4.2.3.50: (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

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Reaction

Synonyms

SBS

ECTree

4 Lyases

4.2 Carbon-oxygen lyases

4.2.3 Acting on phosphates

4.2.3.50 (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

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Systematic Name on EC 4.2.3.50 - (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

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(2Z,6Z)-farnesyl diphosphate lyase [cyclizing; (+)-alpha-santalene-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 (EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (+)-endo-beta-bergamotene (see EC 4.2.3.53) as well as (-)-endo-alpha-bergamotene (see EC 4.2.3.54). 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].