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The tetraacetylated N-(4-pentynoyl)-mannosamine (Ac4ManNAl) is an alkyne-labeled monosaccharide that provides a highly specific tool for studying glycoproteins through metabolic labeling in vivo and subsequent chemoselective ligation.

Ac4ManNAl is cell-permeable unnatural sugar that is intracellularly processed and incorporated instead of its natural monosaccharide counterpart N-acetylmannosamine (ManNAc).

The resulting alkyne-contained glycoprotein can be detected via Cu(I)-catalyzed (CuAAC) click reaction with either fluorescent-labeled azides or biotin-azide.