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Literature summary for 4.2.3.75 extracted from

  • Lopez-Gallego, F.; Agger, S.A.; Abate-Pella, D.; Distefano, M.D.; Schmidt-Dannert, C.
    Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers (2010), ChemBioChem, 11, 1093-1106.
    View publication on PubMedView publication on EuropePMC
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KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.011
-
 (2E,6E)-farnesyl diphosphate pH 8.0, 30°C Coprinopsis cinerea

Metals/Ions

Metals/Ions Comment Organism Structure
K+ replacement of Mg2+ by Mn2+ results in loss of product beta-copaene. Presence of K+ decreases the (?)-germacrene D yield and instead increases the overall yield of tricyclic sesquiterpene olefins Coprinopsis cinerea
Mg2+
-
 Coprinopsis cinerea
Mn2+ replacement of Mg2+ by Mn2+ results in loss of product beta-copaene. In the presence of the Mn2+, Cop4 favors a reaction path that ends after one cyclization in (?)-germacrene D Coprinopsis cinerea

Organism

Organism UniProt Comment Textmining
Coprinopsis cinerea
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate conversion of (E,E)-FPP proceeds via an (E,E)-germacradienyl carbocation Coprinopsis cinerea (-)-germacrene D + diphosphate main products at pH 8.0 are 29.3% (-)-germacrene D, 28.2% cubebol, 10.4% delta-cadinene, at pH 10.0 is 91% (-)-germacrene D, at pH 5.0 84% (-)-germacrene D plus 12% delta-cadinene ?
additional information Coprinus cinereus Cop4 additionally accepts (2Z,6E)-farnesyl diphosphate to produce 27.7% alpha-acoradiene, 10% amorpha-4,11-diene, and 13.3% cadina-4,11-diene Coprinopsis cinerea ?
-
 ?

Synonyms

Synonyms Comment Organism
Cop4
-
 Coprinopsis cinerea

Temperature Range [°C]

Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
4 25 lowering the reaction temperature from 25°C to 4°C increases the selectivity of Cop4 for (?)-germacrene D and decreases the fraction of structurally unidentified sesquiterpene olefins by half Coprinopsis cinerea
37
-
 increasing the reaction temperature to 37°C decreases the fidelity of Cop4. At 37°C Cop4 generates a relative larger fraction of products beta-cubebene, sativene, delta-cadinene and beta-copaene that are derived from a cadinyl cation intermediate Coprinopsis cinerea

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.012
-
 (2E,6E)-farnesyl diphosphate pH 8.0, 30°C Coprinopsis cinerea

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
additional information
-
 under both alkaline and acidic conditions Cop4 becomes a very selective enzyme with only one major product (?)-germacrene D compared to three major compounds produced under neutral reaction conditions. At pH 10, the cyclization reaction ends with the hydride shift and deprotonation of the germacradienyl cation to yield (?)-germacrene D, 91% of total sesquiterpene products, while at pH 5.0 cyclization can proceed via a 1,6 ring closure to also yield a small amount of delta-cadinene, 12% of total sesquiterpene products, in addition to (?)-germacrene D Coprinopsis cinerea
5
-
 at pH 5.0 cyclization can proceed via a 1,6 ring closure to also yield a small amount of delta-cadinene, 12% of total sesquiterpene products, in addition to (?)-germacrene D Coprinopsis cinerea
10
-
 at pH 10, the cyclization reaction ends with the hydride shift and deprotonation of the germacradienyl cation to yield (?)-germacrene D, 91% of total sesquiterpene products Coprinopsis cinerea

pH Range

pH Minimum pH Maximum Comment Organism
additional information
-
 the catalytic fidelity of Cop4 can be drastically altered by varying reactions conditions Coprinopsis cinerea

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1
-
 (2E,6E)-farnesyl diphosphate pH 8.0, 30°C Coprinopsis cinerea