Application of fluorine NMR for structure identification of steroids

Magnetic Resonance in Chemistry

Volumn 49, Issue 5, 2011, Pages 221-230

  Ampt, Kirsten A M ^a   Aspers, Ruud L E G ^b   Jaeger, Martin ^b   Geutjes, Pepijn E T J ^b   Honing, Maarten ^b   Wijmenga, Sybren S ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

absolute configuration; diastereotopic fluorines; HOESY; steroids

Indexed keywords

DRUG PRODUCTS; LIPIDS;

ABSOLUTE CONFIGURATION; COUPLING PATTERN; DIASTEREOTOPIC FLUORINE; FLUORINATED COMPOUND; HETERONUCLEAR; HOESY; HOMONUCLEAR; SPECTRAL SIMPLIFICATION; STEROID; STRUCTURE IDENTIFICATION;

FLUORINE;

EID: 79955022189     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.2737     Document Type: Article

References (68)

1. H. J. Bohm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Muller, U. Obst-Sander, M. Stahl, ChemBioChem 2004, 5, 637.
2. K. L. Kirk, J. Fluor. Chem. 2006, 127, 1013.
3. M. Morgenthaler, E. Schweizer, A. Hoffmann-Roder, F. Benini, R. E. Martin, G. Jaeschke, B. Wagner, H. Fischer, S. Bendels, D. Zimmerli, J. Schneider, F. Diederich, M. Kansy, K. Mueller, ChemMedChem 2007, 2, 1100.
4. K. L. Kirk, Curr. Top. Med. Chem. 2006, 6, 1447.
5. J. P. Begue, D. Bonnet-Delpon, J. Fluor. Chem. 2006, 127, 992.
6. B. K. Park, N. R. Kitteringham, P. M. O'Neill, Annu. Rev. Pharmacol. Toxicol. 2001, 41, 443.
7. H. Ali, J. Rousseau, T. G. Gantchev, J. E. Vanlier, J. Med. Chem. 1993, 36, 4255.
8. O. Corcoran, I. D. Wilson, J. K. Nicholson, Anal. Commun. 1999, 36, 259.
9. R. Martino, V. Gilard, F. Desmoulin, M. Malet-Martino, J. Pharm. Biomed. Anal. 2005, 38, 871.
10. H. Orhan, J. N. M. Commandeur, G. Sahin, U. Aypar, A. Sahin, N. P. E. Vermeulen, Xenobiotica 2004, 34, 301.
11. W. R. Dolbier, Guide to Fluorine NMR for Organic Chemists, Wiley: Hoboken, NJ, 2009.
12. P. A. Stanley, in The Handbook of Environmental Chemistry, Vol. 3, Part N, Organofluorines (Ed.:, A. H. Neilson,), Springer-Verlag: Heidelberg, 2002, pp. 3.
13. J. W. Emsley, L. Phillips, V. Wray, Prog. Nucl. Magn. Reson. Spectrosc. 1976, 10, 83.
14. S. Berger, S. Braun, H. O. Kalinowski, in NMR Spectroscopy of the Non-Metallic Elements, Wiley: New York, 1997, pp. 398.
15. T. S. Everett, in Chemistry of Organic Fluorine Compounds II, A Critical Review, ACS Monograph, vol. 187 (Eds.:, M. Hudlicky, A. E. Pavlath,), American Chemical Society: Washington, 1995, pp. 1037.
16. X. Xie, Y. Yuan, R. Kruger, M. Broring, Magn. Reson. Chem. 2009, 47, 1024.
17. J. Hilton, L. H. Sutcliffe, Prog. Nucl. Magn. Reson. Spectrosc. 1975, 10, 27.
18. R. H. Contreras, J. E. Peralta, Prog. Nucl. Magn. Reson. Spectrosc. 2000, 37, 321.
19. J. Battiste, R. A. Newmark, Prog. Nucl. Magn. Reson. Spectrosc. 2006, 48, 1.
20. M. Liu, R. D. Farrant, J. K. Nicholson, J. C. Lindon, J. Magn. Reson. Ser. B 1995, 106, 270.
21. J. A. R. Garcia, F. A. V. Navarro, H. T. V. Castro, Magn. Reson. Chem. 1994, 32, 547.
22. N. Mistry, I. M. Ismail, M. S. Smith, J. K. Nicholson, J. C. Lindon, J. Pharm. Biomed. Anal. 1997, 16, 697.
23. N. Mistry, I. M. Ismail, R. D. Farrant, M. L. Liu, J. K. Nicholson, J. C. Lindon, J. Pharm. Biomed. Anal. 1999, 19, 511.
24. A. Foris, Magn. Reson. Chem. 2004, 42, 534.
25. D. N. Kirk, H. C. Toms, C. Douglas, K. A. White, K. E. Smith, S. Latif, R. W. P. Hubbard, J. Chem. Soc. Perkin Trans. 2 1990, 1567.
26. J. S. B. de Vlieger, A. J. Kolkman, K. A. M. Ampt, J. N. M. Commandeur, N. P. E. Vermeulen, J. Kool, S. S. Wijmenga, W. M. A. Niessen, H. Irth, M. Honing, J. Chromatogr. B 2010, 878, 667.
27. V. Rea, A. J. Kolkman, E. Vottero, E. J. Stronks, K. A. M. Ampt, M. Honing, N. P. E. Vermeulen, S. S. Wijmenga, J. N. M. Commandeur, Biochemistry 2011, (in press).
28. T. D. W. Claridge, High-Resolution NMR Techniques in Organic Chemistry, vol. 27 (2nd edn), Elsevier: Oxford, 2009.
29. C. E. Hadden, G. E. Martin, V. V. Krishnamurthy, Magn. Reson. Chem. 2000, 38, 143.
30. R. T. Williamson, B. L. Marquez, W. H. Gerwick, G. E. Martin, V. V. Krishnamurthy, Magn. Reson. Chem. 2001, 39, 127.
31. C. E. Hadden, D. T. Angwin, Magn. Reson. Chem. 2001, 39, 1.
32. A. A. Ribeiro, Magn. Reson. Chem. 1997, 35, 215.
33. R. A. Newmark, R. J. Webb, J. Fluor. Chem. 2005, 126, 355.
34. A. A. Ribeiro, M. J. Glen, J. Magn. Reson. Ser. A 1994, 107, 158.
35. A. A. Ribeiro, J. Magn. Reson. Ser. A 1995, 117, 257.
36. A. Bax, R. Freeman, J. Magn. Reson. 1981, 45, 177.
37. W. S. Brey, M. L. Brey, in Encyclopedia of NMR, vol. 3 (Eds.:, D. M. Grant, R. K. Harris,), Wiley: Chichester, 1996, pp. 2063.
38. B. L. Marquez, W. H. Gerwick, R. T. Williamson, Magn. Reson. Chem. 2001, 39, 499.
39. C. Schorn, D. Naumann, H. Scherer, J. Hahn, J. Fluor. Chem. 2001, 107, 159.
40. M. Takasaki, K. Kimura, K. Kawaguchi, A. Abe, G. Katagiri, Macromolecules 2005, 38, 6031.
41. E. E. Kwan, S. G. Huang, Eur. J. Org. Chem. 2008, 2008, 2671.
42. S. L. Cobb, C. D. Murphy, J. Fluor. Chem. 2009, 130, 132.
43. M. Masson, J. F. Sigurjonsdottir, S. Jonsdottir, T. Loftsson, Drug Dev. Ind. Pharm. 2003, 29, 107.
44. W. S. Brey, D. Richardson, B. Bechtel, A. Aksenov, Magn. Reson. Chem. 2007, 45, 205.
45. K. L. Williamson, Y. F. L. Hsu, F. H. Hall, S. Swager, M. S. Coulter, J. Am. Chem. Soc. 1968, 90, 6717.
46. M. Karplus, J. Chem. Phys. 1959, 30, 11.
47. J. San Fabian, J. Guilleme, Chem. Phys. 1996, 206, 325.
48. CambridgeSoft, ChemBio3D, version 12.0, ChemBioOffice 2010, CambridgeSoft: Cambridge, USA, 2010.
49. J. San Fabian, J. Guilleme, E. Diez, J. Magn. Reson. 1998, 133, 255.
50. C. Thibaudeau, J. Plavec, J. Chattopadhyaya, J. Org. Chem. 1998, 63, 4967.
51. B. Coxon, in Advances in Carbohydrate Chemistry and Biochemistry, vol. 62 (Ed.:, D. Horton,), Elsevier: Burlington, 2009, pp. 17.
52. A. M. Ihrig, S. L. Smith, J. Am. Chem. Soc. 1970, 92, 759.
53. L. D. Hall, R. N. Johnson, J. Adamson, A. B. Foster, J. Chem. Soc. D 1970, 463.
54. S. Kurtkaya, V. Barone, J. E. Peralta, R. H. Contreras, J. P. Snyder, J. Am. Chem. Soc. 2002, 124, 9702.
55. T. Tuttle, J. Grafenstein, D. Cremer, Chem. Phys. Lett. 2004, 394, 5.
56. M. Michalik, M. Hein, M. Frank, Carbohydr. Res. 2000, 327, 185.
57. N. Castillo, C. F. Matta, R. J. Boyd, J. Chem. Inf. Model. 2005, 45, 354.
58. A. J. Liu, K. E. Carlson, J. A. Katzenellenbogen, J. Med. Chem. 1992, 35, 2113.
59. A. D. Cross, J. Am. Chem. Soc. 1964, 86, 4011.
60. A. D. Cross, P. W. Landis, J. Am. Chem. Soc. 1962, 84, 1736.
61. A. D. Cross, P. W. Landis, J. Am. Chem. Soc. 1962, 84, 3784.
62. A. D. Cross, P. W. Landis, J. Am. Chem. Soc. 1964, 86, 4005.
63. F. B. Mallory, C. W. Mallory, W. M. Ricker, J. Am. Chem. Soc. 1975, 97, 4770.
64. S. Rozen, G. Benshushan, J. Org. Chem. 1986, 51, 3522.
65. U. Burkert, N. L. Allinger, in Molecular Mechanics, ACS monograph 177, American Chemical Society: Washington DC, 1982.
66. D. Vikictopic, Z. Meic, J. Mol. Struct. 1986, 142, 371.
67. E. Sievanen, V. Noponen, V. Kral, T. Briza, E. Kolehmainen, Magn. Reson. Chem. 2008, 46, 392.
68. Advanced Chemistry Development, Inc., ACD/NMR Workbook, Version 12, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com, 2009.