Work

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

Year: 2000

Type: article

Abstract: HIV-1 has been shown to infect CD4 negative cells by the binding of HIV gp120 to the glycolipid galactosylceramide (1Download : Download high-res image (14KB)Download : Download full-size imageFigure 1. Galactosylceramide (GalCer) 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 (Figure 2, Scheme 3Download : Download high-res image (64KB)Download : Download full-size imageFigure 2. Synthetic GalCer analogues.Download : Download high-res image (15KB)Download : Download full-size imageScheme 3. (a) C17H35CHO, 2:1:1 THF:H2O:CH3OH, rt, 3 days; (b) NaBH3CN, ZnCl2; (c) C17H35CHO, EtOH-HOAc, Pd/C, H2, 4 h, rt.) 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. Figure 1. Galactosylceramide (GalCer) 1. Figure 2. Synthetic GalCer analogues. Scheme 3. (a) C17H35CHO, 2:1:1 THF:H2O:CH3OH, rt, 3 days; (b) NaBH3CN, ZnCl2; (c) C17H35CHO, EtOH-HOAc, Pd/C, H2, 4 h, rt.

Source: Bioorganic & Medicinal Chemistry Letters

DOI: 10.1016/s0960-894x(00)00153-0

Authors: Kevin T. Weber, Djilali Hammache, Jacques Fantini, Bruce Ganem

Institutions: Cornell University, Centre National de la Recherche Scientifique

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: hybrid

Estimated APC paid: $3,880