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
4.2.3.38
-
RECOMMENDED NAME
GeneOntology No.
alpha-bisabolene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (E)-alpha-bisabolene + diphosphate
show the reaction diagram
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-
-
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(2E,6E)-farnesyl diphosphate = (E)-alpha-bisabolene + diphosphate
show the reaction diagram
electrophilic reaction mechanism
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
bisabolene biosynthesis
-
-
oleoresin sesquiterpene volatiles biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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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.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
(E)-alpha-bisabolene synthase
-
(E)-alpha-bisabolene synthase
-
-
(E)-alpha-bisabolene synthase
-
-
apha-bisabolene synthase
-
bisabolene synthase
-
-
-
-
E-alpha-bisabolene synthase
-
additional information
the enzyme belongs to the terpenoid synthases, subgroup sesquiterpene synthases
additional information
the enzyme belongs to the sesquiterpene synthase family of enzymes, TPS-d subfamily
CAS REGISTRY NUMBER
COMMENTARY
211049-94-4
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene ag1
UniProt
Manually annotated by BRENDA team
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)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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)-alpha-bisabolene + diphosphate
show the reaction diagram
-
product identification by GC-MS
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
-
(E)-alpha-bisabolene is the precursor in Abies species of todomatuic acid, juvabione, and related insect juvenile hormone mimics, overview
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
a step in the terpene synthesis pathway, overview
-
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
the recombinant enzymes is substrate-specific and produces (E)-alpha-bisabolene as sole product
-
?
(2E,6E)-farnesyl diphosphate
(E)-gamma-bisabolene + diphosphate
show the reaction diagram
-
product identification by GC-MS, overview
-
?
additional information
?
-
induced (E)-alpha-bisabolene biosynthesis constitutes part of a defense response targeted to insect herbivores, and possibly fungal pathogens, that is distinct from induced oleoresin monoterpene production
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-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
O81086
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-
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
O81086
-
(E)-alpha-bisabolene is the precursor in Abies species of todomatuic acid, juvabione, and related insect juvenile hormone mimics, overview
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
Q675L6
a step in the terpene synthesis pathway, overview
-
?
additional information
?
-
O81086
induced (E)-alpha-bisabolene biosynthesis constitutes part of a defense response targeted to insect herbivores, and possibly fungal pathogens, that is distinct from induced oleoresin monoterpene production
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
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
Mg2+
activates, saturation with Mg2+ is reached at 5 mM, and no apparent inhibition of catalysis occurs up to 100 mM
Mg2+
required
Mn2+
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
additional information
the activity of recombinant ag1 requires a divalent cation cofactor, Mg2+ or Mn2+, which is employed to neutralize the negative charge of the diphosphate leaving group in the substrate ionization step of the reaction sequence. Mg2+ is more efficient in catalysis than is Mn2+. With GDP as substrate, however, Mn2+ at 0.5 mM yields a 4fold higher rate of monoterpene synthase activity compared to Mg2+ at concentrations up to 50 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
alendronate
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etidronate
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farnesyl thiophosphate
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geranyl thiodiphosphate
-
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Mn2+
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
pamidronate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
the enzyme is wound-inducible
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
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
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
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
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.03
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
from 1-year-old rooted saplings
Manually annotated by BRENDA team
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determination of enzyme expression
Manually annotated by BRENDA team
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fresh, green, with needles, from 1-year-old rooted saplings
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
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
expressed in Escherichia coli BL21(DE3) cells
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
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
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cloning from a cDNA library, DNA and amino acid sequence determination and analysis, sequence comparisons, functional expression in Escherichia coli strain BL21
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