Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide

HIV-1 has been shown to infect CD3 negative cells by the binding of HIV gp1 20 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membran e bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deo xynojirimycin (8) displayed potent and specific affinity for gp 120 equal t o that of 1, a finding that may shed light on the antiviral activity of N-b utyl-1-deoxynojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved .