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  • Title: Synthesis of analogues of salacinol containing a carboxylate inner salt and their inhibitory activities against human maltase glucoamylase.
    Author: Chen W, Sim L, Rose DR, Pinto BM.
    Journal: Carbohydr Res; 2007 Sep 03; 342(12-13):1661-7. PubMed ID: 17597595.
    Abstract:
    The syntheses of analogues of the naturally occurring glycosidase inhibitor, salacinol, containing a carboxylate inner salt are described. Salacinol is a sulfonium ion with an internal sulfate counterion. The synthetic strategy relies on the nucleophilic attack of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D- or L-arabinitol at the least hindered carbon of 4,5-anhydro-2,3-O-isopropylidene-D-ribonic acid benzyl ester to yield coupled adducts. Deprotection of the coupled products gives the target compounds. The compound derived from D-arabinitol inhibits recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the small intestine, with a Ki value of 10+/-1 microM.
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