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Issue 5, 2013
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Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

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Abstract

Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2–4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases.

Graphical abstract: Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

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Publication details

The article was received on 29 Jan 2013, accepted on 26 Feb 2013 and first published on 28 Feb 2013


Article type: Concise Article
DOI: 10.1039/C3MD00033H
Citation: Med. Chem. Commun., 2013,4, 783-791
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    Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors

    J. Wang, T. Lin, Y. Chen, C. Lin and J. Fang, Med. Chem. Commun., 2013, 4, 783
    DOI: 10.1039/C3MD00033H

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