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

Author(s): Simona De Marino, Carmen Festa, Maria Iorizzi, Franco Zollo.

Journal Name: Letters in Organic Chemistry

Volume 14 , Issue 2 , 2017

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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.

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Article Details

VOLUME: 14
ISSUE: 2
Year: 2017
Page: [69 - 73]
Pages: 5
DOI: 10.2174/1570178614666170123122831
Price: $58

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