+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

Preparation of radio labeled 3 alpha hydroxy 7 keto 5 beta cholanic acid and its glycine and taurine conjugates

Preparation of radio labeled 3 alpha hydroxy 7 keto 5 beta cholanic acid and its glycine and taurine conjugates

Journal of Labelled Compounds & Radiopharmaceuticals 16(3): 421-434

3.alpha.-Hydroxy-7-keto-5.beta.-cholanic acid was prepared from cholic acid by a route which allowed introduction of 3H into positions 11 and 12 of the steroid C ring. Labeling with 14C was done by halodecarboxylation and resynthesis of the carboxyl function with 14C cyanide. The conjugates of both 3H- and 14C-labeled compounds with glycine and taurine were prepared. 14C-labeled compounds were prepared by degradation of the carboxyl-containing side chain to the norchloride, which was used to prepare the homologous 14C-containing nitrile. Hydrolysis afforded the acid in good yield. 3H was introduced into the C ring of the steroid nucleus by dehydration of 3.alpha.,12.alpha.-dihydroxy-7-keto-5.beta.-cholanic acid to the .DELTA.11-alkene which was catalytically tritiated. Physical and spectral data are presented to characterize the new compounds and TLC methods for purification are reported.

(PDF 0-2 workdays service: $29.90)

Accession: 006173766

Download citation: RISBibTeXText

Related references

Improved method for measuring the glycine and taurine conjugates of bile salts by high-performance liquid chromatography with tauro-7 alpha,12 alpha-dihydroxy-5 beta-cholanic acid as internal standard. Journal of Chromatography 386: 367-370, 1987

Chemical synthesis of (22E)-3 alpha,6 beta,7 beta-trihydroxy-5 beta-chol-22-en-24-oic acid and its taurine and glycine conjugates: a major bile acid in the rat. Journal of Lipid Research 45(3): 567-573, 2003

Is 3 alpha hydroxy 12 keto cholanic acid a marker of cholesterol gall stone. Digestion 18(1/2): 142-143, 1978

Phytochemical reduction of 3,6-di-keto-cholanic acid to 3 alpha-oxy-6-keto-cholanic acid. Bollettino Della Societa Italiana di Biologia Sperimentale 28(4): 611-612, 1952

Biosynthesis of valine and i43soleucine, 3. alpha-Keto-beta-hydroxy acid reductase and alpha-hydroxy-beta-Keto acid reductoisomerase. Journal of Biological Chemistry 235: 2322-2331, 1960

New syntheses of 5 acyl hydantoins and of 5 acyl 4 hydroxy oxazoles precursors of beta keto alpha amino acids and of beta keto alpha hydroxy acid amides. Tetrahedron 25(4): 771-782, 1969

The preparation of chenodeoxycholic acid and its glycine and taurine conjugates. Acta Chem Scand 17(1): 173-186, 1963

Potential bile acid metabolites 8. 7 12 di hydroxy 5 beta cholanic acids and 7 beta hydroxy 5 beta cholanic acids. Journal of Organic Chemistry 48(8): 1194-1197, 1983

Microbiological reduction of cholic acid and 3 alpha 7 beta 12 alpha tri hydroxy cholanic acid. Annali di Chimica 61(10): 695-702, 1971

Modified bile acids preparation of 7 alpha 12 alpha dihydroxy 3 beta and 7 alpha 12 alpha dihydroxy 3 alpha 2 hydroxyethoxy 5 beta cholanic acid and their biological activity. Tetrahedron Letters 33(2): 195-198, 1992

Inhibition of glycine oxidation by pyruvate alpha ketoglutarate and branched chain alpha keto acids in rat liver mitochondria presence of interaction between the glycine cleavage system and alpha keto acid dehydrogenase complexes. Archives of Biochemistry & Biophysics 249(2): 263-272, 1986

Bile acid composition in pancreatic and control subjects by 3 alpha hydroxy steroid dehydrogenase and 7 alpha hydroxy steroid dehydrogenase assays and a direct selective assay for taurine conjugates. Gastroenterology 66(4): 802, 1974

3 6 di hydroxy 5 alpha cholanic acids biliary metabolites of 5 alpha cholestane 3 beta 26 diol and 5 alpha cholestan 3 beta ol. Federation Proceedingspart 2: 1574, 1974

Development and mass spectrometric evaluation of a radio immunoassay for 9 alpha 11 alpha di hydroxy 15 keto prost 5 enoic acid. Febs Letters 26(1): 211-214, 1972