Synthesis of sulfated oligosaccharide glycosides having high anti-HIV activity and the relationship between activity and chemical structure

Sulfated laminara-oligosaccharide glycosides having high anti-human immunod eficiency virus (HIV) activities were synthesized from laminara-tetraose, - pentaose and -hexaose. The oligosaccharide glycosides were synthesized by t reating peracetylated beta-oligosaccharides with various alcohols and Lewis acid catalysts. The effects of the number of glucose residues and the alky l chain-length on anti-HIV activity were examined. The anti-HIV activity of sulfated dodecyl laminara-pentaosides and -hexaosides increased with incre asing degree of sulfation (DS) and the pentaoside having an almost fully-su lfated saccharide portion had the highest activity, whereas for the hexaosi de a somewhat lower DS manifested the highest activity. Sulfated laminara-o ligosaccharide glycosides having fluoroalkyl-containing aglycons of high hy drophobicity showed potent inhibitory effects against HIV infection, in con trast, hydrophilic substituents containing oligo(ethyleneoxy) groups as agl ycons in the sulfated oligosaccharides did not show high anti-HIV activity. (C) 1999 Elsevier Science Ltd. All rights reserved.