyclases β-pinacene synthase from Dictyostelium discoideum and hydropyrene synthase from Streptomyces clavuligerus. Chem. Eur. J. 23 (2017) 10501–10505. [PMID: 28696553] |
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[EC 4.2.3.200 created 2018] |
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