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Literature summary extracted from

  • Ho, C.W.; Lin, Y.N.; Chang, C.F.; Li, S.T.; Wu, Y.T.; Wu, C.Y.; Chang, C.F.; Liu, S.W.; Li, Y.K.; Lin, C.H.
    Discovery of different types of inhibition between the human and thermotoga maritima alpha-fucosidases by fuconojirimycin-based derivatives (2006), Biochemistry, 45, 5695-5702.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.2.1.51 through pET21b expression vector Thermotoga maritima
3.2.1.51 through pET21b expression vector Homo sapiens

Protein Variants

EC Number Protein Variants Comment Organism
3.2.1.51 F59A slow tight-binding inhibition, affinity for compound 1 comparable to the wild-type level Thermotoga maritima
3.2.1.51 L191A slow tight-binding inhibition, kinetics like wild type, affinity for compound 1 comparable to the wild-type level Thermotoga maritima
3.2.1.51 M225A slow tight-binding inhibition, kinetics like wild type, affinity for compound 1 comparable to the wild-type level Thermotoga maritima
3.2.1.51 W58A instabile Thermotoga maritima
3.2.1.51 Y267A affinity for compound 1 comparable to the wild-type level Thermotoga maritima
3.2.1.51 Y64A affinity for compound 1 comparable to the wild-type level Thermotoga maritima

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.51 (2R,3R,4R,5R,6S)-2-(aminomethyl)-6-methylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 (2S,3R,4R,5R)-5-(3-aminopropoxy)-2-methylpiperidine-3,4-diol
-
 Homo sapiens
3.2.1.51 (2S,3R,4R,5R,6S)-2-(hydroxymethyl)-6-methylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 (2S,3R,4S,5R)-1-(3-aminopropyl)-2-methylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 (2S,3R,4S,5R)-2-benzylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 (2S,3R,4S,5R)-2-isopropylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 2-cyclopentyl-2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)acetamide
-
 Homo sapiens
3.2.1.51 2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)quinoline-4-carboxamide
-
 Homo sapiens
3.2.1.51 3-(1H-indol-3-yl)-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)propanamide
-
 Homo sapiens
3.2.1.51 5-fluoro-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)-1H-indole-2-carboxamide
-
 Homo sapiens
3.2.1.51 fuconojirimycin majority of C1-substituted fuconojirimycins act as reversible inhibitors of the human fucosidase Homo sapiens
3.2.1.51 fuconojirimycin majority of C1-substituted fuconojirimycins are slow tight-binding inhibitors of the Thermotoga enzyme, Tyr64 and Tyr267 are critically involved in closely interacting with the aglycon of inhibitors Thermotoga maritima

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.51 Homo sapiens P04066
-
-
3.2.1.51 Thermotoga maritima
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.2.1.51 by ion-exchange chromatography, more than 95% homogeneity Homo sapiens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.51 4-methylumbelliferyl alpha-L-fucopyranoside + H2O
-
 Thermotoga maritima 4-methylumbelliferone + alpha-L-fucose
-
 ?
3.2.1.51 4-methylumbelliferyl alpha-L-fucopyranoside + H2O
-
 Homo sapiens 4-methylumbelliferone + alpha-L-fucose
-
 ?
3.2.1.51 p-nitrophenyl-alpha-L-fucopyranoside + H2O
-
 Thermotoga maritima p-nitrophenol + alpha-L-fucose
-
 ?
3.2.1.51 p-nitrophenyl-alpha-L-fucopyranoside + H2O
-
 Homo sapiens p-nitrophenol + alpha-L-fucose
-
 ?

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.2.1.51 0.0000056
-
 3-(1H-indol-3-yl)-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)propanamide
-
 Homo sapiens
3.2.1.51 0.0000097
-
 5-fluoro-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)-1H-indole-2-carboxamide
-
 Homo sapiens
3.2.1.51 0.0000117
-
 2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)quinoline-4-carboxamide
-
 Homo sapiens
3.2.1.51 0.0000152
-
 (2R,3R,4R,5R,6S)-2-(aminomethyl)-6-methylpiperidine-3,4,5-triol
-
 Homo sapiens
3.2.1.51 0.000018
-
 2-cyclopentyl-2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)acetamide
-
 Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.2.1.51 0.000052
-
-
 Homo sapiens (2S,3R,4R,5R,6S)-2-(hydroxymethyl)-6-methylpiperidine-3,4,5-triol
3.2.1.51 0.000064
-
-
 Homo sapiens (2R,3R,4R,5R,6S)-2-(aminomethyl)-6-methylpiperidine-3,4,5-triol
3.2.1.51 0.00007
-
-
 Homo sapiens (2S,3R,4S,5R)-1-(3-aminopropyl)-2-methylpiperidine-3,4,5-triol
3.2.1.51 0.000267
-
-
 Homo sapiens (2S,3R,4R,5R)-5-(3-aminopropoxy)-2-methylpiperidine-3,4-diol
3.2.1.51 0.006
-
-
 Homo sapiens (2S,3R,4S,5R)-2-isopropylpiperidine-3,4,5-triol
3.2.1.51 0.007
-
-
 Homo sapiens (2S,3R,4S,5R)-2-benzylpiperidine-3,4,5-triol