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Literature summary for 3.2.1.3 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

Application Comment Organism
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

Inhibitors Comment Organism Structure
(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
(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
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
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
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
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
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
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
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
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
additional information ghavamiol, a nitrogen analogue of salacinol, is inactive as inhibitor Homo sapiens
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)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
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

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
small intestine
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl beta-D-glucopyranoside + H2O
-
Homo sapiens 4-nitrophenol + beta-D-glucose
-
?
starch + H2O
-
Homo sapiens beta-D-glucose + ?
-
?
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

Synonyms Comment Organism
maltase glucoamylase
-
Homo sapiens
MGA
-
Homo sapiens

Temperature Optimum [°C]

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

pH Optimum

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
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
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
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
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
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
0.00019
-
salacinol pH 6.5, 37°C Homo sapiens
0.00049
-
blintol pH 6.5, 37°C Homo sapiens
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
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
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