Synthesis of novel glycolipids that bind HIV-1 Gp120

Rachel Y. LaBell, Neil E. Jacobsen, Jacquelyn Gervay-Hague, David F. O'Brien

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

As part of a research effort to design and prepare high affinity ligands for the galactosyl ceramide (GalCer) binding site on the HIV cell surface glycoprotein, gp120, several GalCer analogues have been prepared and characterized. The molecular design of analogues permits independent variations of the carbohydrate, the length of a hydrophilic spacer between the ligand and the lipid, and the composition of the hydrophobic lipid chains. Five different galactosyl analogues were synthesized having hydrophilic spacers of tri-, tetra-, and penta-ethylene glycol separating the carbohydrate from the lipid region which has either oleoyl or stearoyl lipid chains. The synthetic design allows for a convergent synthesis of the three components of the glycolipid conjugate. The structural characterization includes the proton and carbon chemical shifts, which were assigned after analysis of 1D and 2D NMR spectra.

Original languageEnglish (US)
Pages (from-to)143-149
Number of pages7
JournalBioconjugate Chemistry
Volume13
Issue number1
DOIs
StatePublished - 2002
Externally publishedYes

Fingerprint

Glycolipids
Lipids
HIV-1
Ceramides
Galactosylceramides
Carbohydrates
Ligands
Rubiaceae
Glycoproteins
Ethylene Glycol
Membrane Glycoproteins
Chemical shift
Binding sites
Ethylene glycol
Protons
Carbon
Binding Sites
Nuclear magnetic resonance
HIV
Chemical analysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Synthesis of novel glycolipids that bind HIV-1 Gp120. / LaBell, Rachel Y.; Jacobsen, Neil E.; Gervay-Hague, Jacquelyn; O'Brien, David F.

In: Bioconjugate Chemistry, Vol. 13, No. 1, 2002, p. 143-149.

Research output: Contribution to journalArticle

LaBell, Rachel Y. ; Jacobsen, Neil E. ; Gervay-Hague, Jacquelyn ; O'Brien, David F. / Synthesis of novel glycolipids that bind HIV-1 Gp120. In: Bioconjugate Chemistry. 2002 ; Vol. 13, No. 1. pp. 143-149.
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