Abstract
Metabolic oligosaccharide engineering (MOE) provides a method to install novel chemical functional groups into the glycocalyx of living cells. In this Letter we use this technology to compare the impact of replacing natural sialic acid, GalNAc, and GlcNAc with their thiol-bearing counterparts in Jurkat and HL-60 cells. When incubated in the presence of gold-coated nanofibers, only Jurkat cells incubated with Ac(5)ManNTGc-an analogue that installs thiols into sialosides-experienced a distinctive 'spreading' morphology. The comparison of Ac(5)ManNTGc with Ac(5)GalNTGc and Ac(5)GlcNTGc in the two cell lines implicated sialosides of N-linked glycans as critical molecular mediators of the unusual responses evoked in the Jurkat line.