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Enantiomeric resolution of kielcorin derivatives by HPLC on polysaccharide stationary phases using multimodal elution
Author(s) -
Sousa Emília P.,
Tiritan M.E.,
Oliveira Regina V.,
Afonso C.M.M.,
Cass Q.B.,
Pinto Madalena M.M.
Publication year - 2004
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.20031
Subject(s) - chemistry , enantiomer , amylose , elution , tris , chromatography , high performance liquid chromatography , carbamate , cellulose , resolution (logic) , chiral column chromatography , phase (matter) , organic chemistry , starch , biochemistry , artificial intelligence , computer science
Analytical HPLC methods using carbamate chiral stationary phases of polysaccharide derivatives were developed for the enantiomeric resolution of five racemic mixtures of xanthonolignoids: rac‐trans ‐kielcorin C, rac‐cis ‐kielcorin C, rac‐trans ‐kielcorin D, rac‐trans ‐isokielcorin D, and rac‐trans ‐kielcorin E. The separations were evaluated with the stationary phases cellulose tris ‐3,5‐dimethylphenylcarbamate, amylose tris ‐3,5‐dimethylphenylcarbamate, amylose tris ‐(S)‐1‐phenylethylcarbamate, and amylose tris ‐3,5‐dimethoxyphenylcarbamate under normal, reversed‐phase, and polar organic elution conditions. Chiral recognition of those chiral stationary phases, the influence of mobile phases on the enantiomers separation, and the effects of structural features of the solutes on the chiral discrimination observed are discussed. The best performance was achieved on an amylose tris ‐3,5‐dimethylphenylcarbamate phase. Polar organic conditions gave shorter retention factors and better resolutions and were a valuable alternative to the alcohol‐hexane or reversed‐phase conditions. Chirality 16:279–285, 2004 . © 2004 Wiley‐Liss, Inc.