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HO
OH
O
HO
O
O
N
N
N
OH
N
H
O
N
OH
O
N
O
HO
N
O
S
O
O
CdSe
ZnS
N
H
HO
HN
N
O
OH
N
N
O
O
O
OH
O
O
N
H
HO
O
HO
103
OH
n
FIGURE 6.8
Glyconanoparticles obtained by thiol coupling of trivalent galactosyl click
glycodendrons with ZnS/CdSe nanoparticles.
Noncovalent stabilization of nanoparticles by interaction with click glycodendrimers
also has been achieved [153].
The groups of Chiara and coworkers [154] and Fessner and coworkers [155] have
reported the preparation of a new family of octavalent cube-shaped click glyconano-
materials with an inorganic-organic hybrid core (
105
) based on the azide functional
octahydrosilsesquioxane platform
104
(Scheme 6.19). Clickable azide-functionalized
Q
bacteriophage capsid particles have also been used as scaffolds for CuAAC with
alkyne-armed sialic acid residues on the glycan chain of transferrin (Tf) to target the
Tf receptors overexpressed on the surface of a variety of tumor cells [156].
Silica-based click hybrid glycomaterials represent one of the most important func-
tional materials [157]. Click ligation of carbohydrates onto the surface of silica
N
3
N
N
N
3
N
N
N
O
Si
S
i
N
N
N
N
N
O
O
N
3
N
N
O
O
Si
O
N
Si
N
N
3
N
3
Si
O
Si
N
N
O
Cu(I)
O
N
O
N
O
N
3
Si
N
Si
O
N
N
N
N
N
N
3
104
N
3
105
sugar (mannose, galactose)
SCHEME 6.19
Synthesis
of
octahydrosilsesquioxane
cube-shaped
click
glyconano-
materials.
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