Sialic Acids and Other Nonulosonic Acids

Review
In: Essentials of Glycobiology [Internet]. 4th edition. Cold Spring Harbor (NY): Cold Spring Harbor Laboratory Press; 2022. Chapter 15.

Excerpt

Sialic acids (Sias) are abundant on vertebrate glycoproteins, glycolipids, and milk oligosaccharides, as well as on some microbial surface glycans, mediating diverse functional roles. Originally discovered within the Deuterostome lineage of animals and associated microbes, they are actually a subset of a more ancient family of α-keto acid monosaccharides with a 9-carbon backbone called nonulosonic acids (NulOs), which are also found in some Eubacteria and Archaea. Biosynthesis of all NulO-glycans requires the activation of NulO to a CMP-sugar, before the NulO is transferred to glycan acceptors. NulOs are remarkable for the number and the type of functional groups on one monosaccharide. Further complexity arises from various epimers, modifications, and diverse linkages to other glycans, making these molecules well-suited to carry information for glycan–protein, cell–cell, and pathogen–host recognition. NulOs are among the most rapidly evolving classes of monosaccharides in nature and exist in tremendous variety, particularly in the microbial world. Given their high density and widespread location on vertebrate cells, Sias also exert many functions via electronegative charge, such as repulsion of cell–cell interactions, protein stabilization, ion binding, and ion transport.

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