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Information on EC 4.2.3.126 - gamma-muurolene synthase
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4.2.3.126 gamma-muurolene synthaseIUBMB Comments
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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The enzyme appears in viruses and cellular organisms
Synonyms
Cop3, SasesquiTPS1, sesquiterpene synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Cop3
Cop3
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-
ambiguous
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = gamma-muurolene + diphosphate
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-
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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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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
-
-
-
?
(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
-
?
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
-
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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-
?
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NATURAL SUBSTRATE
NATURAL 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
significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures
-
-
?
(2E,6E)-farnesyl diphosphate
gamma-muurolene + diphosphate
-
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
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
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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-
?
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
role of the active site H-alpha1 loop in catalysis, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). AGR3_AGRAE
358
0
40819
Swiss-Prot
other Location (Reliability: 5)
AGR4_AGRAE
342
0
38560
Swiss-Prot
other Location (Reliability: 1)
AGR8_AGRAE
353
0
40511
Swiss-Prot
other Location (Reliability: 1)
AGR9_AGRAE
372
0
42668
Swiss-Prot
other Location (Reliability: 4)
STS1_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38401
Swiss-Prot
other Location (Reliability: 3)
TPS1_PHYPO
334
0
38880
Swiss-Prot
other Location (Reliability: 3)
COP3_COPC7
Coprinopsis cinerea (strain Okayama-7 / 130 / ATCC MYA-4618 / FGSC 9003)
425
0
47766
Swiss-Prot
other Location (Reliability: 2)
AGR1_AGRAE
346
0
39574
Swiss-Prot
Mitochondrion (Reliability: 4)
STS10_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
336
0
38275
Swiss-Prot
other Location (Reliability: 4)
STS2_POSPM
Postia placenta (strain ATCC 44394 / Madison 698-R)
338
0
38419
Swiss-Prot
other Location (Reliability: 4)
A0A2P6QUB3_ROSCH
148
0
16888
TrEMBL
Secretory Pathway (Reliability: 3)
A0A4Y6GMI9_9ROSI
114
0
13501
TrEMBL
other Location (Reliability: 4)
A0A2P6SQN2_ROSCH
105
0
12187
TrEMBL
other Location (Reliability: 1)
A0A4Y6GLI6_9ROSI
133
0
15837
TrEMBL
other Location (Reliability: 2)
A0A396JJK2_MEDTR
431
0
50491
TrEMBL
other Location (Reliability: 5)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
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
-
SasesquiTPS1 shows the R(R/P)X8W motif at positions 19-29, and the DDXXD motif
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H255P
-
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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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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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Agger, S.; Lopez-Gallego, F.; Schmidt-Dannert, C.
Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus
Mol. Microbiol.
72
1181-1195
2009
Coprinopsis cinerea (A8NE23), Coprinopsis cinerea ATCC MYA-4618 (A8NE23)
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Lopez-Gallego, F.; Wawrzyn, G.; Schmidt-Dannert, C.
Selectivity of fungal sesquiterpene synthases: Role of the active sites H-1alpha loop in catalysis
Appl. Environ. Microbiol.
76
7723-7733
2010
Coprinopsis cinerea
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Jones, C.G.; Keeling, C.I.; Ghisalberti, E.L.; Barbour, E.L.; Plummer, J.A.; Bohlmann, J.
Isolation of cDNAs and functional characterisation of two multi-product terpene synthase enzymes from sandalwood, Santalum album L
Arch. Biochem. Biophys.
477
121-130
2008
Santalum album (B5A435), Santalum album
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