Synthesis of bile acid 24-acyl glucuronides

Steroids

Volumn 63, Issue 4, 1998, Pages 180-185

  Goto, Junichi ^a   Murao, Naoaki ^a   Oohashi, Junji ^a   Ikegawa, Shigeo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Benzyl 2,3,4 tri O benzyl D glucopyranuronate; Bile acid; Carboxyl linked glucuronide; Mitsunobu reaction

Indexed keywords

BILE ACID; BILE ACID CONJUGATE; CHENODEOXYCHOLIC ACID; CHOLIC ACID; GLUCURONIC ACID; LITHOCHOLIC ACID; URSODEOXYCHOLIC ACID;

ARTICLE; BILE ACID METABOLISM; BILE ACID SYNTHESIS; CONJUGATION; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

ACYLATION; BILE ACIDS AND SALTS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; GLUCURONATES;

EID: 0032055625     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00160-8     Document Type: Article

References (17)

1. 1. Dutton GJ (1980). Glucuronidation of Drugs and Other Compounds. CRC Press, Boca Raton, Florida.
2. 2. Back P, Spaczinski K, Gerok W (1974). Bile-salt glucuronides in urine. Hoppe-Seyler's Z Physiol Chem 355:749-752.
3. 3. Back P (1976). Bile acid glucuronides. II. Isolation and identification of a chenodeoxycholic acid glucuronide from human plasma in intrahepatic cholestasis. Hoppe-Seyler's Z Physiol Chem 357:213-217.
4. 4. Almé B, Sjövall J (1980). Analysis of bile acid glucuronides in urine. Identification of 3α, 6α, 12α-trihydroxy-5β-cholanoic acid. J Steroid Biochem 13:907-916.
5. 5. Radominska-Pyrek A, Zimniak P, Irshaid YM, Lester R, Tephly TR, St Pyrek J (1987). Glucuronidation of 6α-hydroxy bile acids by human liver microsomes. J Clin Invest 80:234-241.
6. 6. Ikegawa S, Murao N, Motoyama T, Yanagihara T, Niwa T, Goto J (1996). Separetory and detection of bile acid 3-glucuronides in human urine by liquid chromatography/electrospray ionization-mass spectrometry. Biomed Chromatogr 10:313-317.
7. 7. Shattuck KE, Radominska-Pyrek A, Zimniak P, Adcok EW, Lester R, St Pyrek J (1986). Metabolism of 24-norlithocholic acid in the rat: Formation of hydroxyl- and carboxyl-linked glucuronides and effect on bile flow. Hepatology 6:869-873.
8. 8. Radominska-Pyrek A, Zimniak P, Chari M, Golunski E, Lester R, St Pyrek J (1986). Glucuronides of monohydroxylated bile acids: specificity of microsomal glucuronyltransferase for the glucuronidation site, C-3 configuration, and side chain length. J Lipid Res 27:89-101.
9. 9. Zimniak P, Radominska A, Zimniak M, Lester R (1988). Formation of three types of glucuronides of 6-hydroxy bile acids by rat liver microsomes. J Lipid Res 29:183-190.
10. 10. Radominska A, Green MD, Zimniak P, Lester R, Tephly TR (1988). Biosynthesis of hydroxyl-linked glucuronides of short-chain bile acids by rat liver 3-hydroxysteroid UDP-glucuronosyltransferase. J Lipid Res 29:501-508.
11. 11. Panfil I, Lehman PA, Zimniak P, Ernst B, Franz T, Lester R, Radominska A (1992). Biosynthesis and chemical synthesis of carboxyl-linked glucuronide of lithocholic acid. Biochem Biophys Acta 1126:221-228.
12. 12. Goto J, Murao N, Nakada C, Motoyama T, Oohashi J, Yanagihara T, Niwa T, Ikegawa S (1998). Separation and characterization of carboxyl-linked glucuronides of bile acids in incubation mixture of rat liver microsomes. Steroids, in press.
13. 13. Mitsunobu O (1981). The use of diethylazodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 7:1-28.
14. 14. Pravdic N, Keglevic D (1965). Glucuronic esters-III. The synthesis of the fully benzylated C-1 hydroxyl free glucuronic acid. Tetrahedron 21:1897-1901.
15. 15. Kirschning A, Ries M, Domann S, Martin W, Albrecht W, Arnold P, Laufer S (1997). Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-300. Bioorg Med Chem Lett 7:903-906.
16. 16. Compernolle F (1980). Synthesis of biliverdin and bilirubin 1-O-acyl-β-D-glucuropyranuronic acids. Biochem J 187:857-862.
17. 17. Juteau H, Gareau Y, Labelle M (1997). A convenient synthesis of β-acyl glucuronides. Tetrahedron Lett. 38:1481-1484.