Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

Bioorg Med Chem Lett. 2008 Nov 15;18(22):5945-7. doi: 10.1016/j.bmcl.2008.09.010. Epub 2008 Sep 6.


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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosynthetic Pathways
  • Cell Membrane / drug effects
  • Combinatorial Chemistry Techniques
  • Fibronectins / drug effects
  • HL-60 Cells
  • Halogenation*
  • Humans
  • Hydrocarbons, Fluorinated / chemistry*
  • Hydrocarbons, Fluorinated / pharmacology
  • Jurkat Cells
  • Oligosaccharides / metabolism*
  • Sialic Acids / biosynthesis
  • Sialic Acids / metabolism*


  • Fibronectins
  • Hydrocarbons, Fluorinated
  • Oligosaccharides
  • Sialic Acids