Direct stereochemical resolution of aspartame stereoisomers and their degradation products by high-performance liquid chromatography on a chiral crown ether based stationary phase |
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Authors: | S Motellier I W Wainer |
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Institution: | Pharmaceutical Division, St. Jude Children's Research Hospital, Memphis, TN 38105. |
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Abstract: | The direct stereochemical resolution of the four stereoisomers of aspartame (N-DL-alpha-aspartyl-DL-phenylalanine methyl ester) and their degradation products was achieved on a high-performance liquid chromatography chiral stationary phase based upon a chiral crown ether. The chromatographic conditions included a mobile phase composed of aqueous perchloric acid adjusted to a pH of 2.8 and modified with 1.5% of 2-propanol and a temperature gradient. The active L,L-isomer (sold under the brand name NutraSweet) was measured in a diet cola and coffee sweetened with NutraSweet. Degradation products of NutraSweet were also detected but no racemization of stereochemical contamination was observed. |
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