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Literature summary extracted from

  • Nakano, C.; Hoshino, T.; Sato, T.; Toyomasu, T.; Dairi, T.; Sassa, T.
    Substrate specificity of the CYC2 enzyme from Kitasatospora griseola: production of sclarene, biformene and novel bicyclic diterpenes by the enzymatic reactions of labdane- and halimane-type diterpene diphosphates (2010), Tetrahedron Lett., 51, 125-128.
No PubMed abstract available

Application

EC Number Application Comment Organism
4.2.3.36 synthesis CYC2 is a promising tool for introducing a buta-1,3-diene moiety into molecules by the enzymatic reactions Kitasatospora griseola

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.B26 Mg2+ presence is essential for enzymic activity Kitasatospora griseola
4.2.3.B27 Mg2+ presence is essential for enzymic activity Kitasatospora griseola
4.2.3.B28 Mg2+ presence is essential for enzymic activity Kitasatospora griseola
4.2.3.B29 Mg2+ presence is essential for enzymic activity Kitasatospora griseola
4.2.3.36 Mg2+ presence is essential for enzymic activity Kitasatospora griseola
4.2.3.36 Mg2+ the divalent metal ion is essential for the enzyme activities of all diterpene cyclases including the dephosphorylating CYC2 enzyme. Therefore, the CYC2 catalyzes Type A-like reaction, that is, the diphosphate-removal reaction followed by the formation of allylic carbocation Kitasatospora griseola

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.36 additional information Kitasatospora griseola CYC2 is not a cyclase, it shows broad substrate specificity. All of the three bicyclic diterpenes labdane, halimane, and clerodane, occuring in nature, are accepted as substrates of the CYC2, reactivity in a coupled assay with ent-CDP synthase, EC 5.5.1.13, overview ?
-
 ?
4.2.3.36 terpentedienyl diphosphate Kitasatospora griseola
-
 terpentetriene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.B26 Kitasatospora griseola Q9AJE3
-
-
4.2.3.B27 Kitasatospora griseola Q9AJE3
-
-
4.2.3.B28 Kitasatospora griseola Q9AJE3
-
-
4.2.3.B29 Kitasatospora griseola Q9AJE3
-
-
4.2.3.36 Kitasatospora griseola
-
-
-
4.2.3.36 Kitasatospora griseola Q9AJE3
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.B27 syn-copalyl diphosphate = (4aS,5R,8aS)-1,1,4a-trimethyl-6-methylidene-5-(3-methylidenepent-4-en-1-yl)decahydronaphthalene + diphosphate compound has not been found in nature Kitasatospora griseola
a
4.2.3.B28 tuberculosinyl diphosphate = (4aS,5R,6S)-1,1,5,6-tetramethyl-5-(3-methylidenepent-4-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene + diphosphate compound has not been found in nature Kitasatospora griseola
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.B26 (+)-copalyl diphosphate
-
 Kitasatospora griseola sclarene + diphosphate single product, yield about 50%. Cyc2 does not catalyze further cyclization reaction of (+)-copalyl diphosphate ?
4.2.3.B27 syn-copalyl diphosphate
-
 Kitasatospora griseola (4aS,5R,8aS)-1,1,4a-trimethyl-6-methylidene-5-(3-methylidenepent-4-en-1-yl)decahydronaphthalene + diphosphate yield about 55% ?
4.2.3.B28 tuberculosinyl diphosphate
-
 Kitasatospora griseola (4aS,5R,6S)-1,1,5,6-tetramethyl-5-(3-methylidenepent-4-en-1-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene + diphosphate yield about 50%. Compound has not been found in nature ?
4.2.3.B29 (-)-ent-copalyl diphosphate
-
 Kitasatospora griseola (Z)-biformene + diphosphate yield about 60%, no formation of (E)-biformene ?
4.2.3.36 additional information CYC2 is not a cyclase, it shows broad substrate specificity. All of the three bicyclic diterpenes labdane, halimane, and clerodane, occuring in nature, are accepted as substrates of the CYC2, reactivity in a coupled assay with ent-CDP synthase, EC 5.5.1.13, overview Kitasatospora griseola ?
-
 ?
4.2.3.36 terpentedienyl diphosphate
-
 Kitasatospora griseola terpentetriene + diphosphate
-
 ?
4.2.3.36 terpentedienyl diphosphate generation of terpentetriene from through a diphosphate-removal reaction Kitasatospora griseola terpentetriene + diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.B26 Cyc2 ambiguous Kitasatospora griseola
4.2.3.B26 diterpene cyclase-2 ambiguous Kitasatospora griseola
4.2.3.B27 Cyc2 ambiguous Kitasatospora griseola
4.2.3.B27 diterpene cyclase-2 ambiguous Kitasatospora griseola
4.2.3.B28 Cyc2 ambiguous Kitasatospora griseola
4.2.3.B28 diterpene cyclase-2 ambiguous Kitasatospora griseola
4.2.3.B29 Cyc2 ambiguous Kitasatospora griseola
4.2.3.B29 diterpene cyclase-2 ambiguous Kitasatospora griseola
4.2.3.36 Cyc2
-
 Kitasatospora griseola
4.2.3.36 diterpene cyclase-2
-
 Kitasatospora griseola

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.3.B26 30
-
 assay at Kitasatospora griseola
4.2.3.B26 50
-
-
 Kitasatospora griseola
4.2.3.B27 30
-
 assay at Kitasatospora griseola
4.2.3.B27 50
-
-
 Kitasatospora griseola
4.2.3.B28 30
-
 assay at Kitasatospora griseola
4.2.3.B28 50
-
-
 Kitasatospora griseola
4.2.3.B29 30
-
 assay at Kitasatospora griseola
4.2.3.B29 50
-
-
 Kitasatospora griseola
4.2.3.36 30
-
 assay at Kitasatospora griseola
4.2.3.36 50
-
-
 Kitasatospora griseola

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.3.B26 6.8
-
-
 Kitasatospora griseola
4.2.3.B26 7.5
-
 assay at Kitasatospora griseola
4.2.3.B27 6.8
-
-
 Kitasatospora griseola
4.2.3.B27 7.5
-
 assay at Kitasatospora griseola
4.2.3.B28 6.8
-
-
 Kitasatospora griseola
4.2.3.B28 7.5
-
 assay at Kitasatospora griseola
4.2.3.B29 6.8
-
-
 Kitasatospora griseola
4.2.3.B29 7.5
-
 assay at Kitasatospora griseola
4.2.3.36 6.8
-
-
 Kitasatospora griseola
4.2.3.36 7.5
-
 assay at Kitasatospora griseola

pH Range

EC Number pH Minimum pH Maximum Comment Organism
4.2.3.B26 6.8 7.5
-
 Kitasatospora griseola
4.2.3.B27 6.8 7.5
-
 Kitasatospora griseola
4.2.3.B28 6.8 7.5
-
 Kitasatospora griseola
4.2.3.B29 6.8 7.5
-
 Kitasatospora griseola
4.2.3.36 6.8 7.5
-
 Kitasatospora griseola

General Information

EC Number General Information Comment Organism
4.2.3.36 additional information the CYC2 enzyme involves a DDXXD motif in the sequence that is characteristic to type-A cyclase and responsible for the diphosphate-removal reaction through Mg2+ chelation Kitasatospora griseola