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Direct and Regioselective Di-?-fucosylation on the Secondary Rim of ?-Cyclodextrin.

ABSTRACT: A straightforward glycosylation method is described to regio- and stereoselectively introduce two ?-l-fucose moieties directly to the secondary rim of ?-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 ?-cyclodextrins to make well-defined multivalent glycoclusters.

SUBMITTER: Verkhnyatskaya SA

PROVIDER: S-EPMC6563713 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin.

Verkhnyatskaya Stella A SA de Vries Alex H AH Douma-de Vries Elmatine E Sneep Renze J L RJL Walvoort Marthe T C MTC

Chemistry (Weinheim an der Bergstrasse, Germany) 20190321 27

A straightforward glycosylation method is described to regio- and stereoselectively introduce two α-l-fucose moieties directly to the secondary rim of β-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 β-cyclodextrins to make well-defined multivalent glycoclusters ...[more]

PMID: 30801812

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