Synthesis of the N-terminal lipohexapeptide of human Gαo-protein and fluorescent-labeled analogues for biological studies

Chemistry - A European Journal

Volumn 5, Issue 3, 1999, Pages 922-936

  Cotté, Alain ^a   Bader, Benjamin ^b   Kuhlmann, Jürgen ^b   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

^b MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

Cell signaling; Enzyme reactions; Lipopeptides; Protecting groups; Proteins

Indexed keywords

CARBOXYLIC ACID; CHOLINESTERASE; FLUORESCENT DYE; GUANINE NUCLEOTIDE BINDING PROTEIN; HEXAPEPTIDE; MORPHOLINE; PALMITIC ACID; PEPTIDE FRAGMENT; RHODAMINE B;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL REACTION; CONJUGATION; ENZYME SYNTHESIS; FLUORESCENCE; HYDROLYSIS; PALMITOYLATION; PEPTIDE SYNTHESIS; PRENYLATION; PROTEIN DEGRADATION; PROTEIN STRUCTURE; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

EID: 0032986772     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990301)5:3<922::aid-chem922>3.0.co;2-o     Document Type: Article

References (44)

1. a) A. G. Gilman, Annu. Rev. Biochem. 1987, 615-649;
2. b) J. R. Hepler, A. G. Gilman, Trends Biochemn. Sci. 1992, 17, 383-387;
3. c) M. I. Simon, M. P. Strathmann, N. Gautam, Science 1991, 252, 802-808;
4. d) P. B. Wedegaertner, P. T. Wilson, H. R. Bourne, J. Biol. Chem. 1995, 270, 503-506.
5. M. E. Linder, P. Middleton, J. R. Hepler, R. Taussig, A. G. Gilman, S. M. Mumby, Proc. Natl. Acad. Sci. USA 1993, 90, 3675-3679.
6. A. M. Shenoy-Scaria, L. K. Timson Gauen, J. Kwong, A. S. Shaw, D. M. Lublin, Mol. Cell Biol. 1993, 13, 6385-6392.
7. a) G. Milligan, M. Parenti, A. I. Magee, Trends Biochem. Sci. 1995,20, 191-186;
8. b) J.-Y. Lu, L. A. Verkruyse, S. L. Hofmann, Proc. Natl. Acad. Sci. USA 1996, 93, 10046-10050.
9. S. Moffet, B. Mouillac, H. Bouin, M. Bouvier, EMBO J. 1993, 12, 349-35
10. P. B. Wedegaertner, H. R. Bourne, Cell 1994, 77, 1063-1070.
11. K. Hinterding, D. Alonso-Diaz, H. Waldmann, Angew. Chem. 1998, 110, 716-780; Angew. Chem. Int. Ed. 1998, 37, 688-749.
12. K. Hinterding, D. Alonso-Diaz, H. Waldmann, Angew. Chem. 1998, 110, 716-780; Angew. Chem. Int. Ed. 1998, 37, 688-749.
13. Part of this research was published in preliminary form: T. Schmittberger, A. Cotté, H. Waldmann, Chem. Commun. 1998, 937-938.
14. S. M. Mumby, C. Kleuss, A. G. Gilman, Proc. Natl. Acad. Sci USA 1994, 91, 2800-2804.
15. a) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, Angew. Chem. 1996, 108, 82-85; Angew. Chem. Int. Ed. Engl. 1996, 35, 106-109;
16. a) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, Angew. Chem. 1996, 108, 82-85; Angew. Chem. Int. Ed. Engl. 1996, 35, 106-109;
17. b) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
18. b) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
19. c) P. Stöber, M. Schelhaas, E. Nägele, P. Hagenbuch, J. Rétey, H. Waldmann, Bioorg. Med. Chem. 1997, 5, 75-83.
20. a) E. Nägele, M. Schelhaas, N. Kuder, H. Waldmann, J. Am. Chem. Soc. 1998, 120, 6889;
21. b) M. Schelhaas, E. Nägele, N. Kuder, H. B. Bader, J. Kuhlmann, A. Wittinghofer, H. Waldmann, Chem. Eur. J. 1999, 5, in press.
22. H. Garg, R. W. Jeanloz, Adv. Carbohydr. Chem. Biochem. 1985, 43, 135.
23. S. Friedrich-Bochnitschek, H. Waldmann, H. Kunz, J. Org. Chem. 1989, 54, 751.
24. H. Kunz, Angew. Chem. 1987, 99, 297; Angew. Chem. Int. Ed. Engl. 1987, 26, 294.
25. H. Kunz, Angew. Chem. 1987, 99, 297; Angew. Chem. Int. Ed. Engl. 1987, 26, 294.
26. M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056.
27. M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056.
28. a) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911;
29. b) T. Kappes, H. Waldmann, Liebigs Ann./Recueil 1997, 803.
30. H. Kunz, M. Buchholz, Chem. Ber. 1979, 112, 2145-2157.
31. T. Zelinski, M.-R. Kula, Biocatalysis Biotransform. 1997, 15, 57.
32. R. L. van Etten, J. F. Sebastian, G. A. Clowes, M. L. Bender, J. Am. Chem. Soc. 1967, 89, 3242-3253; J. Am. Chem. Soc. 1967, 89, 3253-3262.
33. R. L. van Etten, J. F. Sebastian, G. A. Clowes, M. L. Bender, J. Am. Chem. Soc. 1967, 89, 3242-3253; J. Am. Chem. Soc. 1967, 89, 3253-3262.
34. a) S. Shahinian, J. R. Silvius, Biochemistry 1995, 34, 3813;
35. b) H. Schröder, R. Leventis, S. Shahinian, P. A. Walton, J. R. Silvius, J. Cell. Biol. 1996, 134, 647.
36. a) H. Schröder, R. Leventis, S. Rex, M. Schelhaas, E. N gele, H. Waldmann, J. R. Silvius, Biochemistry 1997, 36, 13102;
37. b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schröder, J. R. Silvius, Angew. Chem. 1997, 109, 2334; Angew. Chem. Int. Ed. Engl. 1997, 36, 2238.
38. b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schröder, J. R. Silvius, Angew. Chem. 1997, 109, 2334; Angew. Chem. Int. Ed. Engl. 1997, 36, 2238.
39. S. McLaughlin, A. Achren, Trends Biochem. Sci. 1995, 20, 272.
40. G. T. Hermanson, Bioconjugate Techniques, Academic Press, San Diego, 1996.
41. R. C. Macdonald, R. I. Macdonald, B. P. M. Menco, K. Takeshita, N. K. Subbarao, L. R. Hu, Biochim. Biophys. Acta 1991, 1061, 297.
42. S. Lin, W. S. Struve, Photochem. Photobiol. 1991, 54, 361.
43. J. S. Palston, A. R. Main, B. F. Kilpatrick, A. L. Chasson, Biochem. J. 1983, 211, 243-250.
44. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon, Oxford, 1988.