Chemical synthesis of (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid and its taurine and glycine conjugates

Kakiyama, Genta; Iida, Takashi; Yoshimoto, Atsushi; Goto, Takaaki; Mano, Nariyasu; Goto, Junichi; Nambara, Toshio; Hagey, Lee R.; Hofmann, Alan F.

doi:10.1194/jlr.d300027-jlr200

Cited by 16 publications

(23 citation statements)

References 29 publications

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“…Видовою особливістю щурів є те, що в них близько 90% жовчних кислот перебуває в кон'югованому стані, а тауро-кон'югати переважають над глікокон'юга-тами [13]. Кон'юговані з таурином холати є більш полярними сполуками, ніж такі з гліци-ном [14].…”

Section: результати та їх обговоренняunclassified

Exocrine Function of the Liver in Rats With Exposure to Cоrvitin

Vovkun¹,

Yanchuk²,

Shtanova³

et al. 2016

Fiziol Zh

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Section: результати та їх обговоренняunclassified

Exocrine Function of the Liver in Rats With Exposure to Cоrvitin

Vovkun¹,

Yanchuk²,

Shtanova³

et al. 2016

Fiziol Zh

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“…Oxidation of the 24-nor-22x,23-diol 5 with sodium periodate (NaIO 4 ) 14,16) in methanol and water mixture for 12 h at room temperature proceeded satisfactorily to give exclusively the corresponding C 22 23,24-dinor-aldehyde 6 in good isolated yield (89%). The resulting aldehyde 6, when subjected to coupling reaction with methyl (triphenylphosphoranylidene)acetate 14,16) in refluxing benzene for 12 h, underwent Wittig reaction to afford the C 24 (22E)-tetraformyl-22-ene ester 7 in isolated yield of 50%.…”

Section: Resultsmentioning

confidence: 99%

“…2. Although the synthetic pathways as well as the procedures are essentially application for the preparation of (22E)-3a,6b,7b-trihydroxy-5b-chol-22-en-24-oic acid and its conjugates which are major bile acids in the rat, 14) the targeted compounds in this study are especially useful for studies on the hepatobiliary dispoisition of these bile acids as substrates for multiple canalicular transporters as mentioned above.…”

Section: Resultsmentioning

confidence: 99%

“…The resulting aldehyde 6, when subjected to coupling reaction with methyl (triphenylphosphoranylidene)acetate 14,16) in refluxing benzene for 12 h, underwent Wittig reaction to afford the C 24 (22E)-tetraformyl-22-ene ester 7 in isolated yield of 50%. Finally, elimination of the protecting groups in 7 was carried out by treatment with methanolic KOH, yielding the crude 6a-OH-D 22 -CA 1a.…”

Section: Resultsmentioning

confidence: 99%

“…Thus, treatment of 2 with formic acid and perchloric acid resulted in the formation of the corresponding tetraformate 3, which in turn was converted to the C 23 24-nor-22-ene 4 by the side chain degradation with lead tetraacetate and cuprous acetate 15) in boiling pyridine for 14) in a mixture of tetrahydrofuran (THF), tert-butyl alcohol (t-BuOH) and water at room temperature for 12 h afforded the C-22 epimeric mixture (22R and 22S) of the C 23 24-nor-22x,23-diol 5 in 76% yield. Without isolation of each of the 22-epimers, the mixture was subjected to the subsequent reaction.…”

Section: Resultsmentioning

confidence: 99%

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Chemical Synthesis of (22E)-3.ALPHA.,6.ALPHA.,7.ALPHA.,12.ALPHA.-Tetrahydroxy-5.BETA.-chol-22-en-24-oic Acid and Its N-Acylamidated Conjugates with Glycine or Taurine: Precursors of the [22,23-3H] Labelled Tracers

Ogawa

Adachi

Kakiyama

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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(22E)-3a,6a,7a,12a-Tetrahydroxy-5b-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C 24 3a,6a,7a,12a-tetrahydroxylated bile acid to the corresponding C 22 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-D 22-5b-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.Key words bile acid; tetrahydroxy-D 22-5b-cholenoic acid; gycine conjugate; taurine conjugate; Wittig reaction; N-acylamidation Chem. Pharm. Bull. 58(8) 1103-1106 (2010) © 2010 Pharmaceutical Society of Japan * To whom correspondence should be addressed. e-mail: takaiida@chs.nihon-u.ac.jp Fig. 1. Structure of (22E)-3a,6a,7a,12a-Tetrahydroxy-5b-chol-22-en-24-oic Acid and Its Glycine and Taurine Conjugates (1a-c)

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Bile Acids: Chemistry, Pathochemistry, Biology, Pathobiology, and Therapeutics

Hofmann

Hagey

2008

Cell. Mol. Life Sci.

729

565

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Bile acids and bile alcohols in the form of their conjugates are amphipathic end products of cholesterol metabolism with multiple physiological functions. The great variety of bile acids and bile alcohols that are present in vertebrates are tabulated. Bile salts have an enterohepatic circulation resulting from efficient vectorial transport of bile salts through the hepatocyte and the ileal enterocyte; such transport leads to the accumulation of a pool of bile salts that cycles between the liver and intestine. Bile salt anions promote lipid absorption, enhance tryptic cleavage of dietary proteins, and have antimicrobial effects. Bile salts are signaling molecules, activating nuclear receptors in the hepatocyte and ileal enterocyte, as well as an increasing number of G-protein coupled receptors. Bile acids are used therapeutically to correct deficiency states, to decrease the cholesterol saturation of bile, or to decrease the cytotoxicity of retained bile acids in cholestatic liver disease.

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Chemical synthesis of (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid and its taurine and glycine conjugates

Cited by 16 publications

References 29 publications

Exocrine Function of the Liver in Rats With Exposure to Cоrvitin

Exocrine Function of the Liver in Rats With Exposure to Cоrvitin

Chemical Synthesis of (22E)-3.ALPHA.,6.ALPHA.,7.ALPHA.,12.ALPHA.-Tetrahydroxy-5.BETA.-chol-22-en-24-oic Acid and Its N-Acylamidated Conjugates with Glycine or Taurine: Precursors of the [22,23-3H] Labelled Tracers

Bile Acids: Chemistry, Pathochemistry, Biology, Pathobiology, and Therapeutics

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