Synthesis of novel glycolipids that bind HIV-1 Gp120.
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.
LaBell
Rachel Y
RY
Department of Chemistry, The University of Arizona, Tucson. Arizona 85721, USA.
Jacobsen
Neil E
NE
Gervay-Hague
Jacquelyn
J
O'Brien
David F
DF
D005690:Galactose / Q000737:chemistry; D005699:Galactosylceramides / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000494:pharmacology*; D015699:HIV Envelope Protein gp120 / Q000187:drug effects*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D005699:Galactosylceramides; D006017:Glycolipids; D015699:HIV Envelope Protein gp120; D007202:Indicators and Reagents; D005690:Galactose