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Literature summary extracted from

  • Agger, S.; Lopez-Gallego, F.; Schmidt-Dannert, C.
    Diversity of sesquiterpene synthases in the basidiomycete Coprinus cinereus (2009), Mol. Microbiol., 72, 1181-1195.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.13 expressed in Escherichia coli Coprinopsis cinerea
4.2.3.13 expressed in Escherichia coli BL21(DE3) cells Coprinopsis cinerea
4.2.3.23 expressed in Escherichia coli Coprinopsis cinerea
4.2.3.95 expressed in Escherichia coli JM109 cells and in Saccharomyces cerevisiae strain YPH 500 Coprinopsis cinerea
4.2.3.125 gene cop3, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli strain JM109 leading to production of alpha-muurolene Coprinopsis cinerea
4.2.3.126 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 Coprinopsis cinerea
4.2.3.127 gene cop4, phylogenetic analysis Coprinopsis cinerea
4.2.3.128 gene cop4, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli strain JM109 Coprinopsis cinerea
4.2.3.129 gene cop4, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression in Escherichia coli strain JM109 Coprinopsis cinerea

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.128 Mg2+ required Coprinopsis cinerea
4.2.3.129 Mg2+ required Coprinopsis cinerea

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.125 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea
-
 alpha-muurolene + diphosphate
-
 ?
4.2.3.125 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea ATCC MYA-4618
-
 alpha-muurolene + diphosphate
-
 ?
4.2.3.125 additional information Coprinopsis cinerea 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 ?
-
 ?
4.2.3.125 additional information Coprinopsis cinerea ATCC MYA-4618 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 ?
-
 ?
4.2.3.126 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures gamma-muurolene + diphosphate
-
 ?
4.2.3.126 additional information Coprinopsis cinerea 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 ?
-
 ?
4.2.3.126 additional information Coprinopsis cinerea ATCC MYA-4618 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 ?
-
 ?
4.2.3.127 additional information Coprinopsis cinerea Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13. Cop4 cultures produce several sesquiterpene compounds betacubebene, sativene, beta-copaene, and cubebol ?
-
 ?
4.2.3.127 additional information Coprinopsis cinerea ATCC MYA-4618 Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13. Cop4 cultures produce several sesquiterpene compounds betacubebene, sativene, beta-copaene, and cubebol ?
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 beta-cubebene + diphosphate
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea ATCC MYA-4618 Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 beta-cubebene + diphosphate
-
 ?
4.2.3.128 additional information Coprinopsis cinerea Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol ?
-
 ?
4.2.3.128 additional information Coprinopsis cinerea ATCC MYA-4618 Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol ?
-
 ?
4.2.3.129 (2E,6E)-farnesyl diphosphate Coprinopsis cinerea Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 (+)-sativene + diphosphate
-
 ?
4.2.3.129 additional information Coprinopsis cinerea Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.13 Coprinopsis cinerea
-
-
-
4.2.3.23 Coprinopsis cinerea
-
-
-
4.2.3.95 Coprinopsis cinerea
-
-
-
4.2.3.95 Coprinopsis cinerea ATCC MYA-4618
-
-
-
4.2.3.125 Coprinopsis cinerea A8NE23 gene cop3
-
4.2.3.125 Coprinopsis cinerea ATCC MYA-4618 A8NE23 gene cop3
-
4.2.3.126 Coprinopsis cinerea A8NE23 gene cop3
-
4.2.3.126 Coprinopsis cinerea ATCC MYA-4618 A8NE23 gene cop3
-
4.2.3.127 Coprinopsis cinerea A8NU13 gene cop4
-
4.2.3.128 Coprinopsis cinerea A8NU13
-
-
4.2.3.128 Coprinopsis cinerea ATCC MYA-4618 A8NU13
-
-
4.2.3.129 Coprinopsis cinerea A8NU13
-
-
4.2.3.129 Coprinopsis cinerea ATCC MYA-4618 A8NU13
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.127 (2E,6E)-farnesyl diphosphate = beta-copaene + diphosphate the reaction mechanism requires first the isomerization of all-trans (E,E)-FPP at the 2,3 double bond to generate a cisoid-farnesyl cation. Cop4 then catalyzes a 1,10 ring closure of this farnesyl cation isomer to form the secondary cis-germacrene-dienyl cation. Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products beta-cubebene, cubebol, beta-copaene, and sativene Coprinopsis cinerea
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.13 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea delta-cadinene + diphosphate major product ?
4.2.3.13 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 delta-cadinene + diphosphate major product ?
4.2.3.13 (2E,6E)-farnesyl diphosphate + H2O Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene) Coprinopsis cinerea delta-cadinene + diphosphate
-
 ?
4.2.3.13 (2E,6E)-farnesyl diphosphate + H2O Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene) Coprinopsis cinerea ATCC MYA-4618 delta-cadinene + diphosphate
-
 ?
4.2.3.23 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea germacrene A + diphosphate
-
 ?
4.2.3.23 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 germacrene A + diphosphate
-
 ?
4.2.3.95 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea (-)-alpha-cuprenene + diphosphate
-
 ?
4.2.3.95 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 (-)-alpha-cuprenene + diphosphate
-
 ?
4.2.3.125 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea alpha-muurolene + diphosphate
-
 ?
4.2.3.125 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea alpha-muurolene + diphosphate recombinant Escherichia coli produces alpha-muurolene to 30% of total terpenoid compounds, but also other sesquiterpenes ?
4.2.3.125 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 alpha-muurolene + diphosphate
-
 ?
4.2.3.125 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 alpha-muurolene + diphosphate recombinant Escherichia coli produces alpha-muurolene to 30% of total terpenoid compounds, but also other sesquiterpenes ?
4.2.3.125 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 Coprinopsis cinerea ?
-
 ?
4.2.3.125 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 Coprinopsis cinerea ATCC MYA-4618 ?
-
 ?
4.2.3.126 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea gamma-muurolene + diphosphate
-
 ?
4.2.3.126 (2E,6E)-farnesyl diphosphate significant amounts of beta-elemene, gamma-muurolene, germacrene D, and delta-cadinene are synthesized in the headspace of Cop3 cultures Coprinopsis cinerea gamma-muurolene + diphosphate
-
 ?
4.2.3.126 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 gamma-muurolene + diphosphate
-
 ?
4.2.3.126 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 Coprinopsis cinerea ?
-
 ?
4.2.3.126 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 Coprinopsis cinerea ATCC MYA-4618 ?
-
 ?
4.2.3.127 additional information Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13. Cop4 cultures produce several sesquiterpene compounds betacubebene, sativene, beta-copaene, and cubebol Coprinopsis cinerea ?
-
 ?
4.2.3.127 additional information Escherichia coli strains expressing Cop4 accumulate delta-cadinene as the major terpenoid, accounting for about 40% of the total sesquiterpenes detected Coprinopsis cinerea ?
-
 ?
4.2.3.127 additional information Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13. Cop4 cultures produce several sesquiterpene compounds betacubebene, sativene, beta-copaene, and cubebol Coprinopsis cinerea ATCC MYA-4618 ?
-
 ?
4.2.3.127 additional information Escherichia coli strains expressing Cop4 accumulate delta-cadinene as the major terpenoid, accounting for about 40% of the total sesquiterpenes detected Coprinopsis cinerea ATCC MYA-4618 ?
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea beta-cubebene + diphosphate
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 Coprinopsis cinerea beta-cubebene + diphosphate
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea ATCC MYA-4618 beta-cubebene + diphosphate
-
 ?
4.2.3.128 (2E,6E)-farnesyl diphosphate Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 Coprinopsis cinerea ATCC MYA-4618 beta-cubebene + diphosphate
-
 ?
4.2.3.128 additional information Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol Coprinopsis cinerea ?
-
 ?
4.2.3.128 additional information Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol Coprinopsis cinerea ATCC MYA-4618 ?
-
 ?
4.2.3.129 (2E,6E)-farnesyl diphosphate
-
 Coprinopsis cinerea (+)-sativene + diphosphate
-
 ?
4.2.3.129 (2E,6E)-farnesyl diphosphate Cop4 synthesizes delta-cadinene as its major product, cf. EC 4.2.3.13 Coprinopsis cinerea (+)-sativene + diphosphate
-
 ?
4.2.3.129 additional information Cop4 cultures produce several sesquiterpene compounds, e.g. beta-cubebene, sativene, beta-copaene, and cubebol Coprinopsis cinerea ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.13 Cop4
-
 Coprinopsis cinerea
4.2.3.13 delta-cadinene synthase
-
 Coprinopsis cinerea
4.2.3.23 germacrene A synthase
-
 Coprinopsis cinerea
4.2.3.95 (-)-alpha-cuprenene synthase
-
 Coprinopsis cinerea
4.2.3.95 Cop6
-
 Coprinopsis cinerea
4.2.3.125 Cop3
-
 Coprinopsis cinerea
4.2.3.126 Cop3
-
 Coprinopsis cinerea
4.2.3.127 Cop4
-
 Coprinopsis cinerea
4.2.3.127 sesquiterpene synthase
-
 Coprinopsis cinerea
4.2.3.129 Cop4
-
 Coprinopsis cinerea

General Information

EC Number General Information Comment Organism
4.2.3.125 additional information Cop3 is a terpene synthase Coprinopsis cinerea
4.2.3.126 additional information Cop3 is a terpene synthase Coprinopsis cinerea
4.2.3.127 additional information Cop4 is a delta-cadinene synthase Coprinopsis cinerea