A Highly Sensitive HPLC Method to Determine the Absolute Configuration of Glycosyl Diacylglycerols Using a Fluorescent Chiral Derivatizing Reagent

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Abstract
Structural elucidations of naturally occurring glycosyl diacylglycerols have been hampered by the difficulty of the assignment of the absolute configuration at the glycerol moiety. Although several approaches towards solving this problem have been proposed,1-6 they were not satisfactory in their simplicity or sensitivity. Hence, the absolute configurations have been usually determined through total syntheses starting from chiral glycerols with known configurations.7-9 Previously,10 we have developed a fluorescent chiral derivatizing agent, (S)-(+)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid [(S)-TBMB carboxylic acid, Scheme]. This agent or its ester having strong fluorescence with the maximum emission wavelength at ca. 380 nm and the excitation maximum at ca. 310 nm has provided useful ways to discriminate d,l-isomers of amino acids,10 monosaccharides,11 and diacylglycerols.12 In this paper, we report a highly sensitive HPLC way to determine the absolute configuration of glycosyl diacylglycerols using (S)-TBMB carboxylic acid.