Structures of ceramide tetrasaccharides from various sources: uniqueness of rat kidney ceramide tetrasaccharide

• Published in: Journal of lipid research Vol. 13; no. 5; pp. 657 - 662
• Main Authors: Siddiqui, B, Kawanami, J, Li, Y T, Hakomori, S
• Format: Journal Article
• Language: English
• Published: United States Elsevier 01-09-1972
• Subjects: Animals; bovine kidney; Carbohydrates - analysis; Cattle; Ceramides - analysis; Ceramides - isolation & purification; Chromatography, Gas; Chromatography, Thin Layer; Erythrocytes - analysis; Glycolipids - analysis; Haplorhini; horse spleen; Horses; human erythrocytes; Humans; Hydrolysis; Kidney; Mass Spectrometry; Methylation; Molecular Conformation; monkey kidney; Optical Rotation; Oxidation-Reduction; Periodic Acid; Polysaccharides - analysis; Polysaccharides - isolation & purification; rat kidney; Rats; Spectrophotometry, Infrared; Spleen - analysis
• ISSN: 0022-2275
• DOI: 10.1016/S0022-2275(20)39371-8

Methylation analysis of ceramide tetrasaccharide isolated from human erythrocytes gave acetates of 2,3,6-tri-O-methylgalactitol and 2,4,6-tri-O-methylgalactitol in a ratio of 1:1, and about 50% of the galactose was oxidized by periodate. Rat kidney ceramide tetrasaccharide gave, in contrast, a much larger proportion of the acetates of 2,4,6-tri-O-methylgalactitol (ratio 1:0.3), and less than 20% of the galactose was oxidized by periodate. Sequential degradation by beta-N-acetylhexosaminidase, alpha-galactosidase, and beta-galactosidase showed ceramide tetrasaccharides to have identical carbohydrate sequences and anomeric structures. The major part of ceramide trihexoside derived from rat kidney ceramide tetrasaccharide migrated on thin-layer chromatography more slowly than that derived from other ceramide tetrasaccharides. The structure of a major part of rat kidney ceramide tetrasaccharide was thus determined to be GalNAcbeta(1-->3)Galalpha(1-->3)Galbeta(1-->4)Glcbeta(1-->1)Cer, whereas other ceramide tetrasaccharides have Galalpha(1-->4) structure at the penultimate residue.