Information on EC 4.2.3.81 - exo-alpha-bergamotene synthase

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The expected taxonomic range for this enzyme is: Magnoliophyta

EC NUMBER
COMMENTARY
4.2.3.81
-
RECOMMENDED NAME
GeneOntology No.
exo-alpha-bergamotene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = (-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
bergamotene biosynthesis I
-
santalene biosynthesis II
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate lyase (cyclizing, (-)-exo-alpha-bergamotene-forming)
The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (-)-exo-alpha-bergamotene (74%) there were (E)-nerolidol (10%), (Z)-alpha-bisabolene (6%), (E)-beta-farnesene (5%) and beta-sesquiphellandrene (1%).
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
LaBERS
Q2XSC4
-
SaSSy
E3W202
-
SspiSy
E3W204
-
SSy
E3W202
-
SSy
E3W204
-
TPS10
Q2NM15
gene name
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
-
UniProt
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
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
Q2NM15
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W202, -
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W203, -
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
Q2XSC4
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
Q2NM15
after herbivory by lepidopteran larvae, maize releases a mixture of volatiles that is highly attractive to females of various parasitic wasp species. The terpene synthase TPS10 forms (E)-beta-farnesene, (E)-alpha-bergamotene, and other herbivory-induced sesquiterpene hydrocarbons from the substrate farnesyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W202, -
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W203, -
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W202, -
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W203, -
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
additional information
?
-
E3W202, -
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene. The product profile resulting from incubations of SaSSy with (6E,6E)-farnesyl diphosphate resembles the authentic essential oil of Santalum album more closely than that of the (6Z,6Z)-farnesyl diphosphate incubations
-
-
-
additional information
?
-
E3W203, -
Santalum austrocaledonicum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranxyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
-
additional information
?
-
E3W204
Santalum spicatum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
-
additional information
?
-
E3W202, -
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
-
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
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W202, -
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W203, -
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
Q2XSC4
-
-
-
?
(2E,6E)-farnesyl diphosphate
(-)-exo-alpha-bergamotene + diphosphate
show the reaction diagram
Q2NM15
after herbivory by lepidopteran larvae, maize releases a mixture of volatiles that is highly attractive to females of various parasitic wasp species. The terpene synthase TPS10 forms (E)-beta-farnesene, (E)-alpha-bergamotene, and other herbivory-induced sesquiterpene hydrocarbons from the substrate farnesyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W204
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W202, -
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
exo-alpha-bergamotene + diphosphate
show the reaction diagram
E3W203, -
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
additional information
?
-
E3W202, -
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene. The product profile resulting from incubations of SaSSy with (6E,6E)-farnesyl diphosphate resembles the authentic essential oil of Santalum album more closely than that of the (6Z,6Z)-farnesyl diphosphate incubations
-
-
-
additional information
?
-
E3W203, -
Santalum austrocaledonicum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranxyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
-
additional information
?
-
E3W204
Santalum spicatum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q2XSC4
product formation is highest in the presence of the cofactor Mg2+ with product concentration peaking at 50 mM
Mg2+
E3W202, -
required; when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mg2+
E3W203, -
required; when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mg2+
E3W204
required; when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
Q2XSC4
the assays with Mn2+ shows highest activity at 0.05 mM with 49% of the maximum product level
Mn2+
E3W202, -
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
E3W203, -
incubation in presence of Mn2+ yields mainly alpha-exo-bergamotene; when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
E3W204
incubation in presence of Mn2+ yields mainly alpha-exo-bergamotene; when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0014
-
(2E,6E)-farnesyl diphosphate
E3W202, -
30C, pH 8.0; pH 7.4, 25C
0.0014
-
(2E,6E)-farnesyl diphosphate
E3W203, -
30C, pH 8.0; pH 7.4, 25C
0.0014
-
(2E,6E)-farnesyl diphosphate
E3W204
30C, pH 8.0; pH 7.4, 25C
0.0047
-
(2E,6E)-farnesyl diphosphate
Q2XSC4
pH 7.5, 23C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.033
-
(2E,6E)-farnesyl diphosphate
Q2XSC4
pH 7.5, 23C
0.34
-
(2E,6E)-farnesyl diphosphate
E3W202, -
30C, pH 8.0; pH 7.4, 25C
0.91
-
(2E,6E)-farnesyl diphosphate
E3W203, -
30C, pH 8.0; pH 7.4, 25C
2.6
-
(2E,6E)-farnesyl diphosphate
E3W204
30C, pH 8.0; pH 7.4, 25C
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.7
-
(2E,6E)-farnesyl diphosphate
Q2XSC4
pH 7.5, 23C
263972
242.9
-
(2E,6E)-farnesyl diphosphate
E3W202, -
pH 7.4, 25C
263972
650
-
(2E,6E)-farnesyl diphosphate
E3W203, -
pH 7.4, 25C
263972
1857
-
(2E,6E)-farnesyl diphosphate
E3W204
pH 7.4, 25C
263972
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.4
-
E3W202, -
assay at
7.4
-
E3W203, -
assay at
7.4
-
E3W204
assay at
7.5
-
Q2XSC4
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
23
-
Q2XSC4
assay at
25
-
E3W202, -
assay at
25
-
E3W203, -
assay at
25
-
E3W204
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
66000
-
E3W202, -
-
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
E3W202, -
x * 65163, calculated from sequence; x * 66000, SDS-PAGE of recombinant His-tagged protein
?
E3W203, -
x * 65268, calculated from sequence
?
E3W204
x * 65407, calculated from sequence
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
bovine serum albumin stabilizes
Q2XSC4
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli; heterologous expression of a His6-tagged protein in Escherichia coli
E3W202, -
expression in Escherichia coli; heterologous expression of a His6-tagged protein in Escherichia coli
E3W203, -
expression in Escherichia coli; heterologous expression of a His6-tagged protein in Escherichia coli
E3W204
overexpression of tps10 in Arabidopsis thaliana results in plants emitting high quantities of TPS10 sesquiterpene products identical to that released by maize
Q2NM15
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in response to herbivore attack and is regulated at the transcript level
Q2NM15