[Determination of the D- and L-configurations of amino deoxy sugars by (S)-TBMB carboxylic acid, a fluorescent chiral derivatization reagent].
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.
Bai
Chen
C
Department of Biochemistry, School of Life Sciences, Fudan University, Shanghai 200433, China. baichen@fudan.edu.cn
Liang
Bo
B
Wang
Shu-Zhen
SZ
Zheng
Xiao-Xun
XX
Lin
Zhi-Ping
ZP
Huang
Wei-Da
WD
D000606:Amino Sugars / Q000032:analysis*; D002236:Carbohydrate Conformation; D002264:Carboxylic Acids; D003837:Deoxy Sugars / Q000032:analysis*; D004149:Dioxoles; D005456:Fluorescent Dyes; D015394:Molecular Structure
C435704:2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid; D000606:Amino Sugars; D002264:Carboxylic Acids; D003837:Deoxy Sugars; D004149:Dioxoles; D005456:Fluorescent Dyes