Chiral Chromatography of amino acids on porous graphitic carbon coated with a series of N-substituted L-phenylalanine selectors - Effect of the anchor molecule on enantioselectivity

Wan, Qian-Hong, Shaw, P.Nicholas, Davies, Martyn C. and Barrett, David A. (1997) Chiral Chromatography of amino acids on porous graphitic carbon coated with a series of N-substituted L-phenylalanine selectors - Effect of the anchor molecule on enantioselectivity. Journal of Chromatography A, 765 2: 187-200. doi:10.1016/S0021-9673(96)00928-4


Author Wan, Qian-Hong
Shaw, P.Nicholas
Davies, Martyn C.
Barrett, David A.
Title Chiral Chromatography of amino acids on porous graphitic carbon coated with a series of N-substituted L-phenylalanine selectors - Effect of the anchor molecule on enantioselectivity
Journal name Journal of Chromatography A   Check publisher's open access policy
ISSN 0021-9673
1873-3778
Publication date 1997-03
Sub-type Article (original research)
DOI 10.1016/S0021-9673(96)00928-4
Volume 765
Issue 2
Start page 187
End page 200
Total pages 14
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Language eng
Formatted abstract
Six chiral stationary phases were prepared by coating the surface of porous graphitic carbon (PGC) with a series of N-substituted L-phenylalanine 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 (methoxybenzyl, naphthylmethyl, anthrylmethyl) anchor molecules on retention and enantioselectivity was studied using 36 amino acid enantiomers as probe compounds. The surface concentrations of the chiral selectors, determined using the breakthrough method, were found to be in the range 0.55-1.26 μmol/m2. The coated PGC phases all showed appreciable enantioselectivity for both non-polar and acidic amino acids, but basic amino acids were predominantly unretained. The order of retention of a pair of amino acid enantiomers was L>D On the alkyl-L-phenylalanine phases but a reversed retention order (D>L) was observed on the aryl-substituted L-phenylalanine phases. The chromatographic properties of each of the chiral stationary phases were compared in terms of retention order, enantioselectivity and diastereomeric complex stability. The reversal of the elution order on these two types of phases is discussed in relation to competitive intramorecular interactions involved in transient diasteriomeric complexes.
Keyword Enantiomer separation
Stationary phases, Lc
Porous graphitic carbon
Enantioselectivity
Amino Acids
Ligand-exchange chromatography
Liquid-chromatography
Enantiomers
Performance
Separation
Hplc
Recognition
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, 14:12:14 EST