Chemistry Reference
In-Depth Information
TABLE 12.2 Comparison of
-Glucosidase, Glycogen Phosphorylase, and
Glucose-6-Phosphatase Inhibitory Activities of 1,2,3-1
H
-Triazolyl Glycohybrids (49-52)
at 100
mol Conc w.r.t. Acarbose and Sodium-Ortho-Vandate
Glycogen
Phosphorylase
Inhibitory
Activities
Glucose-6-
Phosphatase
Inhibitory
Activities
-Glucosidase
Inhibitory
Activities
1
H
-Triazolyl
Glycohybrids
Acarbose
60%
-
-
Sodium-ortho-vandate
-
-
36%
49
-
47.7%
≈
25%
50
-
34.1%
-
51
29.6%
20%
≈
25%
52
31.4%
-
-
armed-oligoethyl linked thiogalactosides as appropriate choice for click reaction
precursor furnishing clusters (
53
) and (
54
) (Fig. 12.19) [70].
Gouin et al. have synthesized carbohydrate-centered multi-mannoside clusters
through an efficient four step strategy including direct regioselective azidation of
unprotected D-glucose, maltose, and maltotriose cores using triphenylphosphine-
carbon tetrabromide-sodium azide and their successive acetylation to prepare tem-
plate over which acetyl protected mannosyl alkynes were grafted. Click reaction
followed by deprotection of clustered sugars afforded multivalent mannoside-based
clusters (
55-56
) exhibiting remarkable cluster effects toward concanavalin A (Con A)
lectin by an enzyme-linked lectin assay (ELLA) (Fig. 12.20) [71].
OH
HO
OH
OH
HO
OH OH
O
O
OH
OH
HO
S
OH
S
OH
O
OH
OH
OH
OH
O
O
S
O
OH
n
OH
N
N
O
OH
S
O
N
N
O
OH
N
N
N
N
S
HO
S
n
OH
HO
O
O
HO
HO
N
O
O
N
N
HO
OH
O
N
O
n
HO
O
O
HO
O
OH
OH
n
N
N
HO
N
O
HO
HO
O
HO
N
N
N
HO
n = 0
n = 2
n = 5
n = 0
n = 2
n = 5
53
54
FIGURE 12.19
1-Thio-
-D-galactose derived glyco-clusters exhibiting
-galactosidase
inhibitor.
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