RESOLUTION OF CHIRAL THIOL COMPOUNDS DERIVATIZED WITH N-(1-PYRENYL)-MALEIMIDE AND THIOGLO™3

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Abstract
Many chiral thiols such as cysteine, homocysteine, N-acetylcysteine (NAC), and penicillamine are biologically important compounds. Among other roles, they act as antioxidants, therapeutic agents and indicators of disease. When analyzing low levels of these compounds, they are often derivatized in order to increase the sensitivity of the determination. However, it is generally an associated amine functional group that is derivatized. By selectively derivatizing only the thiol moiety with a fluorescent group, one is able to eliminate the large number of amine containing background compounds that are present in biological samples. However, there have been few reports on the enantiomeric resolution of thiol containing amino acids in which the fluorescent tag is linked exclusively through the sulfhydryl group. The first HPLC enantioresolution of N(1-pyrenyl)maleimide (NPM) and ThioGlo™3 derivatized compounds is reported on Teicoplanin and naphthylethyl-carbamate-β-cyclodextrin (NEC-β-CD) chiral stationary phases.