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Literature summary extracted from

  • Faraldos, J.A.; OMaille, P.E.; Dellas, N.; Noel, J.P.; Coates, R.M.
    Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate (2010), J. Am. Chem. Soc., 132, 4281-4289.
    View publication on PubMed

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.3.9 0.0143
-
 (2Z,6E)-farnesyl diphosphate in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C Nicotiana tabacum
4.2.3.B17 0.01403
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B18 0.01403
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B19 0.01403
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.61 0.0084
-
 (2E,6E)-farnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum
4.2.3.61 0.014
-
 (2E,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.61 0.0197
-
 (2E,6Z)-6-fluorofarnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.9 Mg2+ required Nicotiana tabacum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.B17 (2Z,6E)-farnesyl diphosphate Nicotiana tabacum 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 (+)-2-epi-prezizaene + diphosphate
-
 ?
4.2.3.B18 (2Z,6E)-farnesyl diphosphate Nicotiana tabacum 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 (-)-alpha-cedrene + diphosphate
-
 ?
4.2.3.B19 (2Z,6E)-farnesyl diphosphate Nicotiana tabacum 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 (-)-beta-curcumene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.9 Nicotiana tabacum
-
-
-
4.2.3.B17 Nicotiana tabacum
-
 recombinant enzyme
-
4.2.3.B18 Nicotiana tabacum
-
 recombinant enzyme
-
4.2.3.B19 Nicotiana tabacum
-
 recombinant enzyme
-
4.2.3.61 Nicotiana tabacum
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.9 (2E,6E)-farnesyl diphosphate
-
 Nicotiana tabacum (+)-5-epiaristolochene + diphosphate in addition to the major products (+)-5-epiaristolochene (78.9%), its DELTA1(10) isomer (-)-4-epieremophilene (6.2%), and (R)-germacrene A (3.7%), incubations of (2Z,6E)-farnesyl diphosphate with the enzyme lead to 22 additional sesquiterpenes (11% of total products), among the identified minor products are (-)-R-cedrene, an isomer of (-)-prezizaene and an acoradiene (together accounting for 2.5% of the total hydrocarbon fraction) ?
4.2.3.9 (2Z,6E)-farnesyl diphosphate
-
 Nicotiana tabacum (+)-2-epiprezizaene + (-)-alpha-cedrene + (-)-beta-curcumene + alpha-acoradiene + 4-epi-alpha-acoradiene + alpha-bisabolol + epi-alpha-bisabolol + nerolidol + (2Z,6E)-farnesol + diphosphate (+)-2-epiprezizaene (44% yield), (-)-alpha-cedrene (21.5% yield), (-)-beta-curcumene (15.5% yield), alpha-acoradiene (3.9% yield), 4-epi-alpha-acoradiene (1.3% yield), alpha-bisabolol (1.8% yield), epi-alpha-bisabolol (1.8% yield), nerolidol (3.6% yield), (2Z,6E)-farnesol (6.7% yield) ?
4.2.3.B17 (2Z,6E)-farnesyl diphosphate 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 Nicotiana tabacum (+)-2-epi-prezizaene + diphosphate
-
 ?
4.2.3.B17 (2Z,6E)-farnesyl diphosphate 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%) Nicotiana tabacum (+)-2-epi-prezizaene + diphosphate
-
 ?
4.2.3.B18 (2Z,6E)-farnesyl diphosphate 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 Nicotiana tabacum (-)-alpha-cedrene + diphosphate
-
 ?
4.2.3.B18 (2Z,6E)-farnesyl diphosphate 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%) Nicotiana tabacum (-)-alpha-cedrene + diphosphate
-
 ?
4.2.3.B19 (2Z,6E)-farnesyl diphosphate 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 Nicotiana tabacum (-)-beta-curcumene + diphosphate
-
 ?
4.2.3.B19 (2Z,6E)-farnesyl diphosphate 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%) Nicotiana tabacum (-)-beta-curcumene + diphosphate
-
 ?
4.2.3.61 (2E,6E)-farnesyl diphosphate
-
 Nicotiana tabacum (+)-5-epiaristolochene + diphosphate
-
 ?
4.2.3.61 (2E,6Z)-6-fluorofarnesyl diphosphate the fluoro substitution at the C6 position of farnesyl diphosphate has negligible effects on enzyme binding, substrate orientation, diphosphate ionization, and the initial 1,10 ring closure catalyzed by TEAS Nicotiana tabacum (-)-1-fluorogermacrene A sole product, 58% yield ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.9 5-epi-aristolochene synthase
-
 Nicotiana tabacum
4.2.3.9 TEAS
-
 Nicotiana tabacum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.3.B17 22
-
 assay at Nicotiana tabacum
4.2.3.B18 22
-
 assay at Nicotiana tabacum
4.2.3.B19 22
-
 assay at Nicotiana tabacum

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.2.3.9 0.095
-
 (2Z,6E)-farnesyl diphosphate in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C Nicotiana tabacum
4.2.3.B17 0.095
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B18 0.095
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B19 0.095
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.61 0.042
-
 (2E,6E)-farnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum
4.2.3.61 0.095
-
 (2E,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.61 0.11
-
 (2E,6Z)-6-fluorofarnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.3.B17 7.5
-
 assay at Nicotiana tabacum
4.2.3.B18 7.5
-
 assay at Nicotiana tabacum
4.2.3.B19 7.5
-
 assay at Nicotiana tabacum

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
4.2.3.9 0.0068
-
 (2Z,6E)-farnesyl diphosphate in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C Nicotiana tabacum
4.2.3.9 5
-
 (2E,6E)-farnesyl diphosphate
-
 Nicotiana tabacum
4.2.3.B17 6.77
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B18 6.77
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.B19 6.77
-
 (2Z,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum
4.2.3.61 5
-
 (2E,6E)-farnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum
4.2.3.61 5.6
-
 (2E,6Z)-6-fluorofarnesyl diphosphate pH 7.0, 22°C Nicotiana tabacum
4.2.3.61 6.7
-
 (2E,6E)-farnesyl diphosphate pH 7.5, 22°C Nicotiana tabacum