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

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Poaceae

EC NUMBER
COMMENTARY
4.2.3.55
-
RECOMMENDED NAME
GeneOntology No.
(S)-beta-bisabolene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(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
Q1EG72, Q5GJ60
(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 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.
Q1EG72, Q5GJ60
PATHWAY
KEGG Link
MetaCyc Link
bisabolene biosynthesis
-
santalene biosynthesis II
-
Sesquiterpenoid and triterpenoid biosynthesis
-
zealexin biosynthesis
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
Os08g07100
Q0J7R9
gene name
TPS11
Q1EG72
-
TPS6
Q5GJ60
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
L. variety B73
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
the enzyme may be involved in plant defense
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
(S)-beta-bisabolene + diphosphate
show the reaction diagram
Q1EG72, Q5GJ60, -
-
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
Q0J7R9
-
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
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
-
?
(2Z,6E)-farnesyl diphosphate
(S)-beta-bisabolene + diphosphate
show the reaction diagram
Q1EG72, Q5GJ60, -
-
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
?
-
Q1EG72, Q5GJ60, -
no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity
-
-
-
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
(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 ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q1EG72, Q5GJ60
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+
Q1EG72, Q5GJ60
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]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0021
-
(2E,6E)-farnesyl diphosphate
Q1EG72, Q5GJ60
30°C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
-
Q1EG72, Q5GJ60
in presence of 5 mM Mg2+
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.2
8.6
Q1EG72, Q5GJ60
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
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
Q1EG72, Q5GJ60
assay at; assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
the enzyme is predominantly active in the roots
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
partial; partial
Q1EG72, Q5GJ60
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overexpression in Escherichia coli; overexpression in Escherichia coli
Q1EG72, Q5GJ60
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
L405V
Q0J7R9
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
Q0J7R9
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
Q0J7R9
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
Q1EG72, Q5GJ60
mutation inactivates the enzyme completely
Y522F
Q1EG72, Q5GJ60
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