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Information on EC 4.2.3.9 - aristolochene synthase and Organism(s) Nicotiana tabacum and UniProt Accession Q40577

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EC Tree
     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.9 aristolochene synthase
IUBMB Comments
The initial internal cyclization produces the monocyclic intermediate germacrene A; further cyclization and methyl transfer converts the intermediate into aristolochene. While in some species germacrene A remains as an enzyme-bound intermediate, it has been shown to be a minor product of the reaction in Penicillium roqueforti (see also EC 4.2.3.23, germacrene-A synthase). The enzyme from Penicillium roqueforti requires Mg2+. Mn2+ can partially substitute, at low concentrations. Aristolochene is the likely parent compound for a number of sesquiterpenes produced by filamentous fungi.
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This record set is specific for:
Nicotiana tabacum
UNIPROT: Q40577
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The taxonomic range for the selected organisms is: Nicotiana tabacum
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
sesquiterpene cyclase, aristolochene synthase, 5-epi-aristolochene synthase, farnesylpyrophosphate cyclase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5-epi-aristolochene synthase
-
5-epi-aristolochene synthase
-
-
AS
-
-
-
-
cyclase, farnesyl pyrophosphate
-
-
-
-
farnesylpyrophosphate cyclase
-
-
-
-
FPP-carbocyclase
-
-
-
-
sesquiterpene cyclase
-
-
-
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synthase, aristolochene
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
internal cyclization
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-
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate diphosphate-lyase (cyclizing, aristolochene-forming)
The initial internal cyclization produces the monocyclic intermediate germacrene A; further cyclization and methyl transfer converts the intermediate into aristolochene. While in some species germacrene A remains as an enzyme-bound intermediate, it has been shown to be a minor product of the reaction in Penicillium roqueforti [5] (see also EC 4.2.3.23, germacrene-A synthase). The enzyme from Penicillium roqueforti requires Mg2+. Mn2+ can partially substitute, at low concentrations. Aristolochene is the likely parent compound for a number of sesquiterpenes produced by filamentous fungi.
CAS REGISTRY NUMBER
COMMENTARY hide
94185-89-4
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-5-epi-aristolochene + diphosphate
show the reaction diagram
-
-
-
?
anilinogeranyl diphosphate
(4E,8E)-4,8-dimethyl-2-azabicyclo[9.2.2]pentadeca-1(13),4,8,11,14-pentaene + diphosphate
show the reaction diagram
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-5-epiaristolochene + diphosphate
show the reaction diagram
-
-
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)
-
?
(2Z,6E)-farnesyl diphosphate
(+)-2-epiprezizaene + (-)-alpha-cedrene + (-)-beta-curcumene + alpha-acoradiene + 4-epi-alpha-acoradiene + alpha-bisabolol + epi-alpha-bisabolol + nerolidol + (2Z,6E)-farnesol + diphosphate
show the reaction diagram
-
-
(+)-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)
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-5-epi-aristolochene + diphosphate
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
required
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
anilinogeranyl diphosphate
potent noncompetitive inhibitor
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00447
(2E,6E)-farnesyl diphosphate
at pH 7.5 and 37°C
0.0082
anilinogeranyl diphosphate
at pH 7.5 and 37°C
0.0143
(2Z,6E)-farnesyl diphosphate
-
in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.032
(2E,6E)-farnesyl diphosphate
at pH 7.5 and 37°C
0.00012
anilinogeranyl diphosphate
at pH 7.5 and 37°C
0.095
(2Z,6E)-farnesyl diphosphate
-
in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5 - 11.8
(2E,6E)-farnesyl diphosphate
5
(2E,6E)-farnesyl diphosphate
-
-
0.0068
(2Z,6E)-farnesyl diphosphate
-
in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00041
anilinogeranyl diphosphate
at pH 7.5 and 37°C
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
5EAS_TOBAC
548
0
62987
Swiss-Prot
-
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
His-bind Ni2+ column chromatography, Mono Q column chromatography, and Superdex 200 gel filtration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
J. Am. Chem. Soc.
132
4281-4289
2010
Nicotiana tabacum
Manually annotated by BRENDA team
Rising, K.A.; Crenshaw, C.M.; Koo, H.J.; Subramanian, T.; Chehade, K.A.; Starks, C.; Allen, K.D.; Andres, D.A.; Spielmann, H.P.; Noel, J.P.; Chappell, J.
Formation of a novel macrocyclic alkaloid from the unnatural farnesyl diphosphate analogue anilinogeranyl diphosphate by 5-epi-aristolochene synthase
ACS Chem. Biol.
10
1729-1736
2015
Nicotiana tabacum (Q40577), Nicotiana tabacum
Manually annotated by BRENDA team