Evaluation of π-acid chiral stationary phases deriving from tyrosine and related amino acids for the chromatographic resolution of racemates: Specific requirements for enantiorecognition ability
✍ Scribed by M. Liene; P. Macaudìre; M. Caude; R. Rosset; A. Tambut´
- Publisher
- John Wiley and Sons
- Year
- 1989
- Tongue
- English
- Weight
- 977 KB
- Volume
- 1
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
Chromatographic applications of three novel chiral stationary phases (CSPs) deriving from (S)-(N)-(3,5-dinitrobenzoyl)tyrosine are reported, under liquid chromatographic (LC) and subcritical fluid chromatographic (SubFC) conditions. Two grafting modes of the chiral moiety have been experimented starting either from y-mercaptopropyl-silanized (type 1) or y-aminopropyl-silanized (type 2) silica gels. For type 2 CSPs an evaluation of the stability of the amide linkage was achieved by means of SubFC; the relative contribution of ionic and covalent bindings to the chiral recognition ability was then outlined. The chromatographic properties of these CSPs were compared with those of the corresponding CSPs deriving from phenylglycine, p-hydroxyphenylglycine, and phenylalanine for the resolution of some tertiary phosphine oxide, naphthoyl amide, and a-methylene y-lactam enantiomers. Some simple requirements regarding the solute and CSP structures for chiral recognition ability can be inferred from these results. In addition, the resolution of a-acid a-N-(3,5-dinitrobenzoyl)amino esters was investigated on these a-acid CSPs. An example of preparative scale chromatography is also presented.