Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers
Table 3
Sulfation and anti-HIV activity of 3-O-octadecyl(16)--D-glucopyranansa.
Number
Free 3-O-octadecyl glucopyranan
Sulfated 3-O-octadecyl glucopyranan
Proportion of 3-O-octadecyl group
PSA
Temp.
Time
Yield
DPb
Elemental analysis
DSc
mg
mol%
g
°C
h
mg
×103
C, %
H, %
S, %
g/mL
g/mL
1
115
2.8
1.50
85
1.5
145
5.1
25.2
26.5
4.5
12.2
1.03
0.05
>162
2
120
2.8
1.06
85
1.5
145
4.3
30.6
30.6
4.4
10.3
0.75
0.09
>163
3
80
2.8
0.49
85
1.5
130
5.1
26.1
26.1
4.3
11.8
1.02
0.04
>200
4
75
4.7
0.69
85
1.5
103.5
2.5
13.5
34.9
4.9
8.6
0.55
1.25
>147
5
60.5
6.7
0.58
85
1
95.4
—f
—f
37.6
4.7
9.5
0.57
20.34
>200
6
155.4
15.7
0.92
85
1
262.5
5.5
29.7
47.5
6.1
8.4
0.52
6.50
>200
Dextran sulfate
8.5
18.4
2.1
0.05
>621
Curdlan sulfate
79.0
14.1
1.4
0.18
>100
Sulfation was carried out with piperidine-N-sulfonic acid (PSA) in DMSO. bDegree of polymerization. cDegree of sulfation. d50% effective concentration on HIV. e50% cytotoxic concentration on MT4 cell. fNot determined. It was difficult to dissolve in water.
