HPLC Separation of Metyrosine Enantiomers as Methyl Esters Derivatized with 2, 3, 4, 6-Tetra-O-acetyl-β-D-glucopyranosyl Isothiocyanate

Abstract

Enantiomeric resolution of racemic metyrosine as methyl esters was investigated following the formation of diastereomeric thioureas with 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (TAGIT). Baseline separation (R_s>1.5) was achieved for the derivatized enantiomers on an octadecylsilane column under isocratic conditions using a mobile phase consisting of 35:65 v/v acetonitrile-distilled water containing 0.1% triethylamine pH 4.0 (adjusted with trifluoroacetic acid) at a flow rate of 1.0 mL and detection at 250 nm. Retention times, peak resolution, and separation factors were tabulated and a possible mechanism of separation is discussed.