Preparation and characterization of 3-monohydroxylated bile acids of different side chain length and configuration at C-3. Novel approach to the synthesis of 24-norlithocholic acid

Journal Article · Tue Dec 31 23:00:00 EST 1985 · J. Lipid Res.; (United States)

OSTI ID:5692290

Radominska-Pyrek, A; Huynh, T; Lester, R; Pyrek, J

A series of 3-monohydroxylated bile acids, in unlabeled and radioactive form, of varying side chain length and configuration at C-3 has been synthesized and rigorously characterized. They include: 3 alpha- and 3 beta-hydroxy-5 beta-androstane-17 beta-carboxylic acids (C20); 3 alpha- and 3 beta-hydroxy-5 beta-pregnan-21-oic acids (C21); 3 alpha- and 3 beta-hydroxy-23,24-bisnor-5 beta-cholan-22-oic acids (C22); 3 alpha- and 3 beta-hydroxy-24-nor-5 beta-cholan-23-oic acids (C23, norlithocholic and isonorlithocholic acids); and 3 beta-hydroxy-5 beta-cholan-24-oic acid (C24, isolithocholic acid). A novel approach to the degradation of lithocholic acid acetate to 24-norlithocholic acid is described. This degradation involves the photochemical modification of a Hunsdiecker reaction and Kornblum oxidation of the intermediate 23-bromide. The availability of these compounds makes it possible to study the metabolism and biological effects of short chain bile acids.

• Research Organization: Univ. of Texas Medical School, Houston
• OSTI ID: 5692290
• Journal Information: J. Lipid Res.; (United States), Journal Name: J. Lipid Res.; (United States) Vol. 1; ISSN JLPRA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
BILE ACIDS
CARBOXYLIC ACIDS
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
CHEMICAL REACTIONS
DECOMPOSITION
HYDROXY COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
STEROIDS
STEROLS
STRUCTURE-ACTIVITY RELATIONSHIPS
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS