Synthesis of glycolipid analogues that disrupt binding of HIV-1 gp120 to galactosylceramide.
HIV-1 has been shown to infect CD4 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1) (GalCer). Several analogues of 1 were prepared to investigate the specific orientation of 1 in the membrane bilayer that is involved in gp120 binding. Interestingly, N-stearyl-1-deoxynojirimycin (8) displayed potent and specific affinity for gp120 equal to that of 1, a finding that may shed light on the antiviral activity of N-butyl-1-deoxynojirimycin.
Weber
K T
KT
Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853-1301, USA.
Hammache
D
D
Fantini
J
J
Ganem
B
B
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D005699:Galactosylceramides / Q000378:metabolism*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D015699:HIV Envelope Protein gp120 / Q000378:metabolism*; D008051:Lipid Bilayers; D013329:Structure-Activity Relationship
D019380:Anti-HIV Agents; D005699:Galactosylceramides; D006017:Glycolipids; D015699:HIV Envelope Protein gp120; D008051:Lipid Bilayers; C413763:N-stearoyl-1-deoxynojirimycin; D017485:1-Deoxynojirimycin