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Entry M0061    5.3.2.-    4-oxalocrotonate tautomerase

Next Step

Step 01

The N-terminal proline deprotonates the CH2 of the substrate, initiating double bond rearrangement and forming the enol form of the substrate.

GIF of Reaction Step M0061.stg01


Comment: Pro1 can function as a general base under physiological conditions because of its unusually low pKa of 6.4 [1].



Mechanisms

Proton Transfer
Assisted Keto-Enol Tautomerisation

Mechanism Components

Overall Reactant Used
Bond Cleavage
Bond Formation
Bond Order Change
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Phe50 Side Chain spectator Activator
Polar Non-polar interaction
Arg39B Side Chain spectator Electrostatic Stabiliser
Hydrogen Bond Donor
Pro1 Main Chain N Terminus reactant Proton Acceptor
Hydrogen Bond Acceptor
Polar Non-polar interaction

Reactive Centre

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

View similar reactions in MACiE.


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