Chiral stationary phases table

The inherent chirality of proteins makes them very good candidates for the separation of enantiomers. Proteins which can tolerate organic solvents, as well as high temperatures, and which can function over a wide range of pH are useful as chiral stationary phases. Table 22-2 shows some of the characteristics of these proteins [138]. 

Table 2. Classes of Hplc Chiral Stationary Phases...

Table 6. Chiral Stationary Phases, Manufacturers, and Prices...

Possible differences are also well illustrated by 3-thio- and 3-methyl-thiohex-anols and their esters (Table 1). Among these compounds, there is a tendency for the (R) enantiomers to have a typical, fruity aroma. However, for 3-methylthiohexanol (an aroma component of yellow passion fruit) this situation is reversed the (S) enantiomer had the characteristic fruity aroma ( exotisch, fruchtig ).52 For the separation of enantiomers of odorous compounds, enan-tioselective GLC with chiral stationary phases, and MGDC techniques using a conventional capillary column and an enantioselective column are commonly used.53... 

A large number of chiral molecules have been separated with ligand-exchange chiral stationary phases. A few examples with commercially available columns are given in Table 4. 

A lot of published data on the separation of enantiomers of flavors and fragrances by GC is reviewed by Chirbase/Flavor database. Table 1. summarizes the enantiomer separation of oxygenated monoterpenes on chiral stationary phases of cyclodextrin derivatives by high resolution gas chromatography. 

Table 1. Enantiomer Separation of Oxygenated Monoterpenes on Chiral Stationary Phases of Cyclodextrin Derivatives by High Resolution Gas Chromatography...

Table 1 includes many but not all, chiral stationary phases used to separate the oxygenated monoterpenes. 

Table 7. Commercially Available Chiral Stationary Phases for Enantiomer Separation by LC...

The low thermal stability and the volatility of some of the low molecular weight stationary phases restricted their general use. Therefore, thermally stable and nonvolatile polymeric chiral stationary phases were developed by coupling the diamide phase, via the amino functionality, to a statistical copolymer of dimethylsiloxane and (2-carboxypropyl)methylsiloxane of appropriate viscosity131. The fluid polymeric phase, referred to as Chirasil-Val (Table 2), exhibits excellent properties for the enantiomer separation of a variety of compound classes over a broad temperature range141142. 

Using a chiral column, coated with a definite modified cyclodextrin as the chiral stationary phase, the elution orders of furanoid and pyranoid linalool oxides are not comparable [11, 12]. Consistently, the chromatographic behaviour of diastereomers and/or enantiomers on modified cyclodextrins is not predictable (Fig. 17.1, Table 17.1). Even by changing the non-chiral polysiloxane part of the chiral stationary phase used, the order of elution may significantly be changed [13]. The reliable assignment of the elution order in enantio-cGC implies the coinjection of structurally well defined references [11-13]. 

Table 17.1 Elution order of the furanoid linalool oxides using different modified cyclodextrins (CD) as chiral stationary phases [11, 13]...

TABLE 2. CLASSES OF HPLC CHIRAL STATIONARY PHASES... 

Temperature is also an important parameter for controlling the resolution of enantiomers in HPLC. The enthalpy and entropy control of chiral resolution on antibiotic CSPs is similar to the case of polysaccharide-based CSPs (Chapter 2). Armstrong et al. [1] have studied the effect of temperature on the resolution behavior of proglumide, 5-methyl-5-phenylhydantoin and A-carbamyl-D-pheny-lalanine on the vancomycin column. The experiments were carried out from 0°C to 45°C. These results are given in Table 6 for three chiral compounds. It has been observed that the values of k, a, and Rs for the three studied molecules have decreased with the increase in temperature, indicating the enhancement of chiral resolution at low temperature. In another work, the same workers [22] have also studied the effect of temperature on the resolution of certain amino acid derivatives on the teicoplanin chiral stationary phase. They further observed poor resolution at ambient temperature, whereas the resolution increased at low... 

Table 3 Some Examples of Chiral Stationary Phases Used in CEC Applications, Resulting Resolution, and Efficiency... 

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