Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:18

Article

Dafik, Laila²  d'Alarcao, Marc¹  Kumar, Krishna^2,3 

[1] San Jose State Univ, Dept Chem, San Jose, CA 95192 USA

[2] Tufts Univ, Dept Chem, Medford, MA 02155 USA

[3] Tufts Med Ctr, Ctr Canc, Boston, MA 02110 USA

关键词: Glycoengineering;    Sialic acid;    Fluorination;    Cell adhesion;   

DOI  :  10.1016/j.bmcl.2008.09.010

来源: Elsevier

【 摘 要 】

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. (C) 2008 Elsevier Ltd. All rights reserved.

【 授权许可】

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