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Overview for MACiE Entry M0263

Version history

General Information

EC Number: 4.2.3.37 (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:

  • Unassigned Domain

Display structure information

Overall Reaction:

Image of 2-trans,6-trans-farnesyl diphosphate

right arrow

Image of (+)-epi-isozizaene

Image of diphosphate

2-trans,6-trans-farnesyl diphosphate
C00448
CHEBI:175763
(+)-epi-isozizaene
C16269
CHEBI:23925
diphosphate
C00013
CHEBI:33019

Overall Comment: A member of the the terpene synthase family.


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Stepwise Description of the Reaction

Step 1The binding of the substrate causes a conformation change in the active site, which promotes the elimination of the pyrophosphate.
Step 2The pyrophosphate attacks the C3 cationic carbon in a nucleophilic addition reaction.
Step 3Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring with concomitant elimination of the pyrophosphate.
Step 4A 1,2-Hydride shift.
Step 5Spirocyclisation to form the five and six membered ring intermediate.
Step 6Intramolecular electrophilic addition to form the second six-membered ring.
Step 7The six-membered ring contracts to a five membered ring.
Step 8The pyrophosphate deprotonates the substrate, which initiates the final methyl migration.

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Catalytic Residues Involved

Type Number Chain Location of Function
Phe 198 A Side Chain
Phe 95 A Side Chain
Phe 96 A Side Chain
Arg 338 A Side Chain

Metal Cofactors for M0263

Type Het group Number Chain
magnesium MG 700 A Overview
magnesium MG 701 A Overview
magnesium MG 702 A Overview

References

  1. 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.
    Medline: 20131801
  2. 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.
    Medline: 16669656

Homologue information for M0263 (3kb9)

MACiE Homologues (within the PDB)

MACiE Homologues (within UniprotKB/SwissProt)


Links to this entry in other databases

Link to EC-PDB-SUM Link to PDB-SUM Link to RCSB PDB Link to PDBe Link to CSA
Link to MetaCyc Link to KEGG Link to BRENDA Link to ExplorENZ

GOA logo
magnesium ion binding (molecular function)
lyase activity (molecular function)
metal ion binding (molecular function)
epi-isozizaene synthase activity (molecular function)
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