|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 188.8.131.52
In Pathway: santalene biosynthesis I
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.
Mass balance status: Balanced.
Enzyme Commission Primary Name: (+)-α-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
Enzyme Commission Synonyms: SBS (ambiguous)
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -53.649994 [Latendresse13]
Enzyme Commission Summary:
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 (EC 184.108.40.206), while the (6S)-bisabolyl cation will give rise to (-)-endo-α-bergamotene (see EC 220.127.116.11) and (+)-endo-β-bergamotene (see EC 18.104.22.168). 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 [Sallaud09].
Unification Links: Rhea:30466
Huikuri09: Huikuri HV, Raatikainen MJ, Moerch-Joergensen R, Hartikainen J, Virtanen V, Boland J, Anttonen O, Hoest N, Boersma LV, Platou ES, Messier MD, Bloch-Thomsen PE, Cardiac Arrhythmias and Risk Stratification after Acute Myocardial Infarction study group (2009). "Prediction of fatal or near-fatal cardiac arrhythmia events in patients with depressed left ventricular function after an acute myocardial infarction." Eur Heart J 30(6);689-98. PMID: 19155249
Sallaud09: Sallaud C, Rontein D, Onillon S, Jabes F, Duffe P, Giacalone C, Thoraval S, Escoffier C, Herbette G, Leonhardt N, Causse M, Tissier A (2009). "A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites." Plant Cell 21(1);301-17. PMID: 19155349
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