Synthesis of S-alkylated sulfonium-ions and their glucosidase inhibitory activities against recombinant human maltase glucoamylase |
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Authors: | Mohan Sankar Sim Lyann Rose David R Pinto B Mario |
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Affiliation: | Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada V5A 1S6. |
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Abstract: | The syntheses of nine S-alkylated, cyclic sulfonium-ions with varying alkyl chain lengths, as mimics of N-alkylated imino sugars, and their glucosidase inhibitory activities are described. The target compounds were synthesized by alkylation of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-d-arabinitol at the ring sulfur atom using various alkyl halides, followed by deprotection using boron trichloride. Enzyme inhibitory assays against recombinant human maltase glucoamylase (MGA), a critical enzyme in the small intestine involved in the breakdown of glucose oligosaccharides into glucose itself, shows that they are effective inhibitors of MGA with K(i) values ranging from 6 to 75 microM. |
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Keywords: | Glucosidase inhibitors Maltase glucoamylase S-Alkylated sulfonium-ions N-Alkylated imino sugars |
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