Astec CHIROBIOTIC® TAG Chiral HPLC Separations

By: Tom Beesley, Reporter EU Volume 30

Broad chiral selectivity, easy method development protocols, good resolution, fast analysis time, robustness, and reproducibility are all desired attributes of a superior chiral stationary phase (CSP). Astec CHIROBIOTIC® CSPs offer many of these attributes for a wide variety of chiral compounds.

CHIROBIOTIC stationary phases are manufactured by linking various macrocyclic glycopeptides through multiple covalent bonds to silica surfaces. To date, vancomycin (V/V2), teicoplanin (T/T2) and ristocetin (R) glycopeptides have been commercialized. The difference in V/V2 and T/T2 pairs is the technology used in the bonding process. The alternative attachment to the surface often provides complementary differences in chiral selectivity. An additional CSP has been developed whereby the sugar moiety of teicoplanin glycopeptide has been removed prior to bonding. This is referred to as teicoplanin aglycone or TAG.

The CHIROBIOTIC TAG CSP has proven especially unique in the CHIROBIOTIC series. TAG has demonstrated effectiveness in resolving the enantiomers of underivatized amino acids with simple mobile phases like methanol/water with excellent selectivity. TAG has been applied to chiral amino acid separations of serine, isoleucine, and many other underivatized amino acids. Separation conditions are often appropriate for LC-MS analyses. Figure 1 shows an excellent separation of serine enantiomers using a very simple, LC-MS compatible mobile phase. The CHIROBIOTIC TAG has not only shown improved separation over other CSPs, it also provides unique selectivity. TAG is the only known CSP to separate carnitine (gamma amino acid) and all of its analogs. See Figure 2.

Figure 1. Separation of Serine Enantiomers using CHIROBIOTIC TAG (referenced above: 14024AST)

Figure 2. LC-MS Chromatogram of Carnitine (referenced above: 14024AST)

 

Astec CHIROBIOTIC CSPs offer many desirable attributes for chiral separations. Alternative bonding strategies as in the V/V2 and T/T2 series, as well as modifications of the glycopeptide itself as in the T/TAG series show unique and complementary selectivity towards a wide variety of chiral compounds. Selectivity of TAG towards amino acid enantiomers using simple, LC-MS compatible mobile phases is just a sample of what the CHIROBIOTIC series of CSPs can accomplish.

 

For more information on all our Chiral Stationary Phases, visit sigma-aldrich.com/chiral

 

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Trademark Attributions:

  • CHIROBIOTIC is a registered trademark of Sigma-Aldrich Co.

 

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