Lipoconjugates: Structure-activity studies for pheromone analogues of Ustilago maydis with varied lipophilicity

International Journal of Peptide and Protein Research

Volumn 48, Issue 4, 1996, Pages 377-390

  Koppitz, M ^a   Spellig, T ^a   Kahmann, R ^a   Kessler, H ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Activities; Conformational analysis; Lipophilic amino acids; Mating factors; NMR spectroscopy; S alkylation; Synthesis; Ustilago maydis

Indexed keywords

BETA GLUCURONIDASE; LIPOPEPTIDE; PHEROMONE; PHEROMONE DERIVATIVE; SYNTHETIC PEPTIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS GROWTH; LIPOPHILICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; USTILAGO MAYDIS;

FUNGI; USTILAGO MAYDIS;

EID: 0029910723     PISSN: 03678377     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1996.tb00855.x     Document Type: Article

References (53)

1. Rowell, J.B., DeVay, J.E. (1954) Phytopathology 44, 356-362
2. Holliday, R. (1961) Genet. Res. 2, 204-230
3. Banuett, F. (1992) Trends Genet. 8, 174-179
4. Bölker, M., Urban, M. & Kahmann, R. (1992) Cell 68, 441-450
5. Spellig, T., Bölker, M., Lottspeich, F., Frank, R.W. & Kahmann, R. (1994) EMBO J. 13, 1620-1627
6. Bölker, M. & Kahmann, R. (1993) Plant Cell 5, 1461-1469
7. McLaughlin & Aderem, A. (1995) Trends Biochem. Sci. 20, 272-276
8. Schwyzer, R. (1991) Biochemistry 31, 785-792
9. Schwyzer, R. (1986) Biochemistry 25, 4281-4286
10. Cuba, W., Haener, R., Breipohl, G., Henke, S., Knolle, J., Santagada, V. & Kassier, H. (1994) J. Am. Chem. Soc. 116, 7532-7540
11. Wider, G., Lee, K.H. & Wüthrich, K. (1981) J. Mo!. Biol. 42, 159-163
12. Takahashi, S. (1990) Biochemistry 29, 6255-6264
13. Fields, G.B. & Noble, R.L. (1990) Int. J. Protein Res. 35, 161-214
14. Barlos, K., Chatzi, O., Gatos, D. & Stavropoulos, G. (1991) Int. J. Peptidc Protein Res. 37, 513-520
15. Barlos, K., Gatos, D., Kallistis, J., Papahotiu, G., Sotiriu, P., Wenqing, Y. & Schäfer, W. (1989) Tetrahedron Lett. 30, 3943-3946
16. Xue, C.-B., Ewenson, A., Decker, J.M. & Naider, F. (1990) Int. J. Peptide Protein Res. 36, 362-373
17. Waldmann, H. & Nagele, E. (1995) Angew. Client. 107, 2425-2428
18. Yang, C.-C., Marlowe, C.K. & Kania, R. (1991) J. Am. Cliem. Soc. 113, 3177-3178
19. Stephenson, R.C. & Clarke, S. (1990) J. Biol. Chem. 265, 16248-16254
20. Brown, M.J., Milano, P.D., Lever, D.C., Epstein, W.W. & Poulter, C.D. (1991) J. Am. Client. Soc. 113, 3176-3177
21. Sherill, C., Khouri, O., Zeman, S. & Roise, D. (1995) Biochemistry 34, 3553-3560
22. Brenner, M. & Huber, W. (1953) Heir. Chim. Ada 36, 1109-1115
23. Hiskey, R.G. & Adams, J.B. (1965) J. Org. Client. 30, 1340
24. Braunschweiler, L. & Ernst, R.R. (1983) J. Magn. Reson. 53, 521-528
25. Bax, A., Byrd, R.A. & Aszalos, A. (1984) J. Am. Chem. Soc. 106, 7632-7633
26. Jeener, J., Meier, B.H., Bachmann, P. & Ernst, R.R. (1979) J. Chem. Phys. 71, 4546-4553
27. Müller, L. (1979) J. Am. Chem. Soc. 101, 4481-4484
28. Bax, A., GrifTey, R.H. & Hawkins, L.B. (1983) J. Magn. Reson. 55, 301-315
29. Kessler, H., Bermel, W. & Griesinger, C. (1985) 6th Symp. Magn. Resonanzspektroskopie
30. Lerner, L. & Bax, A. (1986) J. Magn. Reson. 69, 375-380
31. Bax, A., Sklenar, V., Clore, G.M. & Gronenborn, A.M. (1987) J. Am. Client. Soc. 109, 6511-6513
32. Hwang, T.-L. & Shaka, AJ. (1994) J. Magn. Reson. 112, 275-279
33. Neuhaus, D. & Williamson, M. (1989) The Nuclear Overhouser Effect in Structural and Conformational Analysis . 34. Jelicks, L.A., Shenbagamurthi, Becker & J.M. Naider, F.R. ( 1988) Biopolymers 27, 431-449
34. Jelicks, L.A., Broido, M.S., Becker, J.M. & Naider, F.R., (1989) Biochemistry 28, 4233-4240
35. Dyson, H.J. & Wright, P.E. (1991) Anna. Rev. Biophys. Chem. 20, 519-538
36. Dyson, H.J., Norrby, E., Hoey, K., Parks, D.E., Lerner, R.E. & Wright, P.E. (1992) Biochemistry 31, 1458-1463
37. Havel, T.F., DISGEO (1986) Quantum Chemistry Exchange Program, Exchange No. 507, Indiana University
38. Silvius, J.R. & l'Heureux, F. (1994) Biochemistry 32, 30143022
39. Peitzsch, R.M. & McLaughlin, S. (1993) Biochemistry 32, 10436-10443
40. Tanford, C. (1991) The Hydrophobie Effect: Formation of Micelles and Biological Membranes, 2nd edn., Krieger, Dordrecht
41. McLaughlin, S. & Aderem, A. (1995) Trends Biochem. Sci. 20, 272-276
42. Silvius, J.R. & l'Heureux, F. (1994) Biochemistry 33, 30143022
43. Marcus, S., Caldwell, O.A., Miller, D., Xue, C.B., Naider, F. & Decker, J.M. (1991) Mol. Cell. Biol. 11, 3603-3612
44. Fujino, M., Kitada, C., Sakagami, Y., Isogai, A., Tamura, S. & Suzuki, A. (1980) Naturwissenschaften 67, 406-408
45. Xue, C.-B., Eriotou-Bargiota, E., Miller, D., Becker, J.M. & Naider, F. (1989) J. Biol. Client. 264, 19161-19168
46. Caldwell, O.A., Wang, S.-H., Xue, C.-B., Jiang, Y., Lu, H.-F., Naider, F. & Becker^J-M. (1994) J. Biol. Client. 269, 1981719826
47. Gounarides, J.S., Broido, M.S., Xue, C.-B., Becker, J.M. & Naider, F. (1991) Biochem. Biophys. Res. Commun. 31, 11251130
48. Ten Kortenaar, P.B.W., Van Djik, E.G., Peelers, M., Raaben, B.J., Adams, P.J.H.M. & Tesser, G.I. (1986) Int. J. Peptide Protein Res. 27, 398-400
49. König, W. & Geiger, G. (1970) Client. Ber. 103, 788-798
50. Urban, M., Kahmann, R. & Bölker, M. (1996) Mol. Gen. Genet., in press
51. Holliday, R. (1974) in King R.C. (ed.), Handbook of Genetics. Plenum, New York, vol. 1, pp. 575-595
52. Jefferson, R.A. (1987) Plant. Mol. Biol. Rep. S, 387-405
53. Richard, G., Bailey, J.A., Keon, J.P.R. & Hargreaves, J.A. (1992) Physiol. Mol. Plant Pathol. 40, 383-393