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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

Reaction

[protein]-3-O-(N-acetyl-beta-D-glucosaminyl)-L-serine
+
H2O
=
[protein]-L-serine
+
N-acetyl-D-glucosamine

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

     3 Hydrolases
         3.2 Glycosylases
             3.2.1 Glycosidases, i.e. enzymes that hydrolyse O- and S-glycosyl compounds
                3.2.1.169 protein O-GlcNAcase

Inhibitors

Inhibitors on EC 3.2.1.169 - protein O-GlcNAcase

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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
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
-
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
2-((6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)acetate
-
NAGstatin
2-(acetylamino)-2-deoxy-1-S-hexanoyl-1-thio-beta-D-glucopyranose
-
inhibits activity at 10 mM, 47.5% relative activity compared with activity without any addition of effector
2-acetamido-2-deoxy-D-gluconhydroxime-1,5-lactone
-
inhibits activity at 0.1 mM, 6.7% relative activity compared with activity without any addition of effector
2-acetamindo-1-amino-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 3.2% relative activity compared with activity without any addition of effector
2-acetamindo-1-azido-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 19.3% relative activity compared with activity without any addition of effector
2-acetamindo-1-bromo-1,2-dideoxy-beta-D-glucopyranose
-
inhibits activity at 10 mM, 34.8% relative activity compared with activity without any addition of effector
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
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
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
Hg2+
-
inhibits activity at 1 mM, 6% relative activity compared with activity without any addition of effector
HPDP-biotin
treatment with a sulfhydrylspecific biotinylation reagent, HPDP-biotin, to biotinylate any accessible free cysteine residue in the native enzyme. Treatment is able to inhibit enzymatic activity, suggesting that the cysteine residue playing a role in catalysis is modified
LOGNAc
i.e. 2-acetamido-2-deoxy-D-gluconhydroximo-1,5-lactone
methyl alpha-D-mannose
-
inhibits activity at 10 mM, 11.3% relative activity compared with activity without any addition of effector. Other sugars and sugar analogs do not inhibit with exception of methyl-alpha-D-mannose
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide
-
1-acetamido-epi-valienamine
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide
-
acetamido-azepane
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide
-
butyl-PUGNAc
N-((6S,7R,8R)-6,7-dihydroxy-5-(hydroxymethyl)-2-phenethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-yl)isobutyramide
-
GlcNAcstatin
N-(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
-
inhibits activity at 10 mM, 40% relative activity compared with activity without any addition of effector
N-acetylglucosamino-1,5-lactone oxime
-
LOGNAc
N-ethylmaleimide
N-methyl-deoxynojirimycin
-
inhibits activity at 10 mM, 73.5% relative activity compared with activity without any addition of effector
N-[(2Z,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(phenylcarbamoyl)oxy]imino]tetrahydro-2H-pyran-3-yl]acetamide
-
PUGNAc, inhibits also other functionally related enzymes
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
-
high salt, 1.0 M NaCl, inhibits enzyme activity by 50% compared with activity without any addition of effector
NAG-thiazoline
naphthalimide
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
O-(2-deoxy-2-butamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-hexamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isobutamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-isovaleramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-propamido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
O-(2-deoxy-2-valeramido-D-glucopyranosylidene)amino N-phenylcarbamate
-
inhibitor of both human O-GlcNAcase and human beta-hexosaminidase
p-aminophenyl-S-GlcNAc
-
inhibits activity at 10 mM, 76.3% relative activity compared with activity without any addition of effector
PUGNAc
Sn2+
-
inhibits activity at 1 mM, 57.6% relative activity compared with activity without any addition of effector
streptozotocin
thiamet G
Tris
-
high salt, 75 mM, inhibits enzyme activity by 50% compared with activity without any addition of effector
UDP-GlcNAc
-
inhibits activity at 10 mM, 78.1% relative activity compared with activity without any addition of effector
Zn2+
-
inhibits activity at 1 mM, 7.3% relative activity compared with activity without any addition of effector
additional information
-