Reaction: (2Z,6Z)-farnesyl diphosphate = ()-endo-α-bergamotene + diphosphate
For diagram of reaction click here.
Other name(s): SBS
Systematic name: (2Z,6Z)-farnesyl-diphosphate lyase (cyclizing; ()-endo-α-bergamotene-forming)
Comments: 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 184.108.40.206), while the (6S)-bisabolyl cation will give rise to (+)-endo-β-bergamotene (EC 220.127.116.11) as well as ()-endo-α-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 .
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
1. Sallaud, C., Rontein, D., Onillon, S., Jabes, F., Duffe, P., Giacalone, C., Thoraval, S., Escoffier, C., Herbette, G., Leonhardt, N., Causse, M. and Tissier, A. A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites. Plant Cell 21 (2009) 301-317. [PMID: 19155349]