2,3,4,6-TETRA-O-BENZOYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE - AN EFFICIENT REAGENT FOR THE DETERMINATION OF ENANTIOMERIC PURITIES OF AMINO-ACIDS, BETA-ADRENERGIC BLOCKERS AND ALKYLOXIRANES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY USING STANDARD REVERSED-PHASE COLUMNS

The use of the chiral derivatization reagent 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl isothiocyanate (BGIT) is described for the conversion of a variety of amino acids and beta-adrenergic blockers into diastereomeric thioureas, which can be separated on achiral RP-18 HPLC columns. In comparison with the established reagent 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (AGIT), BGIT shows increased sensitivity owing to the higher molar absorptivity on the BGIT derivatives. Also a series of monosubstituted alkyloxiranes was transformed with 2-propylamine into the corresponding amino alcohols, which were then further reacted with BGIT, 2,3,4,6-tetra-O-pivaloyl-beta-D-galactopyranosyl isothiocyanate (PGIT) or AGIT, leading to the corresponding thiourea derivatives. The diastereomers derived from BGIT could be separated with excellent resolution on a standard RP-18 column, whereas the PGIT and AGIT derivatives showed less or no resolution.