A Convenient Method for the Synthesis of (S)-Dolichol and (S)-Nordolichol

Abstract

A procedure for the preparation of (S)-dolichol and (S)-nor-dolichol starting from the polyprenyl fraction extracted from Gingko Biloba integer or extracted leaves is described. Two chiral isoprenoid compounds in good yields and high degree of enantiomeric excess were obtained. The (S)-nordolichol appears to be a good chiral precursor for the preparation of ¹⁴C-labeled (S)-dolichol which is to be used in investigations aimed at gaining further information with respect to the role of dolichol in the function of living cells.

Get full access to this article

View all access options for this article.

References

1. Burgos, J., Hemming, F.W., Pennock, J.F. and Morton, R.A. (1963). Biochem. J., 88: 470-470 .

2. Chojnacki, T. and Dallner, G. (1988). Biochem. J., 251: 1-1 .

3. Carroll, K.K., Guthrie, N. and Ravi, K. (1992). Biochem. Cell Biol., 70(6): 382-382 .

4. Hemming, F.W. (1992). Biochem. Cell Biol., 70(6): 377-377 .

5. Krag, S.S. (1998). Biochem. Biophys. Res. Comm., 243: 1-1 .

6. Adair, W.L. and Robertson, S. (1980). Biochem. J., 189: 441-441 .

7. Eggens, I., Chojnacki, T., Kenne, L. and Dallner, G. (1983). Biochim. Biophys. Acta., 751: 355-355 .

8. Beytia, E.D. and Porter, J.W. (1976). Ann. Rev. Biochem.: 113-113.

9. Grunler, J., Ericsson, J. and Dallner, G. (1994). Biochim. Biophys. Acta., 1212: 259-259 .

10.

10. Krag, S.S. (2000). In: Ernst, B., Hart, G.W. and Sinay, P. (eds), Carbohydrates in Chemistry and Biology, Vol. 3, p. 37-37, Wiley-VCH Verlag, Weinheim .

11.

11. Tateyama, S. and Sagami, H. (2001). J. Biochem., 129: 297-297 .

12.

12. Marino, M., Distefano, E., Pallottini, V., Caporali, S., Bruscalupi, G. and Trentalance, A. (2001). Exp. Physiol., 86: 39-39 .

13.

13. Thiel, C., Schwarz, M., Peng, J., Grzmil, M., Hasilik, M., Braulke, T., Kohlschuetter, A., von Figura, K., Lehle, L. and Koerner, C. (2003). J. Biol. Chem., 278: 22498-22498 .

14.

14. Endo, S., Zhang, Y-W., Takahashi, S. and Koyama, T. (2003). Biochim. Biophys. Acta, 1625: 291-291 .

15.

15. Kaiden, A. and Krag, S.S. (1992). Biochem. Cell Biol., 70(6): 385-385 .

16.

16. Van-Houte, H.A., Van-Veldhoven, P.P., Mannaerts, G.P., Baes, M.I. and Declercq, P.E. (1997). Biochim. Biophys. Acta, 1347: 93-93 .

17.

17. Leloir, L.F. (1977). Adv. Exp. Med., 83: 9-9 .

18.

18. Kurup, R.K.A., Devi, D., Augustine, J. and Kurup, P.A. (2001). Neurosci. Res. Commun., 28(2): 95-95 .

19.

19. Hemming, F.W. (1977). Biochem. Soc. Trans., 5: 1682-1682 .

20.

20. Low, P., Peterson, E., Mizuno, M., Tagikawa, T., Chojnacki, T. and Dallner, G. (1985). Biochem. Biophys. Res. Comm., 130(1): 460-460 .

21.

21. Tanner, W. and Lehle, L. (1987). Biochim. Biophys. Acta, 906: 81-81 .

22.

22. Burda, P. and Aebi, M. (1999). Biochim. Biophys. Acta, 1426: 239-239 .

23.

23. Marino, M., Dolfi, C., Paradiso, C., Cavallini, G., Masini, M., Gori, Z., Pollera, M., Trentalance, A. and Bergamini, E. (1998). J. Geron.: Biol. Sci., 53A(2): B87-B87 .

24.

24. De-Ropp, J.S. and Troy, F.A. (1985). J. Biol. Chem., 260(29): 15669-15669 .

25.

25. De-Ropp, J.S. and Troy, F.A. (1984). Biochemistry, 23: 2691-2691 .

26.

26. Valtersson, C., Van-Duyn, G., Verkleij, A.J., Chojnacki, T., De-Kruijff, B. and Dallner, G. (1985). J. Biol. Chem., 260(5): 2742-2742 .

27.

27. Van-Duijn, G., Valtersson, C., Chojnacki, T., Verkleij, A.J., Dallner, G. and De-Kruijff, B. (1986). Biochim. Biophys. Acta, 861: 211-211 .

28.

28. Jakobsson-Borin, A., Aberg, F. and Dallner, G. (1994). Biochim. Biophys. Acta, 1213: 159-159 .

29.

29. Hjertman, M., Wejde, J., Dricu, A., Carlberg, M., Griffiths, W.J., Sjovall, J. and Larsson, O. (1997). FEBS Lett., 416: 235-235 .

30.

30. Pullarkat, R.K., Pullarkat, P.S. and Morris, G.N. (1990). Biochem. J., 265: 891-891 .

31.

31. Pullarkat, R.K. and Reha, H. (1982). J. Biol. Chem., 257: 5591-5591 .

32.

32. Pullarkat, R.K., Reha, H. and Pullarkat, P.S. (1984). Biochim. Biophys. Acta, 793: 494-494 .

33.

33. Keller, R.K. and Nellis, S.W. (1986). Lipids, 21: 353-353 .

34.

34. Kalen, A., Appelkvist, E.L. and Dallner, G. (1989). Lipids, 24: 579-579 .

35.

35. Wood, W.G., Sun, G.Y. and Schroeder, F. (1989). Chem. Phys. Lipids, 51: 219-219 .

36.

36. Daniels, I. and Hemming, F.W. (1990). Lipids, 25: 586-586 .

37.

37. Edlund, C., Soderberg, M., Kristensson, K. and Dallner, G. (1992). Biochem. Cell Biol., 70: 422-422 .

38.

38. Dini, B., Dolfi, C., Santucci, V., Cavallini, G., Donati, A., Gori, Z., Maccheroni, M. and Bergamini, E. (2001). Exp. Gerontol., 37: 99-99 .

39.

39. Marino, M., Pallottini, V., D’Eramo, C., Cavallini, G., Bergamini, E. and Trentalance, A. (2002). Mech. Ageing Dev., 123(8): 1183-1183 .

40.

40. Mankowski, T., Jankowski, W., Chojnacki, T. and Franke, P. (1976). Biochemistry, 15(10): 2125-2125 .

41.

41. Suzuki, S., Mori, F., Takigawa, T., Ibata, K., Ninagawa, Y., Nishida, T., Mizuno, M. and Tanaka, Y. (1983). Tetrahedron Lett., 24: 5103-5103 .

42.

42. Imperiali, B. and Zimmerman, J.W. (1988). Tetrahedron Lett., 29(42): 5343-5343 .

43.

43. Takigawa, T., Ibata, K. and Mizuno, M. (1989). Chem. Phys. Lipids, 51: 171-171 .

44.

44. Van-Houte, H.A., Busson, R.H., Parmentier, G.G., Declercq, P.E., Van-Veldhoven, P.P., Mannaerts, G.P. and Eyssen, H.J. (1994). Chem. Phys. Lipids, 72: 103-103 .

45.

45. Ibata, K., Mizuno, M., Takigawa, T. and Tanaka, Y. (1983). Biochem. J., 213: 305-305 .

46.

46. Balcom, B.B. and Petersen, N.O. (1996). Can. J. Chem., 74: 253-2531 .

47.

47. Uneyama, K., Matsuda, H. and Torii, S. (1984). J. Org. Chem., 49: 4315-4315 .

48.

48. Backvall, J.E., Sellen, M. and Grant, B. (1990). J. Am. Chem. Soc., 112: 6615-6615 .

49.

49. Widmer, U. (1987). Synthesis: 568-568.

50.

50. Brown, H.C. and Zweifel, G. (1960). J. Am. Chem. Soc., 82: 4708-4708 .

51.

51. Wang, Y.-F., Lalonde, J.L., Momongan, M., Bergbreiter, D.E. and Wong, C.-H. (1988). J. Am. Chem. Soc., 110: 7200-7200 .

52.

52. Weissfloch, A.N.E. and Kazlauskas, R.J. (1995). J. Org. Chem., 60: 6959-6959 .

53.

53. Grisenti, P., Ferraboschi, P., Casati, S. and Santaniello, E. (1993). Tetrahedron: Asymmetry, 4(5): 997-997 .

54.

54. Chen, C.-S., Fujimoto, Y., Girdaukas, G. and Sih, C.J. (1982). J. Am. Chem. Soc., 104: 7294-7294 .

55.

55. Classon, B. and Liu, Z. (1988). J. Org. Chem., 53: 6126-6126 .

56.

56. Huh, H. (2000). Hoon, Medicinal and Aromatic Plants-Industrial Profiles, 12(Ginkgo Biloba): 215-215 .

57.

57. Carlson, T., Skorupinska-Tudek, K., Hertel, J., Chojnacki, T., Olsson, J.M. and Swiezewska, E. (2000). J. Lipid Res., 41: 1177-1177 .

58.

58. Suzuki, S., Shiono, M. and Fujita, Y. (1983). Synthesis: 804-804.