system, which displayed great potential in enhancing lectin binding and an encapsulation ability that could be used in site-specific drug delivery [39–42] (Fig. 8).
14.3.2.3 Primary-Rim-Conjugated Heptavalency Glycol Ligands
The hydroxyls on the primary rim of CDs were selectively substituted by nucleophilic atoms, then the saccharide ligands were connected with spacers to form
CD–saccharide conjugates. This strategy to synthesize primary-rim glycoclusters
is one of the most efficient methods, with a satisfactory yield that can provide a
reliable chemical resource for testing the suitability of different spacers and
saccharide ligands [43–45] (Fig. 9).
A well-designed synthetic multivalent mannotriose would be a promising tool for
investigation of the allergenicity and antigenicity of yeast mannans. Crohn’s disease
(inflammatory bowel disease) is caused by a disturbed immune response to antigens of
yeast mannans [46, 47]. However, achievement of polysaccharide synthesis is still a real
challenge. On the basis of the above concept, Carpenter and Nepogodiev employed
per-6-thio cyclodextrins, 71, as a platform coupled with halogen-armed carbohydrates
(α-Man-(1–3), α-Man-(1–2), α-Man mannotriose, 72) through multiple SN2 reactions to
afford CD 73 in a 57% yield, which was a great help for similar research [48]
(Scheme 15).
Fig. 6 Cyclodextrin (CD)based monovalency drug
carrier
14 Functionalized Cyclodextrins and Their Applications in Biodelivery
403
14.3.2.3 Primary-Rim-Conjugated Heptavalency Glycol Ligands
The hydroxyls on the primary rim of CDs were selectively substituted by nucleophilic atoms, then the saccharide ligands were connected with spacers to form
CD–saccharide conjugates. This strategy to synthesize primary-rim glycoclusters
is one of the most efficient methods, with a satisfactory yield that can provide a
reliable chemical resource for testing the suitability of different spacers and
saccharide ligands [43–45] (Fig. 9).
A well-designed synthetic multivalent mannotriose would be a promising tool for
investigation of the allergenicity and antigenicity of yeast mannans. Crohn’s disease
(inflammatory bowel disease) is caused by a disturbed immune response to antigens of
yeast mannans [46, 47]. However, achievement of polysaccharide synthesis is still a real
challenge. On the basis of the above concept, Carpenter and Nepogodiev employed
per-6-thio cyclodextrins, 71, as a platform coupled with halogen-armed carbohydrates
(α-Man-(1–3), α-Man-(1–2), α-Man mannotriose, 72) through multiple SN2 reactions to
afford CD 73 in a 57% yield, which was a great help for similar research [48]
(Scheme 15).
Fig. 6 Cyclodextrin (CD)based monovalency drug
carrier
14 Functionalized Cyclodextrins and Their Applications in Biodelivery
403