AMACE1: versatile aminoacetamide electrophore reagent

Acetamide, 2-amino-N-[[3,5-bis(trifluoromethyl)phenyl]-methyl]-N-methyl-, monohydrochloride, which we have named AMACE1, was synthesized in three steps starting from N-tritylglycine. AMACE1 was coupled via its primary amine group (pKa 8.2) under aqueous conditions to four model analytes for oxidative sugar damage to DNA: glycolate, 3-hydroxy-2-butanone, 3-phenylbutyraldehyde, and alpha-hydroxy-gamma-butyrolactone, relying on cyanoborohydride for coupling to a keto function and a water-soluble carbodiimide for coupling to a carboxyl function. Further reaction with butyric anhydride led to products that could be detected by gas chromatography/electron capture mass spectrometry when 1 microL of ethyl acetate containing essentially 20 amol of each product was injected, on the basis of selected ion monitoring of the analyte characteristic anion fragment from dissociative loss of the 3,5-bis-(trifluoromethyl)phenylmethyl moiety: m/z 215, 289, 299, and 329, respectively. Since many small, organic analytes contain a keto or carboxylic acid group, AMACE1 should be useful in general in the area of trace organic analysis.