Metabolism of Natural and Unnatural Sialic Acid

Akiko Fujita, Jennifer J. Kohler

Research output: Chapter in Book/Report/Conference proceedingChapter

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.

Original languageEnglish (US)
Title of host publicationGlycoscience: Biology and Medicine
PublisherSpringer Japan
Pages1119-1128
Number of pages10
ISBN (Print)9784431548416, 9784431548409
DOIs
StatePublished - Jan 1 2015

Keywords

  • 2-Keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN)
  • Bioorthogonal
  • Metabolic glycoengineering
  • Metabolism
  • N-Acetylmannosamine (ManNAc)
  • N-Glycolylneuraminic acid (Neu5Gc)
  • Sialic acid (Sia)
  • Sialic acid analogs (Sia analogs)
  • Sialyltransferase
  • Uridine diphosphate N-acetylglucosamine (UDP-GlcNAc)

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Medicine(all)

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  • Cite this

    Fujita, A., & Kohler, J. J. (2015). Metabolism of Natural and Unnatural Sialic Acid. In Glycoscience: Biology and Medicine (pp. 1119-1128). Springer Japan. https://doi.org/10.1007/978-4-431-54841-6_70