Acid-catalyzed reductive amination of aldoses with 8-aminopyrene-1,3,6-trisulfonate.
The reductive amination 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 pKa 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 degrees C in less than 60 min.
Evangelista
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Beckman Instruments Inc., Fullerton, CA 92634, USA.
Guttman
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Chen
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D000143:Acids / Q000737:chemistry*; D000586:Amination; D004305:Dose-Response Relationship, Drug; D009005:Monosaccharides / Q000032:analysis*; D010084:Oxidation-Reduction; D011721:Pyrenes / Q000737:chemistry*; D013997:Time Factors
C103430:8-aminopyrene-1,3,6-trisulfonic acid; D000143:Acids; D009005:Monosaccharides; D011721:Pyrenes