Synthesis and glycosidase inhibition potency of all-trans substituted 1-C-perfluoroalkyl iminosugars

Synthesis and glycosidase inhibition potency of all-trans substituted 1-C-perfluoroalkyl iminosugars 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 –C4F9 proved detrimental for enzyme binding, introduction of a –C3F7 moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Carbohydrate Research Elsevier

Synthesis and glycosidase inhibition potency of all-trans substituted 1-C-perfluoroalkyl iminosugars

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier Ltd
ISSN
0008-6215
eISSN
1873-426X
D.O.I.
10.1016/j.carres.2018.05.004
Publisher site
See Article on Publisher Site

Abstract

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 –C4F9 proved detrimental for enzyme binding, introduction of a –C3F7 moiety tuned the inhibitory activity spectrum selectively towards α-fucosidase and α-glucosidase from yeast.

Journal

Carbohydrate ResearchElsevier

Published: Jul 15, 2018

References

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