Abstract
Ring-opening copolymerization in various ratios of 1,4-anhydro deoxy-ribose monomers, 1,4-anhydro-2(or 3)-O-tert-butyldimethylsilyl-3(or 2)-deoxy-α-D-ribopyranose (A3DSR or A2DSR), with 1,4-anhydro-2,3-di-O-tert-butyldimethylsilyl-α-D-ribopyranose (ADSR) was investigated with boron trifluoride etherate catalyst to give the corresponding copolymers having number average molecular weights of 90.1×103–270.0×103 for copoly(A3DSR-ADSR)s and 39.1×103–93.4×103 for copoly(A2DSR-ADSR)s. The molecular weights of copoly(A3DSR-ADSR)s were higher than those of copoly(A2DSR-ADSR)s, suggesting that the substituent at C2 position works more effectively for regulating the ring-opening copolymerization than that at C3. After deprotection of hydroxyl groups followed by sulfation, sulfated heteroribofuranans consisting of various ratios of 2- or 3-deoxy-ribofuranosidic and ribofuranosidic units were obtained. It was found that both sulfated 2- and 3-deoxy-ribofuranans had no anti-AIDS virus activity. The anti-AIDS virus activity increased with decreasing ratio of the deoxy unit to give as high as EC50=0.6μg ml−1, indicating that the number of sulfate groups in the polysaccharide chain was important for the high anti-AIDS virus activity. The sulfated deoxy-ribofuranans had relatively low blood anticoagulant activity of 2–18 unit mg−1 compared with sulfated ribofuranan of 56 unit mg−1.
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Choi, Y., Kang, B., Lu, R. et al. Synthesis of Sulfated Deoxy-Ribofuranans Having Selective Anti-AIDS Virus Activity by Ring-Opening Copolymerization of 1,4-Anhydro Ribose Derivatives. Polym J 29, 374–379 (1997). https://doi.org/10.1295/polymj.29.374
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DOI: https://doi.org/10.1295/polymj.29.374