RESUMEN
Methods of stereoselective synthesis of oxysterols are considered by the examples of (25R)-26-hydroxycholesterol, (24S)-24,25-epoxycholesterol, and (24S)-24-hydroxycholesterol containing functional groups in the terminal fragments of their side chains. Special attention is paid to the problems of construction of chiral centers C24 and C25.
Asunto(s)
Colesterol/análogos & derivados , Hidroxicolesteroles/síntesis química , Colesterol/síntesis química , Colesterol/química , Hidroxicolesteroles/química , EstereoisomerismoRESUMEN
The structural peculiarities of the most widespread oxysterols, the products of oxidative transformations of cholesterol are discussed. The transformations proceed with the participation of enzymatic systems of the body or as a result of various nonenzymatic reactions. The pathways of their formation from cholesterol are also considered. The role of oxysterols in the maintenance of cholesterol homeostasis and in the development of atherosclerosis is reviewed. The possibility of using oxysterols as markers of pathological processes is demonstrated.
Asunto(s)
Colesterol/metabolismo , Hidroxicolesteroles/metabolismo , Animales , Arteriosclerosis/metabolismo , Transporte Biológico Activo , Biomarcadores/metabolismo , Homeostasis , Humanos , Hidroxicolesteroles/química , Metabolismo de los Lípidos , Hígado/metabolismo , Oxidación-ReducciónRESUMEN
A new method for the synthesis of both isomers of 24-hydroxycholesterol starting from lithocholic acid is proposed.
Asunto(s)
Hidroxicolesteroles/síntesis química , Ácido Litocólico/química , IsomerismoRESUMEN
A new approach to the synthesis of a series of isomeric 24-hydroxy- and 24,25-epoxysteroids starting from lithocholic acid was proposed. Sharpless asymmetric hydroxylation of intermediate delta24-olefines was used as a reaction determining the stereochemistry of target compounds. The resulting derivatives are potential agonists of nuclear receptors LXRalpha and LXRbeta and are potentially useful in the structure-function studies.