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MetaCyc Reaction: 4.2.3.50

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 4.2.3.50

Enzymes and Genes:

Solanum habrochaites: santalene and bergamontene synthaseInferred from experiment: SBS

In Pathway: santalene biosynthesis I

The direction shown, i.e. which substrates are on the left and right sides, 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): -53.649994Inferred by computational analysis [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 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (-)-endo-α-bergamotene (see EC 4.2.3.54) and (+)-endo-β-bergamotene (see EC 4.2.3.53). 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].

Citations: [Huikuri09]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: Rhea:30466

Relationship Links: BRENDA:EC:4.2.3.50, ENZYME:EC:4.2.3.50, IUBMB-ExplorEnz:EC:4.2.3.50

Credits:
Created 18-Jul-2011 by Pujar A, Boyce Thompson Institute


References

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

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Feb 13, 2016, biocyc11.