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Characterization of mono-, di-, and tri-O-acetylated sialic acids on human cells.

Abstract
The presence of mono-, di-, and tri-O-acetylated sialic acids on human cells was demonstrated by using radiochromatographic and chemical techniques. Human melanoma cells and fresh colon tissue were biosynthetically labeled with 6- (3H) glucosamine. Radiolabeled sialic acids were hydrolytically removed from cellular glycoconjugates, purified by ion-exchange chromatography, and separated by paper chromatography on the basis of the number of O-substitutions on each sialic molecule. This analytical technique characterized radiolabeled sialic acids that migrated with the same Rf as synthetic mono-, di-, and tri-O-acetylated 14C-labeled sialic acids. The mono-O-acetylated sialic acids were characterized by their sensitivity to sodium periodate oxidation and a crude mouse liver esterase preparation. The di- and tri-O-acetylated sialic acids were characterized by their resistance to sodium periodate oxidation and sensitivity to the action of crude mouse liver esterase. Chromatographically separated di- and tri-O-acetylated sialic acids from normal human colon tissue were characterized by their respective ion molecular weights by using fast-atom bombardment-mass spectrometry. Using these methods, we chemically characterized mono, di-, and tri-O-acetylated sialic acids expressed on human cells. Aberrant expression of O-acetylated sialic acids was associated with adenocarcinoma of the colon, leading to a nearly complete loss of di- and tri-O-acetylated sialic acids.
AuthorsJ T Hutchins, C L Reading
JournalJournal of cellular biochemistry (J Cell Biochem) Vol. 37 Issue 1 Pg. 37-48 (May 1988) ISSN: 0730-2312 [Print] United States
PMID3392109 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Sialic Acids
Topics
  • Acetylation
  • Animals
  • Chromatography, Paper
  • Humans
  • Hydrolysis
  • Mass Spectrometry
  • Melanoma (metabolism)
  • Mice
  • Sialic Acids (metabolism)
  • Tumor Cells, Cultured (metabolism)

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