3.2.1.169: protein O-GlcNAcase
This is an abbreviated version!
For detailed information about protein O-GlcNAcase, go to the full flat file.
Word Map on EC 3.2.1.169
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3.2.1.169
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o-glcnacylation
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streptozotocin
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o-glycosylation
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nucleocytoplasmic
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beta-cell
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diabetogenic
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perfringens
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thiamet
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pugnacity
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tetratricopeptide
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thetaiotaomicron
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substrate-assisted
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hexosaminidases
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medicine
- 3.2.1.169
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o-glcnacylation
- streptozotocin
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o-glycosylation
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nucleocytoplasmic
-
beta-cell
-
diabetogenic
- perfringens
-
thiamet
-
pugnacity
-
tetratricopeptide
- thetaiotaomicron
-
substrate-assisted
- hexosaminidases
- medicine
Reaction
Synonyms
beta-N-acetylglucosaminidase, BtGH84, CP40, CpNagJ, CpOGA, cytoplasmic O-GlcNAcase, endo-beta-N-acetylglucosaminidase, EndoS-like endoglycosidase, glycoside hydrolase O-GlcNAcase, hexosaminidase, hOGA, mNCOAT, NagJ, NCOAT, neutral hexosaminidase C, neutral O-GlcNAcase, O-GlcNAc hydrolase, 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-linked beta-N-acetyl glucosaminase, O-linked N-acetylglucosaminase, OGA, OGA-FL, OGA-NV
ECTree
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Inhibitors
Inhibitors on EC 3.2.1.169 - protein O-GlcNAcase
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(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
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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
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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
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PUGNAc-imidazole hybrid
2-((6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)acetate
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NAGstatin
2-(acetylamino)-2-deoxy-1-S-hexanoyl-1-thio-beta-D-glucopyranose
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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
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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
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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
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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
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inhibits activity at 10 mM, 34.8% relative activity compared with activity without any addition of effector
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
alpha-D-mannose
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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
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thiamet-G
castanospermine
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inhibits activity at 10 mM, 32.7% relative activity compared with activity without any addition of effector
Cd2+
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inhibits activity at 1 mM, 7.7% relative activity compared with activity without any addition of effector
Cu2+
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inhibits activity at 1 mM, 1% relative activity compared with activity without any addition of effector
D-glucosamine
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inhibits activity at 10 mM, 60.7% relative activity compared with activity without any addition of effector
GlcNAcstatin A
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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 D
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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
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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+
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inhibits activity at 1 mM, 6% relative activity compared with activity without any addition of effector
HPDP-biotin
treatment with a sulfhydrylspecific biotinylation reagent, HPDP-biotin, to biotinylate any accessible free cysteine residue in the native enzyme. Treatment is able to inhibit enzymatic activity, suggesting that the cysteine residue playing a role in catalysis is modified
methyl alpha-D-mannose
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inhibits activity at 10 mM, 11.3% relative activity compared with activity without any addition of effector. Other sugars and sugar analogs do not inhibit with exception of methyl-alpha-D-mannose
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide
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1-acetamido-epi-valienamine
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide
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acetamido-azepane
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide
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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
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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-acetyl-D-glucosamine
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inhibits activity at 10 mM, 40% relative activity compared with activity without any addition of effector
N-methyl-deoxynojirimycin
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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
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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
NaCl
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high salt, 1.0 M NaCl, inhibits enzyme activity by 50% compared with activity without any addition of effector
O-(2-deoxy-2-butamido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-hexamido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isobutamido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isovaleramido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-propamido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-valeramido-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
p-aminophenyl-S-GlcNAc
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inhibits activity at 10 mM, 76.3% relative activity compared with activity without any addition of effector
Sn2+
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inhibits activity at 1 mM, 57.6% relative activity compared with activity without any addition of effector
Tris
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high salt, 75 mM, inhibits enzyme activity by 50% compared with activity without any addition of effector
UDP-GlcNAc
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inhibits activity at 10 mM, 78.1% relative activity compared with activity without any addition of effector
Zn2+
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inhibits activity at 1 mM, 7.3% relative activity compared with activity without any addition of effector
NAG-thiazoline
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
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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
GlcNAcstatin B
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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 carriesa phenylethyl moiety. GlcNAcstatins are the most potent human OGA inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
GlcNAcstatin C
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GlcNAcstatin C carriesa phenylethyl moiety. GlcNAcstatins are the most potent human O-GlcNAcase inhibitors, inhibiting the enzyme in the sub-nanomolar to nanomolar range
treatment is able to inhibit enzymatic activity, suggesting that the cysteine residue playing a role in catalysis is modified
N-ethylmaleimide
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inhibits activity at 10 mM, 15.3% relative activity compared with activity without any addition of effector
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
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inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
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PUGNAc
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
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PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
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PUGNAc
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
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inhibits activity at 0.1 mM, 4.1% relative activity compared with activity without any addition of effector
i.e. O-(2-acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate, 98.9% inhibition at 0.1 mM
PUGNAc
i.e. O-(2-acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate
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
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STZ, significantly dose-dependently inhibited recombinant O-GlcNAcase
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methylnitrosourea (MNU), the nitric oxide-containing portion of streptozotocin: no significant inhibition observed
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additional information
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streptozotocin does not appear to act as an irreversible inhibitor
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additional information
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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
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additional information
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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
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