Concerning the thermolability of cholesta-5,8-dien-3β-ol, a sterol that accumulates in blood and tissues in a human genetic developmental disorder

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 20, 1996, Pages 2421-2424

  Ruan, B ^a   Pang, J ^a   Wilson, W K ^a   Schroepfer Jr , G J ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTA 5,8 DIEN 3BETA OL; CHOLESTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEGRADATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; TEMPERATURE;

EID: 0030598199     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00437-4     Document Type: Article

References (27)

1. 1. Wolthers, B. G.; Waltrecht, H. T.; van der Molen, J, C.; Nagel, G. T.; Van Doormal, J. J., Wijnandts, P. N. J. Lipid Res. 1991, 32, 603.
2. 2. Axelson, M. J. Lipid Res. 1991, 32, 1441.
3. 3. Batta, A. K.; Tint, G. S.; Shefer, S.; Abuelo, D.; Salen, G. J. Lipid Res. 1995, 36, 705.
4. 4. Batta, A. K.; Salen, G.; Tint, G. S.; Shefer, S. J. Lipid Res. 1995, 36, 2413.
5. 5. Smith, D. W.; Lemli, L.; Opitz, J. M. J. Pediatr. 1964, 64, 210.
6. 6. Fumagalli, R.; Bernini, F.; Galli, G.; Anastasia, M.; Fiecchi, A. Steroids 1980, 35, 665.
7. 7. Ruan, B.; Shey, J.; Gerst, N.; Wilson, W. K.; Schroepfer, G. J., Jr. Proc. Natl. Acad. Sci. U.S.A., in press.
8. 8. Heard, R. D. H.; Hoffman, M. M. J. Biol. Chem. 1940, 135, 801.
9. 9. Heard, R. D. H.; Hoffman, M. M. J. Biol Chem. 1941, 138, 1941.
10. 10b
11. (b) Wilson, W. K.; Sumpter, R. M; Warren, J. J.; Rogers, P. S.; Ruan, B.; Schroepfer, G. J., Jr. J. Lipid Res. 1996, 37, 1529.
12. 13C NMR.
13. (b) van der Gen, A; Lakeman, J.; Gras, M. A. M. P.; Huisman, H. O. Tetrahedron 1964, 20, 2521.
14. 13C NMR, high resolution MS, and by GC-MS of its TMS derivative.
15. +-HPLC.
16. 14. Varian 3400 GC, helium carrier gas, falling needle injector, 30-m DB-5MS column (0.25 mm id, 0.1 mm film thickness), injector and column at 250 °C, GC-MS transfer line at 260 °C, Extrel ELQ-400 quadrupole mass spectrometer, 70 eV.
17. 15. Hewlett Packard 5890 GC.
18. 16. Same GC-MS conditions as in note 14, with injector head pressure of 18 psi.
19. 7 with 9.1% acetone in hexane as eluting solvent and sample application with hexane. Under these conditions Ia and IIIa showed retention times of ∼31 min and ∼15 min, respectively).
20. 7 elution with 3% acetone in hexane. Under these conditions, Ib and IIIb showed retention times of 37 min and 17.5 min, respectively.
21. 19
22. 15 at 150 °C. The oven temperature was increased from 150 °C to 200 °C over 0.5 min and then maintained at 200 °C for 10 min.
23. 15 at 200 °C. The oven temperature was increased from 200 °C to 250 °C over 0.5 min and then maintained at 250 °C for 10 min.
24. 7 column (30 cm × 1 cm) using 15% acetone in hexane.
25. 10b matched those of an authentic standard of nia to within 0.001 ppm (methyl and olefinic signals) or 0.002 ppm (other signals).
26. 25. Salen, G.; Shefer, S.; Batta, A. K.; Tint, G. S.; Xu, G.; Honda, A.; Irons, M.; Elias, E. R. J. Lipid Res. 1996, 57, 1169.
27. 26. Wolf, C.; Chevy, F.; Pham, J.; Kolf-Clauw, M.; Citadelle, D.; Mulliez, N.; Roux, C. J. Lipid Res. 1996, 37, 1325.