Structure of phosphonoglycosphingolipid containing pyruvylated galactose in nerve fibers of Aplysia kurodai.
A phosphonoglycosphingolipid, designated as FGL-IIb, was identified in nerve fibers of Aplysia kurodai by two-dimensional thin layer chromatography (Abe, S., Araki, S., and Satake, M. (1986) Biomed. Res. (Tokyo) 7, 47-51). FGL-IIb was isolated from the nervous system of A. kurodai by Iatrobeads column chromatography using three solvent systems. Pyruvic acid was identified by thin layer chromatography as its 2,4-dinitrophenylhydrazone and established by permethylation studies to be attached as a ketal to O-3 and O-4 of the terminal galactose of the oligosaccharide chain in FGL-IIb. By sugar analysis, permethylation studies, fast atom bombardment-mass spectrometry, and proton magnetic resonance spectrometry, the structure of FGL-IIb was concluded to be [3,4-O-(1-carboxyethylidene)]Gal beta 1----3GalNAc alpha 1----3(Fuc alpha 1----2) (2-aminoethylphosphonyl----6)Gal beta 1----4Glc beta 1----1ceramide. Its major aliphatic components were palmitic acid, octadeca-4-sphingenine and anteisononadeca-4-sphingenine. This is the first report of the occurrence of pyruvylated galactose as a constituent of animal sphingolipid.
Araki
S
S
Department of Neurochemistry, Brain Research Institute, Niigata, Japan.
Abe
S
S
Ando
S
S
Kon
K
K
Fujiwara
N
N
Satake
M
M
D020384:Acidic Glycosphingolipids; D000818:Animals; D001048:Aplysia / Q000032:analysis*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002849:Chromatography, Gas; D005690:Galactose / Q000032:analysis; D006028:Glycosphingolipids / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D009412:Nerve Fibers / Q000032:analysis*; D011773:Pyruvates; D019289:Pyruvic Acid
D020384:Acidic Glycosphingolipids; D006028:Glycosphingolipids; D011773:Pyruvates; C061817:phosphonoglycosphingolipid FGL-IIb; D019289:Pyruvic Acid; D005690:Galactose