Information on EC 4.2.3.72 - alpha-gurjunene synthase

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The expected taxonomic range for this enzyme is: Solidago canadensis

EC NUMBER
COMMENTARY hide
4.2.3.72
-
RECOMMENDED NAME
GeneOntology No.
alpha-gurjunene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-alpha-gurjunene + diphosphate
show the reaction diagram
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-
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(-)-alpha-gurjunene-forming]
Initial cyclization probably gives biyclogermacrene in an enzyme bound form which is not released to the medium. The enzyme from Solidago canadensis also forms a small amount of (+)-gamma-gurjunene [1].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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
(-)-alpha-gurjunene + diphosphate
show the reaction diagram
-
initial step is the formation of a germacrenyl cation after abstraction of the diphosphate group. Internal shifts of electron pairs lead to the patchoulenyl cation, which then undergoes a double 1,2-hydride shift. Rearrangement leads to the aromadendrenyl cation, which then undergoes a 1,2-hydride shift. Abstraction of a proton by the enzyme yields isoledene, which is reprotonated at the active site of the enzyme. At this junction two proton abstractions are possible, one leading to (-)-alpha-gurjunene and the other to (+)-gamma-gurjunene
product ratio 91% (-)-alpha-gurjunene and 9% (+)-gamma-gurjunene
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
required
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0055
(2E,6E)-farnesyl diphosphate
-
pH 7.0, 30°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
49.9
-
pH 7.0, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.8
-
presence of Mg2+
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
48000
-
gel filtration
60000
-
1 * 60000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 60000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE