Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
9748571 | Journal of Chromatography A | 2005 | 5 Pages |
Abstract
Novel N-acylated-(S)-cysteine derivative-N-(R)-mandelyl-(S)-cysteine (R-NMC), containing additional chiral center, aromatic and polar α-substituents in contrast to the traditionally used enantiomerically pure thiols, has been demonstrated to be an efficient SH-reagent for enantiomeric HPLC analysis of primary nonfunctionalized amines and amino alcohols after precolumn derivatization with o-phthalaldehyde. The R-NMC-derived isoindoles as well as adducts formed using traditional SH-reagents had a characteristic absorption maximum at 340 nm with a molar absorbance 6000 Mâ1 cmâ1, were stable during the HPLC-analysis and highly fluorescent allowing to detect 1 fmol of amino compound. Using diastereomeric R-NMC all tested amino alcohols were resolved effectively as well as nonfunctionalized amines, some of which were not resolved by a direct method on a chiral phase. Applying traditional enantiomeric N-acetyl-(S)-cysteine (NAC) only some isoindoles formed by aliphatic amino alcohols have been separated satisfactorily. The enhanced selectivity for R-NMC-derived isomers has been achieved, obviously, due to the involvement of the substituents at an extra chiral center into additional intramolecular interactions.
Related Topics
Physical Sciences and Engineering
Chemistry
Analytical Chemistry
Authors
Dorel T. Guranda, Pavel A. Kudryavtsev, Andrei Y. Khimiuk, Vytas K. Å vedas,