A novel ganglioside with a free amino group in bovine brain.
A novel ganglioside which binds cholera-toxin B-subunit was purified from bovine brain by an h.p.l.c. system using an Aquasil column subsequent to Q-Sepharose column chromatography. T.l.c./immunostaining showed that the isolated ganglioside had about 60% of the binding reactivity of the authentic ganglioside GM1 for cholera-toxin B-subunit. On h.p.l.c., this ganglioside migrated between ganglioside GD1a and GD1b, and was found to give positive reactions with ninhydrin and fluorescamine reagents which specifically react with amino groups. The presence of a free amino group was further confirmed by chemical re-N-acetylation. The N-acetylated product had an identical RF value on h.p.l.c. and similar reactivity with cholera-toxin B-subunit as the authentic GM1. H.p.t.l.c., t.l.c./immunostaining, negative-ion fast-atom-bombardment (f.a.b.)-m.s., and 1H-n.m.r. spectroscopy of the novel ganglioside unequivocally demonstrated that it has the basal structure of GM1 with de-N-acetylated neuraminic acid instead of N-acetylneuraminic acid. In the present study we report for the first time that a ganglioside derivative containing de-N-acetylated neuraminic acid, de-N-acetylated GM1, exists in natural brain tissues.
Hidari
K I
KI
Laboratory for Glyco Cell Biology, Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Irie
F
F
Suzuki
M
M
Kon
K
K
Ando
S
S
Hirabayashi
Y
Y
D000107:Acetylation; D000818:Animals; D001923:Brain Chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002417:Cattle; D002772:Cholera Toxin / Q000378:metabolism; D002855:Chromatography, Thin Layer; D005732:Gangliosides / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011485:Protein Binding; D016339:Spectrometry, Mass, Fast Atom Bombardment
D005732:Gangliosides; D002772:Cholera Toxin