Direct Experimental Evidence of Ternary Diastereomeric Complexes in Chiral Separations of Phenylglycine Enatiomers with Chiral Mobile Phase by RP-HPLC

Abstract

Abstract:

Chiral separation of D-,L-phenylglycine by RP-HPLC was accomplished by adding a complex of optically active L-Phe-Cu²⁺ to the mobile phase. Chiral separation mechanism was further elucidated in light of unambiguously assigning the structure of the elutents from RP-HPLC by taking advantage of tandem mass spectrometry due to its unique capability of structural identification of the unknows. Mass spectrometry results revealed that the pair of eluents respresented a pair of ternary copper complexes with mixed ligands, providing the first experimental evidence. These complexes are diastereoisomer in nature. The optimized configuration of the diastereoisomer was predicted by theoretical calculation. In addition, the effects of the ratio of Cu²⁺ to L-Phe, pH of chiral mobile phase as well as the concentrations of methanol were investigated.

Key words: Chiral mobile phase, RP-HPLC, Phenylglycin, Mass spectrometry, Theoretical calculation

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YU Qing, CAO Jie*, ZHANG Cheng-Gen. Direct Experimental Evidence of Ternary Diastereomeric Complexes in Chiral Separations of Phenylglycine Enatiomers with Chiral Mobile Phase by RP-HPLC[J]. Chem. J. Chinese Universities, 2009, 30(5): 988.

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Direct Experimental Evidence of Ternary Diastereomeric Complexes in Chiral Separations of Phenylglycine Enatiomers with Chiral Mobile Phase by RP-HPLC

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