[Preparations and biological properties of chiral compounds].
Enantiomers of chiral compounds may express various biological activities and also different toxicities. Examples of different pharmacological effects of some chiral drugs such as fluoxetine, penicillamine, ibuprofen and albuterol are provided in this paper. Due to possible differences in activity, the chiral drugs are required to be pure enantiomeric compounds in order to be more effective and safer to use. In the laboratory, enantiomers are mainly synthesized as racemates (an equimolar mixture of enantiomers) while in biological pathways only one enantiomeric form is produced, such as amino acids, sugars and lipids. This paper presents the principles of chirality, general information about enantiomers and their biological aspects. It gives an outline of stereoselective methods for chromatographic resolution of enantiomers with stereoselective protein stationary phases, i.e. capillary electrochromatography (CEC) and high performance liquid chromatography (HPLC). The use of enzyme biotransformations (hydrolysis, oxidation and reduction) in chiral syntheses of carboxyl-, phosphoryl- or beta-hydroxy esters, alcohols, epoxides and cis-carboxyl sulphoxide is described. This article also includes an example of lipase stereoselectivity improvement by amino acid mutations within the enzyme active site.
Sinko
Goran
G
Institut za medicinska istrazivanja i medicinu rada, Zagreb, Hrvatska. gsinko@imi.hr
D002626:Chemistry, Pharmaceutical; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D010600:Pharmacology; D013237:Stereoisomerism
D004364:Pharmaceutical Preparations