Direct and Regioselective Di-alpha-fucosylation on the Secondary Rim of beta-Cyclodextrin

Stella A. Verkhnyatskaya, Alex H. de Vries, Elmatine Douma-de Vries, Enze J. L. Sneep, Marthe T. C. Walvoort*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

A straightforward glycosylation method is described to regio- and stereoselectively introduce two alpha-L-fucose moieties directly to the secondary rim of beta-cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram-scale, and may be generally applied to directly glycosylate beta-cyclodextrins to make well-defined multivalent glycoclusters.

Original languageEnglish
Pages (from-to)6722-6727
Number of pages6
JournalChemistry
Volume25
Issue number27
DOIs
Publication statusPublished - 10-May-2019

Keywords

  • beta-cyclodextrin
  • fucosylation
  • mass fragmentation
  • molecular dynamics simulations
  • regioselectivity
  • DE-O-BENZYLATION
  • BIOLOGICAL EVALUATION
  • MOLECULAR-DYNAMICS
  • MASS-SPECTROMETRY
  • FUCOSE
  • CYCLOMALTOHEPTAOSE
  • RECOGNITION
  • POWERFUL
  • HYDRIDE
  • DESIGN

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