4.2.3.53: (+)-endo-beta-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
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Reaction
Synonyms
SBS
ECTree
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Systematic Name
Systematic Name on EC 4.2.3.53 - (+)-endo-beta-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
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(2Z,6Z)-farnesyl diphosphate lyase (cyclizing; (+)-endo-beta-bergamotene-forming)
The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl diphosphate. Following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the (2Z,6Z)-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-alpha-santalene (see EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (-)-endo-alpha-bergamotene (see EC 4.2.3.54), as well as (+)-endo-beta-bergamotene. Small amounts of (-)-epi-beta-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-alpha-bergamotene are formed from the (6S)-bisabolyl cation [1].