Information on EC 3.2.1.169 - protein O-GlcNAcase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.2.1.169
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RECOMMENDED NAME
GeneOntology No.
protein O-GlcNAcase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
[protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine + H2O = [protein]-L-serine + N-acetyl-D-glucosamine
show the reaction diagram
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[protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-theronine + H2O = [protein]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
protein O-[N-acetyl]-glucosylation
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SYSTEMATIC NAME
IUBMB Comments
[protein]-3-O-(N-acetyl-D-glucosaminyl)-L-serine/threonine N-acetylglucosaminyl hydrolase
Within higher eukaryotes post-translational modification of protein serines/threonines with N-acetylglucosamine (O-GlcNAc) is dynamic, inducible and abundant, regulating many cellular processes by interfering with protein phosphorylation. EC 2.4.1.255 (protein O-GlcNAc transferase) transfers GlcNAc onto substrate proteins and EC 3.2.1.169 (protein O-GlcNAcase) cleaves GlcNAc from the modified proteins.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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caspase-3 efficiently cleaved O-GlcNAcase
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-acetamido-2-deoxy-5-fluoro-beta-D-glucopyranosyl fluoride + H2O
fluoride + N-acetyl-beta-D-glucosaminide
show the reaction diagram
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a substrate contains a modest leaving group as well as a poor nucleophile, the catalytic efficiency of the enzyme is synergistically impaired. Testing a wide range of such substrates and obtained co-crystals of BtGH84, to test if under the right conditions, such a substrate might be trapped in the active site unhydrolyzed
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3,4-difluorophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 3,4-difluorophenol
show the reaction diagram
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?
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 3,4-difluorophenol
show the reaction diagram
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3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 3,4-difluorophenol
show the reaction diagram
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3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 3,4-difluorophenol
show the reaction diagram
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?
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 3,4-difluorophenol
show the reaction diagram
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3,4-difluorophenyl 2-deoxy-2-difluoroacetamido-beta-D-glucopyranoside + H2O
3,4-difluorophenol + 2-deoxy-2-difluoroacetamido-beta-D-glucopyranose
show the reaction diagram
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a substrate contains a modest leaving group as well as a poor nucleophile, the catalytic efficiency of the enzyme is synergistically impaired. Testing a wide range of such substrates and obtained co-crystals of BtGH84, to test if under the right conditions, such a substrate might be trapped in the active site unhydrolyzed
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3,4-dinitrophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 3,4-dinitrophenol
show the reaction diagram
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3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 3,4-dinitrophenol
show the reaction diagram
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3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 3,4-dinitrophenol
show the reaction diagram
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3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 3,4-dinitrophenol
show the reaction diagram
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3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 3,4-dinitrophenol
show the reaction diagram
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3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3,4-dinitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
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3-fluoro-4-nitrophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 3-fluoro-4-nitrophenol
show the reaction diagram
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?
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 3-fluoro-4-nitrophenol
show the reaction diagram
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?
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 3-fluoro-4-nitrophenol
show the reaction diagram
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?
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 3-fluoro-4-nitrophenol
show the reaction diagram
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?
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 3-fluoro-4-nitrophenol
show the reaction diagram
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?
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3-fluoro-4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
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?
3-nitrophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 3-nitrophenol
show the reaction diagram
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?
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 3-nitrophenol
show the reaction diagram
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?
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 3-nitrophenol
show the reaction diagram
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?
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 3-nitrophenol
show the reaction diagram
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?
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 3-nitrophenol
show the reaction diagram
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?
3-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
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?
4-aminophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside + H2O
?
show the reaction diagram
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67% relative activity compared to 4-nitrophenyl-beta-D-GlcNac
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?
4-chloro-3-nitrophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 4-chloro-3-nitrophenol
show the reaction diagram
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?
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-chloro-3-nitrophenol
show the reaction diagram
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?
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-chloro-3-nitrophenol
show the reaction diagram
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?
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-chloro-3-nitrophenol
show the reaction diagram
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?
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-chloro-3-nitrophenol
show the reaction diagram
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?
4-chlorophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 4-chlorophenol
show the reaction diagram
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?
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-chlorophenol
show the reaction diagram
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?
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-chlorophenol
show the reaction diagram
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?
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-chlorophenol
show the reaction diagram
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?
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-chlorophenol
show the reaction diagram
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?
4-chlorophenyl N-acetyl-beta-D-glucosaminide + H2O
4-chlorophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
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?
4-cyanophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 4-cyanophenol
show the reaction diagram
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?
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-cyanophenol
show the reaction diagram
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?
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-cyanophenol
show the reaction diagram
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-
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?
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-cyanophenol
show the reaction diagram
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?
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-cyanophenol
show the reaction diagram
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?
4-methoxyphenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + 4-methoxyphenol
show the reaction diagram
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?
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-methoxyphenol
show the reaction diagram
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-
-
-
?
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-methoxyphenol
show the reaction diagram
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-
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?
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-methoxyphenol
show the reaction diagram
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?
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-methoxyphenol
show the reaction diagram
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?
4-methylumbelliferyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside + H2O
?
show the reaction diagram
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33% relative activity compared to 4-nitrophenyl-beta-D-GlcNac
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4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside + H2O
4-methylumbelliferone + 2-acetamido-2-deoxy-beta-D-glucopyranose
show the reaction diagram
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substrate with a 4-methylumbelliferone leaving group. A substrate contains a modest leaving group as well as a poor nucleophile, the catalytic efficiency of the enzyme is synergistically impaired. Testing a wide range of such substrates and obtained co-crystals of BtGH84, to test if under the right conditions, such a substrate might be trapped in the active site unhydrolyzed
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4-methylumbelliferyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 4-methylumbelliferone
show the reaction diagram
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?
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-methylumbelliferone
show the reaction diagram
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?
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-methylumbelliferone
show the reaction diagram
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?
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-methylumbelliferone
show the reaction diagram
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?
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-methylumbelliferone
show the reaction diagram
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?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-difluoroacetyl-beta-D-glucosamine
show the reaction diagram
4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-fluoroacetyl-beta-D-glucosamine
show the reaction diagram
4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-trifluoroacetyl-beta-D-glucosamine
show the reaction diagram
4-methylumbelliferyl-2-acetamido-2-deoxy-beta-D-glucopyranoside + H2O
4-methylumbelliferol + N-acetyl-beta-D-glucosamine
show the reaction diagram
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4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
fluorogenic substrate, 4MU-NAG
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?
4-nitrophenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + 4-nitrophenol
show the reaction diagram
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?
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + 4-nitrophenol
show the reaction diagram
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?
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + 4-nitrophenol
show the reaction diagram
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?
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + 4-nitrophenol
show the reaction diagram
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?
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + 4-nitrophenol
show the reaction diagram
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?
4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
4-nitrophenyl N-acetyl-beta-D-thioglucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-thioglucosamine
show the reaction diagram
4-nitrophenyl-beta-D-GlcNAc + H2O
4-nitrophenol + N-acetyl-D-glucosamine
show the reaction diagram
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Ala-Ser(O-GlcNAc)-Tyr + H2O
Ala-Ser-Tyr + N-acetyl-beta-D-glucosamine
show the reaction diagram
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is synthesized using standard N-(9-fluorenyl)methoxycarbonyl (FMOC) chemistry
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?
fluorescein di(N-acetyl-beta-D-glucosaminide) + H2O
fluorescein mono(N-acetyl-beta-D-glucosaminide) + N-acetyl-D-glucosamine
show the reaction diagram
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FDGlcNAc, fluorogenic substrate
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GlcNAc beta(1-4)GlcNAc + H2O
N-acetyl-D-glucosamine + N-acetyl-D-glucosamine
show the reaction diagram
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4% relative activity. Enzyme can cleave terminal Glc-NAc from disaccharides to a limited extent as long as GlcNAc is linked to the other saccharides beta-linkage at the C-1 position
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GlcNAc beta(1-6)Gal + H2O
N-acetyl-D-glucosamine + beta-D-galactose
show the reaction diagram
-
29% relative activity. Enzyme can cleave terminal Glc-NAc from disaccharides to a limited extent as long as GlcNAc is linked to the other saccharides beta-linkage at the C-1 position
-
-
?
GlcNAcbeta(1-6)Man-beta-1-OMe + H2O
N-acetyl-D-glucosamine + methyl beta-D-mannoside
show the reaction diagram
-
33% relative activity. Enzyme can cleave terminal Glc-NAc from disaccharides to a limited extent as long as GlcNAc is linked to the other saccharides beta-linkage at the C-1 position
-
-
?
methyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + methanol
show the reaction diagram
-
-
-
-
?
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + methanol
show the reaction diagram
-
-
-
-
?
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + methanol
show the reaction diagram
-
-
-
-
?
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + methanol
show the reaction diagram
-
-
-
-
?
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + methanol
show the reaction diagram
-
-
-
-
?
N-acetyl-4-aminophenyl N-acetyl-beta-D-glucosaminide + H2O
N-acetyl-4-aminophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
P-(GlcNAc)STST + H2O
PSTST + N-acetyl-D-glucosamine
show the reaction diagram
-
-
-
-
?
phenyl 2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-N,O3,O4,O6-tetraacetyl-beta-D-glucopyranose + phenol
show the reaction diagram
-
-
-
-
?
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranose + phenol
show the reaction diagram
-
-
-
-
?
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranose + phenol
show the reaction diagram
-
-
-
-
?
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranose + phenol
show the reaction diagram
-
-
-
-
?
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside + H2O
2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranose + phenol
show the reaction diagram
-
-
-
-
?
phenyl N-acetyl-beta-D-glucosaminide + H2O
phenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
YSD-(GlcNAc)SPSTST + H2O
YSDSPSTST + N-acetyl-D-glucosamine
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cd2+
-
inhibits activity at 1 mM
Cu2+
-
inhibits activity at 1 mM
Hg2+
-
inhibits activity at 1 mM
Zn2+
-
inhibits activity at 1 mM
additional information
-
EDTA, Mg2+, Fe3+, Ca2+, Mn2+, and Co2+ do not affect the activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3aS,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
-
NAG-thiazoline, inhibits also other functionally related enzymes
(3aS,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-propyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
-
NButGT, selective O-GlcNAcase inhibitor
(6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide
-
PUGNAc-imidazole hybrid
1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
2-((6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)acetate
-
NAGstatin
2-(acetylamino)-2-deoxy-1-S-hexanoyl-1-thio-beta-D-glucopyranose
-
inhibits activity at 10 mM, 47.5% relative activity compared with activity without any addition of effector
2-acetamido-2-deoxy-D-gluconhydroxime-1,5-lactone
-
inhibits activity at 0.1 mM, 6.7% relative activity compared with activity without any addition of effector
2-acetamindo-1-amino-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 3.2% relative activity compared with activity without any addition of effector
2-acetamindo-1-azido-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 19.3% relative activity compared with activity without any addition of effector
2-acetamindo-1-bromo-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 34.8% relative activity compared with activity without any addition of effector
Ala-Cys(S-GlcNAc)-Ala
-
pseudosubstrate
alpha-D-mannose
-
inhibits activity at 10 mM, 62.6% relative activity compared with activity without any addition of effector
amen ändern: (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
-
thiamet-G
castanospermine
-
inhibits activity at 10 mM, 32.7% relative activity compared with activity without any addition of effector
Cd2+
-
inhibits activity at 1 mM, 7.7% relative activity compared with activity without any addition of effector
Cu2+
-
inhibits activity at 1 mM, 1% relative activity compared with activity without any addition of effector
D-glucosamine
-
inhibits activity at 10 mM, 60.7% relative activity compared with activity without any addition of effector
deoxynojirimycin
-
slight inhibition
GalNAc
-
an inhibitor of other hexosaminidases
GlcNAcstatin A
-
GlcNAcstatin A carries a carboxymethyl group, GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
GlcNAcstatin B
-
GlcNAcstatin B carries a phenylethyl moiety. GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
GlcNAcstatin C
GlcNAcstatin D
-
GlcNAcstatin D carries a phenylethyl moiety. GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
GlcNAcstatin E
-
GlcNAcstatin E carries a phenylethyl moiety. GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
Hg2+
-
inhibits activity at 1 mM, 6% relative activity compared with activity without any addition of effector
HPDP-biotin
treatment with a sulfhydrylspecific biotinylation reagent, HPDP-biotin, to biotinylate any accessible free cysteine residue in the native enzyme. Treatment is able to inhibit enzymatic activity, suggesting that the cysteine residue playing a role in catalysis is modified
methyl alpha-D-mannose
-
inhibits activity at 10 mM, 11.3% relative activity compared with activity without any addition of effector. Other sugars and sugar analogs do not inhibit with exception of methyl-alpha-D-mannose
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide
-
1-acetamido-epi-valienamine
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide
-
acetamido-azepane
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide
-
butyl-PUGNAc
N-((6S,7R,8R)-6,7-dihydroxy-5-(hydroxymethyl)-2-phenethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-yl)isobutyramide
-
GlcNAcstatin
N-acetyl-D-glucosamine
-
inhibits activity at 10 mM, 40% relative activity compared with activity without any addition of effector
N-acetylglucosamino-1,5-lactone oxime
-
LOGNAc
N-ethylmaleimide
N-methyl-deoxynojirimycin
-
inhibits activity at 10 mM, 73.5% relative activity compared with activity without any addition of effector
N-[(2Z,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(phenylcarbamoyl)oxy]imino]tetrahydro-2H-pyran-3-yl]acetamide
-
PUGNAc, inhibits also other functionally related enzymes
NaCl
-
high salt, 1.0 M NaCl, inhibits enzyme activity by 50% compared with activity without any addition of effector
NAG-thiazoline
-
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
O-(2-deoxy-2-butamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-hexamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isobutamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isovaleramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-propamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-valeramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
p-aminophenyl-S-GlcNAc
-
inhibits activity at 10 mM, 76.3% relative activity compared with activity without any addition of effector
Sn2+
-
inhibits activity at 1 mM, 57.6% relative activity compared with activity without any addition of effector
streptozotocin
Tris
-
high salt, 75 mM, inhibits enzyme activity by 50% compared with activity without any addition of effector
UDP-GlcNAc
-
inhibits activity at 10 mM, 78.1% relative activity compared with activity without any addition of effector
Zn2+
-
inhibits activity at 1 mM, 7.3% relative activity compared with activity without any addition of effector
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.21 - 0.56
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide
0.3 - 0.73
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide
0.47 - 0.95
3-nitrophenyl N-acetyl-beta-D-glucosaminide
0.56
4-chlorophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.08 - 1
4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
0.0029 - 1.4
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
0.45
4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide
-
-
0.49
4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide
-
-
0.38
4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide
-
-
0.0029 - 0.1
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
0.016 - 36
4-nitrophenyl N-acetyl-beta-D-glucosaminide
1.4
4-nitrophenyl N-acetyl-beta-D-thioglucosaminide
-
-
2.5 - 5
4-nitrophenyl-beta-D-GlcNAc
-
-
0.0849 - 2.1
fluorescein di(N-acetyl-beta-D-glucosaminide)
0.84
N-acetyl-4-aminophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
1.5 - 3.6
N-acetyl-beta-D-glucosamine
0.62 - 0.95
phenyl N-acetyl-beta-D-glucosaminide
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0013 - 11
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
10.5 - 65
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
0.2 - 54.9
4-nitrophenyl N-acetyl-beta-D-glucosaminide
1.3 - 2.1
fluorescein di(N-acetyl-beta-D-glucosaminide)
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.84
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190116
0.098
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156569
0.68
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156551
2.07
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156539
0.15
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156562
19.89
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190109
8.59
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156564
11.93
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156544
18.24
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156532
0.49
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156555
12.15
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190110
1.11
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156565
1.67
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156545
7.67
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156533
0.49
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156556
8.49
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190115
0.154
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156568
1.96
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156550
2.71
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156538
1.16
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156561
10.36
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190113
1.47
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156548
4.81
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156536
0.41
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156559
6.69
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190117
0.086
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156570
0.49
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156552
1.07
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156540
0.107
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156563
10.27
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190114
2.17
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156549
4.51
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156537
0.85
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156560
5.04
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190119
0.11
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156554
0.73
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156542
10.61
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190112
0.241
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156567
1.14
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156547
5.41
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156535
0.23
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156558
0.0683 - 3620
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
12.78
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190111
0.197
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156566
0.5
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156546
2.95
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156534
0.13
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156557
3.09 - 112
4-nitrophenyl N-acetyl-beta-D-glucosaminide
1 - 15.3
fluorescein di(N-acetyl-beta-D-glucosaminide)
0.44
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190120
0.088
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156543
5.82
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
190118
0.066
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
Homo sapiens
-
-
156571
0.15
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156553
0.94
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
Homo sapiens
-
-
156541
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0006 - 0.0015
(3aS,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-propyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
0.0038
(6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-N-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide
-
-
0.0015
1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.00012
1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.0057
1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.0016
1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.00007 - 0.00018
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
0.057
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.00023 - 0.0006
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
0.00042
2-((6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)acetate
-
-
0.00168
2-acetamido-2-deoxy-D-gluconhydroxime-1,5-lactone
-
-
0.151
2-acetamindo-1-amino-1,2-dideoxy-beta-D-glucopyranose
-
-
1.14
2-acetamindo-1-azido-1,2-dideoxy-beta-D-glucopyranose
-
-
0.000021
amen ändern: (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
-
-
1.5
GlcNAc
-
pH 6.5
0.0000043
GlcNAcstatin A
-
-
0.00000042
GlcNAcstatin B
-
-
0.0000044 - 0.0000981
GlcNAcstatin C
0.00000074
GlcNAcstatin D
-
-
0.0085
GlcNAcstatin E
-
-
0.0062
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide
-
-
0.011
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide
-
-
0.0024
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide
-
-
0.000004
N-((6S,7R,8R)-6,7-dihydroxy-5-(hydroxymethyl)-2-phenethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-yl)isobutyramide
-
-
3.9
N-acetyl-D-glucosamine
-
-
0.0016
N-acetylglucosamino-1,5-lactone oxime
-
-
0.00008
NAG-thiazoline
-
-
0.000035 - 0.000046
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
0.00005
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
-
-
0.0000054 - 0.000052
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
0.0024
O-(2-deoxy-2-butamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
0.21
O-(2-deoxy-2-hexamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
0.009
O-(2-deoxy-2-isobutamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
0.19
O-(2-deoxy-2-isovaleramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
0.0012
O-(2-deoxy-2-propamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
0.04
O-(2-deoxy-2-valeramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
1.5
streptozotocin
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.007
2-acetamido-2-deoxy-D-gluconhydroxime-1,5-lactone
Rattus norvegicus
-
-
0.16
2-acetamindo-1-amino-1,2-dideoxy-beta-D-glucopyranose
Rattus norvegicus
-
-
1.5
2-acetamindo-1-azido-1,2-dideoxy-beta-D-glucopyranose
Rattus norvegicus
-
-
0.0049
Ala-Cys(S-GlcNAc)-Ala
Clostridium perfringens
-
-
30
D-glucosamine
Rattus norvegicus
-
-
7
N-acetyl-D-glucosamine
Rattus norvegicus
-
-
0.0000086 - 0.00015
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
0.064
streptozotocin
Clostridium perfringens
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.78
-
fluorescein di(N-acetyl-beta-D-glucosaminide) as a substrate
1.68
-
splice variant v-O-GlcNAcase, fluorescein di(N-acetyl-beta-D-glucosaminide) as a substrate
2.035
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide as a substrate
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 5.5
D174N mutant displayed a reduced catalytic efficiency at the wild type enzyme's optimal pH as well as in the basic pH range. It exhibits a marked shift in pH optimum to the pH 5-5.5 range
6
-
bell-shaped pH-activity profile
6.4
-
at pH below 5.0, it begins to lose activity dramatically, at pH 6 or higher, it maintains high activity
6.5 - 7
optimum for the wild-type enzyme
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 37
-
most active at 37°C, and less active at room temperature, and very little activity at 4°C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
expressed in every human tissue examined but is the highest in the brain, placenta, and pancreas
Manually annotated by BRENDA team
-
enzyme is ubiquitously present in all rat tissues
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
enriched in nuclei
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Bacteroides thetaiotaomicron (strain ATCC 29148 / DSM 2079 / NCTC 10582 / E50 / VPI-5482)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / DSM 756 / JCM 1290 / NCIMB 6125 / NCTC 8237 / Type A)
Oceanicola granulosus (strain ATCC BAA-861 / DSM 15982 / KCTC 12143 / HTCC2516)
Oceanicola granulosus (strain ATCC BAA-861 / DSM 15982 / KCTC 12143 / HTCC2516)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
106000
-
SDS-PAGE and sucrose density gradient
130000
-
recombinant O-GlcNAcase, Coomassie blue staining following one-dimensional gel electrophoresis and Western blotting
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
-
1 * 54000 (alpha-subunit) and 1 * 51000 (beta-subunit)
monomer
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
visualization of the reaction coordinate of O-GlcNAc hydrolases
-
X-ray crystal structure of BtGH84 in complex with the inhibitor NAG-thiazoline. Hanging drop vapor diffusion method
-
X-ray crystallography
-
significant sequence homology to the human O-GlcNAcase N-terminus
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
-
enzyme is unstable below pH 4.5
708967
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 37
-
enzyme loses activity very fast (within 5 min) at 57°C, stable at 37°C and room temperature
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography using nickel-affinity chromatography followed by gel filtration
-
glutathione affinity chromatography
-
Ni2+-affinity chromotography
-
nickel affinity chromatography
-
nickel-affinity and ion-exchange chromatography
-
on a nickel column via the His6-tag
-
over 22000fold, gel filtration chromatography
-
the N-terminal His6-tagged recombinant BtGH84 protein is purified
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned and overexpressed in Escherichia coli
-
construction of a pUC118-pTM hybrid expression vector containing the full length and splice variant mouse NCOAT
expressed in Escherichia coli
-
expressed in Escherichia coli BL21
-
O-GlcNAcase and its splice variant (v-O-GlcNAcase) expressed in Escherichia coli
-
overexpress human O-GlcNAcase as a fusion protein with thioredoxin in an Escherichia coli expression system
-
soluble BtGH84 is expressed in the cytoplasm of Escherichia coli
-
the N-terminal His6-tagged recombinant BtGH84 protein is expressed
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
neonatal rat cardiac myocytes (NRCM) are treated with 60 nmol/l O-GlcNAcase RNAi or Scr RNAi for 72 hours to knockdown O-GlcNAcase expression. Knockdown of O-GlcNAcase reduces posthypoxic cardiac myocyte injury
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D242A
-
site-directed mutant, 2800fold lower catalytic efficiency than wild-type
D243A
-
site-directed mutant, 110fold lower catalytic efficiency than wild-type
N372A
-
site-directed mutant
Y137F
-
site-directed mutant
Y282F
-
site-directed mutant
D297N
-
rather inactive mutant
D298N
-
rather inactive mutant
D401A
-
rather inactive mutant
N390A
-
as active as wild-type
N396A
-
rather inactive mutant
V331C
-
mutation of Val331 to cysteine results in a mutant enzyme with unaltered steady-state kinetics compared with wild-type CpOGA
Y335F
-
rather inactive mutant
C896W
-
site-specific mutagenesis, in the tryptic peptide LGCFEIAK (894-901). Site-specific mutagenesis of the C-terminal glycine and cysteine residues (G895A and C896W) present in the tryptic peptide LGCFEIAK (894–901) causes little or no inhibition of O-GlcNAcase activity (72.3% of control and 129.9% of control, respectively)
D174A
-
generated mutant, reveals severely impaired catalytic activity across a broad range of substrates alongside a pH-activity profile consistent with deletion of a key catalytic residue
D175A
-
generated mutant, significant decrease in catalytic efficiency with substrates bearing poor leaving groups (up to 3000fold), while for substates bearing good leading groups the difference is much smaller (7fold). Mutant enzyme cleaves thioglycosides with essentially the same catalytic efficiency as the wild-type enzyme
DELTA1-350
-
deletion construct comprising amino acids 1-350 of human O-GlcNAcase
DELTA351-916
-
deletion construct comprising amino acids 351-916 of human O-GlcNAcase
E130A
-
site-specific mutagenesis, in the tryptic peptide EYEIEFIYAISPGLDITFSNPK (128-149), retains almost full enzymatic activity (97.3% of control)
F133V
-
site-specific mutagenesis, in the tryptic peptide EYEIEFIYAISPGLDITFSNPK (128-149), no O-GlcNAcase activity (3.3% of control)
G895A
-
site-specific mutagenesis, in the tryptic peptide LGCFEIAK (894-901). Site-specific mutagenesis of the C-terminal glycine and cysteine residues (G895A and C896W) present in the tryptic peptide LGCFEIAK (894–901) causes little or no inhibition of O-GlcNAcase activity (72.3% of control and 129.9% of control, respectively)
S138I
-
site-specific mutagenesis, in the tryptic peptide EYEIEFIYAISPGLDITFSNPK (128-149), exhibits greatly reduced activity (15.4% of control)
v-O-GlcNAcase
-
variant OGlcNAcase, isoform lacking the C-terminal third of the full-length O-GlcNAcase
Y129F
-
site-specific mutagenesis, in the tryptic peptide EYEIEFIYAISPGLDITFSNPK (128-149), retains almost full enzymatic activity (90.5% of control)
C166S
site-directed mutagenesis
C878S
site-directed mutagenesis, comparable level of O-GlcNAcase activity as wild-type enzyme
D174N
site-directed mutagenesis
D175A
site-directed mutagenesis
D177N
site-directed mutagenesis
DELTA250-345
protein missing amino acids 250-345, due to the removal of exon 8
DELTA250-398
lacks amino acids 250-398 in the protein due to the specific excision of exons 8 and 9