Structure of triphosphonoglycosphingolipid containing N-acetylgalactosamine 6-O-2-aminoethylphosphonate in the nervous system of Aplysia kurodai.
A phosphonoglycosphingolipid, named F-21, was found in the nervous system of Aplysia kurodai by two-dimensional thin-layer chromatography (Abe, S., Araki, S., and Satake, M. (1986) Biomed. Res. (Tokyo) 7, 47-51). F-21 was isolated from the nervous tissue of Aplysia in this study, and its chemical structure was characterized as follows, where 2-AEP is 2-aminoethylphosphonate. (Formula; see text) The major aliphatic components of the ceramide portion were palmitic acid (75%), stearic acid (22%), octadeca-4-sphingenine (43%), and anteisononadeca-4-sphingenine (54%). Some information on the steric interactions in the sugar moiety was obtained by NMR spectroscopy. The ring protons of the internal galactose, H1, H3, and H4 and the H3 of the side chain galactose were shifted, as compared to the corresponding protons of dephosphonylated F-21. This may indicate the interactions between the 2-AEP residue of N-acetylgalactosamine and the internal galactose and between the N-acetyl group of N-acetylgalactosamine and the side chain galactose, implying a sterically restricted and unique structure that may relate to some biological functions of F-21.
Abe
S
S
Department of Neurochemistry, Niigata University, Japan.
Araki
S
S
Satake
M
M
Fujiwara
N
N
Kon
K
K
Ando
S
S
D000116:Acetylgalactosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D000615:Aminoethylphosphonic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D001048:Aplysia; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D006028:Glycosphingolipids / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008958:Models, Molecular; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009420:Nervous System / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011233:Precipitin Tests; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006028:Glycosphingolipids; D009943:Organophosphorus Compounds; C068861:N-acetylgalactosamine 6-O-2-aminoethylphosphonate; D000615:Aminoethylphosphonic Acid; D000116:Acetylgalactosamine