13587-11-6Relevant academic research and scientific papers
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
Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles
Costa, Stefania,Maldonado Rodriguez, Maria Elena,Rugiero, Irene,De Bastiani, Morena,Medici, Alessandro,Tamburini, Elena,Pedrini, Paola
, p. 969 - 975 (2016)
The biotransformations of cholic acid (1a), deoxycholic acid (1b), and hyodeoxycholic acid (1c) to bendigoles and other metabolites with bacteria isolated from the rural slaughterhouse of Cayambe (Pichincha Province, Ecuador) were reported. The more active strains were characterized, and belong to the genera Pseudomonas and Rhodococcus. Various biotransformation products were obtained depending on bacteria and substrates. Cholic acid (1a) afforded the 3-oxo and 3-oxo-4-ene derivatives 2a and 3a (45% and 45%, resp.) with P.?mendocina ECS10, 3,12-dioxo-4-ene derivative 4a (60%) with Rh.?erythropolis ECS25, and 9,10-secosteroid 6 (15%) with Rh.?erythropolis ECS12. Bendigole F (5a) was obtained in 20% with P.?fragi ECS22. Deoxycholic acid (1b) gave 3-oxo derivative 2b with P.?prosekii ECS1 and Rh.?erythropolis ECS25 (20% and 61%, resp.), while 3-oxo-4-ene derivative 3b was obtained with P.?prosekii ECS1 and P.?mendocina ECS10 (22% and 95%, resp.). Moreover, P.?fragi ECS9 afforded bendigole A (8b; 80%). Finally, P.?mendocina ECS10 biotransformed hyodeoxycholic acid (1c) to 3-oxo derivative 2c (50%) and Rh.?erythropolis ECS12 to 6α-hydroxy-3-oxo-23,24-dinor-5β-cholan-22-oic acid (9c, 66%). Bendigole G (5c; 13%) with P.?prosekii ECS1 and bendigole H?(8c) with P.?prosekii ECS1 and Rh.?erythropolis ECS12 (20% and 16%, resp.) were obtained.
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
COMPETITIVE IMMUNOASSAY METHODS
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Paragraph 0183, (2018/03/25)
The invention provides assay methods and kits for detecting, measuring or quantitating the level of 7α-hydroxy-4-cholesten-3-one (7C4) in a biological sample from a subject, such as a human subject. In some embodiments, the human subject has a condition associated with bile acid malabsorption or diarrhea of unknown origin. The invention also provides isolated antibodies or antibody fragment thereof that specifically binds to 7α- hydroxy-4-cholesten-3-one (7C4) and have less than 1% cross-reactivity to one or more members selected from the group consisting of 7-ketocholesterol, 7α-hydroxycholesterol, and trihydroxycholestanoic acid.
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
IMPROVED SYNTHESIS OF 3-KETO, 4-ENE-3-KETO, AND 4,6-DIENE-3-KETO BILE ACIDS
Leppik, Raymond A.
, p. 475 - 484 (2007/10/02)
Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80percent yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups.The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60percent yield, via bromination, dehydrobromination, and deformylation.By extending the dehydrobromination reaction, the 7α-formoxyl group of the intermediate 4-ene-3-keto-7α,12α-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.
