Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

Ahmad Ghavami, Blair D. Johnston, Matthew D. Maddess, Sarah M. Chinapoo, Morten T. Jensen, Birte Svensson, B. Mario Pinto

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-Xylitol at the least-hindered carbon of 2,4- O-benzylidene-L-erythritol-1, 3 -cyclic sulfate. The sulfonium ion 8 inhibited barley-alpha-amylase (AMY1) and porcine pancreatic-alpha-amylase (PPA), with K-i values of 109 +/- 11 and 55 +/- 5 muM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.
Original languageEnglish
JournalCanadian Journal of Chemistry
Volume80
Issue number8
Pages (from-to)932-947
ISSN0008-4042
DOIs
Publication statusPublished - 2002
Externally publishedYes

Fingerprint Dive into the research topics of 'Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors'. Together they form a unique fingerprint.

Cite this