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Literature summary 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

EC Number Inhibitors Comment Organism Structure
3.2.1.52 1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 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. About 17000fold more tightly than GlcNAc Homo sapiens
3.2.1.52 1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 GlcNAc
-
 Homo sapiens
3.2.1.52 additional information streptozotocin does not appear to act as an irreversible inhibitor Homo sapiens
3.2.1.52 O-(2-acetamido-2-deoxy-D-glucopyranosylidene) amino-N-phenylcarbamate PUGNAc Homo sapiens
3.2.1.169 1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 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
3.2.1.169 1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 GlcNAc
-
 Homo sapiens
3.2.1.169 additional information streptozotocin does not appear to act as an irreversible inhibitor Homo sapiens
3.2.1.169 O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate PUGNAc Homo sapiens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.2.1.52 0.88
-
 4-methylcoumar-7-yl-beta-N-acetyl-D-glucosamine
-
 Homo sapiens
3.2.1.52 3.8
-
 4-methylcoumar-7-yl-beta-N-fluoroacetyl-D-glucosamine
-
 Homo sapiens
3.2.1.169 0.38
-
 4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide
-
 Homo sapiens
3.2.1.169 0.43
-
 4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
-
 Homo sapiens
3.2.1.169 0.45
-
 4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide
-
 Homo sapiens
3.2.1.169 0.49
-
 4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.169 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

EC Number Organism UniProt Comment Textmining
3.2.1.52 Homo sapiens
-
-
-
3.2.1.169 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.2.1.52 placenta
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.52 4-methylcoumar-7-yl-beta-N-acetyl-D-glucosamine + H2O
-
 Homo sapiens ?
-
 ?
3.2.1.52 4-methylcoumar-7-yl-beta-N-fluoroacetyl-D-glucosamine + H2O
-
 Homo sapiens ?
-
 ?
3.2.1.169 4-methylumbelliferyl N-acetyl-beta-D-glucosaminide + H2O
-
 Homo sapiens 4-methylumbelliferone + N-acetyl-beta-D-glucosamine
-
 ?
3.2.1.169 4-methylumbelliferyl N-difluoroacetyl-beta-D-glucosaminide + H2O
-
 Homo sapiens 4-methylumbelliferone + N-difluoroacetyl-beta-D-glucosamine
-
 ?
3.2.1.169 4-methylumbelliferyl N-fluoroacetyl-beta-D-glucosaminide + H2O
-
 Homo sapiens 4-methylumbelliferone + N-fluoroacetyl-beta-D-glucosamine
-
 ?
3.2.1.169 4-methylumbelliferyl N-trifluoroacetyl-beta-D-glucosaminide + H2O
-
 Homo sapiens 4-methylumbelliferone + N-trifluoroacetyl-beta-D-glucosamine
-
 ?
3.2.1.169 4-nitrophenyl N-acetyl-beta-D-glucosaminide + H2O
-
 Homo sapiens 4-nitrophenol + N-acetyl-beta-D-glucosamine
-
 ?
3.2.1.169 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

EC Number Synonyms Comment Organism
3.2.1.52 beta-hexosaminidase
-
 Homo sapiens
3.2.1.52 lysosomal beta-hexosaminidase
-
 Homo sapiens
3.2.1.169 O-GlcNAcase
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.52 37
-
 assay at Homo sapiens
3.2.1.169 37
-
 assay at Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.2.1.52 0.000036
-
 O-(2-acetamido-2-deoxy-D-glucopyranosylidene) amino-N-phenylcarbamate
-
 Homo sapiens
3.2.1.52 0.00007
-
 1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 0.032
-
 1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 0.34
-
 1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 0.72
-
 1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 1.2
-
 GlcNAc
-
 Homo sapiens
3.2.1.52 4
-
 1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 4.6
-
 1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.52 11
-
 1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.000046
-
 O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate
-
 Homo sapiens
3.2.1.169 0.00007
-
 1,2-dideoxy-2'-methyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.00012
-
 1,2-dideoxy-2'-ethyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 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
3.2.1.169 0.00023
-
 1,2-dideoxy-2'-propyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.0015
-
 1,2-dideoxy-2'-butyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.0016
-
 1,2-dideoxy-2'-isopropyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.0057
-
 1,2-dideoxy-2'-isobutyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 0.057
-
 1,2-dideoxy-2'-pentyl-alpha-D-glucopyranoso-[2,1-d]-DELTA2'-thiazoline
-
 Homo sapiens
3.2.1.169 1.5
-
 GlcNAc pH 6.5 Homo sapiens