Direct stereochemical resolution of aspartame stereoisomers and their degradation products by high-performance liquid chromatography on a chiral crown ether based stationary phase.
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.
Motellier
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Pharmaceutical Division, St. Jude Children's Research Hospital, Memphis, TN 38105.
Wainer
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IW
D000433:1-Propanol; D001218:Aspartame / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004988:Ethers, Cyclic; D013237:Stereoisomerism; D013549:Sweetening Agents / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D013696:Temperature
D004988:Ethers, Cyclic; D013549:Sweetening Agents; D000433:1-Propanol; D001218:Aspartame