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Entry M0181    3.11.1.1    phosphonoacetaldehyde hydrolase

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Step 04

Asp12 attacks the phosphate of the covalently bound intermediate in a nucleophilic substitution that cleaved the C-P bond and results in a phosphorylated Asp12 and alkylated Lys53

GIF of Reaction Step M0181.stg04



Mechanisms

Bimolecular Nucleophilic Substitution

Mechanism Components

Bond Formation
Enzyme-Substrate Bond Formation
Bond Cleavage
Enzyme-Substrate Bond Cleavage
Bond Order Change
Intermediate Collapse
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
His56 Side Chain spectator Hydrogen Bond Acceptor
Hydrogen Bond Donor
Ala45 Main Chain Carbonyl spectator Hydrogen Bond Acceptor
Met49 Side Chain spectator Hydrogen Bond Acceptor
Arg160 Side Chain spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Asp12 Side Chain reactant Hydrogen Bond Acceptor
Metal Ligand
Nucleophile
Lys53 Side Chain reactant Covalently Attached
Two Electron Acceptor

Metal Cofactors involved in Step 04

Metal Type Metal Identity Chain Activity Function
magnesium MG 502 x spectator Substrate Binding
Electrostatic Stabiliser
Activator
Increase Electrophilicity

Reactive Centre

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

View similar reactions in MACiE.


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