Structural analysis of glycosyl-phosphatidylinositol antigens of Leishmania major.
Three glycosyl-phosphatidylinositol glycolipids recognized by antibodies from patients with cutaneous leishmaniasis were extracted from Leishmania major promastigotes by hexane:isopropanol and then purified by thin layer chromatography and LH-20 gel chromatography. Structural analysis was carried out using chemical analyses, fast atom bombardment mass spectrometry, and 1H NMR. The major structures deduced can be summarized as follows: (formula: see text) where n = 0, 1, 2; R1 = (CH2)23-CH3; R2 = (CH2)14-CH3 or (CH2)16-CH3. Alkyl-acyl substitutions in the glycerol backbone showed considerable heterogeneity. These three glycolipids belong to a relatively new class of compounds and may represent sequential steps in the biosynthesis of glycosyl-phosphatidylinositols which anchor proteins or other glycoconjugates to Leishmania cell membranes.
Rosen
G
G
Department of Parasitology, Kuvin Centre for the Study of Infectious and Tropical Diseases, Hebrew University, Hadassah Medical School, Jerusalem, Israel.
Påhlsson
P
P
Londner
M V
MV
Westerman
M E
ME
Nilsson
B
B
D000818:Animals; D000953:Antigens, Protozoan / Q000302:isolation & purification*; D002240:Carbohydrate Sequence; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D006017:Glycolipids / Q000302:isolation & purification*; D017261:Glycosylphosphatidylinositols; D007895:Leishmania tropica / Q000276:immunology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010716:Phosphatidylinositols / Q000302:isolation & purification*
D000953:Antigens, Protozoan; D006017:Glycolipids; D017261:Glycosylphosphatidylinositols; D010716:Phosphatidylinositols