Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1

Steroids

Volumn 71, Issue 1, 2006, Pages 18-29

  Iida, Takashi ^a   Kakiyama, Genta ^a   Hibiya, Yohei ^a   Miyata, Shohei ^a   Inoue, Takehiko ^b   Ohno, Kohsaku ^b   Goto, Takaaki ^c   Mano, Nariyasu ^c   Goto, Junichi ^c   Nambara, Toshio ^c   Hofmann, Alan F ^d  

^a NIHON UNIVERSITY   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

^d UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

Electrospray ionization mass spectrometry; Tandem mass spectrometry; Unsaturated bile acid; Unusual bile acid multi conjugates

Indexed keywords

3BETA,7BETA DIHYDROXY 5 CHOLEN 24 OIC ACID; 4 (4,6 DIMETHOXY 1,3,5 TRIAZIN 2 YL) 4 METHYLMORPHOLINIUM CHLORIDE; BILE ACID; CHOLANE DERIVATIVE; GLYCINE; MORPHOLINE DERIVATIVE; PYRIDINE; SULFUR DERIVATIVE; SULFUR TRIOXIDE; SULFURIC ACID; TAURINE; TOLUENE; TRIMETHYLAMINE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CASE REPORT; CHEMICAL REACTION; CONJUGATION; ELECTROSPRAY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; NIEMANN PICK DISEASE; SULFATION; SYNTHESIS; URINE;

BILE ACIDS AND SALTS; CHOLESTANOLS; CHOLIC ACIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MASS SPECTROMETRY; NIEMANN-PICK DISEASES; SAPONINS;

EID: 28544435981     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2005.07.008     Document Type: Article

References (26)

1. J. Sjövall, and K.D.R. Setchell Techniques for extraction and group separation of bile acids Setchell KDR D. Kritchevsky P.P. Nair The Bile Acids-Chemistry, Physiology, and Metabolism (Methods and Applications) vol. 4 1988 Plenum Press New York 1 42
2. H.-U. Marschall, B. Egestad, H. Matern, S. Matern, and J. Sjövall N-Acetylglucosamines J Biol Chem 264 1989 12989 12993
3. H.-U. Marschall, H. Matern, H. Wietholtz, B. Egestad, S. Matern, and J. Sjövall Bile acid N-acetylglucosaminidation J Clin Invest 89 1992 1981 1987
4. H.-U. Marschall, W.J. Griffiths, J. Zhang, H. Wietholtz, H. Matern, and S. Matern Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro J Lipid Res 35 1994 1599 1610
5. N. Yamaga, and H. Kohara Conjugation types of 7β-hydroxylated bile acids detected in healthy human urine J Biochem 116 1994 1123 1126
6. M.C. Patterson, M.T. Vanier, K. Suzuki, J.A. Morris, E. Carstera, and E.B. Neufeld Niemann-Pick disease type C: A Lipid Trafficking Disorder C.R. Scriver A.L. Beaudet W.S. Sly D. Valle The Metabolic and Molecular Bases of Inherited Disease 2001 McGraw-Hill New York 3611 3633
7. P.C. Reid, S. Sugii, and T.-Y. Chang Trafficking defects in endogenously synthesized cholesterol in fibroblasts, macrophages, hepatocytes, and glial cells from Niemann-Pick type C1 mice J Lipid Res 44 2003 1010 1019
8. 1 J Lipid Res 42 2001 1571 1577
9. D. Horton, M.L. Wolfrom, and I. Tiosugers Synthesis of 2-Amino-2-deoxy-1-thio-d-glucose J Org Chem 27 1962 1794 1800
10. H.V. Belle Cholesterol Bile Acids and Atheroscleosis. 1965 North-Holland Publishing Co Amsterdam
11. T. Iida, T. Momose, T. Tamura, T. Matsumoto, F.C. Chang, and J. Goto Potential bile acid metabolites. 13. Improved routes to 3β,6β- and 3β,6α-dihydroxy-5β-cholanoic acids J Lipid Res 29 1988 165 171
12. N. Chidambaram Chandrasekaran S. tert-Butyl hydroperoxide-pyridinium dichromate: A convenient reagent system for allylic and benzylic oxidations J Org Chem 52 1987 5048 5051
13. Haines AH, Methods for the Oxidation of Organic Compounds. London: Academic Press; 1985. p. 58-9.
14. ER.H. Walker The functional selectivity of complex hydride reducing agents Chem Soc Rev 5 1976 23 50
15. T. Iida, T. Momose, T. Tamura, T. Matsumoto, F.C. Chang, and J. Goto Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers J Lipid Res 30 1989 1267 1280
16. M. Tohma, R. Mahara, H. Takeshita, and T. Kurosawa A convenient synthesis of 3β,12α-, 3β,7α-, and 3β,7β-dihydroxy-5- cholen-24-oic acids: Unusual bile acids in human biological fluids Steroids 48 1986 331 338
17. T. Akihisa, T. Matsumoto, H. Sakamaki, M. Take, and Y. Ichinohe Platinum-catalyzed oxidation of cholesterol Bull Chem Soc Jpn 59 1986 680 682
18. T. Niwa, T. Koshiyama, J. Goto, and T. Nambara Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids Steroids 57 1992 522 529
19. E. Suzuki, S. Namba, H. Kurihara, J. Goto, Y. Matsuki, and T. Nambara Synthesis of 15α-hydroxyestrogen 15-N-acetylglucosaminides Steroids 60 1995 277 284
20. K. Mori, K. Fukamatsu, and M. Kido Synthesis of chlorinated steroids related to the structures proposed for blattellastanoides A and B, the aggregation pheromone of the German cockroach, Blattella germanica L Liebigs Ann Chem 1993 657 663
21. K. Mori, K. Fukamatsu, and M. Kido Synthesis of blattellastanoides A and B, chlorinated steroids glucosides isolated as the aggregation pheromone of the German cockroach, Blattella germanica L Liebigs Ann Chem 1993 665 670
22. 1H NMR in the structural and conformational analysis of oligosaccharides and glycoconjugates Prog Nuclear Magenetic Reson Spectros 27 1994 445 474
23. J. Goto, Y. Sano, T. Chikai, and T. Nambara Synthesis of disulfates of unconjugated and conjugated bile acids Chem Pharm Bull 35 1987 4562 4567
24. T. Momose, T. Tsubaki, T. Iida, and T. Nambara An improved synthesis of taurine- and glycine-conjugated bile acids Lipids 32 1997 775 778
25. T. Iida, S. Nishida, Y. Yamaguchi, M. Kodake, F.C. Chang, and T. Niwa Potential bile acid metabolites. 23. Synthesis of 3-glucosides of nonamidated and glycine- and taurine-amidated conjugates of bile acids J Lipid Res 36 1995 628 638
26. M. Kunishima, C. Kawachi, K. Hioki, K. Terao, and S. Tani Formation of carboxamides by direct condensation of carboxylic acids and amines in alcohols using a new alcohol- and water-soluble condensing agent: DMT-MM Tetrahedron 57 2001 1551 1558