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Acid‐catalyzed reductive amination of aldoses with 8‐aminopyrene‐1,3,6‐trisulfonate
Author(s) -
Evangelista Ramon A.,
Guttman András,
Chen FuTai A.
Publication year - 1996
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.1150170210
Subject(s) - reductive amination , amination , catalysis , chemistry , combinatorial chemistry , organic chemistry
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 p K a 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.