Determination of the D- and L-configurations of Amino Deoxy Sugars by (S)-TBMBª¤Carboxylic Acid, a Fluorescent Chiral Derivatization Reagent

BAI Chen^*, LIANG Bo, WANG Shu-Zhen¹, ZHENG Xiao-Xun, LIN Zhi-Ping²ªª, HUANG Wei-Da

ª¤( Department of Biochemistry, School of Life Sciences, Fudan University, Shanghai 200433, China; Department of Biology,ª¤College of Life and Sciences, Shanghai Teachers University, Shanghai 200234, China;ªª Department of Chemistry, Fudan University,ª¤Shanghai 200433, China)

Abstract D- and L- amino sugars were coupled with (S)-TBMB £Û(S)-TBMB = (S)-2-tert-butyl-2-methyl-1, 3-benzodioxole£Ýcarbonyl chloride, a fluorescent chiral reagent, followed by per-O-acetylation. The reactions yielded diastereomeric per-O-acetylated ª«N-(S)-TBMB carbonyl amino sugars. Their ¹HNMR 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.
Key words D-ª«and L- configuration of amino deoxy sugars; fluorescent chiral reagent; (S)-TBMB carboxylic acid

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