Effect of Degree of Sulfation on Anti-Hiv Activity of Synthetic (1→5)-α-D-Ribofuranan Sulfate

ABSTRACT

Stereoregular (1→5)-α-D-ribofuranan prepared by selective ring-opening polymerization of anhydro-ribose derivatives was sulfated with piperidine N-sulfonic acid to give ribofuranan sulfates (RFS) with various degrees of sulfation (DS). NMR analysis of RFS indicated a similar reactivity of two hydroxyl groups (2-OH and 3-OH). Anti-HIV effects of RFS were investigated by using MT-4 cells, i.e., an HTLV-I-carrying CD-4 positive cell line in vitro. RFS with higher DS showed remarkably higher anti-HIV activity. Anticoagulant activity of RFS was also investigated. RFS with a high DS interacted more selectively with virus protein rather than other proteins in the blood than RFS with a low DS.