Abstract

Background: Several GC and HPLC methods have been proposed for the separation of aldose enantiomers.

Method: We developed a general HPLC method for the discrimination of (D,L)-monosaccharide components from natural products. The reaction involves the preparation of L-cysteine (3-nitrophenyl) methyl ester hydrochloride, which reacts with aldoses leading to thiazolidine derivatives.

Results: Direct HPLC analysis with reversed-phase column and UV detection, discriminated enantiomeric D- and L-monosaccharides in a highly sensitive manner.

Conclusion: This method was applied for the determination of the absolute configurations of monosaccharides in the natural poliumoside B, a tetraglycoside obtained from Teucrium polium.

Keywords: 2-polyhydroxyalkyl-thiazolidine-4(R)-carboxylic acids (3-nitrophenyl)methyl esters, enantioseparation, HPLC-UV, L-cysteine (3-nitrophenyl)methyl ester, monosaccharides.

Graphical Abstract