TY - JOUR
T1 - Oxidative degradation of glycosphingolipids revisited
T2 - a simple preparation of oligosaccharides from glycosphingolipids
AU - Miljkovic, Momcilo
AU - Schengrund, Cara Lynne
N1 - Funding Information:
*This work was supported, in part, by grant CA-14319 from the National Cancer Institute, National Institutes of Health .
PY - 1986/11/1
Y1 - 1986/11/1
N2 - In order to cleave gangliosides and isolate the oligosaccharide portion, the allylic nature of OH-3 of the sphigenine base was utilized in its selective oxidation to a ketone group by 2,3-dichloro-5,6-dicyanobenzoquinone. Triethylamine treatment of the oxidation products resulted in the β-elimination of the intact oligosaccharide. The isolation of the pure oligosaccharide from the modified ceramide residue and unreacted ganglioside was obtained by liquid chromatography. Preliminary investigations suggest that the same reaction conditions can be used for an analogous elimination of oligosaccharides linked to the serine or threonine residues of glycoproteins.
AB - In order to cleave gangliosides and isolate the oligosaccharide portion, the allylic nature of OH-3 of the sphigenine base was utilized in its selective oxidation to a ketone group by 2,3-dichloro-5,6-dicyanobenzoquinone. Triethylamine treatment of the oxidation products resulted in the β-elimination of the intact oligosaccharide. The isolation of the pure oligosaccharide from the modified ceramide residue and unreacted ganglioside was obtained by liquid chromatography. Preliminary investigations suggest that the same reaction conditions can be used for an analogous elimination of oligosaccharides linked to the serine or threonine residues of glycoproteins.
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U2 - 10.1016/S0008-6215(00)90143-5
DO - 10.1016/S0008-6215(00)90143-5
M3 - Article
C2 - 3791298
AN - SCOPUS:0022814418
SN - 0008-6215
VL - 155
SP - 175
EP - 181
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -