Liu Ying, Berthod Alain, Mitchell Clifford R, Xiao Tom Ling, Zhang Bo, Armstrong Daniel W
Iowa State University, Department of Chemistry, Gilman Hall, Ames, IA 50011, USA.
J Chromatogr A. 2002 Nov 29;978(1-2):185-204. doi: 10.1016/s0021-9673(02)01356-0.
The chiral recognition capabilities of three macrocyclic glycopeptide chiral selectors, namely teicoplanin (Chirobiotic T), its aglycone (Chirobiotic TAG) and ristocetin (Chirobiotic R), were evaluated with supercritical and subcritical fluid mobile phases. A set of 111 chiral compounds including heterocycles, analgesics (nonsteroidal antiinflamatory compounds), beta-blockers, sulfoxides, N-protected amino acids and native amino acids was separated on the three chiral stationary phases (CSPs). All separations were done with an outlet pressure regulated at 100 bar, 31 degrees C and at 4 ml/min. Various amounts of methanol ranging from 7 to 67% (v/v) were added to the carbon dioxide along with small amounts (0.1 to 0.5%, v/v) of triethylamine and/or trifluoroacetic acid. The Chirobiotic TAG CSP was the most effective closely followed by the Chirobiotic T column. Both columns were able to separate, partially or fully, 92% of the enantiomers of the compound set. The ristocetin chiral selector could partially or baseline resolve only 60% of the enantiomers tested. All separations were done in less than 15 min and 70% were done in less than 4 min. The speed of the separations is the main advantage of the use of SFC compared to normal-phase HPLC. In addition, SFC is advantageous for preparative separations with easy solute recovery and solvent disposal.
采用超临界和亚临界流体流动相评估了三种大环糖肽手性选择剂的手性识别能力，这三种手性选择剂分别是替考拉宁（手性抗生素T）、其苷元（手性抗生素TAG）和瑞斯托菌素（手性抗生素R）。在这三种手性固定相（CSP）上分离了一组111种手性化合物，包括杂环化合物、镇痛药（非甾体抗炎化合物）、β-受体阻滞剂、亚砜、N-保护氨基酸和天然氨基酸。所有分离均在出口压力为100 bar、温度为31℃、流速为4 ml/min的条件下进行。向二氧化碳中加入7%至67%（v/v）不等的各种量的甲醇，以及少量（0.1%至0.5%，v/v）的三乙胺和/或三氟乙酸。手性抗生素TAG CSP最有效，紧随其后的是手性抗生素T柱。两根柱子都能够部分或完全分离化合物组中92%的对映体。瑞斯托菌素手性选择剂只能部分或基线分离60%的测试对映体。所有分离均在不到15分钟内完成，70%的分离在不到4分钟内完成。与正相高效液相色谱相比，超临界流体色谱分离速度快是其主要优势。此外，超临界流体色谱有利于制备分离，溶质回收和溶剂处理都很容易。
