Preparation of (25)- and (25)-26-functionalized steroids as tools for biosynthetic studies of cholic acids
| Autor: | A. V. Antonchick, Vladimir N. Zhabinskii, Vladimir A. Khripach, Andrey P. Antonchick, Natalya B. Khripach, Olga V. Konstantinova, Bernd Schneider |
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| Rok vydání: | 2005 |
| Předmět: |
Magnetic Resonance Spectroscopy
medicine.medical_treatment Clinical Biochemistry Sodium chlorite Carboxylic Acids Stigmasterol Biochemistry Catalysis Steroid chemistry.chemical_compound Endocrinology Biosynthesis medicine Side chain Organic chemistry Sulfones Molecular Biology Pharmacology Carbon Isotopes Molecular Structure Organic Chemistry Cholic acid Cholic Acids Stereoisomerism Pregnanes Cholestanones chemistry Alcohols Steroids Chromatography Thin Layer CYP8B1 Oxidation-Reduction |
| Zdroj: | Steroids. 70:551-562 |
| ISSN: | 0039-128X |
| Popis: | A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3beta-hydroxy-Delta(5)- or a Delta(4)-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3beta-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach. |
| Databáze: | OpenAIRE |
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