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The neoglycolipid (NeoGL)  N -acetyl-1-deoxy-1-phosphatidylethanolamino lacto-N-tetraositol [Lc 4 Ose-PtdEtn( N Ac)] and the radioactivly labeled analog [Lc 4 Ose-PtdEtn( N [ 14 C]Ac)] were synthesized by coupling the corresponding oligosaccharide to phosphatidylethanolamine (dihexadecyl) via reductive amination and subsequent  N -acetylation with unlabeled and [ 14 C]acetic acid anhydride, respectively. Lc 4 Ose-PtdEtn( N [ 14 C]Ac) was then incubated with homogenates of rat small intestine epithelial cells (IEC-6) at pH 4. The reaction products were shown to be the degradation products formed by glycosidases by fast atom bombardment mass spectrometry (FAB MS). On the other hand, incubation of Lc 4 Ose-PtdEtn( N Ac) with IEC-6 cell homogenates in sialyltransferase assays yielded the corresponding sialylated product. When Lc 4 Ose-PtdEtn( N [ 14 C]Ac) was fed to IEC-6 cells as BSA complex, up to 5% of the NeoGL administered were taken up by the cells. After extraction of the NeoGL and separation by thin layer chromatography (TLC) the catabolic products Lc 3 Ose-PtdEtn( N [ 14 C]Ac), Lac-PtdEtn( N [ 14 C]Ac), and Glc-PtdEtn( N [ 14 C]Ac), as well as the main anabolic product NeuGc-Lc 4 Ose-PtdEtn( N [ 14 C]Ac) could be identified by FAB MS. These results demonstrate that PtdEtn-derived NeoGL can be used as probes for studies on the metabolism of specific oligosaccharide structures in cell culture.

Neoglycolipids Derived from Phosphatidylethanolamine Serve as Probes in Cell Culture Studies on Glycolipid Metabolism