13587-11-6Relevant articles and documents
The "triamino-analogue" of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry
Bhattarai, Khadga M.,Del Amo, Vicente,Magro, Germinal,Sisson, Adam L.,Joos, Jean-Baptiste,Charmant, Jonathan P. H.,Kantacha, Anob,Davis, Anthony P.
, p. 2335 - 2337 (2006)
Cholic acid 1 has been converted into triamine 5 with the all-trans polycyclic allocholanoyl skeleton and co-directed, axial amino groups; the potential of this system as a scaffold is illustrated by conversion to a preorganised anion receptor. The Royal
Bile acid transformations by Alcaligenes recti
Mazumder, Ipsita,Mahato, Shashi B.
, p. 79 - 86 (1993)
Metabolism of cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid by the grown cells of the bacterium Alcaligenes recti suspended in water was studied.Each isolated metabolite was characterized by the application of various spectroscopic methods.Cholic acid, chenodeoxycholic acid, ursodeoxycholic acid, and deoxycholic acid yielded methylated derivatives 3α-methoxy-7α,12α-dihydroxy-5β-cholanoic acid, 3α-methoxy-7α-hydroxy-5β-cholanoic acid, 3α-methoxy-7β-hydroxy-5β-cholanoic acid, and 3α-methoxy-12α-hydroxy-5β-cholanoic acid, respectively.In addition, cholic acid furnished 7α,12α-dihydroxy-3-oxochol-4-en-24-oic acid; chenodeoxycholic acid gave 7α-hydroxy-3-oxo-5β-cholanoic acid and 7α-hydroxy-3-oxochol-4-en-24-oic acid while ursodeoxycholic acid yielded 7β-hydroxy-3-oxochol-4-en-24-oic acid and 3-oxochola-4,6-dien-24-oic acid.The formation of various metabolites showed that two competitive enzymic reactions, i.e., selective methylation of the 3α-hydroxy group and dehydrogenation in the A/B rings, were operative.The methylation process was found to be enzymic involving an S-adenosyl-L-methionine (AdoMet)-dependent methyl transferase, and this reaction appeared to be inhibitory to the process of degradation of the ring system.In the other reaction sequence, degradation of the ring system was initiated by dehydrogenation of the 3α-hydroxy group.A 7β-dehydratase activity producing the Δ6 double bond was also noticeable in the metabolism of ursodeoxycholic acid. Keywords: sterols; bile acids; metabolites; microbial transformation; Alcaligenes recti; bacterial transformation
POTENTIAL BILE ACID METABOLITES. XI. SYNTHESES OF STEREOISOMERIC 7,12-DIHYDROXY-5α-CHOLANIC ACIDS
Iida, Takashi,Momose, Toshiaki,Chang, Frederic C.,Nambara, Toshio
, p. 1934 - 1938 (2007/10/02)
Three new compounds, 7α,12β-, 7β,12α-, and 7β,12β-dihydroxy-5α-cholanic acids, were synthesized.The principal reactions employed were 1) selective acylation at C-7 of a 7α,12α-dihydroxy ester with the propionic anhydride-4-dimethylaminopyridine system, 2) potassium superoxide-18-crown-6 ether inversion of the 7α-hydroxyl group, and 3) stereoselective reduction of the 12-ketones with the sodium borohydride-palladium chloride system and tert-butylamine-borane complex.High-performance liquid chromatography was of key impotance in characterizing the compounds and determining their purity.Keywords-- bile acid; allobile acid; 7,12-dihydroxy-5-α-cholanic acid; selective acylation; potassium superoxide-18-crown-6 ether reaction; sodium borohydride-palladium chloride reduction; tert-butylamine-borane complex reduction; HPLC
