Structure of a triphosphonopentaosylceramide containing 4-O-methyl-N-acetylglucosamine from the skin of the sea hare, Aplysia kurodai.
A novel phosphonoglycosphingolipid named SGL-I containing 3 mol of 2-aminoethylphosphonate residues was isolated from the skin of a sea gastropod, Aplysia kurodai. The saccharide moiety of the glycolipid was characterized as 4-O-methyl-GlcNAc alpha 1----4GalNAc alpha-1----3 [6'-O-(2-aminoethylphosphonyl)Gal alpha 1----2] (2-aminoethylphosphonyl----6)Gal beta 1----4(2-aminoethylphosphonyl----6) Glc beta 1----1-ceramide. The major aliphatic components of the ceramide portion were palmitic acid, stearic acid, octadeca-4-sphingenine, and anteisononadeca-4-sphingenine. This glycolipid is unique in containing 4-O-methyl-N-acetylglucosamine and 3 mol of 2-aminoethylphosphonate residues, one of which is attached to C-6 of glucose.
Araki
S
S
Department of Neurochemistry, Niigata University, Japan.
Abe
S
S
Odani
S
S
Ando
S
S
Fujii
N
N
Satake
M
M
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000032:analysis; D000596:Amino Acids / Q000032:analysis; D000818:Animals; D001048:Aplysia / Q000032:analysis*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002849:Chromatography, Gas; D005944:Glucosamine / Q000031:analogs & derivatives*; D006028:Glycosphingolipids / Q000302:isolation & purification*; D013058:Mass Spectrometry; D009844:Oligosaccharides / Q000302:isolation & purification; D012867:Skin / Q000032:analysis
D000596:Amino Acids; D006028:Glycosphingolipids; D009844:Oligosaccharides; C014088:methyl-2-acetamido-2-deoxy-D-glucopyranoside; D005944:Glucosamine; D000117:Acetylglucosamine