Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells

Neil W. Charter, Lara Mahal, Daniel E. Koshland, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

Abstract

In this study we demonstrate that polysialyltransferases are capable of accepting unnatural substrates in terminally differentiated human neurons. Polysialyltransferases catalyze the glycosylation of the neural cell adhesion molecule (NCAM) with polysialic acid (PSA). The unnatural sialic acid analog, N-levulinoyl sialic acid (SiaLev), was incorporated into cell surface glycoconjugates including PSA by the incubation of cultured neurons with the metabolic precursor N-levulinoylmannosamine (ManLev). The ketone group within the levulinoyl side chain of SiaLev was then used as a chemical handle for detection using a biotin probe. The incorporation of SiaLev residues into PSA was demonstrated by protection from sialidases that can cleave natural sialic acids but not those bearing unnatural N-acyl groups. The presence of SiaLev groups on the neuronal cell surface did not impede neurite outgrowth or significantly affect the distribution of PSA on neuronal compartments. Since PSA is important in neural plasticity and development, this mechanism for modulating PSA structure might be useful for functional studies.

Original languageEnglish (US)
Pages (from-to)1049-1056
Number of pages8
JournalGlycobiology
Volume10
Issue number10
StatePublished - 2000

Fingerprint

Sialic Acids
Neurons
Bearings (structural)
Glycosylation
Neural Cell Adhesion Molecules
Neuronal Plasticity
Glycoconjugates
N-Acetylneuraminic Acid
Biotin
Ketones
Plasticity
polysialic acid
N-levulinoylsialic acid
Substrates

Keywords

  • Biosynthesis
  • NCAM
  • Polysialyltransferase
  • Sialic acid

ASJC Scopus subject areas

  • Biochemistry

Cite this

Charter, N. W., Mahal, L., Koshland, D. E., & Bertozzi, C. R. (2000). Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells. Glycobiology, 10(10), 1049-1056.

Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells. / Charter, Neil W.; Mahal, Lara; Koshland, Daniel E.; Bertozzi, Carolyn R.

In: Glycobiology, Vol. 10, No. 10, 2000, p. 1049-1056.

Research output: Contribution to journalArticle

Charter, NW, Mahal, L, Koshland, DE & Bertozzi, CR 2000, 'Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells', Glycobiology, vol. 10, no. 10, pp. 1049-1056.
Charter, Neil W. ; Mahal, Lara ; Koshland, Daniel E. ; Bertozzi, Carolyn R. / Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells. In: Glycobiology. 2000 ; Vol. 10, No. 10. pp. 1049-1056.
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