Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation

E Saxon, SJ Luchansky, HC Hang, C Yu…

Index: Saxon, Eliana; Luchansky, Sarah J.; Hang, Howard C.; Yu, Chong; Lee, Sandy C.; Bertozzi, Carolyn R. Journal of the American Chemical Society, 2002 , vol. 124, # 50 p. 14893 - 14902

Full Text: HTML

Citation Number: 241

Abstract

The structure of sialic acid on living cells can be modulated by metabolism of unnatural biosynthetic precursors. Here we investigate the conversion of a panel of azide- functionalized mannosamine and glucosamine derivatives into cell-surface sialosides. A key tool in this study is the Staudinger ligation, a highly selective reaction between modified triarylphosphines and azides that produces an amide-linked product. A preliminary study ...