Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway.
Metabolic oligosaccharide engineering has been employed to introduce fluorine-containing groups onto mammalian cell surfaces. Incubation of HeLa, Jurkat, and HL60 cells in culture with fluorinated sialic acid and mannosamine analogues resulted in cell-surface presentation of fluorinated glycans. Metabolic conversion of fluorinated precursors was detected and quantified by DMB-derivatization and HPLC ESI-MS analysis. Between 7% and 72% of total membrane-associated sialosides were fluorinated, depending on the precursor used and the cell type. Fluorination of mammalian cell surfaces provides a means for introducing a bioorthogonal surface for modulating noncovalent interactions such as those involved in cell adhesion.
Dafik
Laila
L
Department of Chemistry, Tufts University, Medford, 62 Talbot Avenue, MA 02155-5813, USA.
d'Alarcao
Marc
M
Kumar
Krishna
K
D053898:Biosynthetic Pathways; D002462:Cell Membrane / Q000187:drug effects; D020650:Combinatorial Chemistry Techniques; D005353:Fibronectins / Q000187:drug effects; D018922:HL-60 Cells; D054879:Halogenation; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry* / Q000494:pharmacology; D019169:Jurkat Cells; D009844:Oligosaccharides / Q000378:metabolism*; D012794:Sialic Acids / Q000096:biosynthesis / Q000378:metabolism*
D005353:Fibronectins; D006845:Hydrocarbons, Fluorinated; D009844:Oligosaccharides; D012794:Sialic Acids