title: Synthesis of S-alkylated sulfonium-ions and their glucosidase inhibitory activities against recombinant human maltase glucoamylase.
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.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada V5A 1S6.
authors.forename: Sankar
authors.initials: S
authors.lastname: Mohan
authors.forename: Lyann
authors.initials: L
authors.lastname: Sim
authors.forename: David R
authors.initials: DR
authors.lastname: Rose
authors.forename: B Mario
authors.initials: BM
authors.lastname: Pinto
mesh_terms: D000478:Alkylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D006801:Humans; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011994:Recombinant Proteins / Q000378:metabolism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000235:genetics / Q000378:metabolism*
chemical_list: D004791:Enzyme Inhibitors; D011994:Recombinant Proteins; D013452:Sulfonium Compounds; D005959:Glucosidases; D000520:alpha-Glucosidases