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Literature summary for 3.2.1.20 extracted from

  • Ferreira, S.B.; Sodero, A.C.; Cardoso, M.F.; Lima, E.S.; Kaiser, C.R.; Silva, F.P.; Ferreira, V.F.
    Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as alpha-glucosidases inhibitors (2010), J. Med. Chem., 53, 2364-2375.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1,2:3,4-di-O-isopropylidene-6-(4-phenyl-1H-1,2,3-triazole-1-yl)-alpha-D-galactopyranose 99.4% inhibition at 0.5 mM Saccharomyces cerevisiae
1,2:5,6-di-O-isopropylidene-3-(4-phenyl-1H-1,2,3-triazole-1-yl)-alpha-D-allofuranose 73.1% inhibition at 0.5 mM Saccharomyces cerevisiae
5-deoxy-1,2-O-isopropylidene-5-(4-hydroxymethyl-1H-1,2,3-triazole-1-yl)-alpha-D-xylofuranose 68.8% inhibition at 0.5 mM Saccharomyces cerevisiae
5-deoxy-1,2-O-isopropylidene-5-(4-phenyl-1H-1,2,3-triazole-1-yl)-alpha-D-xylofuranose 87.9% inhibition at 0.5 mM Saccharomyces cerevisiae
5-deoxy-1,2-O-isopropylidene-5-[4-(1-cyclohexene)-1H-1,2,3-triazole-1-yl]-alpha-D-xylofuranose 33.3% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-(4-phenyl-1H-1,2,3-triazol-1-yl)-b-D-ribofuranoside 94.4% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-(4-phenyl-1H-1,2,3-triazol-1-yl)-beta-D-ribofuranoside
-
Saccharomyces cerevisiae
methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-(4-propyl-1H-1,2,3-triazol-1-yl)-beta-D-ribofuranoside 44.9% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]-beta-D-ribofuranoside 98.4% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-[4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1H-1,2,3-triazol-1-yl]-beta-D-ribofuranoside 79.5% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(1-hydroxycyclohexyl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 98.5% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(2-hydroxy-4-methylpentan-2-yl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
-
Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(2-hydroxybutan-2-yl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 41.1% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 60.2% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 98.0% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-deoxy-5-[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 46.5% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-[4-(3-chloropropyl)-1H-1,2,3-triazol-1-yl]-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside 99.5% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-5-deoxy-2,3-O-(1-methylethylidene)-b-D-ribofuranoside 98.1% inhibition at 0.5 mM Saccharomyces cerevisiae
methyl 5-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
-
Saccharomyces cerevisiae
methyl 5-[4-[(acetyloxy)methyl]-1H-1,2,3-triazol-1-yl]-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
-
Saccharomyces cerevisiae
additional information synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as alpha-glucosidases inhibitors. Methyl-2,3-O-isopropylidene-beta-D-ribofuranosides, such as the 4-(1-cyclohexenyl)-1,2,3-triazole derivative, are among the most active compounds, showing up to 25fold higher inhibitory potency than the complex oligosaccharide acarbose. Docking study and homology modeling, transition-state-mimicking mechanism, overview Saccharomyces cerevisiae

Organism

Organism UniProt Comment Textmining
Saccharomyces cerevisiae
-
-
-

Synonyms

Synonyms Comment Organism
MAL12
-
Saccharomyces cerevisiae
maltase
-
Saccharomyces cerevisiae

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0038
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-5-deoxy-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
0.0052
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-deoxy-5-[4-(1-hydroxycyclohexyl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
0.0057
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]-beta-D-ribofuranoside
0.0149
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-(4-phenyl-1H-1,2,3-triazol-1-yl)-beta-D-ribofuranoside
0.0151
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-deoxy-5-[4-(ethoxycarbonyl)-1H-1,2,3-triazol-1-yl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranoside
0.0247
-
pH and temperature not specified in the publication Saccharomyces cerevisiae methyl 5-deoxy-2,3-O-(1-methylethylidene)-5-[4-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1H-1,2,3-triazol-1-yl]-beta-D-ribofuranoside