The preparation of 3alpha,7beta-dihydroxy-22,23-methylene-5beta-cholan-24-oic acid( 2-sulfoethy1)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid “cyclopropylog” (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.
BILE-ACIDS WITH CYCLOPROPANE-CONTAINING SIDE-CHAIN .2. SYNTHESIS AND PROPERTIES OF 3-ALPHA,7-BETA-DIHYDROXY-22,23-METHYLENE-5-BETA-CHOLAN-24-OIC ACID (2-SULFOETHYL)AMIDE
PELLICCIARI, Roberto;NATALINI, Benedetto;
1985
Abstract
The preparation of 3alpha,7beta-dihydroxy-22,23-methylene-5beta-cholan-24-oic acid( 2-sulfoethy1)amide (5) by the one-step EEDQ-induced conjugation between ursodeoxycholic acid “cyclopropylog” (4) and taurine is described. The presence of a cyclopropyl ring adjacent to the amide bond is shown to make it resistant to degradation by intestinal bacteria. This new cyclopropylog is neither deconjugated at the C-24 amide bond nor 7-dehydroxylated when incubated with human stools in anaerobic conditions.File in questo prodotto:
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