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Literature summary for 3.2.1.169 extracted from

  • 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 (2005), J. Biol. Chem., 280, 25313-25322.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
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 Homo sapiens
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
GlcNAc
-
Homo sapiens
additional information streptozotocin does not appear to act as an irreversible inhibitor Homo sapiens
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate PUGNAc Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.38
-
4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide
-
Homo sapiens
0.43
-
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
Homo sapiens
0.45
-
4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide
-
Homo sapiens
0.49
-
4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide
-
Homo sapiens

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
-
Homo sapiens 4-methylumbelliferone + N-acetyl-beta-D-glucosamine
-
?
4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide + H2O
-
Homo sapiens 4-methylumbelliferone + N-difluoroacetyl-beta-D-glucosamine
-
?
4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide + H2O
-
Homo sapiens 4-methylumbelliferone + N-fluoroacetyl-beta-D-glucosamine
-
?
4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide + H2O
-
Homo sapiens 4-methylumbelliferone + N-trifluoroacetyl-beta-D-glucosamine
-
?
4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
-
Homo sapiens 4-nitrophenol + N-acetyl-beta-D-glucosamine
-
?
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 Homo sapiens ?
-
?

Synonyms

Synonyms Comment Organism
O-GlcNAcase
-
Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000046
-
O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
Homo sapiens
0.00007
-
1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.00012
-
1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
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 Homo sapiens
0.00023
-
1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.0015
-
1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.0016
-
1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.0057
-
1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
0.057
-
1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
Homo sapiens
1.5
-
GlcNAc pH 6.5 Homo sapiens