Resolution of chiral thiol compounds derivatized with N-(1-pyrenyl)-maleimide and ThioGlo (TM) 3

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