4.2.3.75: (-)-germacrene D synthase
This is an abbreviated version!
For detailed information about (-)-germacrene D synthase, go to the full flat file.
Word Map on EC 4.2.3.75
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4.2.3.75
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cyclization
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sesquiterpene
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cyclases
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carbocation
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geranyl
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epi-isozizaene
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limonene
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chemodiversity
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spearmint
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remold
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4s-limonene
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aristolochene
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oleoresin
- 4.2.3.75
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cyclization
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sesquiterpene
- cyclases
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carbocation
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geranyl
- epi-isozizaene
- limonene
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chemodiversity
- spearmint
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remold
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4s-limonene
- aristolochene
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oleoresin
Reaction
Synonyms
(-)-germacrene D synthase, Cop4, GDS, GerD, germacrene D synthase, Sc19, terpenoid cyclase, TPS, TPS07, TPS1, VitiM1610, ylangene/germacrene synthase
ECTree
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Substrates Products
Substrates Products on EC 4.2.3.75 - (-)-germacrene D synthase
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REACTION DIAGRAM
(2E,6E)-farnesyl diphosphate
(-)-germacrene D + alpha-ylangene + diphosphate
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + beta-caryophyllene + beta-copaene + diphosphate
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(-)-germacrene D + diphosphate
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conversion of (E,E)-FPP proceeds via an (E,E)-germacradienyl carbocation
main products at pH 8.0 are 29.3% (-)-germacrene D, 28.2% cubebol, 10.4% delta-cadinene, at pH 10.0 is 91% (-)-germacrene D, at pH 5.0 84% (-)-germacrene D plus 12% delta-cadinene
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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79.4% of olefinic products
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?
(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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catalyzes the formation of enantiomerically pure (-)-germacrene D
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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main product is germacradienol, about 15% formation of (-)-(7S)-germacrene
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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main product is germacradienol, about 15% formation of (-)-(7S)-germacrene
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(2E,6E)-farnesyl diphosphate
(-)-germacrene D + diphosphate
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plus about 8% dleta-cadinene
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(-)-(7S)-germacrene D + diphosphate
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2-trans,6-trans-farnesyl diphosphate
(-)-(7S)-germacrene D + diphosphate
strictly enantio-specific reaction of (-)-germacrene D synthase
GC-MS product analysis
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Coprinus cinereus Cop4 additionally accepts (2Z,6E)-farnesyl diphosphate to produce 27.7% alpha-acoradiene, 10% amorpha-4,11-diene, and 13.3% cadina-4,11-diene
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additional information
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no substrate: geranyl diphosphate or geranylgeranyl diphosphate
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additional information
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no substrate: geranyl diphosphate or geranylgeranyl diphosphate
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