Evaluation and Comparison of a 3,5-Dimethylphenyl Isocyanate Teicoplanin with Phenyl Isocyanate Teicoplanin Chiral Stationary Phase Using RP-HPLC

• Published in: Chinese journal of chemistry Vol. 30; no. 1; pp. 157 - 162
• Main Author: 沈报春 张大同 余小燕 郭伟 韩亚琼 徐秀珠
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 2012; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: 3,5‐dimethylphenylisocyanate teicoplanin; 5-dimethylphenylisocyanate teicoplanin; Amino acids; chiral stationary phase; Chromatography; Isocyanates; Liquid chromatography; phenylisocyanate teicoplanin; 二甲基; 对映体分离; 手性固定相; 替考拉宁; 甲基异氰酸酯; 苯基异氰酸酯; 评价; 高效液相色谱法
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.201180463

HPLC enantiomeric separations of 8 a-amino acids were achieved using two self-made chiral stationary phases （CSP）-henyl isocyanate teicoplanin （Phe-TE） and 3,5-dimethylphenyl isocyanate teicoplanin （DMP-TE）, using reversed phase mobile phases. The Phe-TE or the DMP-TE CSP was prepared from the TE using derivative agents, phenyl isocyanate or 3,5-dimethylphenyl isocyanate, respectively. The chromatographic results were given as the retention, selectivity, resolution factor and the enantioselective free energy difference corresponding to the separation of the two enantiomers. The effect of pH, organic modifier type and amount were discussed, and the stereose- lectivities for two TE-based CSPs were compared. The chiral selectivity factor for six a-amino acids on DMP-TE is somewhat bigger than that on Phe-TE CSP under reversed phase （RP） mode. Comparison of the enantiomeric separations using self-made Phe-TE and DMP-TE was conducted to gain a better understanding of the chiral recognition mechanism of the macrocyclic glycopeptide CSP.