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HO
HO
COOH
HO
N
AcO
AcO
OAc
N
O
O
O
AcHN
N
N
3
HO
OH
O
AcO
OH
HO
168
173
HO
AcO
AcO
AcO
COOMe
HO
i. CuSO
4
/ Na ascorbate, DMF
MW, 100 °C, 15 min
N
3
AcO
AcO
COOH
O
HO
O
+
O
AcHN
N
HO
N
O
AcO
OH
O
ii. NaOMe, MeOH
iii. KOH 0.2 M
AcHN
O
N
AcO
174
OAc
HO
177
OH
HO
169
HO
HO
OAc
COOH
HO
O
N
AcO
HO
O
N
N
3
OAc
O
AcHN
N
AcO
HO
HO
175
HO
OH
O
HO
170
OAc
AcO
O
HO
OAc
COOH
HO
OAc
N
3
N
HO
O
N
O
AcHN
OH
OH
N
176
HO
HO
O
171
OH
OAc
AcO
O
O
HO
OH
i. CuSO
4
/ Na ascorbate, DMF
MW, 100 °C, 15 min
N
3
O
HO
O
OH
O
+
N
AcO
N
N
OMe
O
HO
HO
ii. H
2
/10% Pd/C
OMe
178
179
O
iii. NaOMe, MeOH
172
SCHEME 13.19
Synthesis of 1,2,3-triazole-linked sialic acid and amino acid glycosides
168-172
by click chemistry.
acid
177
, as well as by click chemistry reaction between the amino acid N
3
-ThrOBn
178
with 3-O-propynyl-GalOMe
179
(Scheme 13.19) [64]. The 1,2,3-triazole linked
sialic acid-6-O-galactose
169
and the sialic acid-galactopyranoside
168
showed high
TcTS inhibitory activity at 1 mM (approx. 90%), whilst only the former displayed rel-
evant trypanocidal activity (IC
50
260
M). These results highlight the 1,2,3-triazole
linked sialic acid-6-O-galactose
169
as a prototype for further design of new neogly-
coconjugates against Chagas' disease.
REFERENCES
1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B.
Angew. Chem., Int. Ed
.
2001
,
40
, 2004-2021.
2. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.
Angew. Chem., Int. Ed
.
2002
,
41
, 2596-2599.
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