Information on EC 4.2.3.56 - gamma-humulene synthase

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The expected taxonomic range for this enzyme is: Abies grandis

EC NUMBER
COMMENTARY
4.2.3.56
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RECOMMENDED NAME
GeneOntology No.
gamma-humulene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = gamma-humulene + diphosphate
show the reaction diagram
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-
-
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PATHWAY
KEGG Link
MetaCyc Link
oleoresin sesquiterpene volatiles biosynthesis
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Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase (gamma-humulene-forming)
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SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
gamma-humulene synthase
O64405
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gammaHS
O64405
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ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
grand fir
SwissProt
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
gamma-humulene + diphosphate
show the reaction diagram
-, O64405
-
gamma-humulene is the main product (30.9% yield) of the wild type enzyme
-
?
(2E,6E)-farnesyl diphosphate
gamma-humulene + diphosphate
show the reaction diagram
-
-
main product with 28.6% yield
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?
additional information
?
-
-, O64405
besides gamma-humulene (30.9% yield), gamma-humulene synthase produces 18.9% siberene, 11.4% longifolene, 7.4% beta-bisabolene, 4.3% sativene, 4.1% alpha-longipinene, 3.0% beta-farnesene, 2.6% alpha-ylangene, 2.1% beta-gurjunene, 2.0% gamma-bisabolene, 1.7% beta-longipinene, 1.3% alpha-bisaolene, 1.3% alpha-himachalene, 1.1% gamma-himachalene, 1.0% cyclosativene, 0.6% beta-ylangene, and 0.2% beta-cubebene
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-
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additional information
?
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gamma-humulene synthase produces mainly gamma-humulene (28.6% yield) from (2E,6E)-farnesyl diphosphate, further products are sibirene (15.1% yield), longifolene (11.8% yield), beta-himachalene (7.2% yield), alpha-himachalene (4.8% yield), beta-bisabolene (3.9% yield), alpha-longipinene (3.4% yield), sativene (3.1% yield), alpha-ylangene (2.7% yield), beta-gurjunene (2.0% yield), gamma-bisabolene (1.9% yield), beta-longipinene (1.5% yield), (E)-beta-farnesene (1.3% yield), (E)-alpha-bisabolene (0.9% yield), delta-amorphene and alpha-amorphene (0.5% yield each), beta-ylangene (0.3% yield), 1,5,9-trimethylcyclododeca-1,5,9-triene and longicyclene (0.2% yield each), as well as beta-cubebene, alpha-copaene, alpha-cubebene, (Z,E)-germacrene B, and cyclosativene (0.1% yield each), along with 26 unknown sesquiterpene olefins (4.1% total yield)
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METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
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gamma-humulene synthase can utilize Mg2+ or Mn2+ with comparable velocities in the cyclization reaction
Mn2+
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gamma-humulene synthase can utilize Mg2+ or Mn2+ with comparable velocities in the cyclization reaction
additional information
-
does not utilize K+ in the cyclization reaction
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
67940
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calculated from amino acid sequence
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
hydroxyapatite column chromatography followed by gradient elution from an anion-exchange matrix
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Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D343A
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the mutation results in severely impaired activity for olefin production (estimated kcat reduction by more than 3000fold), the mutant produces 27.9% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 12.9% gamma-humulene (the main product of the wild type enzyme)
D343E
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the mutant produces 34.4% sativene from (2E,6E)-farnesyl diphosphate as the main product and no gamma-humulene (the main product of the wild type enzyme), the mutant is capable of producing sesquiterpenols (61% nerolidol and 14% bisabolol, very similar to wild type distribution) at a rate comparable to that of olefin formation by the wild type enzyme
D488A
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the mutant produces 40% sativene from (2E,6E)-farnesyl diphosphate as the main product and no gamma-humulene (the main product of the wild type enzyme)
D488E
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the mutant produces 19.6% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 6.0% gamma-humulene (the main product of the wild type enzyme), olefin synthase activity is reduced to 3% of wild type enzyme
D488N
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the mutant produces 21.7% sativene from (2E,6E)-farnesyl diphosphate as the main product and only 18.7% gamma-humulene (the main product of the wild type enzyme)
D570N
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the mutant produces 13.1% sativene from (2E,6E)-farnesyl diphosphate as the main product and 29.3% gamma-humulene (the main product of the wild type enzyme)
Y566F
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the mutant produces 42.6% gamma-humulene (the main product of the wild type enzyme)