Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Abstract

Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

Macrocyclic glycopeptides- and derivatized cyclofructan-based chiral stationary phases for the enantioseparation of fluorinated ß-phenylalanine analogs

“…For the separation of amino acids, amines, and organic acids, macrocyclic glycopeptide-based CSPs can be applied in different chromatographic modes, however, the best performances are usually achieved in polar ionic mode (PIM) and RPM. Among macrocyclic antibiotics, teicoplanin and teicoplanin aglycone-based CSPs are most frequently used for the enantioseparation of αand ß-amino acids [23].…”

“…Functionalized polysaccharides on SPP and FPP support were first applied by Chankvetadze et al [19], while Cinchona alkaloid-based mono-and zwitterionic CSPs applying SPPs and FPPs was developed by Armstrong et al [20] and Lämmerhofer et al [21], respectively. It is worth noting that in addition to the above citations, some very recent review papers have summarized these new results [22][23][24].…”

Enantiomeric separation of bupropion by liquid chromatography on derivatized cyclofructan chiral stationary phase

“…Macrocyclic glycopeptide‐based selectors (e.g., teicoplanin and vancomycin) have proved to be an exceptionally useful class of chiral selectors for the separation of various compounds of biological and pharmacological importance. The advantages of these selectors are their complex structure with multiple interaction sites, broad selectivity under multimodal elution conditions, and long‐term stability, good efficiency, and high reproducibility of the commercially available columns 17–19 . Cyclofructans belong to the class of cyclic oligosaccharides composed of six or more β‐2,1‐linked fructofuranose units.…”

“…The advantages of these selectors are their complex structure with multiple interaction sites, broad selectivity under multimodal elution conditions, and long-term stability, good efficiency, and high reproducibility of the commercially available columns. [17][18][19] Cyclofructans belong to the class of cyclic oligosaccharides composed of six or more β-2,1-linked fructofuranose units. There are papers and recent reviews published on derivatized cyclofructan CSPs and their applications in the enantioseparations.…”

Macromolecular helicity induction and static helicity memory of poly(biphenylylacetylene)s bearing aromatic pendant groups and their use as chiral stationary phases for high‐performance liquid chromatography

“…Direct enantioseparation by high-performance liquid chromatography (HPLC) and supercritical fluid chromatography with chiral stationary phases (CSPs) [1][2][3][4][5][6][7][8][9][10] is recognized as one of the most powerful and widely used techniques for both the trace analyses of chiral molecules and industrial-scale productions of optically pure ingredients. [11][12][13][14][15][16][17][18][19] Okamoto et al achieved the first asymmetric synthesis of a one-handed helical poly(triphenylmethyl methacrylate) (PTrMA) [20][21][22][23][24][25] by the helix-sense-selective polymerization of an achiral bulky vinyl monomer with a chiral catalyst in 1979 and discovered its remarkable chiral separation ability when used as a CSP for HPLC, which was then commercialized in [This article is part of the Special Issue: A Special Issue to Celebrate the 80th Birthday of Professor Yoshio Okamoto.…”