Literature summary for 4.2.3.B18 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.

Search for more literature for 4.2.3.B18

KM Value [mM]

KM Value [mM]	KM Value Maximum [mM]	Substrate	Comment	Organism	Structure
0.01403	-	(2Z,6E)-farnesyl diphosphate	pH 7.5, 22°C	Nicotiana tabacum

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
(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	-	?

Organism

Organism	UniProt	Comment	Textmining
Nicotiana tabacum	-	recombinant enzyme	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
(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	-	?
(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	-	?

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
22	-	assay at	Nicotiana tabacum

Turnover Number [1/s]

Turnover Number Minimum [1/s]	Turnover Number Maximum [1/s]	Substrate	Comment	Organism	Structure
0.095	-	(2Z,6E)-farnesyl diphosphate	pH 7.5, 22°C	Nicotiana tabacum

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7.5	-	assay at	Nicotiana tabacum

kcat/KM [mM/s]

kcat/KM Value [1/mMs^-1]	kcat/KM Value Maximum [1/mMs^-1]	Substrate	Comment	Organism	Structure
6.77	-	(2Z,6E)-farnesyl diphosphate	pH 7.5, 22°C	Nicotiana tabacum

Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.

Release 2023.1 (January 2023)