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Literature summary for 3.2.1.114 extracted from

  • Fiaux, H.; Kuntz, D.A.; Hoffman, D.; Janzer, R.C.; Gerber-Lemaire, S.; Rose, D.R.; Juillerat-Jeanneret, L.
    Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site (2008), Bioorg. Med. Chem., 16, 7337-7346.
    View publication on PubMed
Search for more literature for 3.2.1.114

Crystallization (Commentary)

Crystallization (Comment) Organism
-
 Drosophila melanogaster
in complex with inhibitors (3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one and (3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one, to 1.08 A and 1.74 A resolution, respectively Drosophila melanogaster

Inhibitors

Inhibitors Comment Organism Structure
(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol
-
 Drosophila melanogaster
(2R,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Drosophila melanogaster
(2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Canavalia ensiformis
(2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Drosophila melanogaster
(2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Homo sapiens
(2S,3R,4S)-2-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
-
 Homo sapiens
(3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
-
 Drosophila melanogaster
(3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
-
 Drosophila melanogaster
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one competitive inhibitor Canavalia ensiformis
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one competitive inhibitor Drosophila melanogaster
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
-
 Homo sapiens
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one competitve inhibitor Canavalia ensiformis
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one competitve inhibitor Drosophila melanogaster
(3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one competitve inhibitor Homo sapiens
(3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxy-1-methylpyrrolidin-2-one
-
 Homo sapiens
(3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxypyrrolidin-2-one
-
 Homo sapiens
mannostatin
-
 Homo sapiens
swainsonine competitve inhibitor Canavalia ensiformis
swainsonine competitve inhibitor Drosophila melanogaster
swainsonine competitve inhibitor Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.55
-
 4-methylumbelliferyl-alpha-D-mannopyranoside extracted from endothelial cells HCEC Homo sapiens
0.65
-
 4-methylumbelliferyl-alpha-D-mannopyranoside extracted from human glioblastoma cells LNZ308 Homo sapiens
1.065
-
 4-methylumbelliferyl-alpha-D-mannopyranoside extracted from human glioblastoma cells LN18 Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
Golgi apparatus
-
 Drosophila melanogaster 5794
-
Golgi apparatus
-
 Homo sapiens 5794
-
Golgi apparatus
-
 Canavalia ensiformis 5794
-

Organism

Organism UniProt Comment Textmining
Canavalia ensiformis
-
-
-
Drosophila melanogaster
-
-
-
Drosophila melanogaster Q24451 isoform GMII
-
Homo sapiens
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Drosophila melanogaster

Source Tissue

Source Tissue Comment Organism Textmining
endothelial cell line HCEC Homo sapiens
-
glioblastoma cell line LNZ 308 Homo sapiens
-
LN-18 cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-methyl-umbelliferyl-alpha-D-mannopyranoside + H2O 30 min, 37°C Homo sapiens 4-methyl-umbelliferone + alpha-D-mannopyranose
-
 ?
4-methylumbelliferyl alpha-D-mannoside + H2O
-
 Homo sapiens 4-methylumbelliferone + alpha-D-mannose
-
 ?
4-nitrophenyl-alpha-D-mannopyranoside + H2O 30 min, 37°C Canavalia ensiformis 4-nitrophenol + alpha-D-mannopyranose
-
 ?
4-nitrophenyl-alpha-D-mannopyranoside + H2O 30 min, 20°C Drosophila melanogaster 4-nitrophenol + alpha-D-mannose
-
 ?

Synonyms

Synonyms Comment Organism
alpha-mannosidase II
-
 Drosophila melanogaster
alpha-mannosidase II
-
 Homo sapiens
alpha-mannosidase II
-
 Canavalia ensiformis
dGMII
-
 Drosophila melanogaster
human type II alpha-mannosidase
-
 Homo sapiens
jack bean alpha-mannosidase
-
 Canavalia ensiformis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
20
-
-
 Drosophila melanogaster
37
-
-
 Homo sapiens
37
-
-
 Canavalia ensiformis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00002
-
 swainsonine
-
 Drosophila melanogaster
0.00002
-
 (1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol 20C, pH 6.8 Drosophila melanogaster
0.000135
-
 (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Canavalia ensiformis
0.000155
-
 swainsonine
-
 Canavalia ensiformis
0.000206
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
-
 Canavalia ensiformis
0.00055
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one extracted from human glioblastoma cells LNZ308 Homo sapiens
0.00067
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one extracted from endothelial cells HCEC Homo sapiens
0.001
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
-
 Drosophila melanogaster
0.001
-
 (3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one 20C, pH 6.8 Drosophila melanogaster
0.0032
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one extracted from human glioblastoma cells LN18 Homo sapiens
0.004
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
-
 Canavalia ensiformis
0.022
-
 (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
-
 Drosophila melanogaster
0.022
-
 (3R,4R,5R)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one 20C, pH 6.8 Drosophila melanogaster
0.0233
-
 (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol extracted from endothelial cells HCEC Homo sapiens
0.0325
-
 (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol extracted from human glioblastoma cells LN18 Homo sapiens
0.0415
-
 (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol extracted from human glioblastoma cells LNZ308 Homo sapiens
0.067
-
 (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
-
 Drosophila melanogaster
0.067
-
 (2R,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol 20C, pH 6.8 Drosophila melanogaster

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00001
-
 extracted from endothelial cells HCEC Homo sapiens swainsonine
0.00002
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens swainsonine
0.00005
-
 extracted from human glioblastoma cells LN18 Homo sapiens swainsonine
0.0005
-
 extracted from endothelial cells HCEC Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
0.0005
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
0.00075
-
 extracted from endothelial cells HCEC Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxy-1-methylpyrrolidin-2-one
0.002
-
 extracted from human glioblastoma cells LN18 Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)-1-methylpyrrolidin-2-one
0.0075
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxy-1-methylpyrrolidin-2-one
0.025
-
 extracted from endothelial cells HCEC Homo sapiens (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
0.05
-
 extracted from human glioblastoma cells LN18 Homo sapiens (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
0.05
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (2S,3R,4S)-2-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidine-3,4-diol
0.05
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
0.075
-
 extracted from endothelial cells HCEC Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
0.075
-
 extracted from endothelial cells HCEC Homo sapiens (2S,3R,4S)-2-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.075
-
 extracted from endothelial cells HCEC Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxypyrrolidin-2-one
0.075
-
 extracted from human glioblastoma cells LN18 Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxy-1-methylpyrrolidin-2-one
0.075
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (2S,3R,4S)-2-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.15
-
 extracted from human glioblastoma cells LNZ308 Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxypyrrolidin-2-one
0.2
-
 extracted from human glioblastoma cells LN18 Homo sapiens (2S,3R,4S)-2-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.35
-
 extracted from human glioblastoma cells LN18 Homo sapiens (3R,4R,5S)-3,4-dihydroxy-5-([[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)pyrrolidin-2-one
0.75
-
 extracted from human glioblastoma cells LN18 Homo sapiens (3R,4R,5S)-5-[([(1R)-2-[(4-bromophenyl)(hydroxy)methoxy]-1-phenylethyl]amino)methyl]-3,4-dihydroxypyrrolidin-2-one