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
LITERATURE
(2E,6E)-farnesyl diphosphate = gamma-humulene + diphosphate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
grand fir
SwissProt
Manually annotated by BRENDA team
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
gamma-humulene + diphosphate
show the reaction diagram
O64405
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gamma-humulene is the main product (30.9% yield) of the wild type enzyme
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?
(2E,6E)-farnesyl diphosphate
gamma-humulene + diphosphate
show the reaction diagram
-
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main product with 28.6% yield
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?
additional information
?
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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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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
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
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does not utilize K+ in the cyclization reaction
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
67940
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calculated from amino acid sequence
715436
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hydroxyapatite column chromatography followed by gradient elution from an anion-exchange matrix
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
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ENGINEERING
ORGANISM
UNIPROT
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)