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Entry M0262    4.2.3.6    trichodiene synthase

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Step 02

The pyrophosphate attacks the C3 cationic carbon in a nucleophilic addition reaction.

GIF of Reaction Step M0262.stg02


Comment: Recapture of one of the alpha-phosphate oxygens by the C3 cation results in formation of (3R)-nerolidyl diphosphate [1]



Mechanisms

Bimolecular Nucleophilic Addition

Mechanism Components

Bond Formation
Charge Delocalisation
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Tyr93 Side Chain spectator van der Waals interaction
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
Increase Nucleophilicity
Hydrogen Bond Donor
Lys232 Side Chain spectator Electrostatic Stabiliser
Increase Nucleophilicity
Hydrogen Bond Donor
Arg304 Side Chain spectator Electrostatic Stabiliser
Increase Nucleophilicity
Hydrogen Bond Donor
Tyr305 Side Chain spectator Increase Nucleophilicity
Electrostatic Stabiliser
Hydrogen Bond Donor

Metal Cofactors involved in Step 02

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-O
None
None
C
O

View similar reactions in MACiE.


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