Non-natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant gp120

Katherine D. McReynolds, Abhijit Bhat, John C. Conboy, S. Scott Saavedra, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However, palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor, galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and a hydrophilic component are required for rgp120 recognition. Moreover, structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific.

Original languageEnglish (US)
Pages (from-to)625-637
Number of pages13
JournalBioorganic and Medicinal Chemistry
Issue number3
StatePublished - 2002
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


Dive into the research topics of 'Non-natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant gp120'. Together they form a unique fingerprint.

Cite this