Evaluation and Comparison of a 3,5‐Dimethylphenyl Isocyanate Teicoplanin and Phenyl Isocyanate Teicoplanin Chiral Stationary Phases

Abstract

AbstractTwo chiral stationary phases (CSP), phenyl isocyanate teicoplanin CSP (Ph‐TE) and 3,5‐dimethylphenyl isocyanate teicoplanin CSP (DMP‐TE) were prepared from the macrocyclic glycopeptide teicoplanin CSP (TE) using derivative agents, phenyl isocyanate or 3,5‐dimethylphenyl isocyanate, respectively. The evaluation and comparison of these two self‐made CSP were conducted using HPLC enantiomeric separations in two different mobile phase modes, i.e., the reversed phased (RP) mode and the polar organic (PO) mode. The chromatographic results were given as the retention, selectivity, and resolution factors. Twelve racemic analytes, including eight amino acids and four non‐amino acid compounds, amino‐(4‐hydroxyphenyl) acetic acid, 4‐(1‐hydroxyethyl)‐2‐methoxy phenol, lamivudine and oxazepam reached enantioseparation using the RPLC mobile phase on these two new CSP. The results show that the retention factors and stereoselectivity factors on DMP‐TE are somewhat bigger than those on Ph‐TE for most analytes in the RPLC mobile phase. Six amino alcohols reached enantiomeric separation on these two CSP using the PO mobile phase. The retention of these amino alcohols on DMP‐TE is longer than that on Ph‐TE but the selectivities have little difference between these two CSP. Comparison of the enantiomeric separations using self‐made Ph‐TE and DMP‐TE were conducted in order to gain a better understanding of the chiral recognition mechanism of the macrocyclic glycopeptide CSP.