Cellular metabolism of unnatural sialic acid precursors

Nam D. Pham, Charles S. Fermaintt, Andrea C. Rodriguez, Janet E. McCombs, Nicole Nischan, Jennifer J. Kohler

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


Carbohydrates, in addition to their metabolic functions, serve important roles as receptors, ligands, and structural molecules for diverse biological processes. Insight into carbohydrate biology and mechanisms has been aided by metabolic oligosaccharide engineering (MOE). In MOE, unnatural carbohydrate analogs with novel functional groups are incorporated into cellular glycoconjugates and used to probe biological systems. While MOE has expanded knowledge of carbohydrate biology, limited metabolism of unnatural carbohydrate analogs restricts its use. Here we assess metabolism of SiaDAz, a diazirine-modified analog of sialic acid, and its cell-permeable precursor, Ac4ManNDAz. We show that the efficiency of Ac4ManNDAz and SiaDAz metabolism depends on cell type. Our results indicate that different cell lines can have different metabolic roadblocks in the synthesis of cell surface SiaDAz. These findings point to roles for promiscuous intracellular esterases, kinases, and phosphatases during unnatural sugar metabolism and provide guidance for ways to improve MOE.

Original languageEnglish (US)
Pages (from-to)515-529
Number of pages15
JournalGlycoconjugate Journal
Issue number7
StatePublished - Oct 1 2015


  • Diazirine
  • Esterase
  • Metabolic engineering
  • Photocrosslinking
  • Sialic acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Cell Biology


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