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Entry M0263    4.2.3.37    epi-isozizaene synthase

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Step 03

Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring with concomitant elimination of the pyrophosphate.

GIF of Reaction Step M0263.stg03


Comment: Rotation about the newly formed C2-C3 bond generates the correpsonding cicoid conformer, which readily undergoes ionisation and cyclisation to form the bisabolyl cation [2]



Mechanisms

Intramolecular Electrophilic Substitution

Mechanism Components

Bond Formation
Bond Cleavage
Bond Order Change
Intermediate Formation
Cyclisation
Dephosphorylation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Arg338 Side Chain spectator Electrostatic Stabiliser
Promotes Heterolytic Reactions
Hydrogen Bond Donor
Phe95 Side Chain spectator Steric Role
Electrostatic Stabiliser
Polar Non-polar interaction
Phe96 Side Chain spectator Steric Role
Electrostatic Stabiliser
Polar Non-polar interaction
Phe198 Side Chain spectator Steric Role
Electrostatic Stabiliser
Polar Non-polar interaction

Metal Cofactors involved in Step 03

Metal Type Metal Identity Chain Activity Function
magnesium MG 700 A spectator Substrate Binding
Activator
Promotes Heterolytic Reactions
Electrostatic Stabiliser
magnesium MG 701 A spectator Substrate Binding
Activator
Promotes Heterolytic Reactions
Electrostatic Stabiliser
magnesium MG 702 A spectator Substrate Binding
Activator
Promotes Heterolytic Reactions
Electrostatic Stabiliser

Reactive Centre

Bonds Formed Bonds Cleaved Bonds Changed in Order Atom Types Involved
C-C
C-O
The C-C bond changes from a single to double bond
The C-C bond changes from a double to single bond
The C-C bond changes from a double to single bond
C
O

View similar reactions in MACiE.


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