Role of alkyl and aryl substituents in chiral ligand exchange chromatography of amino acids - Study using porous graphitic carbon coated with N-substituted-L-proline selectors

Wan, Qian-hong, Shaw, P.Nicholas, Davies, Martyn C. and Barrett, David A. (1997) Role of alkyl and aryl substituents in chiral ligand exchange chromatography of amino acids - Study using porous graphitic carbon coated with N-substituted-L-proline selectors. Journal of Chromatography A, 786 2: 249-257. doi:10.1016/S0021-9673(97)00601-8


Author Wan, Qian-hong
Shaw, P.Nicholas
Davies, Martyn C.
Barrett, David A.
Title Role of alkyl and aryl substituents in chiral ligand exchange chromatography of amino acids - Study using porous graphitic carbon coated with N-substituted-L-proline selectors
Journal name Journal of Chromatography A   Check publisher's open access policy
ISSN 0021-9673
1873-3778
Publication date 1997-10
Sub-type Article (original research)
DOI 10.1016/S0021-9673(97)00601-8
Volume 786
Issue 2
Start page 249
End page 257
Total pages 9
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Language eng
Formatted abstract
Five chiral stationary phases were prepared by coating the surface of porous graphitic carbon with a series of N-substituted L-proline chiral selectors. The N-substituents served as anchor molecules for immobilization of chiral selectors on the support material. The effect of the alkyl (C7, C9, C12) and aryl (naphthylmethyl, anthrylmethyl) anchor molecules on retention and enantioselectivity were studied using thirty-six amino acid enantiomers as probe compounds. The surface concentrations of the chiral selectors, determined using the breakthrough method, were found to he in the range 0.39-0.68 μmol m-2. The coated PGC phases all showed appreciable enantioselectivity for both non-polar and acidic amino acids with the naphthylmethyl-L-proline showing the greatest overall values. The N- substituents were shown to have strong influence on retention and enantioselectivity. An increase in the chain length of the alkyl N- substituents resulted in improved enantioselectivity whereas the retention decreased. However, with the aryl N-substituents, both the retention and enantioselectivity decreased with an increase in the ring number of the aryl substituent. The retention order for the majority of the amino acids examined was the same on all the columns, that is D>L. These behaviours were interpreted in terms of the involvement of the N-substituent in intramolecular hydrophobic interactions responsible for the observed chiral recognition.
Keyword Chiral stationary phases, Lc
Amino acids
Liquid-chromatography
Enantiomers
Performance
Separation
Hplc
Recognition
Retention
Silicas
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Pharmacy Publications
 
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Created: Mon, 20 Dec 2010, 14:12:20 EST