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L-Cysteine (3-Nitrophenyl)methyl Ester Hydrochloride: A New Chiral Reagent in the Sugar Analysis

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.

Authors:   De Marino, Simona; Festa, Carmen; Iorizzi, Maria; Zollo, Franco
Journal:   Letters in Organic Chemistry
Facts, background information, dossiers
  • HPLC
  • monosaccharides
  • UV detection
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