Bifunctional Unnatural Sialic Acids for Dual Metabolic
Labeling of Cell-Surface Sialylated Glycans
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Abstract
Sialic acid analogues
containing a unique chemical functionality
or chemical reporter have been metabolically incorporated into sialylated
glycans. This process, termed metabolic glycan labeling, has emerged
as a powerful tool for studying sialylation as well as other types
of glycosylation. Currently, this technique can install only a single
functionality. Here we describe a strategy for dual labeling of sialylated
glycans using a new class of bifunctional sialic acid analogues containing
two distinct chemical reporters at the <i>N</i>-acyl and
C9 positions. These bifunctional unnatural sialic acids were metabolically
incorporated into cellular glycans, where the two chemical reporters
exerted their distinct functions. This approach expands the capability
of metabolic glycan labeling to probe sialylation and glycan–protein
interactions