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J Biol Chem, Vol. 273, Issue 47, 31168-31179, November 20, 1998
From the Department of Chemistry, University of California,
Berkeley, California 94720 and Materials Sciences Division, Lawrence
Berkeley National Laboratory, Berkeley, California 94720
The development of chemical strategies for
decorating cells with defined carbohydrate epitopes would greatly
facilitate studies of carbohydrate-mediated cell surface interactions.
This report describes a general strategy for engineering the display of
chemically defined oligosaccharides on cell surfaces that combines the
concepts of metabolic engineering and selective chemical reactivity.
Using a recently described method (Mahal, L. K., Yarema, K. J., and Bertozzi, C. R. (1997) Science 276, 1125-1128), we delivered a uniquely reactive ketone group to
endogenous cell surface sialic acid residues by treating cells with the
ketone-bearing metabolic precursor N-levulinoylmannosamine
(ManLev). The ketone undergoes highly selective condensation reactions
with complementary nucleophiles such as aminooxy and hydrazide groups.
The detailed quantitative parameters of ManLev metabolism in human and
nonhuman-derived cell lines were determined to establish a foundation
for the modification of cell surfaces with novel epitopes at defined
cell-surface densities. Ketones within the glycoconjugates on
ManLev-treated cells were then reacted with synthetic aminooxy and
hydrazide-functionalized carbohydrates. The remodeled cells were
endowed with novel lectin binding profiles as determined by flow
cytometry analysis. The simplicity and generality of this method make
it well suited for use in the study of carbohydrate-mediated cell
surface interactions.
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