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Literature summary extracted from

  • Liu, H.; Nasi, R.; Jayakanthan, K.; Sim, L.; Heipel, H.; Rose, D.R.; Pinto, B.M.
    New synthetic routes to chain-extended selenium, sulfur, and nitrogen analogues of the naturally occurring glucosidase inhibitor salacinol and their inhibitory activities against recombinant human maltase glucoamylase (2007), J. Org. Chem., 72, 6562-6572.
    View publication on PubMed

Application

EC Number Application Comment Organism
3.2.1.3 medicine enzyme inhibitors are very effective in controlling blood glucose levels, and thus are lead candidates for the treatment of type 2 diabetes Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.2.1.3 (2S,3S,4R,5R)-1-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-selenophenium-1-yl)-2,4,5,7-tetrahydroxyheptan-3-yl sulfate a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 (2S,3S,4R,5R)-1-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophenium-1-yl)-2,4,5,7-tetrahydroxyheptan-3-yl sulfate a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episelenoniumylidene]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episulfoniumylidene]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]iminonium]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episelenoniumylidene]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episulfoniumylidene]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]iminonium]-D-arabinitol a structure analogue of salacinol, synthesis, overview Homo sapiens
3.2.1.3 blintol a selenium analogue of salacinol, is very effective in controlling blood glucose levels in rats after a carbohydrate meal, thus providing a lead candidate for the treatment of type 2 diabetes, synthesis, overview Homo sapiens
3.2.1.3 kotalanol isolated from the roots and stems of the plant Salacia reticulata, contains an intriguing inner-salt sulfonium-sulfate structure, inhibition of glucosidases by salacinol and kotalanol is due to their ability to mimic both the shape and charge of the oxacarbenium-ion-like transition state involved in the enzymatic reactions Homo sapiens
3.2.1.3 additional information ghavamiol, a nitrogen analogue of salacinol, is inactive as inhibitor Homo sapiens
3.2.1.3 salacinol isolated from the roots and stems of the plant Salacia reticulata, contains an intriguing inner-salt sulfonium-sulfate structure, inhibition of glucosidases by salacinol is due to their ability to mimic both the shape and charge of the oxacarbenium-ion-like transition state involved in the enzymatic reactions, the compound is capable of attenuating the spike in blood glucose levels Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.2.1.3 starch + H2O Homo sapiens one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the small intestine beta-D-glucose + ?
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.2.1.3 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.2.1.3 small intestine
-
 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.2.1.3 4-nitrophenyl beta-D-glucopyranoside + H2O
-
 Homo sapiens 4-nitrophenol + beta-D-glucose
-
 ?
3.2.1.3 starch + H2O
-
 Homo sapiens beta-D-glucose + ?
-
 ?
3.2.1.3 starch + H2O one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the small intestine Homo sapiens beta-D-glucose + ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.2.1.3 maltase glucoamylase
-
 Homo sapiens
3.2.1.3 MGA
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.2.1.3 37
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.2.1.3 6.5
-
 assay at Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.2.1.3 0.0001
-
 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episelenoniumylidene]-D-arabinitol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.0001
-
 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episelenoniumylidene]-D-arabinitol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00014
-
 (2S,3S,4R,5R)-1-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-selenophenium-1-yl)-2,4,5,7-tetrahydroxyheptan-3-yl sulfate pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00015
-
 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episulfoniumylidene]-D-arabinitol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00017
-
 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]episulfoniumylidene]-D-arabinitol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00019
-
 salacinol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00049
-
 blintol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.00065
-
 (2S,3S,4R,5R)-1-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophenium-1-yl)-2,4,5,7-tetrahydroxyheptan-3-yl sulfate pH 6.5, 37°C Homo sapiens
3.2.1.3 0.008
-
 1,4-dideoxy-1,4-[[(2S,3S,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]iminonium]-D-arabinitol pH 6.5, 37°C Homo sapiens
3.2.1.3 0.035
-
 1,4-dideoxy-1,4-[[(2S,3R,4R,5S)-2,4,5,6-tetrahydroxy-3-(sulfoxy)hexyl]iminonium]-D-arabinitol pH 6.5, 37°C Homo sapiens