4.2.3.13: (+)-delta-cadinene synthase
This is an abbreviated version!
For detailed information about (+)-delta-cadinene synthase, go to the full flat file.
Word Map on EC 4.2.3.13
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4.2.3.13
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synthases
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terpenoids
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sesquiterpenoids
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germacrene
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geranyl
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linalool
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arboreum
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+-delta-cadinene
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lavandula
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beta-caryophyllene
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multiproduct
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fragrant
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alpha-humulene
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agarwood
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e,e-farnesyl
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e-beta-farnesene
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amorpha-4,11-diene
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ddxxd
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aquilaria
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5-epi-aristolochene
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synthesis
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agriculture
- 4.2.3.13
- synthases
-
terpenoids
- sesquiterpenoids
- germacrene
-
geranyl
- linalool
- arboreum
-
+-delta-cadinene
- lavandula
- beta-caryophyllene
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multiproduct
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fragrant
- alpha-humulene
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agarwood
-
e,e-farnesyl
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e-beta-farnesene
- amorpha-4,11-diene
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ddxxd
- aquilaria
- 5-epi-aristolochene
- synthesis
- agriculture
Reaction
Synonyms
(+)-delta-cadinene synthase, (+)-delta-cadinene synthase isoenzyme XC1, 2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, (+)-alpha-cadinene-forming), bifunctional sesquiterpene synthase 1, CAD, cadinene synthase, cadinol/cadinene synthase, CDN1, Cdn1-C1, Cdn1-C14, Cop4, cyclase, delta-cadinene, DCS, Dcs1, delta-cadinene cyclase, delta-cadinene synthase, EC 4.6.1.11, farnesyl diphosphate-delta-cadinene cyclase, PnCO/CDS, PnTPS2, sesquiterpene synthase, TPS1, TPS2
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.13 - (+)-delta-cadinene synthase
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REACTION DIAGRAM
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + germacradien-4-ol + diphosphate
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-
-
?
(2E,6Z)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
nerolidyl diphosphate
(+)-delta-cadinene + alpha-bisabolol + beta-bisabolene + beta-farnesene + ?
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-
?
(+)-delta-cadinene + diphosphate
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-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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products are about 60% (-)-alpha-copaene, 40% (+)-delta-cadinene
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?
delta-cadinene + diphosphate
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major product
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?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
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major product
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?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
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delta-cadinene is one of the two main products, while alpha-muuorlene, beta-caryophyllene, alpha-humulene and alpha-copaene are minor products
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?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
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bifunctional sesquiterpene synthase producing both alpha-copaene and delta-cadinene
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?
delta-cadinene + diphosphate
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Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene)
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-
?
(2E,6E)-farnesyl diphosphate + H2O
delta-cadinene + diphosphate
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Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene)
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-
?
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
the fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton
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-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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amount of enzyme does not increase significantly in stems treated with Verticillium dahliae due to a high basal level of enzyme in untreated stems
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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nerolidyl diphosphate is an intermediate
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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the first step enzyme in the conversion of farnesyl diphosphate to sesquiterpene phytoalexins. The reaction is induced by the infection of cotton with Verticillium dahliae
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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the product (+)-delta-cadinene is metabolically converted to deoxyhemigossypol, deoxyhemigossypol 6-methyl ether, hemigossypol and hemigossypol 6-methyl ether
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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transcription of cad1-C is activated in stems treated with Verticillium dahliae
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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the sesquiterpenoid (+)-alpha-cadinene is an intermediate in phytoalexin biosynthesis
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?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
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the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
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?
?
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delta-cadinene synthase is a sesquiterpene cyclase that utilises the universal achiral precursor farnesyl diphosphate (FDP) to generate predominantly the bicyclic sesquiterpene delta-cadinene and about 2% germacradien-4-ol
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additional information
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products (in vivo expression in Saccharomyces cerevisiae): delta-cadinene and a compound with a cadinene skeleton, minor products: alpha-muurolene, beta-caryophyllene, alpha-humulene and alpha-copaene
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?