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Published on: August 19, 2012
New α-galactosidase-inhibiting aminohydroxycyclopentanes
Patrick Weber1, Roland Fischer2, Seyed A Nasseri3
1Glycogroup, Institute of Chemistry and Technology of Biobased Systems, Graz University of Technology Stremayrgasse 9 A-8010 Graz Austria patrick.weber@tugraz.at +43 316 873 32078.
None:
A set of cyclopentanoid α-galactosidase ligands was prepared from a partially protected ω-eno-aldose via a reliable (2 + 3)-cycloaddition protocol with slightly modified conditions. The obtained N-benzylisoxazolidine ring was selectively opened and the configuration of the hydroxymethylgroup was inverted. Consecutive deprotection provided an aminocyclopentane, which was N-alkylated to furnish a set of potential α-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.
