Development of highly sensitive system for determination of absolute configuration of natural-products by labelling with chiral fluorescent reagents

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We have developed a chiral fluorescent labelling reagent, (S)-2-tert-butyl-2-methyl[-], 3-benzodioxole-4-carboxylic acid(1), and determined. the absolute configurations of ciguatoxin and ganbieric acid by the system to use 1 as a labelling reagent. We have also developed a new Chiral analysis method, on-line-HPLC-exciton-CD method using 1 for the determination of absolute configuration of vicinal diols, amino alochols, and diamines. A new highly sensitive methylation analysis system of oligosaccharides that can determine D, L of monosaccharide by labelling with a newly developed (S)-2-methyl-2-β-naphthyl-1, 3-benzodioxole-4-carboxylic acid(2)was developed, and the absolute configuration of a naturalproduct, polycaevenoside A was determined by the system.A new chiral flurorescent labelling reagent, (R, R)-and(S, S)-2-(2, 3-anthrac-enecarboximido)cyclohexanol(3), for the descrimimnation of the chirality at the position remote from the derivatizable carboxyl group was developed. and the absolute configurations of a ceramide and a ganglioside were determined by the system using 3.Further, (R, R)- and(S, S)-2-(2, 3-anthracenedicarboximido)cycloh-exane carboxylic acid(4)and 3, 4, 6-tri-O-acetyl-2-deoxy-2-(2, 3-naphthalenedica-roboximido)-β-D-glucopyranosyl bromide(5)for derivatization of chirai alcohols were developed. A system for the. determination of absolute configuration of chiral alchols with chiral center at the position remote from the hydroxy group was developed.