Pr. Ashton et al., SYNTHESIS AND BIOLOGICAL EVALUATION OF ALPHA-D-MANNOPYRANOSIDE-CONTAINING DENDRIMERS, Journal of organic chemistry, 63(10), 1998, pp. 3429-3437
The extension of dendritic synthetic principles to the preparation of
new kinds of dendrimer-based glycoconjugate systems has been investiga
ted. A convergent growth approach to the synthesis of alpha-D-mannopyr
anoside-containing dendrimers of various generations has been used suc
cessfully to obtain high molecular weight and monodisperse dendrimers
in which 3-36 identical copies of the mannopyranoside residues are loc
ated at their peripheries. A repetitive synthetic sequence for forming
amide bonds is employed in the preparation of various dendritic wedge
s and their attachment to a 1,3,5-trisubstituted benzenoid core in the
last step. The protecting groups on the saccharide residues are then
finally removed to obtain free saccharide-containing dendrimers. The e
fficacy of these dendrimers in inhibiting the binding of concanavalin
A lectin to a purified yeast mannan fraction (as measured by an enzyme
-linked lectin assay) is shown to be about four times more pronounced
on a molar basis for the dendrimers possessing nine, 18, and 36 mannos
e residues, when compared to a dendritic wedge possessing three mannos
e residues and methyl alpha-D-mannopyranoside as control inhibitors.