New β-cyclodextrin derivatives possessing biologically active saccharide antennae
- 1 December 1993
- journal article
- research article
- Published by Taylor & Francis in Supramolecular Chemistry
- Vol. 3 (1) , 37-42
- https://doi.org/10.1080/10610279308029836
Abstract
The synthesis of monosubstituted β-cyclodextrin derivatives having the monosaccharides, β-D-glucose, β-D-galactose, α-D-mannose, β-L and β-D-fucose linked to the macrocycle via a C9 spacer chain is described. The approach is based on the highly efficient coupling of the NCS sugar derivatives to monomethyl nonanedicarboxylate to generate a stable amido linkage. The NMR studies show the saccharide antennae to be oriented into the environment and not towards the CD cavity.Keywords
This publication has 13 references indexed in Scilit:
- Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugatesCarbohydrate Research, 1992
- Vectorised transport of drugs: Synthesis of a new glycosyl derivative of β-cyclodextrin.Tetrahedron Letters, 1992
- A novel method for the specific glycosylation of proteinsTetrahedron Letters, 1991
- Carbohydrate protein interactions. Syntheses of agglutination inhibitors of wheat germ agglutinin by phase transfer catalysisCanadian Journal of Chemistry, 1991
- A new efficient acylation of free glycosylaminesTetrahedron Letters, 1991
- Intramolecular host-guest complexes of D- and L-mono-6-phenylalanyl-amino-6-deoxy cyclomalto-heptaosesTetrahedron: Asymmetry, 1990
- GLYCOBIOLOGYAnnual Review of Biochemistry, 1988
- Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)]Angewandte Chemie International Edition in English, 1987
- A New Procedure for the Synthesis of Glycosyl IsothiocyanatesSynthesis, 1984
- Properties of a synthetic antigen related to the human blood-group Lewis aJournal of the American Chemical Society, 1975