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

doi:10.1002/chem.201806090

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	6722-6727
Number of pages	6
Journal	Chemistry
Volume	25
Issue number	27
DOIs	https://doi.org/10.1002/chem.201806090
Publication status	Published - 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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Direct and Regioselective Di‐α‐fucosylation on the Secondary Rim of β‐CyclodextrinFinal publisher's version, 1.2 MBLicence: CC BY-NC-ND

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title = "Direct and Regioselective Di-alpha-fucosylation on the Secondary Rim of beta-Cyclodextrin",

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.",

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",

author = "Verkhnyatskaya, {Stella A.} and {de Vries}, {Alex H.} and {Douma-de Vries}, Elmatine and Sneep, {Enze J. L.} and Walvoort, {Marthe T. C.}",

year = "2019",

month = may,

day = "10",

doi = "10.1002/chem.201806090",

language = "English",

volume = "25",

pages = "6722--6727",

journal = "Chemistry",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag GmbH & Co. KGaA",

number = "27",

}

TY - JOUR

T1 - Direct and Regioselective Di-alpha-fucosylation on the Secondary Rim of beta-Cyclodextrin

AU - Verkhnyatskaya, Stella A.

AU - de Vries, Alex H.

AU - Douma-de Vries, Elmatine

AU - Sneep, Enze J. L.

AU - Walvoort, Marthe T. C.

PY - 2019/5/10

Y1 - 2019/5/10

N2 - 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.

AB - 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.

KW - beta-cyclodextrin

KW - fucosylation

KW - mass fragmentation

KW - molecular dynamics simulations

KW - regioselectivity

KW - DE-O-BENZYLATION

KW - BIOLOGICAL EVALUATION

KW - MOLECULAR-DYNAMICS

KW - MASS-SPECTROMETRY

KW - FUCOSE

KW - CYCLOMALTOHEPTAOSE

KW - RECOGNITION

KW - POWERFUL

KW - HYDRIDE

KW - DESIGN

U2 - 10.1002/chem.201806090

DO - 10.1002/chem.201806090

M3 - Article

SN - 0947-6539

VL - 25

SP - 6722

EP - 6727

JO - Chemistry

JF - Chemistry

IS - 27

ER -

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

Abstract

Keywords

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