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Information on EC 3.2.1.169 - protein O-GlcNAcase and Organism(s) Homo sapiens and UniProt Accession P06865

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IUBMB Comments
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.
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Homo sapiens
UNIPROT: P06865
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The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
o-glcnac hydrolase, o-glcnac-selective n-acetyl-beta-d-glucosaminidase, btgh84, glycoside hydrolase o-glcnacase, cytoplasmic o-glcnacase, cpoga, endos-like endoglycosidase, neutral o-glcnacase, cpnagj, o-glcnac-selective-n-acetyl-beta-d-glucosaminidase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
beta-N-acetylglucosaminidase
-
neutral hexosaminidase C
-
O-GlcNAcase
-
beta-N-acetylglucosaminidase
-
-
glycoside hydrolase O-GlcNAcase
-
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hOGA
-
-
O-GlcNAc hydrolase
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O-GlcNAc specific beta-N-acetylglucosaminidase
-
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O-GlcNAc-selective N-acetyl-beta-D-glucosaminidase
-
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O-GlcNAcase
O-linked beta-N-acetyl glucosaminase
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OGA-FL
-
full-length form of OGA
OGA-NV
-
nuclear variant
PATHWAY SOURCE
PATHWAYS
-
-
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.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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-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-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-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 beta-D-N-acetylglucosaminide + H2O
4-methylumbelliferone + beta-D-N-acetylglucosamine
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-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
-
-
-
-
?
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-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
-
-
?
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
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
[alpha-crystallin B chain]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine + H2O
[alpha-crystallin B chain]-L-serine + N-acetyl-D-glucosamine
show the reaction diagram
the sequence of alpha-crystallin B chain is FPTSTSLSPFYLR
-
-
?
[ELK1 protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-threonine + H2O
[ELK1 protein]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
the sequence of ELK1 protein is FWSTLSPI
-
-
?
[lamin B1]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-threonine + H2O
[lamin B1]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
the sequence of lamin B1 protein is KLSPSPSSRVTVS
-
-
?
[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-threonine + H2O
[protein]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
[TAB1 protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine + H2O
[TAB1 protein]-L-serine + N-acetyl-D-glucosamine
show the reaction diagram
the sequence of TAB1 protein is VPYSSAQS
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
[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-threonine + H2O
[protein]-L-threonine + N-acetyl-D-glucosamine
show the reaction diagram
additional information
?
-
INHIBITOR
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
-
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'-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-amino-1H-benzo[de]isoquinoline-1,3(2H)-dione
22.2% inhibition at 0.1 mM
2-[[1-[(2-acetamido-beta-D-glucopyranosylthiomethyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
18.5% inhibition at 0.1 mM
2-[[1-[2-[(2-acetamido-beta-D-glucopyranosyl)thio]ethyl]-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
27.8% inhibition at 0.1 mM
2-[[1-[3-[(2-acetamido-beta-D-glucopyranosyl)thio]propyl]-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
22.7% inhibition at 0.1 mM
2-[[1-[4-[(2-acetamido-beta-D-glucopyranosyl)thio]butyl]-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
25.1% inhibition at 0.1 mM
2-[[1-[5-[(2-acetamido-beta-D-glucopyranosyl)thio]pentyl]-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
26% inhibition at 0.1 mM
2-[[1-[6-[(2-acetamido-beta-D-glucopyranosyl)thio]hexyl]-1H-1,2,3-triazol-4-yl]methyl]-1H-benzo[de]isoquinoline-1,3(2H)-dione
25.7% inhibition at 0.1 mM
5-(trifluoromethyl)-2,3-dihydro-1H-1,4-diazepine
-
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
GlcNAc
-
-
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 BF
-
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
GlcNAcstatin G
-
LOGNAc
i.e. 2-acetamido-2-deoxy-D-gluconhydroximo-1,5-lactone
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-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-2-[(2-acetamido-beta-D-glucopyranosyl)thio]acetamide
31.1% inhibition at 0.1 mM
N-acetylglucosamino-1,5-lactone oxime
-
LOGNAc
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
N-[2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]-2-[(2-acetamido-beta-D-glucopyranosyl) thio]acetamide
38.6% inhibition at 0.1 mM
N-[2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]-3-[(2-acetamido-beta-D-glucopyranosyl)thio]propanamide
66.9% inhibition at 0.1 mM
N-[3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propyl]-2-[(2-acetamido-beta-D-glucopyranosyl)thio]acetamide
97.6% inhibition at 0.1 mM
N-[3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propyl]-3-[(2-acetamido-beta-D-glucopyranosyl)thio]propanamide
59.4% inhibition at 0.1 mM
N-[4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butyl]-2-[(2-acetamido-beta-D-glucopyranosyl)thio]acetamide
50% inhibition at 0.1 mM
N-[4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butyl]-3-[(2-acetamido-beta-D-glucopyranosyl)thio]propanamide
34.3% inhibition at 0.1 mM
NAG-thiazoline
naphthalimide
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
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-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
PUGNAc
streptozotocin
thiamet G
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
0.2 - 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
-
-
0.04 - 4
4-nitrophenyl N-acetyl-beta-D-glucosaminide
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
0.08 - 3.4
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
-
-
0.098
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
0.68
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
2.07
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.15
3,4-difluorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
19.89
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
8.59
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
11.93
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
18.24
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.49
3,4-dinitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
12.15
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
1.11
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
1.67
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
7.67
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.49
3-fluoro-4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
8.49
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.154
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
1.96
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
2.71
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
1.16
3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
10.36
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
1.47
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
4.81
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.41
4-chloro-3-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
6.69
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.086
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
0.49
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
1.07
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.107
4-chlorophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
10.27
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
2.17
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
4.51
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.85
4-cyanophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
5.04
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.11
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
0.73
4-methoxyphenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
10.61
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.241
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
1.14
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
5.41
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.23
4-methylumbelliferyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
12.78
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.197
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
0.5
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
2.95
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
0.13
4-nitrophenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-trifluoroacetyl-beta-D-glucopyranoside
-
-
0.03 - 37
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
-
-
0.088
methyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
5.82
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-beta-D-glucopyranoside
-
-
0.066
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-butanoyl-beta-D-glucopyranoside
-
-
0.15
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-difluoroacetyl-beta-D-glucopyranoside
-
-
0.94
phenyl 2-deoxy-2-amino-O3,O4,O6-triacetyl-N-fluoroacetyl-beta-D-glucopyranoside
-
-
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
-
-
0.000021
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 - 0.0000232
GlcNAcstatin B
0.0000044
GlcNAcstatin C
-
-
0.00000074
GlcNAcstatin D
-
-
0.0085
GlcNAcstatin E
-
-
0.0000214
GlcNAcstatin G
pH and temperature not specified in the publication
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
-
-
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
-
-
0.000046
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
-
-
0.0000066 - 0.06
PUGNAc
1.5
streptozotocin
0.00000008 - 0.009
thiamet G
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000632
GlcNAcstatin B
Homo sapiens
pH and temperature not specified in the publication
0.0000578
GlcNAcstatin G
Homo sapiens
pH and temperature not specified in the publication
0.1
N-[4-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)butyl]-2-[(2-acetamido-beta-D-glucopyranosyl)thio]acetamide
Homo sapiens
at pH 6.5 and 30°C
0.0001501
thiamet G
Homo sapiens
pH and temperature not specified in the publication
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
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
expressed in every human tissue examined but is the highest in the brain, placenta, and pancreas
Manually annotated by BRENDA team
lowest expression in lung, liver, and kidney
Manually annotated by BRENDA team
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
expressed in every human tissue examined but is the highest in the brain, placenta, and pancreas
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
predominantly localized
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
HEXA_HUMAN
529
0
60703
Swiss-Prot
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
103000
gel filtration
130000
-
recombinant O-GlcNAcase, Coomassie blue staining following one-dimensional gel electrophoresis and Western blotting
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
x-ray crystallography
monomer
-
-
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
enzyme in apo and inhibited states, hanging drop vapor diffusion method
mutant enzyme D175N in complex with alpha-crystallin B, TAB1 protein, ELK1 protein or lamin B1, hanging drop vapor diffusion method, using 0.032 M ammonium citrate tribasic (pH 7.0), 0.02M MES monohydrate, 0.128 M potassium thiocyanate, 0.016M imidazole, 0.002 M zinc sulfate heptahydrate, 12.8% (w/v) polyethylene glycol 3350, 3.2% (w/v) polyethylene glycol monomethyl ether 2000, and 5% (w/v) polyethylene glycol monomethyl ether 550
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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 substrates 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
D175N
inactive
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)
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA resin column chromatography and Superdex S200 gel filtration
Ni-Sepharose column chromatography
Ni2+-affinity chromotography
-
nickel-affinity and ion-exchange chromatography
-
on a nickel column via the His6-tag
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
-
expressed in Escherichia coli BL21
-
expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli Rosetta (DE3) cells
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
the enzyme is a drug target for the treatment of Alzheimer's and cardiovascular disease
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Dorfmueller, H.C.; Borodkin, V.S.; Schimpl, M.; van Aalten, D.M.F.
GlcNAcstatins are nanomolar inhibitors of human O-GlcNAcase inducing cellular hyper-O-GlcNAcylation
Biochem. J.
420
221-227
2009
Clostridium perfringens (Q0TR53), Homo sapiens
Manually annotated by BRENDA team
Lee, T.N.; Alborn, W.E.; Knierman, M.D.; Konrad, R.J.
The diabetogenic antibiotic streptozotocin modifies the tryptic digest pattern for peptides of the enzyme O-GlcNAc-selective N-acetyl-beta-D-glucosaminidase that contain amino acid residues essential for enzymatic activity
Biochem. Pharmacol.
72
710-718
2006
Homo sapiens
Manually annotated by BRENDA team
Cetinbas, N.; Macauley, M.S.; Stubbs, K.A.; Drapala, R.; Vocadlo, D.J.
Identification of Asp174 and Asp175 as the Key Catalytic Residues of Human O-GlcNAcase by Functional Analysis of Site-Directed Mutants
Biochemistry
45
3835-3844
2006
Homo sapiens
Manually annotated by BRENDA team
Macauley, M.S.; Vocadlo, D.J.
Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase
Biochim. Biophys. Acta
1800
107-121
2010
Homo sapiens
Manually annotated by BRENDA team
Kim, E.J.; Kang, D.O.; Love, D.C.; Hanover, J.A.
Enzymatic characterization of O-GlcNAcase isoforms using a fluorogenic GlcNAc substrate
Carbohydr. Res.
341
971-982
2006
Homo sapiens
Manually annotated by BRENDA team
Macauley, M.S.; Vocadlo, D.J.
Enzymatic characterization and inhibition of the nuclear variant of human O-GlcNAcase
Carbohydr. Res.
344
1079-1084
2009
Homo sapiens
Manually annotated by BRENDA team
Macauley, M.S.; Stubbs, K.A.; Vocadlo, D.J.
O-GlcNAcase catalyzes cleavage of thioglycosides without general acid catalysis
J. Am. Chem. Soc.
127
17202-17203
2005
Homo sapiens
Manually annotated by BRENDA team
Greig, I.R.; Macauley, M.S.; Williams, I.H.; Vocadlo, D.J.
Probing synergy between two catalytic strategies in the glycoside hydrolase O-GlcNAcase using multiple linear free energy relationships
J. Am. Chem. Soc.
131
13415-13422
2009
Homo sapiens
Manually annotated by BRENDA team
Gao, Y.; Wells, L.; Comer, F.I.; Parker, G.J.; Hart, G.W.
Dynamic O-glycosylation of nuclear and cytosolic proteins: cloning and characterization of a neutral, cytosolic beta-N-acetylglucosaminidase from human brain
J. Biol. Chem.
276
9838-9845
2001
Chlorocebus aethiops, Homo sapiens (P06865)
Manually annotated by BRENDA team
Wells, L.; Gao, Y.; Mahoney, J.A.; Vosseller, K.; Chen, C.; Rosen, A.; Hart, G.W.
Dynamic O-glycosylation of nuclear and cytosolic proteins: further characterization of the nucleocytoplasmic beta-N-acetylglucosaminidase, O-GlcNAcase
J. Biol. Chem.
277
1755-1761
2002
Bos taurus, Chlorocebus aethiops, Cricetulus griseus, Homo sapiens
Manually annotated by BRENDA team
Macauley, M.S.; Whitworth, G.E.; Debowski, A.W.; Chin, D.; Vocadlo, D.J.
O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors
J. Biol. Chem.
280
25313-25322
2005
Homo sapiens
Manually annotated by BRENDA team
Stubbs, K.A.; Zhang, N.; Vocadlo, D.J.
A divergent synthesis of 2-acyl derivatives of PUGNAc yields selective inhibitors of O-GlcNAcase
Org. Biomol. Chem.
4
839-845
2006
Homo sapiens
Manually annotated by BRENDA team
Borodkin, V.S.; Rafie, K.; Selvan, N.; Aristotelous, T.; Navratilova, I.; Ferenbach, A.T.; van Aalten, D.M.F.
O-GlcNAcase fragment discovery with fluorescence polarimetry
ACS Chem. Biol.
13
1353-1360
2018
Clostridium perfringens (Q0TR53), Clostridium perfringens, Homo sapiens (O60502), Homo sapiens
Manually annotated by BRENDA team
Chen, W.; Shen, S.; Dong, L.; Zhang, J.; Yang, Q.
Selective inhibition of beta-N-acetylhexosaminidases by thioglycosyl-naphthalimide hybrid molecules
Bioorg. Med. Chem.
26
394-400
2018
Homo sapiens (O60502)
Manually annotated by BRENDA team
Elsen, N.L.; Patel, S.B.; Ford, R.E.; Hall, D.L.; Hess, F.; Kandula, H.; Kornienko, M.; Reid, J.; Selnick, H.; Shipman, J.M.; Sharma, S.; Lumb, K.J.; Soisson, S.M.; Klein, D.J.
Insights into activity and inhibition from the crystal structure of human O-GlcNAcase
Nat. Chem. Biol.
13
613-615
2017
Homo sapiens (O60502), Homo sapiens
Manually annotated by BRENDA team
Li, B.; Li, H.; Hu, C.W.; Jiang, J.
Structural insights into the substrate binding adaptability and specificity of human O-GlcNAcase
Nat. Commun.
8
666
2017
Homo sapiens (O60502)
Manually annotated by BRENDA team