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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
Author(s) -
Liene M.,
Macaudìre P.,
Caude M.,
Rosset R.,
Tambut´ A.
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010110
Subject(s) - chemistry , enantiomer , moiety , chromatography , chiral derivatizing agent , amino acid , amide , organic chemistry , resolution (logic) , amino esters , high performance liquid chromatography , silica gel , chiral column chromatography , catalysis , biochemistry , artificial intelligence , computer science
Chromatographic applications of three novel chiral stationary phases (CSPs) deriving from (S)‐(N)‐(3,5‐dinitrobenzoyl)tyrosine are reported, under liquid chromatographic (LC) and subscritical fluid chromatographic (SubFC) conditions. Two grafting modes of the chiral moiety have been experimented starting either from γ‐mercaptopropyl‐silanized (type 1) or γ‐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 contriution of ionic and covalent bindings to the ciral recognitio aility 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 α‐methylene γ‐lactam enantiomers. Some simple requirements regarding the solute and CSP structures for chiral recognition ability can be inferred from these results. In addition, the resolutio of π‐acid α‐N‐(3,5‐dinitrobenzoyl)amino esters was investigated on these π‐acid CSPs. An example of preparative scale chromatography is also presented.