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Synthetic analogues of the naturally occurring iminosugar homoDMDP, which feature a perfluoroalkyl group at the pseudo-anomeric position, have been synthesized from the corresponding sugar-derived cyclic aldonitrone. The new fluorinated iminosugars as well as homoDMDP and its 6-deoxy counterpart were evaluated for their inhibitory activity against a panel of glycosidases. While the replacement of the (1',2')-dihydroxyethyl substituent of homoDMDP with -CF proved detrimental for enzyme binding, introduction of a -CF moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast.
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| http://dx.doi.org/10.1016/j.carres.2018.05.004 | DOI Listing |
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