Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
2011

Synthesis of Amine-Linked Diglycosides

publication Evidence: low

Author Information

Author(s): Ian Cumpstey, Jens Frigell, Elias Pershagen, Tashfeen Akhtar, Elena Moreno-Clavijo, Inmaculada Robina, Dominic S. Alonzi, Terry D. Butters

Primary Institution: Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University

Hypothesis

Amine-linked diglycose derivatives may act as glycosidase inhibitors.

Conclusion

The synthesized amine-linked diglycosides showed weak glycosidase inhibitory activity.

Supporting Evidence

  • The study synthesized diglycose derivatives linked by nitrogen.
  • The synthesis involved converting carbohydrates into unsaturated derivatives to enhance reactivity.
  • The synthesized compounds showed weak inhibitory activity against glycosidases.

Takeaway

The researchers made new sugar-like molecules that are linked by nitrogen and tested them to see if they could stop certain enzymes, but they didn't work very well.

Methodology

The study involved synthesizing amine-linked diglycosides using Mitsunobu coupling and palladium-catalyzed reactions, followed by glycosidase inhibition assays.

Limitations

The glycosidase inhibitory activity of the compounds was weak, and the nature of the binding and basis for inhibition is not clear.

Digital Object Identifier (DOI)

10.3762/bjoc.7.128

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