Information on EC 4.2.3.38 - alpha-bisabolene synthase

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The expected taxonomic range for this enzyme is: Pinaceae

EC NUMBER
COMMENTARY hide
4.2.3.38
-
RECOMMENDED NAME
GeneOntology No.
alpha-bisabolene synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (E)-alpha-bisabolene + diphosphate
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
bisabolene biosynthesis (engineered)
-
-
Metabolic pathways
-
-
oleoresin sesquiterpene volatiles biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(E)-alpha-bisabolene-forming]
This cytosolic sesquiterpenoid synthase requires a divalent cation cofactor (Mg2+ or, to a lesser extent, Mn2+) to neutralize the negative charge of the diphosphate leaving group. While unlikely to encounter geranyl diphosphate (GDP) in vivo as it is localized to plastids, the enzyme can use GDP as a substrate in vitro to produce (+)-(4R)-limonene [cf. EC 4.2.3.20, (R)-limonene synthase]. The enzyme is induced as part of a defense mechanism in the grand fir Abies grandis as a response to stem wounding.
CAS REGISTRY NUMBER
COMMENTARY hide
211049-94-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Norway spruce, gene PaTPS-Bis
UniProt
Manually annotated by BRENDA team
white spruce
-
-
Manually annotated by BRENDA team
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
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
(2E,6E)-farnesyl diphosphate
(E)-gamma-bisabolene + diphosphate
show the reaction diagram
-
product identification by GC-MS, overview
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KCl
only weakly influences GDP conversion with the ag1 enzyme causing a 2fold activation at 100 mM KCl, but the monovalent cation has no effect with FDP as substrate
Mn2+
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alendronate
-
etidronate
-
farnesyl thiophosphate
-
-
geranyl thiodiphosphate
-
-
Mn2+
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
pamidronate
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0495
(2E,6E)-farnesyl diphosphate
in 25 mM Tris, 15 mM MgCl2, pH 7.5, at 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002
(2E,6E)-farnesyl diphosphate
Abies grandis
O81086
in 25 mM Tris, 15 mM MgCl2, pH 7.5, at 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.038
(2E,6E)-farnesyl diphosphate
Abies grandis
O81086
in 25 mM Tris, 15 mM MgCl2, pH 7.5, at 30°C
81
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.03
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
from 1-year-old rooted saplings
Manually annotated by BRENDA team
-
determination of enzyme expression
Manually annotated by BRENDA team
-
fresh, green, with needles, from 1-year-old rooted saplings
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 93776, sequence calculation
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
apo form and bound to five inhibitors, sitting drop vapor diffusion method, using 100 mM Tris pH 8.5, 100 mM NaCl, and 23% (w/v) PEG 3350
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
HisTrap column chromatography and Superdex 200 gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloning from a cDNA library, DNA and amino acid sequence determination and analysis, sequence comparisons, functional expression in Escherichia coli strain BL21
-
expressed in Escherichia coli BL21(DE3) cells
expression of the enzyme under control of the potato proteinase inhibitor II pinII-promoter in Picea glauca seedlings, as well as in Arabidopsis thaliana and Nicotiana tabacum in a cell-specific manner in trichomes, expression analysis of theGUS-(E)-alpha-bisabolene synthase construct, overview
-
gene ag1, cloning from a wound-induced stem-cDNA library, DNA and amino acid sequence determination and analysis, sequence comparisons, phylogenetic tree, functional expression in Escherichia coli strain XL1-Blue
gene PaTPS-Bis, DNA and amino acid sequence determination and analysis, expression and phylogenetic analysis, sequence comparison with other enzymes of the terpene synthase family, functional expression in Escherichia coli