Thiolactosides: Scaffolds for the Synthesis of Glycolipids in Animal Cells

[摘要] Various glycolipids were synthesized using thiolactosides as scaffolds for glycosylation in animal cells. The basic building blocks,n-dodecylβ-D-thiolactoside (β-LacSC12) andn-dodecylα-D-thiolactoside (α-LacSC12), were chemically synthesized in 2 steps: glycosylation followed by deacylation. The thiolactosides were administered to animal cells in culture and served as substrates for cellular enzyme-catalyzed glycosylation. Incubation of mouse melanoma B16 cells in the presence ofβ-LacSC12 orα-LacSC12 resulted in sialylation of the terminal galactose residue and gave a GM3-type ganglioside. Administration ofβ-Lac SC12 in Madin-Darby canine kidney (MDCK) cells likewise gave a GM3-type ganglioside. On the other hand, introduction ofβ-LacSC12 in African green monkey kidney (Vero) cells gave Gb3- and Gb4-type glycolipids aside from GM3-type ganglioside.In the course of the study, significant changes in B16 cell morphology and elevated secretion of melanin were also observed.

[学科分类] 有机化学