Overview for MACiE Entry M0263
EC Number: 184.108.40.206 (A member of the Lyases, Carbon-oxygen lyases, Acting on phosphates)
Enzyme Name: epi-isozizaene synthase
Biological Species: Streptomyces coelicolor (Bacteria)
Catalytic Chain UniprotKB Accession Codes:
- Q9K499 - Epi-isozizaene synthase
Representative PDB Code: 3kb9 - EPI-ISOZIZAENE SYNTHASE: COMPLEX WITH MG, INORGANICPYROPHOSPHATE AND BENZYL TRIETHYL AMMONIUM CATION (Resolution = 1.60 Å).
Catalytic CATH Codes:
Display structure information
Overall Comment: A member of the the terpene synthase family.
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Stepwise Description of the Reaction
|Step 1||The binding of the substrate causes a conformation change in the active site, which promotes the elimination of the pyrophosphate.|
|Step 2||The pyrophosphate attacks the C3 cationic carbon in a nucleophilic addition reaction.|
|Step 3||Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring with concomitant elimination of the pyrophosphate.|
|Step 4||A 1,2-Hydride shift.|
|Step 5||Spirocyclisation to form the five and six membered ring intermediate.|
|Step 6||Intramolecular electrophilic addition to form the second six-membered ring.|
|Step 7||The six-membered ring contracts to a five membered ring.|
|Step 8||The pyrophosphate deprotonates the substrate, which initiates the final methyl migration.|
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Catalytic Residues Involved
||Location of Function
Metal Cofactors for M0263
- J. A. Aaron et al. (2010), Biochemistry, 49, 1787-1797. Structure of epi-isozizaene synthase from Streptomyces coelicolor A3(2), a platform for new terpenoid cyclization templates.
- X. Lin et al. (2006), J. Am. Chem. Soc., 128, 6022-6023. Genome mining in Streptomyces coelicolor: molecular cloning and characterization of a new sesquiterpene synthase.
Homologue information for M0263 (3kb9)
MACiE Homologues (within the PDB)
MACiE Homologues (within UniprotKB/SwissProt)
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