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N
3
O
Ac
AcO
O
O
O
O
AcO
O
N
OAc
H
H
x
OA
OAc
N
3
O
71
70
(i) CuSO
4
/Sodium ascorbate,
1:1
t
-BuOH/H
2
O;
N
N
AcO
O
O
N
OAc
AcO
O
O
O
O
AcO
OAc
AcO
N
O
N
N
H
H
x
n
N
72
(ii) NaOMe/MeOH;
(iii) CF
3
COOH/CH
2
Cl
2
N
N
O
OH
OH
N
HO
O
O
O
N
OH
HO
HO
O
N
N
H
H
x
n
N
73
71a, 72a, 73a, x = 1
71b, 72b, 73b, x = 2
71c, 72c, 73c, x = 3
SCHEME 12.5
Click mediated polymerization.
functionalize via non-covalent assembly with biological receptor-specific targeting
moieties [75].
Wu et al. synthesized unsymmetrical dendrimers (
77
) (Fig. 12.22) contain-
ing mannose units and coumarin fluorescent units via click chemistry [76]. The
synthesized dendrimers were identified as highly efficient, dual-purpose recogni-
tion/detection agents for the inhibition of hemagglutination, a specific form of agglu-
tination that involves red blood cells (RBCs). The dendrimer (
75
) under hemag-
glutination assay using the mannose binding protein concanvalin A and rabbit red
blood cells, exhibited 240-fold greater potency than monomeric mannose, corre-
sponding to a relative activity of 15 per sugar moiety when compared to mannose
(activity
=
1) [76].
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