Thiolactosides: Scaffolds for the Synthesis of Glycolipids in Animal Cells | Zendy

Masako Mori | Zendy; Maria Carmelita Z. Kasuya | Zendy; Mamoru Mizuno | Zendy; Kenichi Hatanaka | Zendy

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Thiolactosides: Scaffolds for the Synthesis of Glycolipids in Animal Cells

Author(s) -

Masako Mori,

Maria Carmelita Z. Kasuya,

Mamoru Mizuno,

Kenichi Hatanaka

Publication year - 2011

Publication title -

international journal of carbohydrate chemistry

Language(s) - English

Resource type - Journals

eISSN - 1687-935X

pISSN - 1687-9341

DOI - 10.1155/2011/267208

Subject(s) - glycolipid , glycosylation , ganglioside , chemistry , secretion , galactose , residue (chemistry) , cell culture , biochemistry , vero cell , cell , biology , in vitro , genetics

Various glycolipids were synthesized using thiolactosides as scaffolds for glycosylation in animal cells. The basic building blocks, n-dodecyl β-D-thiolactoside (β-LacSC12) and n-dodecyl α-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 of β-LacSC12 or α-LacSC12 resulted in sialylation of the terminal galactose residue and gave a GM3-type ganglioside. Administration of β-Lac SC12 in Madin-Darby canine kidney (MDCK) cells likewise gave a GM3-type ganglioside. On the other hand, introduction of β-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

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