Metabolism of Natural and Unnatural Sialic Acid

Akiko Fujita, Jennifer J. Kohler

Research output: Chapter in Book/Report/Conference proceedingChapter


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
Subtitle of host publicationBiology and Medicine
PublisherSpringer Japan
Number of pages10
ISBN (Electronic)9784431548416
ISBN (Print)9784431548409
StatePublished - Jan 1 2015


  • 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

  • General Biochemistry, Genetics and Molecular Biology
  • General Medicine


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