Zerbinati Orfeo, Trotta Francesco
Dipartimento di Scienze e Tecnologie Avanzate, Università del Piemonte Orientale A. Avogadro, Spalto Marengo 33/35, I-15100 Alessandria, Italy.
Electrophoresis. 2003 Aug;24(15):2456-61. doi: 10.1002/elps.200305518.
Five noncommercial and four commercially available cyclodextrin (CD) derivatives were tested as chiral auxiliaries for the capillary electrophoretic (CE) resolution of racemic 1,1'-bi-(2-naphthol) (BN), 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (BNHP), and 1,1'-binaphthyl-2,2'-diamine (BNA) at pH 4.0, 6.5, and 8.6. The noncommercial CDs were ethyloxycarbonyl-gamma-CD (ethylcarbonate-gamma-CD), dimethylamino ethyloxycarbonyl-beta-CD, a mercaptosuccinic acid derivative of beta-CD, a maleic acid derivative of beta-CD and heptakis(6-deoxy-6-amino)-beta-CD derivative with one amino group on the C-6 carbon of each glucose unit. Except for the latter, the remaining derivatives were synthesized for this work. Also commercially available methyl-beta-CD, hydroxypropyl-beta-CD and the native beta- and gamma-CDs were examined. Among the nine CDs tested, the maleic acid derivative of beta-CD gave the most interesting performances, since it resolved the atropisomers of BNA and BNHP in the same electrophoretic run at pH 4.0. It resolved the BNA racemate also at pH 6.5. Both the negatively charged CD tested were found to resolve anionic BNHP enantiomers, while positively charged CDs did not with cationic BNA. Several of the CDs investigated in this work were found to resolve the BNHP racemate, although at nonoptimal concentration. None of the experimented CDs was found to resolve the electrically neutral BN atropisomers pair at the three pHs considered, while some among these nine, experimented in a previous work, did so at higher pH.
测试了五种非商业性和四种市售的环糊精（CD）衍生物作为手性助剂，用于在pH 4.0、6.5和8.6条件下对消旋1,1'-联（2-萘酚）（BN）、1,1'-联萘基-2,2'-二磷酸氢酯（BNHP）和1,1'-联萘基-2,2'-二胺（BNA）进行毛细管电泳（CE）拆分。非商业性CD包括乙氧基羰基-γ-环糊精（碳酸乙酯-γ-环糊精）、二甲基氨基乙氧基羰基-β-环糊精、β-环糊精的巯基琥珀酸衍生物、β-环糊精的马来酸衍生物以及每个葡萄糖单元C-6碳上带有一个氨基的七（6-脱氧-6-氨基）-β-环糊精衍生物。除了后者，其余衍生物均为本研究合成。还检测了市售的甲基-β-环糊精、羟丙基-β-环糊精以及天然的β-和γ-环糊精。在所测试的九种环糊精中，β-环糊精的马来酸衍生物表现出最有趣的性能，因为它在pH 4.0的同一电泳运行中拆分了BNA和BNHP的阻转异构体。它在pH 6.5时也拆分了BNA外消旋体。所测试的两种带负电荷的环糊精都能拆分带阴离子的BNHP对映体，而带正电荷的环糊精对带阳离子的BNA则不能。本研究中研究的几种环糊精能拆分BNHP外消旋体，尽管浓度并非最佳。在所考虑的三个pH值下，未发现所测试的环糊精能拆分电中性的BN阻转异构体对，而在之前的一项研究中测试的这九种环糊精中的一些在更高pH值下能做到。
