Characterization of novel mono-O-acetylated GM3s containing 9-O-acetyl sialic acid and 6-O-acetyl galactose in equine erythrocytes.
Novel mono-O-acetylated GM3s, one containing 9-O-acetyl N-glycolyl neuraminic acid and another containing 6'-O-acetyl galactose, were isolated as a mixture from equine erythrocytes, and the structures were characterized by one- and two-dimensional proton nuclear magnetic resonance (NMR) and fast atom bombardment-mass spectrometry (FAB-MS). The position of the O-acetyl residue was identified by the downfield shift of the methylene protons at C-9 of N-glycolyl neuraminic acid (9-O-Ac GM3) and C-6 of galactose (6'-O-Ac GM3) in the NMR spectrum, in comparison to the respective non-acetylated counterparts. To confirm the presence of 6'-O-Ac GM3, the O-acetylated GM3 mixture was desialylated with Arthrobacter neuraminidase, giving 6-O-acetyl galactosyl glucosylceramide, the structure of which was estimated by NMR and FAB-MS, together with non-acetylated lactosylceramide with a ratio of 1:1.
Yachida
Y
Y
Department of Chemistry, School of Medicine, Sapporo Medical University, Japan.
Tsuchihashi
K
K
Gasa
S
S
D000107:Acetylation; D000818:Animals; D001173:Arthrobacter / Q000201:enzymology; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004910:Erythrocyte Membrane / Q000737:chemistry*; D005679:G(M3) Ganglioside / Q000031:analogs & derivatives* / Q000097:blood* / Q000737:chemistry / Q000302:isolation & purification; D005690:Galactose / Q000031:analogs & derivatives* / Q000032:analysis; D006017:Glycolipids / Q000737:chemistry; D006736:Horses; D009682:Magnetic Resonance Spectroscopy; D008563:Membrane Lipids / Q000097:blood* / Q000737:chemistry / Q000302:isolation & purification; D009439:Neuraminidase; D012794:Sialic Acids / Q000032:analysis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment
C101248:6-O-acetylgalactose; D005679:G(M3) Ganglioside; D006017:Glycolipids; D008563:Membrane Lipids; D012794:Sialic Acids; C025676:9-O-acetyl-N-acetylneuraminic acid; D009439:Neuraminidase; D005690:Galactose