The role of π-acidic and π-basic chiral stationary phases in the high-performance liquid chromatographic enantioseparation of unusual β-amino acids

✍ Scribed by István Ilisz; Róbert Berkecz; Enikő Forró; Ferenc Fülöp; Daniel W. Armstrong; Antal Péter

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 136 KB
• Volume: 21
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20542

✦ Synopsis

Abstract

The application of 3,5‐dimethylphenyl‐carbamoylated‐β‐cyclodextrin (Cyclobond I 2000 DMP) and 2,6‐dinitro‐4‐trifluoromethylphenyl‐ether‐β‐cyclodextrin‐based (Cyclobond DNP) chiral stationary phases for the high‐performance liquid chromatographic enantioseparation of unusual β‐amino acids is reported. The investigated amino acids were saturated or unsaturated alicyclic β‐3‐homo‐amino acids and bicyclic β‐amino acids. Prior to chromatographic analyses, all amino acids were transformed to __N‐__3,5‐dinitrobenzoyl‐ or N‐3,5‐dimethylbenzoyl form to ensure a π‐acidic or π‐basic function and to enhance the π‐acidic‐π‐basic interactions between analytes and chiral selectors. Chromatographic results are given as retention, separation and resolution factors. The chromatographic conditions were varied to achieve optimal separation. The sequence of elution of the enantiomers was determined in some cases. Chirality, 2009. © 2008 Wiley‐Liss, Inc.