Acid-catalyzed reductive amination of aldoses with 8-ammopyrene-1,3,6-trisulfonate

Ramon A. Evangelista, András Guttman, Fu Tai A. Chen

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

The reductive animation of monosaccharides with 8-aminopyrene-1,3,6-trisulfonate (APTS) in seven different organic acids including the commonly used acetic acid was investigated by capillary electrophoresis (CE) with laser-induced fluorescence (LIF) detection. The correlation between the yields of the saccharide-APTS adducts and pK, of the organic acid catalyst is consistent with general acid catalysis of the rate-determining step of the reductive amination reaction. Derivatization in the presence of organic acids of higher strength than acetic acid produced substantially higher yields of APTS-sugar adducts, an effect which is more pronounced for N-acetylamino sugars. Optimum yields were obtained using citric acid as a catalyst. Conversion of a few nanomoles of neutral saccharides to the APTS derivatives is achieved at 75°C in less than 60 min.

Original languageEnglish
Pages (from-to)347-351
Number of pages5
JournalELECTROPHORESIS
Volume17
Issue number2
DOIs
Publication statusPublished - Feb 1996

    Fingerprint

Keywords

  • Acid catalysis
  • Aldoses
  • Capillary electrophoresis
  • Laser-induced fluorescence
  • Reductive animation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

Cite this