[Determination of the D- and L-configurations of amino deoxy sugars by (S)-TBMB carboxylic acid, a fluorescent chiral derivatization reagent].

ABSTRACT

D- and L- amino sugars were coupled with (S)-TBMB (S)-TBMB = (S)-2-tert-butyl-2-methyl-1, 3-benzodioxole carbonyl chloride, a fluorescent chiral reagent, followed by per-O-acetylation. The reactions yielded diastereomeric per-O-acetylated N-(S)-TBMB carbonyl amino sugars. Their (1)HNMR signals, especially the strong singlet peaks of tert-Bu and Me groups were diagnostic for the determination of the D-, L- configurations of amino sugar. Furthermore, a simple and highly sensitive method for the determination of the D-, L- configuration of amino deoxy sugars was developed based on the same fluorescent labeling method and reverse phase HPLC. The total time in analysis is less than two hours and the detection limit of the method is 0.2 picomolar.