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Entry M0288    3.5.1.93    glutaryl-7-aminocephalosporanic-acid acylase

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Step 04

The structurally conserved water molecule is activated by the non-protonated terminal amine of Ser170 to attack at the enzyme-substrate intermediate's carbonyl group, forming a second tetrahedral intermediate.

GIF of Reaction Step M0288.stg04



Mechanisms

Bimolecular Nucleophilic Addition
Proton Transfer

Mechanism Components

Bond Formation
Bond Cleavage
Bond Order Change
Intermediate Formation
Overall Product Formed

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Val140A Main Chain Amide spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Asn314A Side Chain spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Glu525A Side Chain spectator Hydrogen Bond Acceptor
Increase Acidity
His193A Side Chain spectator Hydrogen Bond Donor
Hydrogen Bond Acceptor
Increase Acidity
Electrostatic Stabiliser
Ser170A Side Chain reactant Covalently Attached
Ser170A Main Chain N Terminus reactant Proton Donor
Hydrogen Bond Donor

Reactive Centre

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

View similar reactions in MACiE.


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