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. Direct HPLC analysis with reversed-phase column and UV detection, discriminated enantiomeric D- and L-monosaccharides in a highly sensitive manner. This method was applied for the determination of the absolute configurations of monosaccharides in the natural poliumoside B, a tetraglycoside obtained from Teucrium polium.
L-Cysteine (3-Nitrophenyl)methyl ester hydrochloride: a new chiral reagent in the sugar analysis / DE MARINO, Simona; Festa, Carmen; Iorizzi, M.; Zollo, Franco. - In: LETTERS IN ORGANIC CHEMISTRY. - ISSN 1570-1786. - 14:(2017), pp. 69-73. [doi: 10.2174/1570178614666170123122831]
L-Cysteine (3-Nitrophenyl)methyl ester hydrochloride: a new chiral reagent in the sugar analysis
DE MARINO, SIMONAPrimo
;FESTA, CARMENSecondo
;ZOLLO, FRANCO
Ultimo
2017
Abstract
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. Direct HPLC analysis with reversed-phase column and UV detection, discriminated enantiomeric D- and L-monosaccharides in a highly sensitive manner. This method was applied for the determination of the absolute configurations of monosaccharides in the natural poliumoside B, a tetraglycoside obtained from Teucrium polium.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
