3.2.1.49: alpha-N-acetylgalactosaminidase
This is an abbreviated version!
For detailed information about alpha-N-acetylgalactosaminidase, go to the full flat file.
Word Map on EC 3.2.1.49
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3.2.1.49
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n-acetylgalactosamine
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sialidase
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fabry
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schindler
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exoglycosidase
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neuroaxonal
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d3-binding
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gcmaf
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angiokeratoma
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alpha-linked
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beta-galnac
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macrophage-activating
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pomatia
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corporis
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diffusum
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biflorus
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mucin-type
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medicine
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alpha-n-acetylgalactosaminyltransferase
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alpha-n-acetylgalactosamine
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asialo
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diagnostics
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biotechnology
- 3.2.1.49
- n-acetylgalactosamine
- sialidase
- fabry
-
schindler
-
exoglycosidase
-
neuroaxonal
-
d3-binding
-
gcmaf
- angiokeratoma
-
alpha-linked
-
beta-galnac
-
macrophage-activating
- pomatia
-
corporis
- diffusum
- biflorus
-
mucin-type
- medicine
-
alpha-n-acetylgalactosaminyltransferase
- alpha-n-acetylgalactosamine
-
asialo
- diagnostics
- biotechnology
Reaction
Synonyms
2-acetamido-2-deoxy-alpha-D-galactoside acetamidodeoxygalactohydrolase, 4-nitrophenyl-alpha-N-acetylgalactosaminidase, AglA, alpha-acetylgalactosaminidase, alpha-galactosidase B, alpha-GalNAc, alpha-GalNAc-ase, alpha-GalNAcase, alpha-GalNAcase I, alpha-GalNAcase II, alpha-N acetylgalactosaminidase, alpha-N-acetylgalactosaminidase blood group A2 degrading enzyme, alpha-N-galactosaminidase IV, alpha-NAGA, alpha-NAGAL, alpha-NaGalase, envelope glycoprotein gp160, exo-alpha-N-acetylgalactosaminidase, N-acetyl-alpha-D-galactosaminidase, N-acetyl-alpha-galactosaminidase, NagA, NaGalase
ECTree
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Reaction
Reaction on EC 3.2.1.49 - alpha-N-acetylgalactosaminidase
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alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
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alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
double-displacement mechanism. First step: an oxygen atom from Asp140 attacks the electrophilic C1 of the hexose ring, cleaving the glycosidic linkage and creating a covalent enzyme-substrate intermediate. The second step involves a nucleophilic attack by a water molecule, which has been deprotonated by Asp201, on the covalent intermediate.
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alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
the enzyme exhibits an endo-enzyme activity in addition to an exo-activity
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alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
double-displacement, or ping-pong, reaction mechanism and active site structure, overview
alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
a hydride at C3, activated by the interaction of the OH-3 hydroxyl with the conserved His228, is abstracted by NAD+ with oxidation of the OH-3 hydroxyl to a ketone. This activates H2 for proton abstraction by Tyr179, accompanied by elimination of the aglycone, thereby generating a 1,2-unsaturated intermediate. Water is then added to the anomeric center, followed by the reduction of the C3 ketone by the on-board NADH, completing the catalytic sequence and restoring NADH to NAD+ and the enzyme to its starting state to bind another substrate
alpha-D-GalNAc-(1->3)-beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide + H2O = D-GalNAc + beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-ceramide
E2 elimination following hydride transfer from C3
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