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Enzyme Nomenclature
Information on EC 4.2.3.126 - gamma-muurolene synthase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
4.2.3.126
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RECOMMENDED NAME
GeneOntology No.
gamma-muurolene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = gamma-muurolene + diphosphate
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lase (cyclizing, gamma-muurolene-forming)
The enzyme has been characterized from the fungus Coprinus cinereus. Also gives germacrene A and alpha-muurolene, see EC 4.2.3.23, germacrene-A synthase and EC 4.2.3.125, alpha-muurolene synthase.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
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role of the active site H-alpha1 loop in catalysis, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
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?
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
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the major cyclization products of Cop3 and its loop mutants are derived from an E,E-germacradienyl cation formed after ionization and 1,10 cyclization of E,E-farnesyl diphosphate. alpha-Muurolene is 30% of the products formed from (2E,6E)-farnesyl diphosphate
gamma-muurolene is 12% of the products formed from (2E,6E)-farnesyl diphosphate
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(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
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?
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
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SasesquiTPS1 with (2E,6E)-farnesyl diphosphate as substrate produces a complex mixture of mono- and bicyclic sesquiterpenes. The main products as analysed by GC-MS and GC-FID are the cyclic alcohol germacrene D-4-ol, and helminthogermacrene. Also present are alpha-bulnesene, gamma-muurolene, alpha- and beta-selinenes, as well as several other minor bicyclic compounds, alpha-humulene and nerolidol are detected in proportions below 5%
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additional information
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product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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additional information
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seven different sesquiterpenes products, wild-type Cop3 also shows alpha-muurolene synthase activity, EC 4.2.3.125, and produces 30% alpha-muurolene and 35% gemacrene A, product of germacrene A synthase, EC 4.2.3.23, of total products from (2E,6E)-farnesyl diphosphate, product profiling by GC-MS analysis, overview
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additional information
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product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
A8NE23
significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
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the major cyclization products of Cop3 and its loop mutants are derived from an E,E-germacradienyl cation formed after ionization and 1,10 cyclization of E,E-farnesyl diphosphate. alpha-Muurolene is 30% of the products formed from (2E,6E)-farnesyl diphosphate
gamma-muurolene is 12% of the products formed from (2E,6E)-farnesyl diphosphate
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?
additional information
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A8NE23
product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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additional information
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seven different sesquiterpenes products, wild-type Cop3 also shows alpha-muurolene synthase activity, EC 4.2.3.125, and produces 30% alpha-muurolene and 35% gemacrene A, product of germacrene A synthase, EC 4.2.3.23, of total products from (2E,6E)-farnesyl diphosphate, product profiling by GC-MS analysis, overview
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additional information
?
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A8NE23
product profiling by GC-MS analysis, overview. alpha-Muurolene is the major terpenoid compound detected in Cop3 cultures, accounting for about 30% of the total sesquiterpenes detected. Significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
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steady-state kinetics, overview
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
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structural homology modeling of Cop3 using the crystal structure of aristolochene synthase from Aspergillus terreus. Several polar side chains in the H-alpha1 loops of Cop4 and Cop3 move closer to side chains in the metal-binding DDXXD motif
additional information
SasesquiTPS1 shows the R(R/P)X8W motif at positions 19-29, and the DDXXD motif
additional information
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SasesquiTPS1 shows the R(R/P)X8W motif at positions 19-29, and the DDXXD motif
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant HIs6-tagged SasesquiTPS1 from Escherichia coli by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of wild-type and mutant Cop3s in Escherichia coli strain JM109
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gene cop3, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli strain JM109 leading to production of gamma-muurolene
SasesquiTPS1, DNA and amino acid sequence determination and analysis, sequence comparison, functional expression of His6-tagged full-length enzyme in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H255P
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site-directed mutagenesis, modification of the H-alpha1 loop, the mutant shows highly altered product profile compared to the wild-type enzyme, it does no longer produce gamma-muurolene but large amounts of germacrene A (77%), overview
K251I
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site-directed mutagenesis, modification of the H-alpha1 loop, the mutant shows only slightly altered product profile compared to the wild-type enzyme, it produces also beta-copaene, cf. EC 4.2.3.127, overview
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LINKS TO OTHER DATABASES (specific for EC-Number 4.2.3.126)
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