Adsorption of Binary Solvents on Chiral Stationary Phases with Grafted Macrocyclic Antibiotics

A study is performed of the adsorption of water–methanol and water–acetonitrile mixtures on chiral stationary phases (CSPs) Chirobiotic R, Chirobiotic T, and Nautilus-E with grafted macrocyclic antibiotics ristocetin A, teicoplanin, and eremomycin, respectively. The patterns of adsorption on the indicated CSPs are qualitatively the same, and differ only by quantitative indicators. Adsorption isotherms of excess water from binary solvents have adsorption azeotrope points and show the preferred absorption of water in the range of pure organic component to an azeotrope point in the range of 60–75 mol % for H2О–МеОН and 80–90 mol % for H2O–MeCN systems. It is shown that the thickness of the adsorption phase in the first case is less than one nominal molecular layer (0.10–0.13 nm). For H2O–MeCN, it is 3–4 molecular layers (0.88–1.05 nm). Activity coefficients are calculated for the components of solutions in surface layers. The coefficients indicate the systems deviate considerably from the properties of an ideal adsorption solution. Reasons for this behavior are discussed.

Stationary phase type and temperature effect on HPLC separation of lactic acid enantiomers

Lactic acid is a biologically important organic acid existing in two enantiomeric forms which are differently metabolized in the human body. In this paper, direct chiral separation of lactic acid by high performance liquid chromatography is presented. Five chiral stationary phases based on macrocyclic antibiotics were used for enantioseparation and chromatographic parameters, such as retention factors, resolution and selectivity factors, were determined under different column temperatures ranging from 5 to 45 °C. Optical isomers of lactic acid were efficiently separated using chiral stationary phases based on teicoplanin (R S = 1.9 ) and ristocetin (R S = 1.7 ) in reversed-phase separation mode at the column temperature of 25 °C.

HPLC Enantioseparation of Phenylcarbamic Acid Derivatives by Using Macrocyclic Chiral Stationary Phases

The HPLC by using chiral stationary phases based on macrocyclic antibiotics, dimethylphenyl carbamate cyklofructan 7 and β-cyclodextrin in terms of polar-organic separation mode (mobile phase methanol/acetonitrile/acetic acid/triethylamine) were used for enantioseparation of alkoxy derivatives of phenylcarbamic acid. The effect of the analyte structures on the efficiency of enantioseparation was investigated. The most suitable stationary phase was teicoplanin aglycone, where the separations of the enantiomers were obtained (the resolution value from 0.65 to 2.90, depending on the structure of the analyte). Significant effect on the resolution of the enantiomers has position of alkoxy substituent in the hydrophobic part of the molecule. The enantiorecognition was achieved for 3-alkoxysubstituted derivatives.

Semi-synthetic zwitterionic rifamycins: a promising class of antibiotics; survey of their chemistry and biological activities

Rifamycins are an important group of macrocyclic antibiotics highly active against tuberculosis and various other Gram-positive pathogenic bacteria.