4.2.3.91: cubebol synthase

This is an abbreviated version!
For detailed information about cubebol synthase, go to the full flat file.

Reaction

Synonyms

Cop4

ECTree

     4 Lyases

         4.2 Carbon-oxygen lyases

             4.2.3 Acting on phosphates

                4.2.3.91 cubebol synthase

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Results	in table
1	AA Sequence
2	Cloned(Commentary)
2	KM Value [mM]
3	Metals/Ions
2	Organism
3	pH Optimum
1	pH Range
4	Protein Variants
1	Purification (Commentary)
1	Reaction
2	Reference
6	Substrates and Products (Substrate)
2	Synonyms
1	Systematic Name
2	Temperature Range [°C]
2	Turnover Number [1/s]

Substrates Products

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Substrates Products on EC 4.2.3.91 - cubebol synthase

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SUBSTRATE

PRODUCT                       

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(2E,6E)-farnesyl diphosphate

cubebol + diphosphate

Coprinopsis cinerea

-

conversion of (6E,6E)-farnesyl diphosphate proceeds via an (E,E)-germacradienyl carbocation

714733

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

-

?

(2E,6E)-farnesyl diphosphate + H2O

cubebol + diphosphate

2 entries

additional information

?

-

3 entries

(2E,6E)-farnesyl diphosphate + H2O

cubebol + diphosphate

Coprinopsis cinerea

-

-

714733

-

-

?

(2E,6E)-farnesyl diphosphate + H2O

cubebol + diphosphate

Coprinopsis cinerea

-

-

713839

germacrene D and cubebol are the major products in vitro

-

?

additional information

?

-

Coprinopsis cinerea

-

Cop4 is a catalytically promiscuous enzyme that cyclizes (E,E)-farnesyl diphophate into multiple products, including (-)-germacrene D and cubebol (major products). Conversion of (E,E)-farnesyl diphophate by Cop4 proceeds via an (E,E)-germacradienyl carbocation. Cop4 cyclizes (2Z,6E)-farnesyl diphophate via a (6S)-beta-bisabolyl cation intermediate to (6S)-beta-bisabolene. Cop4 converts E-geranyl diphophate into cyclic and acyclic monoterpenes. Cop4 also cyclizes nerolidyl diphosphate. Under alkaline (pH 10) or acidic (pH 5.0) conditions, Cop4 becomes a very selective germacrene D synthase

714733

-

-

?

additional information

?

-

Coprinopsis cinerea

-

Cop4 rearranges a secondary cisoid, allylic cation derived from farnesyl diphophate after isomerization (cis-trans pathway of catalysis) into multiple products, with delta-cadinene and beta-copaene as the major products when expressed in Escherichia coli

713839

-

-

?

additional information

?

-

Coprinopsis cinerea

-

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

714733

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-

?