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Literature summary for 3.2.1.51 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)

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

Protein Variants

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

Inhibitors

Inhibitors Comment Organism Structure
(2R,3R,4R,5R,6S)-2-(aminomethyl)-6-methylpiperidine-3,4,5-triol
-
Homo sapiens
(2S,3R,4R,5R)-5-(3-aminopropoxy)-2-methylpiperidine-3,4-diol
-
Homo sapiens
(2S,3R,4R,5R,6S)-2-(hydroxymethyl)-6-methylpiperidine-3,4,5-triol
-
Homo sapiens
(2S,3R,4S,5R)-1-(3-aminopropyl)-2-methylpiperidine-3,4,5-triol
-
Homo sapiens
(2S,3R,4S,5R)-2-benzylpiperidine-3,4,5-triol
-
Homo sapiens
(2S,3R,4S,5R)-2-isopropylpiperidine-3,4,5-triol
-
Homo sapiens
2-cyclopentyl-2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)acetamide
-
Homo sapiens
2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)quinoline-4-carboxamide
-
Homo sapiens
3-(1H-indol-3-yl)-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)propanamide
-
Homo sapiens
5-fluoro-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)-1H-indole-2-carboxamide
-
Homo sapiens
fuconojirimycin majority of C1-substituted fuconojirimycins act as reversible inhibitors of the human fucosidase Homo sapiens
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

Organism UniProt Comment Textmining
Homo sapiens P04066
-
-
Thermotoga maritima
-
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
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
0.0000117
-
2-phenyl-N-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methylpiperidin-2-yl)methyl)quinoline-4-carboxamide
-
Homo sapiens
0.0000152
-
(2R,3R,4R,5R,6S)-2-(aminomethyl)-6-methylpiperidine-3,4,5-triol
-
Homo sapiens
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

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