Synthesis and enzymatic phosphorylation of a photoactivatable dolichol analogue

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 10992-10999

  Grassi, D ^b   Lippuner, V ^b   Aebi, M ^a   Brunner, J ^a   Vasella, A ^a  

^a ETH ZURICH   (Switzerland)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; DOLICHOL;

ALKYLATION; ARTICLE; PHOSPHORYLATION; PHOTOREACTIVITY; SYNTHESIS;

EID: 0030693622     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9721677     Document Type: Article

References (55)

1. Pennock, J. F.; Hemmins, F. W.; Morton, R. A. Nature 1960, 186, 470-472.
2. Lechner, J.; Wieland, F.; Sumper, M. J. Biol. Chem. 1985, 260, 8984-8989.
3. Hemming, F. W. Biochem. Cell Biol. 1992, 70, 377-381.
4. Quesada-Allue, L. A.; Parodi, A. J. Biochem. J. 1983, 212, 123-128.
5. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-664.
6. Allen, C. M.; Muth, J. D.; Gildersleeve, N. Biochim. Biophys. Acta 1982, 712, 33-41.
7. Ardail, D.; Lermé, F.; Louisot, P. Biochim. Biophys. Acta 1990, 1024, 131-138.
8. Gandhi, C. R.; Keenan, R. W. J. Biol. Chem. 1983, 258, 7639-7643.
9. Heller, L.; Orlean, P.; Adair, W. L., Jr. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7013-7016.
10. Itami, T.; Mueck, R. L.; Keenan, R. W. Biochim. Biophys. Acta 1988, 960, 374-381.
11. Scher, M. G.; Sumbilla, C. M.; Waechter, C. J. J. Biol. Chem. 1985, 260, 13742-13746.
12. Sumbilla, C.; Waechter, C. J. Methods Enzymol. 1985, 111, 411-482.
13. Szkopinska, A.; Swiezewska, E.; Chojnacki, T. Int. J. Biochem. 1992, 24, 1151-1157.
14. Verbert, A. In Glycoproteins; Montreuil, J., Schachter, H., Vliegenhart, J. F. G., Eds.; Elsevier: Amsterdam, 1995; pp 145-152.
15. Hemming, F. W. In Glycoproteins; Neuberger, A., Van Deenen, L. L. M., Eds.; Elsevier: Amsterdam, 1995; Vol. 29a, pp 127-199.
16. Abeijon, C; Hirschberg, C. B. TIBS 1992, 17, 32-36.
17. Carson, D. D.; Lennarz, W. J. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 5709-5713.
18. Mills, J. T.; Adamany, A. M. J. Biol. Chem. 1978, 253, 5270-5273.
19. Kean, E. L. J. Biol. Chem. 1991, 266, 942-946.
20. Marshall, R. D. Biochem. Soc. Symp. 1974, 40, 17-26.
21. Tanner, W.; Lehle, L. Biochim. Biophys. Acta 1987, 906, 81-99.
22. Bretthauer, R. K.; Wu, S. Arch. Biochem. Biophys. 1975, 167, 151-160.
23. Soliday, C. L.; Kolattukudy, P. E. Arch. Biochem. Biophys. 1979, 197, 367-378.
24. Gold, M. H.; Hahn, H. J. Biochemistry 1976, 15, 1808-1814.
25. Babczinski, P.; Tanner, W. Biochem. Biophys. Res. Commun. 1973, 54, 1119-1124.
26. Kruszewska, J.; Messner, R.; Kubicek, C. P.; Palamarczyk, G. J. Gen. Microbiol. 1989, 135, 301-307.
27. Sharma, C. B.; Babczinski, P.; Lehle, L.; Tanner, W. Eur. J. Biochem. 1974, 46, 35-41.
28. Lechner, J.; Wieland, F. Annu. Rev. Biochem. 1989, 58, 173-194.
29. Fleming, S. A. Tetrahedron 1995, 51, 12479-12520.
30. Brunner, J. Annu. Rev. Biochem. 1993, 62, 483-514.
31. Beck, P. J.; Gething, M.-J.; Sambrook, J.; Lehrman, M. A. Somat. Cell Mol. Genet. 1990, 16, 539-548.
32. Palamarczyk, G.; Lehle, L.; Mankowski, T.; Chojnacki, T.; Tanner, W. Eur. J. Biochem. 1980, 105, 517-523.
33. Weber, T.; Brunner, J. J. Am. Chem. Soc. 1995, 117, 3084-3095.
34. Veselovsky, V. V.; Grigorieva, N. Y.; Moiseenkov, A. M. Chem. Phys. Lipids 1989, 51, 147-157.
35. Moiseenkov, A. M. In Organic Synthesis: Modern Trends; Chizhov, O., Ed.; Blackwell Scientific Publishers: Oxford, 1986; pp 151-160.
36. Griaor'eva, N. Y.; Pinsker, O. A. Russ. Chem. Rev. 1994, 62, 169-183.
37. Sato, K.; Miyamoto, O.; Inoue, S.; Matsuhashi, Y.; Koyama, S.; Kaneko, T. J. Chem. Sac., Chem. Commun. 1986, 1761-1762.
38. Inoue, S.; Kaneko, T.; Takahashi, Y.; Miyamoto, O.; Sato, K. J. Chem. Soc., Chem. Commun. 1987, 1036-1037.
39. Jaenicke, L.; Siegmund, H.-U. Biol. Chem. Hoppe-Seyler 1986, 367, 787-795.
40. Jaenicke, L.; Van Leyen, K.; Siegmund, H.-U. Biol. Chem. Hoppe-Seyler 1991, 372, 1021-1026.
41. Siegmund, H.-U. Dissertation Thesis, Köln, Germany, 1986.
42. Sato, K.; Miyamoto, O.; Inoue, S.; Furusawa, F.; Matsuhashi, Y. Chem. Lett. 198-4, 1105-1108.
43. Muraoka, M.; Itoi, T.; Yamamoto, T. J. Chem. Res. S 1982, 256-257.
44. Madaj, E. J., Jr.; Snyder, D. M.; Truce, W. E. J. Am. Chem. Soc. 1986, 108, 3466-3469.
45. Mohri, M.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1985, 451-454.
46. Bouzbouz, S.; Kirschleger, B. Synthesis 1994, 714-718.
47. Baylis, A. B.; Hillman, M. E. D. Verfahren zur Herstellung von Acrylverbinduneen (Acrylic Compounds). In German Offenlegungs-schrift 2155113; 10 May 1992, US Pat. Appl. 87591; Celanese Corporation: Germany, 1972; pp 1-16.
48. Sato, K.; Miyamoto, O.; Inoue, S.; Furusawa, F.; Matsuhashi, Y. Chem. Lett. 1983, 725-728.
49. Brouwer, H.; Stothers, J. B. Can. J. Chem. 1972, 50, 601-611.
50. Shih, L. B.; Bayley, H. Anal. Biochem. 1985, 144, 132-141.
51. Danilov, L. L.; Chojnacki, T. FEBS Lett. 1981, 131, 310-312.
52. Szkopinska, A.; Nowak, L.; Swiezewska, E.; Palamarczyk, G. Arch. Biochem. Biophys. 1988, 266, 124-131.
53. Knauer, R.; Lehle, L. FEBS Lett. 1994, 344, 83-86.
54. Sherman, F. Methods Enzymol. 1991, 194, 3-21.
55. Elmberger, P. G.; Eggens, I.; Dallner, G. Biomed. Chromatogr. 1989, 3, 20-28.