Katsuraya K, Nakashima H, Yamamoto N, Uryu T
Institute of Industrial Science, University of Tokyo, Japan.
Carbohydr Res. 1999 Feb 28;315(3-4):234-42. doi: 10.1016/s0008-6215(98)00315-2.
Sulfated laminara-oligosaccharide glycosides having high anti-human immunodeficiency virus (HIV) activities were synthesized from laminara-tetraose, -pentaose and -hexaose. The oligosaccharide glycosides were synthesized by treating peracetylated beta-oligosaccharides with various alcohols and Lewis acid catalysts. The effects of the number of glucose residues and the alkyl chain-length on anti-HIV activity were examined. The anti-HIV activity of sulfated dodecyl laminara-pentaosides and -hexaosides increased with increasing degree of sulfation (DS) and the pentaoside having an almost fully-sulfated saccharide portion had the highest activity, whereas for the hexaoside a somewhat lower DS manifested the highest activity. Sulfated laminara-oligosaccharide glycosides having fluoroalkyl-containing aglycons of high hydrophobicity showed potent inhibitory effects against HIV infection. In contrast, hydrophilic substituents containing oligo(ethyleneoxy) groups as aglycons in the sulfated oligosaccharides did not show high anti-HIV activity.
从海带四糖、海带五糖和海带六糖合成了具有高抗人免疫缺陷病毒（HIV）活性的硫酸化海带寡糖糖苷。寡糖糖苷是通过用各种醇和路易斯酸催化剂处理全乙酰化的β-寡糖来合成的。研究了葡萄糖残基数量和烷基链长度对抗HIV活性的影响。硫酸化十二烷基海带五糖苷和六糖苷的抗HIV活性随着硫酸化程度（DS）的增加而增加，具有几乎完全硫酸化糖部分的五糖苷具有最高活性，而对于六糖苷，稍低的DS表现出最高活性。具有高疏水性含氟烷基苷元的硫酸化海带寡糖糖苷对HIV感染显示出强大的抑制作用。相比之下，硫酸化寡糖中含有低聚（环氧乙烷）基团作为苷元的亲水性取代基没有显示出高抗HIV活性。
