The enzyme occurs in plants. The initial cyclization product is a (7R)-β-bisabolyl cation. (–)-α-Cedrene is one of the major products. Other products are (+)-2-epi-prezizaene (cf. EC 4.2.3.226, (+)-2-epi-prezizaene synthase), small amounts of (+)-β-curcumene, and other sesquiterpenes with less than 10% yield. The enzyme from Nicotiana tabacum (tobacco) also catalyses the reaction of EC 4.2.3.61, 5-epiaristolochene synthase.
The expected taxonomic range for this enzyme is: Nicotiana tabacum
The enzyme occurs in plants. The initial cyclization product is a (7R)-beta-bisabolyl cation. (-)-alpha-Cedrene is one of the major products. Other products are (+)-2-epi-prezizaene (cf. EC 4.2.3.226, (+)-2-epi-prezizaene synthase), small amounts of (+)-beta-curcumene, and other sesquiterpenes with less than 10% yield. The enzyme from Nicotiana tabacum (tobacco) also catalyses the reaction of EC 4.2.3.61, 5-epiaristolochene synthase.
Substrates: formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place Products: -
Substrates: formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%) Products: -
Substrates: formation of seven bisabolyl-derived sesquiterpenes through the intermediacy of a common (7R)-beta-bisabolyl cation, (+)-2-epiprezizaene (44%) is the major product, (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisabolol (1.8%). The enzyme may be able to exploit the low natural levels (3-14%) of (2Z,6E)-farnesyl diphosphate generated by farnesyl diphosphate synthases to produce a different array of sesquiterpenes in vivo. If the concentration of (2E,2E)-farnesyl diphosphate is depleted by its diversion into biosynthesis of phytosterols, farnesylated proteins, or diterpenes, the enzyme would be capable of utilizing (2Z,6E)-farnesyl diphosphate in its place Products: -
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop method, crystallographic analyses of wild-type enzyme and a promiscuous mutant, with unreactive 2-fluoro analogues ((2E,6E)-2-fluorofarnesyl diphosphate and (2Z,6E)-2-fluorofarnesyl diphosphate) of (2E,6E)- and (2Z,6E)-farnesyl diphosphate reveals catalytically relevant binding modes and distinct farnesyl chain topologies that are consistent with preorganization by the active-site for cisoid or transoid cyclization
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