Analytical Science, LG Chem. Research Park, LG Chem. Ltd., Yusong-Gu, Daejeon, South Korea.
Chirality. 2012 Dec;24(12):1037-46. doi: 10.1002/chir.22094. Epub 2012 Jul 31.
Enantiomeric separations of N-phthaloyl (N-PHT), N-tetrachlorophthaloyl (N-TCPHT), and N-naphthaloyl (N-NPHT) α-amino acids and their esters were examined on several kinds of polysaccharide-derived chiral stationary phases (CSPs). Resolution capability of CSPs was greater Chiralcel OF than the others for N-PHT and N-NPHT α-amino acids and their esters. In N-TCPHT α-amino acids and their esters, good enantioselectivities showed Chiralcel OG for N-TCPHT α-amino acids, Chiralpak AD for N-TCPHT α-amino acid methyl esters, and Chiralcel OD for N-TCPHT α-amino acid ethyl esters, respectively. From the results of liquid chromatography and computational chemistry, it is concluded that l-form is preferred and more retained with electrostatic interaction in case of interaction between N-PHT α-amino acid derivatives and Chiralcel OF, N-TCPHT α-amino acid derivatives and Chiralcel OD, and N-NPHT α-amino acid derivatives and Chiracel OF. On the other hand, d-form is preferred and more retained with van der Waals interaction in case of interaction between N-TCPHT α-amino acid ester derivatives and Chiralcel OG and Chiralpak AD.
对几种多糖衍生的手性固定相（CSP）进行了 N-邻苯二甲酰基（N-PHT）、N-四氯邻苯二甲酰基（N-TCPHT）和 N-萘邻苯二甲酰基（N-NPHT）α-氨基酸及其酯的对映体分离研究。对于 N-PHT 和 N-NPHTα-氨基酸及其酯，CSP 的分辨能力大于 Chiralcel OF。对于 N-TCPHTα-氨基酸及其酯，Chiralcel OG 对 N-TCPHTα-氨基酸、Chiralpak AD 对 N-TCPHTα-氨基酸甲酯和 Chiralcel OD 对 N-TCPHTα-氨基酸乙酯具有良好的对映选择性。从液相色谱和计算化学的结果可以得出结论，在 N-PHTα-氨基酸衍生物与 Chiralcel OF、N-TCPHTα-氨基酸衍生物与 Chiralcel OD 和 N-NPHTα-氨基酸衍生物与 Chiracel OF 之间的相互作用中，l-构型优先且静电相互作用保留更强。另一方面，在 N-TCPHTα-氨基酸酯衍生物与 Chiralcel OG 和 Chiralpak AD 之间的相互作用中，d-构型优先且范德华相互作用保留更强。
