A series of new derivatized cyclodextrins have been developed for use as chiral stationary phases in capillary gas chromatography. As a result, a large number of the enantiomeric components in food and beverage products can be resolved relatively quickly and easily. The study focuses on compounds other than amino acids (e.g., malic acid, lactic acid, tartaric acid, esters, alcohols, lactone flavors or fragrances, and so on). The ability to separate and quantitate enantiomers at low levels should be useful for detecting adulterated products, for evaluating fermentation processes, and for the accurate characterization of enantiomeric flavor components, growth regulators, pesticides, and herbicides as well as their chiral environmental degradation products and metabolites.A large number of the organic components of foods and beverages are chiral molecules. In addition, a significant number of additives, flavors, fragrances, preservatives, growth regulators, fumigants, pesticides, herbicides, and so on used in the industry also are chiral molecules. Chiral or enantiomeric molecules are known to rotate plane polarized light, and they cannot be superimposed on their mirror image isomer. It is well-known that enantiomers have exactly the same physical and chemical properties
A new class of hydrophilic, relatively polar liquid, cyclodextrin (CD) derivatives have been used as highly selective chiral stationary phases (CSPs) for capillary gas chromatography (GC). Several possible requirements for liquidity in CD derivatives are discussed. O-(S)-2-Hydroxypropyl derivatives of alpha-, beta-, and gamma-cyclodextrins were synthesized, exclusively characterized, permethylated, and evaluated for enantioselectivity. Seventy pairs of enantiomers were resolved. They represent a wide variety of structural types and classes of compounds including chiral alkyl amines, amino alcohols, epoxides, pyrans, furans, sugars, diols, esters, ketones, bicyclic compounds, alcohols, and so on. Many of these compounds were not aromatic and cannot be resolved on any known liquid chromatographic CSP. Often, these enantiomers had far less functionality than required for LC separation. General properties of these CSPs as well as possible insights into the separation mechanism are discussed.
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