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
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = (E)-alpha-bisabolene + diphosphate
show the reaction diagram
-
-
-
-
(2E,6E)-farnesyl diphosphate = (E)-alpha-bisabolene + diphosphate
show the reaction diagram
electrophilic reaction mechanism
-, O81086
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
bisabolene biosynthesis
-
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(E)-alpha-bisabolene synthase
O81086
-
(E)-alpha-bisabolene synthase
-
-
(E)-alpha-bisabolene synthase
-
-
bisabolene synthase
-
-
-
-
E-alpha-bisabolene synthase
Q675L6
-
additional information
O81086
the enzyme belongs to the terpenoid synthases, subgroup sesquiterpene synthases
additional information
Q675L6
the enzyme belongs to the sesquiterpene synthase family of enzymes, TPS-d subfamily
CAS REGISTRY NUMBER
COMMENTARY
211049-94-4
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
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 ACCESSION NO.
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
-, Q675L6
-
product identification by GC-MS
-
?
(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
-
-
?
(2E,6E)-farnesyl diphosphate
(E)-alpha-bisabolene + diphosphate
show the reaction diagram
-, O81086
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
?
-
-, 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
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
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
-
(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 ACCESSION NO.
COMMENTARY
LITERATURE
KCl
-, O81086
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+
-, O81086
activates, saturation with Mg2+ is reached at 5 mM, and no apparent inhibition of catalysis occurs up to 100 mM
Mn2+
-, O81086
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
additional information
-, O81086
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 ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Mn2+
-, O81086
activates, but Mn2+ at concentrations higher than 1 mM results in a decline of activity with either substrate
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-, O81086
the enzyme is wound-inducible
-
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-, O81086
assay at
30
-
-
assay at
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.03
-
-, O81086
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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 ACCESSION NO.
COMMENTARY
LITERATURE
?
-, O81086
x * 93776, sequence calculation
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
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
-, O81086
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
-, Q675L6
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
-
cloning from a cDNA library, DNA and amino acid sequence determination and analysis, sequence comparisons, functional expression in Escherichia coli strain BL21
-