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EC 4.2.3.53 Details
EC number
4.2.3.53
Accepted name
(+)-endo-β-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
Reaction
(2Z,6Z)-farnesyl diphosphate = (+)-endo-β-bergamotene + diphosphate
Other name(s)
SBS (ambiguous)
Systematic name
(2Z,6Z)-farnesyl diphosphate lyase (cyclizing; (+)-endo-β-bergamotene-forming)
Comment
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 (+)-α-santalene (see EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (-)-endo-α-bergamotene (see EC 4.2.3.54), as well as (+)-endo-β-bergamotene. Small amounts of (-)-epi-β-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-α-bergamotene are formed from the (6S)-bisabolyl cation [1].
History
created 2010
EC Tree
2.5.1.12 created 1972, deleted 1976
2.5.1.13 created 1972, deleted 1976
2.5.1.14 created 1972, deleted 1976
2.5.1.37 created 1989, deleted 2004
2.5.1.40 created 1992, deleted 1999