Abstract
Sialic acids are a class of negatively charged nine-carbon sugars produced by many species, including both eukaryotes and prokaryotes. Variations in biosynthesis and modifications result in at least 50 variants of sialic acid occurring in nature. Sialic acids are typically found at the nonreducing terminus of glycoconjugates, a position that enables them to regulate a variety of extracellular recognition events. This chapter describes metabolic pathways for sialic acid biosynthesis and degradation, noting differences among species. The sialic acid biosynthetic pathway has also been exploited to enable metabolic production of unnatural sialic acid analogs that have nonnative functional groups, including bioorthogonal and photocrosslinking moieties. This chapter also describes these metabolic glycoengineering approaches and highlights some applications.
Similar content being viewed by others
References
Angata T, Varki A (2002) Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective. Chem Rev 102:439–469
Du J, Meledeo MA, Wang Z, Khanna HS, Paruchuri VD, Yarema KJ (2009) Metabolic glycoengineering: sialic acid and beyond. Glycobiology 19:1382–1401
Irie A, Koyama S, Kozutsumi Y, Kawasaki T, Suzuki A (1998) The molecular basis for the absence of N-glycolylneuraminic acid in humans. J Biol Chem 273:15866–15871
Kayser H, Zeitler R, Kannicht C, Grunow D, Nuck R, Reutter W (1992) Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-d-hexosamines as precursors. J Biol Chem 267:16934–16938
Li Y, Chen X (2012) Sialic acid metabolism and sialyltransferases: natural functions and applications. Appl Microbiol Biotech 94:887–905
Monti E, Bonten E, D’ Azzo A, Bresciani R, Venerando B, Borsani G, Schauer R, Tettamanti G (2010) Sialidases in vertebrates: a family of enzymes tailored for several cell functions. Adv Carbohydr Chem Biochem 64:403–479
Schwarzkopf M, Knobeloch KP, Rohde E, Hinderlich S, Wiechens N, Lucka L, Horak I, Reutter W, Horstkorte R (2002) Sialylation is essential for early development in mice. Proc Natl Acad Sci U S A 99:5267–5270
Sletten EM, Bertozzi CR (2011) From mechanism to mouse: a tale of two bioorthogonal reactions. Acc Chem Res 44:666–676
Tangvoranuntakul P, Gagneux P, Diaz S, Bardor M, Varki NM, Varki A, Muchmore E (2003) Human uptake and incorporation of an immunogenic non-human dietary sialic acid. Proc Natl Acad Sci U S A 100:12045–12050
Tanner ME (2005) The enzymes of sialic acid biosynthesis. Bioorg Chem 33:216–228
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Japan (outside the USA)
About this entry
Cite this entry
Fujita, A., Kohler, J.J. (2014). Metabolism of Natural and Unnatural Sialic Acid. In: Endo, T., Seeberger, P., Hart, G., Wong, CH., Taniguchi, N. (eds) Glycoscience: Biology and Medicine. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54836-2_70-1
Download citation
DOI: https://doi.org/10.1007/978-4-431-54836-2_70-1
Received:
Accepted:
Published:
Publisher Name: Springer, Tokyo
Online ISBN: 978-4-431-54836-2
eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences