Reactivity Tournament of Isothiocyanato-Functionalized Saccharides with 1,6-Diamino-3,6-oxaoctane |
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Authors: | Mark Walter Thisbe K Lindhorst |
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Institution: | (1) Christiana Albertina University of Kiel, Institute of Organic Chemistry, D-24098 Kiel, Germany, DE |
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Abstract: | Summary. Thiourea-bridged glycoclusters and glycodendrimers are described in the literature as mimetics of (oligoantennary) oligosaccharides
to serve as high-affinity lectin ligands. In extension of this concept, the assembly of different, structurally varied isothiocyanato-functionalized
sugar derivatives on an oligoamine scaffold would lead to novel mixed glycoclusters. To control this approach, the relative
reactivities of the isothiocyanates used in the thiourea-bridging reaction have to be known. Therefore, competition experiments
with six different sugar isothiocyanates were carried out using 1,8-diamino-3,6-dioxaoctane as a symmetrical difunctionalized
core molecule. Reactivities were ranked on the basis of integration ratios in the 1H NMR spectra. A first mixed thiourea-bridged glycocluster was successfully prepared.
Received June 13, 2001. Accepted October 31, 2001 |
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Keywords: | , ,Sugar isothiocyanates, Thiourea bridging, Carbohydrates, Bioorganic chemistry, |
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