The reaction of acetylacetone with amino sugars: implications for the formation of glycosylpyrazole derivatives

Warren C. Kett

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Glycosylpyrazoles are efficiently formed by reaction of saccharide hydrazones with pentan-2,4-dione (acetylacetone), but in aqueous buffer, pyrazole derivatives of amino sugars couple with a further equivalent of acetylacetone affording high yields of ketoenamines. These ketoenamines were considerably more stable than the ketoenamines formed from 2-amino-2-deoxy aldoses that have been described as intermediates in the classical Elson-Morgan reaction. Moreover, high yields of perketoenamine derivatives were achieved with oligosaccharides derived from hydrolysis of chitosan. The removal of the ketoenamine moieties to regenerate the free amine was readily accomplished with aqueous hydrazine.
Original languageEnglish
Pages (from-to)819-826
Number of pages8
JournalCarbohydrate Research
Volume338
Issue number9
DOIs
Publication statusPublished - 2003

Keywords

  • Acetylacetone
  • Carbohydrate labelling
  • Chitosan
  • Ketoenamine
  • Pyrazole
  • Sugar hydrazone

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