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Literature summary for 3.2.1.169 extracted from

  • Macauley, M.S.; Vocadlo, D.J.
    Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase (2010), Biochim. Biophys. Acta, 1800, 107-121.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(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 Homo sapiens
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline NButGT Homo sapiens
2-((6S,7R,8R)-8-acetamido-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)acetate NAGstatin Homo sapiens
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 Homo sapiens
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide 1-acetamido-epi-valienamine Homo sapiens
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide acetamido-azepane Homo sapiens
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide butyl-PUGNAc Homo sapiens
N-((6S,7R,8R)-6,7-dihydroxy-5-(hydroxymethyl)-2-phenethyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-yl)isobutyramide GlcNAcstatin Homo sapiens
N-acetylglucosamino-1,5-lactone oxime LOGNAc Homo sapiens
NAG-thiazoline
-
Homo sapiens
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate PUGNAc Homo sapiens
streptozotocin
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Homo sapiens 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 ?
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 Homo sapiens ?
-
?

Synonyms

Synonyms Comment Organism
O-GlcNAcase
-
Homo sapiens
OGA
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
-
Homo sapiens
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
-
Homo sapiens
0.00005
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenyl carbamate
-
Homo sapiens
0.00008
-
NAG-thiazoline
-
Homo sapiens
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
-
Homo sapiens
0.0006
-
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.0016
-
N-acetylglucosamino-1,5-lactone oxime
-
Homo sapiens
0.0024
-
N-((3S,4R,5R,Z)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylcarbamoyloxyimino)tetrahydro-2H-pyran-3-yl)butyramide
-
Homo sapiens
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
-
Homo sapiens
0.0062
-
N-((1R,2R,5S,6R)-2-amino-5,6-dihydroxycyclohex-3-enyl)acetamide
-
Homo sapiens
0.011
-
N-((3R,4R,5R,6S)-3,5,6-trihydroxy-7-(hydroxymethyl)azepan-4-yl)acetamide
-
Homo sapiens
1.5
-
streptozotocin
-
Homo sapiens