Preparation and application of HPLC chiral stationary phases based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid

• Published in: Journal of separation science 2006-04, Vol.29 (6), p.750-761
• Main Author: Hyun, Myung Ho
• Format: Article
• Language: English
• Subjects: (+)-(18-Crown-6)-2; (+)‐(18‐Crown‐6)‐2,3,11,12‐tetracarboxylic acid; 12-tetracarboxylic acid; Adrenergic beta-Antagonists - chemistry; Adrenergic beta-Antagonists - isolation & purification; Amino Acids - chemistry; Amino Acids - isolation & purification; Analysis; Analytical chemistry; Biological and medical sciences; Chemistry; Chiral crown ether; Chiral separation; Chiral stationary phase; Chromatographic methods and physical methods associated with chromatography; Chromatography, High Pressure Liquid - methods; Crown Ethers - chemistry; Exact sciences and technology; General pharmacology; Liquid chromatography; Medical sciences; Molecular Structure; Other chromatographic methods; Pharmacology. Drug treatments; Silicon Dioxide; Stereoisomerism; Thermodynamics
• ISSN: 1615-9306; 1615-9314
• DOI: 10.1002/jssc.200500431

Preparation of liquid chromatographic chiral stationary phases (CSPs) based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid and their application are reviewed. The various methods of connecting (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid to silica gel covalently or dynamically are demonstrated. The CSPs based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid have been very successful for the resolution of various primary amino compounds with the use of an aqueous mobile phase containing organic and acidic modifiers. In addition, the resolution of secondary amino compounds including β‐blockers and N‐(3,5‐dinitrobenzoyl)‐α‐amino acids has been demonstrated on a CSP based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid with a non‐aqueous mobile phase.