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
3.2.1.169
-
RECOMMENDED NAME
GeneOntology No.
protein O-GlcNAcase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
[protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine + H2O = [protein]-L-serine + N-acetyl-D-glucosamine
show the reaction diagram
-
-
-
-
[protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-theronine + H2O = [protein]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
protein O-[N-acetyl]-glucosylation
-
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.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
beta-N-acetylglucosaminidase
-
-
beta-N-acetylglucosaminidase
-
-
beta-N-acetylglucosaminidase
-
-
beta-N-acetylglucosaminidase
P06865
-
BtGH84
Q89ZI2
a bacterial homolog to the human enzyme
cytoplasmic O-GlcNAcase
-
-
glycoside hydrolase O-GlcNAcase
-
-
hexosaminidase
-
-
hOGA
-
-
mNCOAT
Q9EQQ9
-
NCOAT
Q9EQQ9
bifunctional nucleo-cytoplasmic protein with both O-GlcNAcase and histone acetyltransferase domains
neutral hexosaminidase C
P06865
-
neutral O-GlcNAcase
-
-
O-GlcNAc hydrolase
Q89ZI2
-
O-GlcNAc selective N-acetyl-beta-D-glucosaminidase
-
-
O-GlcNAc specific beta-N-acetylglucosaminidase
-
-
O-GlcNAc-selective N-acetyl-beta-D-glucosaminidase
-
-
O-GlcNAc-selective-N-acetyl-beta-D-glucosaminidase
-
-
O-GlcNAcase
-
-
O-GlcNAcase
Q0TR53
-
O-GlcNAcase
-
-
O-GlcNAcase
-
two forms of O-GlcNAcase have been studied, a full-length isoform that is better characterized, and a shorter nuclear-localized variant, arising from failure to splice out one intron
O-GlcNAcase
P06865
-
O-GlcNAcase
Q9EQQ9
-
O-GlcNAcase
-
-
OGA-FL
-
full-length form of OGA
OGA-NV
-
nuclear variant
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
Sprague-Dawley male rats. GlcN (30 micromol/kg/min) or physiological saline (control) is intravenously infused into the rats for 2 h
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
metabolism
-
caspase-3 efficiently cleaved O-GlcNAcase
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
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
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
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
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3,4-dinitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3-fluoro-4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
3-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
3-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
4-aminophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside + H2O
?
show the reaction diagram
-
67% relative activity compared to 4-nitrophenyl-beta-D-GlcNac
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
4-chlorophenyl N-acetyl-beta-D-glucosaminide + H2O
4-chlorophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
4-methylumbelliferyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside + H2O
?
show the reaction diagram
-
33% relative activity compared to 4-nitrophenyl-beta-D-GlcNac
-
-
?
4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside + H2O
4-methylumbelliferone + 2-acetamido-2-deoxy-beta-D-glucopyranose
show the reaction diagram
-
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
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
Q9EQQ9
-
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
fluorogenic substrate, 4MU-NAG
-
-
?
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
MUGlcNAc
-
-
?
4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-difluoroacetyl-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-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 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
-
-
-
-
?
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide + H2O
4-methylumbelliferone + N-acetyl-beta-D-glucosamine
show the reaction diagram
Q0TR53
fluorogenic substrate, 4MU-NAG
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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-glucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
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-glucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
Q89ZI2
-
-
-
?
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-glucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
Q9EQQ9
-
-
-
?
4-nitrophenyl N-acetyl-beta-D-thioglucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-thioglucosamine
show the reaction diagram
-
-
-
-
?
4-nitrophenyl N-acetyl-beta-D-thioglucosaminide + H2O
4-nitrophenol + N-acetyl-beta-D-thioglucosamine
show the reaction diagram
-
enzyme cleaves p-nitrophenyl-S-GlcNAc with comparable efficiency as p-nitrophenyl-O-GlcNAc
-
-
?
4-nitrophenyl-beta-D-GlcNAc + H2O
4-nitrophenol + N-acetyl-D-glucosamine
show the reaction diagram
-
-
-
-
?
Ala-Ser(O-GlcNAc)-Tyr + H2O
Ala-Ser-Tyr + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
is synthesized using standard N-(9-fluorenyl)methoxycarbonyl (FMOC) chemistry
-
-
?
fluorescein di(N-acetyl-beta-D-glucosaminide) + H2O
fluorescein mono(N-acetyl-beta-D-glucosaminide) + N-acetyl-D-glucosamine
show the reaction diagram
-
FDGlcNAc, fluorogenic substrate
-
-
?
GlcNAc beta(1-4)GlcNAc + H2O
N-acetyl-D-glucosamine + N-acetyl-D-glucosamine
show the reaction diagram
-
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
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
additional information
?
-
-
catalyzes the cleavage of beta-O-linked N-acetyl-beta-D-glucosaminide from modified proteins and is a member of the family 84 glycoside hydrolases
-
-
-
additional information
?
-
-
catalyzing the hydrolytic cleavage of beta-O-linked 2-acetamido-2-deoxy-D-glycopyranose (O-GlcNAc) from serine and threonine residues of posttranslationally modified proteins
-
-
-
additional information
?
-
-
enzyme cleaves 4-nitrophenyl N-acetyl-beta-D-glucosaminide from modified proteins and also cleaves 4-nitrophenyl N-acetyl-beta-D-thioglucosaminide
-
-
-
additional information
?
-
-
enzyme is responsible for removal of the O-GlcNAc post-translational modification, is being increasingly used to aid in discerning the roles played by this form of intracellular glycosylation
-
-
-
additional information
?
-
-
enzyme removes N-acetyl-beta-D-glucosaminide from proteins
-
-
-
additional information
?
-
-
enzyme that removes N-acetyl-beta-D-glucosamine from O-GlcNAcylated proteins
-
-
-
additional information
?
-
Q0TR53
enzyme that removes O-GlcNAc from O-GlcNAcylated proteins
-
-
-
additional information
?
-
-
has O-GlcNAcase activity against O-GlcNAcylated human proteins, suggesting that the enzyme is a suitable model for further studies into the function of human O-GlcNAcase
-
-
-
additional information
?
-
-
O-GlcNAcase uses a catalytic mechanism involving substrate-assisted catalysis. In this mechanism, the leaving group is expelled from the anomeric center by nucleophilic attack of the 2-acetamido group of the substrate to form an oxazoline intermediate
-
-
-
additional information
?
-
-
removes O-N-acetyl-glucosamine residues from O-GlcNAcylated proteins
-
-
-
additional information
?
-
-
when a substrate contains a modest leaving group as well as a poor nucleophile, the catalytic efficiency of the enzyme is synergistically impaired
-
-
-
additional information
?
-
-
fluorescein di-N-acetyl-beta-D-galactosaminide (FDGalNAc) is not cleaved by these enzymes, the O-GlcNAcase has substrate specificity toward O-GlcNAc but not O-GalNAc
-
-
-
additional information
?
-
-
strong selectivity for O-GlcNAc-synthetic glycopeptides. Enzyme does not cleave 4-nitrophenylGalNAc and is highly selective for O-GlcNAc bearing glycopeptides. O-GlcNAcase is involved in the regulated removal of O-GlcNAc from O-GlcNAc-bearing glycoproteins in the nucleoplasmic and cytoplasmic compartments of cells, shows no activity against other monosaccharides either in alpha or beta linkage to 4-nitrophenyl, such as, 4-nitrophenyl-alpha-D-GlcNAc, 4-nitrophenyl-alpha-D-glucose, 4-nitrophenyl-beta-D-glucose, 4-nitrophenyl-alpha-D-GalNAc, 4-nitrophenyl-beta-D-GalNAc, 4-nitrophenyl-alpha-D-galactose, 4-nitrophenyl-beta-D-galactose, 4-nitrophenyl-alpha-D-mannose, 4-nitrophenyl-alpha-L-fructose, substitution of GlcNAc at other positions prevents cleavage, for example, Gal(1-3)GlcNAc-p-nitrophenol, Gal(1-4)GlcNAc, Gal(1-3)GlcNAc, and UDP-GlcNAc, the enzyme specifically cleave GlcNAc at C-1 position in beta-linkage to other groups
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
catalyzes the cleavage of beta-O-linked N-acetyl-beta-D-glucosaminide from modified proteins and is a member of the family 84 glycoside hydrolases
-
-
-
additional information
?
-
-
catalyzing the hydrolytic cleavage of beta-O-linked 2-acetamido-2-deoxy-D-glycopyranose (O-GlcNAc) from serine and threonine residues of posttranslationally modified proteins
-
-
-
additional information
?
-
-
enzyme cleaves 4-nitrophenyl N-acetyl-beta-D-glucosaminide from modified proteins and also cleaves 4-nitrophenyl N-acetyl-beta-D-thioglucosaminide
-
-
-
additional information
?
-
-
enzyme is responsible for removal of the O-GlcNAc post-translational modification, is being increasingly used to aid in discerning the roles played by this form of intracellular glycosylation
-
-
-
additional information
?
-
-
enzyme removes N-acetyl-beta-D-glucosaminide from proteins
-
-
-
additional information
?
-
-
enzyme that removes N-acetyl-beta-D-glucosamine from O-GlcNAcylated proteins
-
-
-
additional information
?
-
Q0TR53
enzyme that removes O-GlcNAc from O-GlcNAcylated proteins
-
-
-
additional information
?
-
-
has O-GlcNAcase activity against O-GlcNAcylated human proteins, suggesting that the enzyme is a suitable model for further studies into the function of human O-GlcNAcase
-
-
-
additional information
?
-
-
O-GlcNAcase uses a catalytic mechanism involving substrate-assisted catalysis. In this mechanism, the leaving group is expelled from the anomeric center by nucleophilic attack of the 2-acetamido group of the substrate to form an oxazoline intermediate
-
-
-
additional information
?
-
-
removes O-N-acetyl-glucosamine residues from O-GlcNAcylated proteins
-
-
-
additional information
?
-
-
when a substrate contains a modest leaving group as well as a poor nucleophile, the catalytic efficiency of the enzyme is synergistically impaired
-
-
-
additional information
?
-
-
strong selectivity for O-GlcNAc-synthetic glycopeptides. Enzyme does not cleave 4-nitrophenylGalNAc and is highly selective for O-GlcNAc bearing glycopeptides. O-GlcNAcase is involved in the regulated removal of O-GlcNAc from O-GlcNAc-bearing glycoproteins in the nucleoplasmic and cytoplasmic compartments of cells
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Cd2+
-
inhibits activity at 1 mM
Cu2+
-
inhibits activity at 1 mM
Zn2+
-
inhibits activity at 1 mM
Hg2+
-
inhibits activity at 1 mM
additional information
-
EDTA, Mg2+, Fe3+, Ca2+, Mn2+, and Co2+ do not affect the activity
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
an inhibitor that mimics the oxazoline intermediate proposed in the catalytic mechanism of family 20 glycoside hydrolases, is shown to act as a potent competitive inhibitor. NAG-thiazoline is therefore a potent inhibitor of O-GlcNAcase, binding about 21000fold more tightly than the parent saccharide, N-acetyl-beta-D-glucosaminide
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
NAG-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
-
NButGT
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 C carriesa phenylethyl moiety. GlcNAcstatins are the most potent human OGA inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
GlcNAcstatin C
-
GlcNAcstatin C carriesa phenylethyl moiety. GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
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
Q9EQQ9
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
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
Q9EQQ9
treatment is able to inhibit enzymatic activity, suggesting that the cysteine residue playing a role in catalysis is modified
N-ethylmaleimide
-
inhibits activity at 10 mM, 15.3% relative activity compared with activity without any addition of effector
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
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
PUGNAc, transition state mimic
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
inhibits activity at 0.1 mM, 4.1% relative activity compared with activity without any addition of effector
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
-
STZ, significantly dose-dependently inhibited recombinant O-GlcNAcase
streptozotocin
-
-
streptozotocin
-
binds in the enzyme active site in its intact form, without the formation of a covalent adduct, weak inhibitor
streptozotocin
-
STZ, diabetogenic compound, acts as a suicide inhibitor
streptozotocin
-
poor inhibitor
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
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
additional information
-
methylnitrosourea (MNU), the nitric oxide-containing portion of streptozotocin: no significant inhibition observed
-
additional information
-
streptozotocin does not appear to act as an irreversible inhibitor
-
additional information
-
GlcN-induced whole-body insulin resistance is related to tissue O-GlcNAcase activity and mRNA expression. O-GlcNAcase activity is posttranslationally inhibited during GlcN-induced insulin resistance
-
additional information
-
addition of 50 mM GalNAc does not inhibit the neutral hexosaminidase activity; GlcNAc analogs with no or small effect on the enzyme activity: N-acetylgalactosamine, 4-aminophenyl 1-thio-beta-D-galactopyranoside, (2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl)-L-asparagine, 2-(acetylamino)-2-deoxy-N-hexanoyl-beta-D-glucopyranosylamine, 2-(acetylamino)-2-deoxy-1-O-phosphono-beta-D-glucopyranose, bromoconduritol, iodoacetic acid, N-acetylneuraminic acid
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-
GlcN is found to provoke hyperglycemia. The insulin resistance index (HOMA-IR) increased. The beta-cell function index (HOMA-beta) diminished. Insulin release index (insulin/glucose) is less in the GlcN group than in the control. Muscle O-GlcNAcase activity diminished
-
additional information
-
addition of Triton X-100 does not increase activity
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.21
-
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.22
-
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide
-
D175A mutant
0.36
-
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 5.0)
0.56
-
3,4-dinitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 7.4)
0.3
-
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.31
-
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D175A mutant
0.38
-
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 7.4)
0.73
-
3-fluoro-4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 5.0)
0.47
-
3-nitrophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.95
-
3-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D175A mutant
0.56
-
4-chlorophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.08
-
4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
-
D242N mutant, at a pH value of 8.5 the apparent Km is 12fold reduced (1 mM to 0.08 mM)
1
-
4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside
-
D242N mutant, at a pH value of 8.5 the apparent Km is 12fold reduced (1 mM to 0.08 mM)
0.0029
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.003
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D297N mutant
0.0031
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N390A mutant
0.004
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D298N mutant
0.013
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N396A mutant
0.015
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D401A mutant
0.028
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
W490A mutant
0.041
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
Y335F mutant
0.2
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D175A mutant; wild-type
0.43
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
-
1.4
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 7.4)
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
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
wild-type
0.0068
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
V331C mutant
0.1
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
W490A mutant
0.016
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D243N mutant
0.092
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D243A mutant
0.121
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
0.16
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
OGA-FL
0.21
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.23
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D175A mutant
0.26
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D177N mutant
0.28
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.3
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
0.32
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
OGA-NV
0.41
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
Y282F mutant
0.46
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 5.0)
0.46
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
C166S mutant
0.49
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
wild-type
0.97
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D174N mutant
0.998
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
in the pancreas of rats treated with GlcN
1
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
compared to the control, pancreas of rats treated with saline
1.1
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
O-GlcNAcase
1.1
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
1.12
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
compared to the control, muscles of rats treated with saline
1.18
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
Y137F mutant
1.24
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
in the liver of rats treated with GlcN
1.29
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
compared to the control, liver of rats treated with saline
1.4
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D174A mutant (pH 7.4)
1.4
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D175A mutant
1.47
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D242N mutant
1.5
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
1.51
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
in the muscels of rats treated with GlcN
4.4
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
D242A mutant
36
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
N372A mutant
1.4
-
4-nitrophenyl N-acetyl-beta-D-thioglucosaminide
-
-
2.5
5
4-nitrophenyl-beta-D-GlcNAc
-
-
0.0849
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
O-GlcNAcase
2.1
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
splice variant (v-O-GlcNAcase)
0.84
-
N-acetyl-4-aminophenyl N-acetyl-beta-D-glucosaminide
-
wild-type
1.5
-
N-acetyl-beta-D-glucosamine
-
for OGA-FL
3.6
-
N-acetyl-beta-D-glucosamine
-
an inhibitor of OGA-NV
0.62
-
phenyl N-acetyl-beta-D-glucosaminide
-
wild-type
0.95
-
phenyl N-acetyl-beta-D-glucosaminide
-
D175A mutant
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0013
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D298N mutant
0.0025
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N396A mutant
0.0028
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
Y335F mutant
0.0044
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D401A mutant
0.0198
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D297N mutant
4
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
W490A mutant
10.5
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
wild-type
11
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N390A mutant
10.5
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
wild-type
17.3
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
V331C mutant
65
-
4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
-
W490A mutant
0.2
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
1
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
2.3
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D177N mutant
3.4
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
6.4
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D175A mutant
18.6
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D174N mutant
21.7
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
C166S mutant
54.9
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
wild-type
1.3
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
-
2.1
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
splice variant (v-O-GlcNAcase)
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
6.84
-
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293851
0.098
-
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293893
0.68
-
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293875
2.07
-
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293863
0.15
-
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293886
19.89
-
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293844
8.59
-
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293888
11.93
-
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293868
18.24
-
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293856
0.49
-
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293879
12.15
-
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293845
1.11
-
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293889
1.67
-
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293869
7.67
-
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293857
0.49
-
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293880
8.49
-
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293850
0.154
-
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293892
1.96
-
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293874
2.71
-
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293862
1.16
-
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293885
10.36
-
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293848
1.47
-
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293872
4.81
-
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293860
0.41
-
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293883
6.69
-
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293852
0.086
-
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293894
0.49
-
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293876
1.07
-
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293864
0.107
-
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293887
10.27
-
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293849
2.17
-
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293873
4.51
-
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293861
0.85
-
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293884
5.04
-
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293854
0.11
-
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293878
0.73
-
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293866
10.61
-
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293847
0.241
-
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293891
1.14
-
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293871
5.41
-
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293859
0.23
-
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293882
0.0683
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
Y335F mutant
252922
0.192
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N396A mutant
252922
0.293
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D401A mutant
252922
0.325
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D298N mutant
252922
6.6
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
D297N mutant
252922
142.9
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
W490A mutant
252922
3548
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
N390A mutant
252922
3620
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
wild-type
252922
12.78
-
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293846
0.197
-
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293890
0.5
-
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293870
2.95
-
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293858
0.13
-
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
293881
3.09
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
-
-
293265
4.6
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D175A mutant
293265
8.8
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D177N mutant
293265
19.2
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
D174N mutant
293265
47.2
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
C166S mutant
293265
112
-
4-nitrophenyl N-acetyl-beta-D-glucosaminide
Q9EQQ9
wild-type
293265
1
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
splice variant (v-O-GlcNAcase)
293266
15.3
-
fluorescein di(N-acetyl-beta-D-glucosaminide)
-
-
293266
0.44
-
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293855
0.088
-
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293867
5.82
-
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
293853
0.066
-
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
293895
0.15
-
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
293877
0.94
-
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
293865
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0006
-
(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
-
OGA-FL
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
-
OGA-NV
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
-
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.00018
-
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
at pH 7.4, using 4-nitrophenyl N-acetyl-beta-D-glucosaminide as a substrat
0.057
-
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
0.00023
-
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
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
-
GlcNAcstatin C
-
-
0.0000046
-
GlcNAcstatin C
-
wild-type
0.000074
-
GlcNAcstatin C
-
W490A mutant
0.0000981
-
GlcNAcstatin C
-
V331C mutant
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
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
-
-
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
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
-
0.000046
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
-
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
-
-
1.5
-
streptozotocin
-
poor inhibitor
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.007
-
2-acetamido-2-deoxy-D-gluconhydroxime-1,5-lactone
-
-
0.16
-
2-acetamindo-1-amino-1,2-dideoxy-beta-D-glucopyranose
-
-
1.5
-
2-acetamindo-1-azido-1,2-dideoxy-beta-D-glucopyranose
-
-
0.0049
-
Ala-Cys(S-GlcNAc)-Ala
-
-
30
-
D-glucosamine
-
-
7
-
N-acetyl-D-glucosamine
-
-
0.0000086
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
wild-type
0.00001
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
N390A mutant
0.000024
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
W490A mutant
0.00015
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
-
0.064
-
streptozotocin
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
-
in the rats treated with GlcN, muscle O-GlcNAcase activity diminished (0.28 vs. 0.36 nmol of p-nitrophenyl/mg protein/min)
additional information
-
-
last purification step: 13046.67 unit/mg. One unit is the amount of enzyme required to catalyze the release of 4-nitrophenyl from 1 mmol of 4-nitrophenylGlcNAc/min at 37°C
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
5.5
Q9EQQ9
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
Q9EQQ9
optimum for the wild-type enzyme
6.5
-
-
measured pH-values range from 4.5 to 9.0, hydrolysis of 4-nitrophenyl N-acetyl-beta-D-glucosaminide resembles a bell-shaped curve with the maximal catalytic efficiency at a pH of 6.5
6.5
-
-
assay at
6.5
-
-
maximum activity
7
-
-
assay at
7
-
Q9EQQ9
assay at
7.4
-
-
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
assay at
37
-
Q9EQQ9
assay at
37
-
-
assay at
37
-
-
assay at
37
-
-
assay at and most active at
TEMPERATURE RANGE
TEMPERATURE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4
37
-
most active at 37°C, and less active at room temperature, and very little activity at 4°C
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
P06865
expressed in every human tissue examined but is the highest in the brain, placenta, and pancreas
Manually annotated by BRENDA team
-
african green monkey kidney
Manually annotated by BRENDA team
P06865
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
P06865
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
P06865
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
P06865
expressed in every human tissue examined but is the highest in the brain, placenta, and pancreas
Manually annotated by BRENDA team
P06865
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 ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
predominantly localized
Manually annotated by BRENDA team
-
enriched in nuclei
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
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 13 / Type A)
Clostridium perfringens (strain 13 / Type A)
Clostridium perfringens (strain 13 / Type A)
Clostridium perfringens (strain 13 / Type A)
Clostridium perfringens (strain 13 / Type A)
Clostridium perfringens (strain 13 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
Clostridium perfringens (strain ATCC 13124 / NCTC 8237 / Type A)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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 ACCESSION NO.
COMMENTARY
LITERATURE
heterodimer
-
1 * 54000 (alpha-subunit) and 1 * 51000 (beta-subunit)
monomer
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.5
-
-
enzyme is unstable below pH 4.5
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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 ACCESSION NO.
LITERATURE
affinity chromatography using nickel-affinity chromatography followed by gel filtration
-
the N-terminal His6-tagged recombinant BtGH84 protein is purified
-
nickel affinity chromatography
-
glutathione affinity chromatography
-
Ni2+-affinity chromotography
-
nickel-affinity and ion-exchange chromatography
-
on a nickel column via the His6-tag
-
-
Q9EQQ9
over 22000fold, gel filtration chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
soluble BtGH84 is expressed in the cytoplasm of Escherichia coli
-
the N-terminal His6-tagged recombinant BtGH84 protein is expressed
-
cloned and overexpressed in Escherichia coli
-
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
-
construction of a pUC118-pTM hybrid expression vector containing the full length and splice variant mouse NCOAT
Q9EQQ9
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
COMMENTARY
LITERATURE
D242A
-
site-directed mutant, 2800fold lower catalytic efficiency than wild-type
D242N
-
mutant is active on the substrate 4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside, with an efficiency 320fold times lower than that of wild-type enzyme. D242 activates the 2-acetamido group for nucleophilic attack
D242N
-
site-directed mutant
D243A
-
site-directed mutant, 110fold lower catalytic efficiency than wild-type
D243N
-
variant in which the general acid/base is impaired. D243 plays the role of general acid to aid departure of the leaving group. Crystals of the D242N variant grown at pH 8.5 with the substrate 4-methylumbelliferyl 2-acetamido-2-deoxy-beta-D-glucopyranoside, an intact trapped oxazoline intermediate is observed
D243N
-
site-directed mutant
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
W490A
-
mutation of Trp490 to alanine results in a mutant enzyme that shows a 30fold reduction in Km when assayed with the pseudosubstrate 4-methylumbelliferyl-N-acetyl-beta-D-glucosaminide
W490A
-
mutant with less activity
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
Q9EQQ9
site-directed mutagenesis
C878S
Q9EQQ9
site-directed mutagenesis, comparable level of O-GlcNAcase activity as wild-type enzyme
D174N
Q9EQQ9
site-directed mutagenesis
D175A
Q9EQQ9
site-directed mutagenesis
D177N
Q9EQQ9
site-directed mutagenesis
DELTA250-345
Q9EQQ9
protein missing amino acids 250-345, due to the removal of exon 8
DELTA250-398
Q9EQQ9
lacks amino acids 250-398 in the protein due to the specific excision of exons 8 and 9