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Entry M0262    4.2.3.6    trichodiene synthase

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Step 04

Intramolecular electrophilic addition across the C1-C6 bond to form the six-membered ring.

GIF of Reaction Step M0262.stg04


Comment: Formation of the C1-C6 bond. Positive charge on the C7 may be stabilised by the cation-pi interaction with the side chain of Tyr93.



Mechanisms

Intramolecular Electrophilic Addition

Mechanism Components

Bond Formation
Bond Order Change
Charge Delocalisation
Cyclisation
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Tyr93 Side Chain spectator Polar Non-polar interaction
Electrostatic Stabiliser
Leu97 Side Chain spectator van der Waals interaction
Thr96 Side Chain spectator van der Waals interaction
Asp100 Side Chain spectator Metal Ligand
Electrostatic Stabiliser
Arg182 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Lys232 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Arg304 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Tyr305 Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor

Metal Cofactors involved in Step 04

Metal Type Metal Identity Chain Activity Function
magnesium MG 701 B spectator Substrate Binding
Electrostatic Stabiliser
magnesium MG 702 B spectator Substrate Binding
Electrostatic Stabiliser
magnesium MG 703 B spectator Substrate Binding
Electrostatic Stabiliser

Reactive Centre

Bonds Formed Bonds Cleaved Bonds Changed in Order Atom Types Involved
C-C
None
The C-C bond changes from a double to single bond
C

View similar reactions in MACiE.


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