Information on EC 4.2.3.55 - (S)-beta-bisabolene synthase

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The expected taxonomic range for this enzyme is: Poaceae

EC NUMBER
COMMENTARY
4.2.3.55
-
RECOMMENDED NAME
GeneOntology No.
(S)-beta-bisabolene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (S)-beta-bisabolene + diphosphate
show the reaction diagram
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(2E,6E)-farnesyl diphosphate = (S)-beta-bisabolene + diphosphate
show the reaction diagram
(S)-beta-bisabolene is a stable intermediate. (S)-beta-Macrocarpene formation requires a protonation of the intermediate; The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second steps is the isomerization to (S)-beta-macrocarpene (c.f. EC 5.5.1.a, (S)-beta-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
bisabolene biosynthesis
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santalene biosynthesis II
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zealexin biosynthesis
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Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(S)-beta-bisabolene-forming]
The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene (cf. EC 5.5.1.17, (S)-beta-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Os08g07100
gene name
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
L. variety B73
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
the enzyme may be involved in plant defense; the enzyme may be involved in plant defense
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
(S)-beta-bisabolene + diphosphate
show the reaction diagram
-
The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS
?
(2E,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
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products of Oryza sativa Os08g07100 gene product are 2.5% 7-epi-sesquithujene, 5.7% (E)-alpha-bergamotene, 5.7% sesquiabinene A, 11.9% (E)-beta-farnesene, 1.5% gamma-curcumene, 30.1% zingiberene, 12.3% beta-bisabolene, 19.1% beta-sesquiphellandrene, 11.2% (E)-gamma-bisabolene
?
(2E,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
the enzyme may be involved in plant defense
-
?
(2E,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
the enzyme may be involved in plant defense
i.e. ((4S)-1-methyl-4-(5-methyl-1-methylidenehex-4-en-1-yl)cyclohexene
?
(2Z,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
-
The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS
?
additional information
?
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no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity
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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
(S)-beta-bisabolene + diphosphate
show the reaction diagram
Q1EG72, Q5GJ60
the enzyme may be involved in plant defense
-
?
(2E,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
Q1EG72, Q5GJ60
the enzyme may be involved in plant defense
i.e. ((4S)-1-methyl-4-(5-methyl-1-methylidenehex-4-en-1-yl)cyclohexene
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mg2+ measured with 0.01 mM farnesyl diphosphate: 0.131 mM
Mn2+
TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mn2+ measured with 0.01 mM farnesyl diphosphate: 0.0234 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0021
(2E,6E)-farnesyl diphosphate
30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7
in presence of 5 mM Mg2+
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.2 - 8.6
half-maximal activity at pH 6.2 and at pH 8.6, in presence of 5 mM Mg2+. Within a pH range from 5.0 to 8.0, the major product is (S)-beta-macrocarpene, but higher pH values favor the formation of (S)-beta-bisabolene
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
assay at; assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
the enzyme is predominantly active in the roots; the enzyme is predominantly active in the roots
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial; partial
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overexpression in Escherichia coli; overexpression in Escherichia coli
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L405V
products are 1.9% 7-epi-sesquithujene, 8.1% (E)-alpha-bergamotene, 8.9% sesquiabinene A, 23.9% (E)-beta-farnesene, 0% gamma-curcumene, 9.7% zingiberene, 12.0% beta-bisabolene, 26.6% beta-sesquiphellandrene, 8.9% (E)-gamma-bisabolene
L405V/Y373S
products are 1.2% 7-epi-sesquithujene, 23.6% (E)-alpha-bergamotene, 17.7% sesquiabinene A, 53.0% (E)-beta-farnesene, 0% gamma-curcumene, 0.6% zingiberene, 1.3% beta-bisabolene, 2.6% beta-sesquiphellandrene, 0% (E)-gamma-bisabolene
Y373S
products are 7.6% 7-epi-sesquithujene, 24.8% (E)-alpha-bergamotene, 18.2% sesquiabinene A, 38.5% (E)-beta-farnesene, 0% gamma-curcumene, 4.7% zingiberene, 2.5% beta-bisabolene, 3.7% beta-sesquiphellandrene, 0% (E)-gamma-bisabolene
D526N
mutation inactivates the enzyme completely
Y522F
mutation reduces the production of (S)-beta-macrocarpene to trace amounts, the enzyme forms (S)-beta-bisabolene almost exclusively, the overall activity of the mutated enzyme is dramatically reduced