Tritium labelling of amino sugars at C-2 by alkaline epimerization in tritiated water

Glycobiology. 1995 Mar;5(2):167-73. doi: 10.1093/glycob/5.2.167.

Abstract

N-Acetyl-D-[2-3H]glucosamine was synthesized from N-acetyl-D-mannosamine by alkaline 2-epimerization in pyridine containing 3H2O and nickelous acetate. The reaction involves reversible formation of an enol intermediate and therefore also resulted in incorporation of tritium into N-acetylmannosamine. After completed reaction, the two N-acetylhexosamines were separated from other radioactive products and Morgan-Elson chromogens by chromatography on a column of Sephadex G-10, which was eluted with 10% ethanol, and were then separated from each other by chromatography on Sephadex G-15 in 0.27 M sodium borate (pH 7.8). The location of the incorporated tritium was established by treatment of the N-acetylhexosamines with borate under the conditions of the Morgan-Elson reaction, which converts the sugars to Kuhn's chromogen I with concomitant loss of the C-2 hydrogen. As expected, this treatment resulted in the formation of 3H2O, indicating that the tritium was located at C-2. [2-3H]Glucosamine was prepared by acid hydrolysis of the labelled N-acetylglucosamine and was converted to [2-3H]glucosamine 6-phosphate by incubation with hexokinase and ATP. The sugar phosphate was used as a substrate for glucosamine 6-phosphate deaminase (isomerase, EC 5.3.1.10) in a simple 3H2O release assay.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetylglucosamine / chemical synthesis*
  • Acetylglucosamine / isolation & purification
  • Acetylglucosamine / metabolism
  • Aldose-Ketose Isomerases*
  • Carbohydrate Epimerases / isolation & purification
  • Carbohydrate Epimerases / metabolism
  • Chromatography, Gel
  • Chromatography, Paper
  • Electrophoresis, Paper
  • Hexosamines
  • Hot Temperature
  • Hydrolysis
  • Indicators and Reagents
  • Isotope Labeling / methods*
  • Kinetics
  • Saccharomyces cerevisiae / enzymology
  • Tritium
  • Water

Substances

  • Hexosamines
  • Indicators and Reagents
  • Water
  • Tritium
  • glucosamine-6-phosphate isomerase
  • Carbohydrate Epimerases
  • Aldose-Ketose Isomerases
  • Acetylglucosamine
  • N-acetylmannosamine