A series of stereoregular azido group-containing copolymers such as poly [3-azido-2-
O-
t-butyldimethylsilyl-3-deoxy-(1→5)-α-D-xylofuranose-co-2, 3-di-
O-
t-butyldimethylsilyl-(1→5)-α-D-ribofuranose] [copoly (A3ASX-ADSR)] were synthesized by selective ring-opening polymerization of 1, 4-anhydro-3-azido-2-
O-
t-butyldimethylsilyl-3-deoxy-α-D-xylopyranose (A3ASX) and 1, 4-anhydro-2, 3-di-
O-
t-butyldimethylsilyl-α-D-ribopyranose (ADSR) with BF
3•OEt
2 catalyst. The number-average molecular weights (_??_
n) were in a range of 3.5×10
4_??_4.2×10
4. The optical rotations ([α]
D) increased from +119°to+143° with increasing mole fraction of the xylofuranosidic units in the copolymers from 30% to 78%.
Reduction of the azido group in the copolymer into an amino group, acetylation of the amino group into an acetamido group, and removal of the
t-butyldimethylsilyl group afforded poly [3-acetamido-3-deoxy-(1→5)-α-D-xylofuranose-co-(1→5)-α-D-ribofuranose] [copoly (A3AAdX-R)] with _??_
n 9.0×10
3 and [α]
D of +150.8°. Sulfation of the 3AAdXF and copoly (A3AAdX-R) produced a sulfated 3-acetamido-3-deoxy-(1→5)-α-D-xylofuranan with _??_
n of 17.1×10
3, and a sulfated poly _??_3-acetamido-3-deoxy-(1→5)-α-D-xylofuranose-co-(1→5)-α-D-ribofuranose_??_ with _??_
n of 10.9×10
3. The degrees of sulfation of homo- and co-polymers were 0.72 and 1.03, respectively. The four kinds of sulfated acetamido group-containing polypentoses exhibited medium-to-high anti-HIV (human immunodeficiency virus) activities in the range of EC
50 of from 0.42μg/mL to 62.86μg/mL, while they showed low anticoagulant activities in the range of 0 to 6unit/mg.
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