Chemoenzymatic synthesis of a characteristic phosphorylated and glycosylated peptide fragment of the large subunit of mammalian RNA polymerase II

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6702-6710

  Pohl, Torsten ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; GLYCOSYLATED PROTEIN; HEXAPEPTIDE; HYDROXYAMINO ACID; PENICILLIN G; PHOSPHOPROTEIN; RNA POLYMERASE II;

ARTICLE; CATALYST; ENZYME MECHANISM; ENZYME SPECIFICITY; PEPTIDE SYNTHESIS;

EID: 0030750029     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970709e     Document Type: Article

References (57)

1. (a) Hunter, T.; Karin, M. Cell 1992, 70, 375.
2. (b) Levitzki, A. Eur. J. Biochem. 1994, 226, 1.
3. (c) Casey, P. J. Science 1995, 268, 221.
4. (d) Egan, S. E.; Weinberg, R. A. Nature 1993, 365, 781.
5. (e) Boguski, M. S.; McCormick, F. Nature 1993, 366, 643.
6. (a) Krebs, E. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122.
7. (a) Krebs, E. Angew. Chem. 1993, 105, 1173; Angew. Chem., Int. Ed. Engl. 1993, 32, 1122.
8. (b) Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 32, 1130.
9. (b) Fischer, E. H. Angew. Chem. 1993, 105, 1181; Angew. Chem., Int. Ed. Engl. 1993, 32, 1130.
10. (c) Bridges, A. J. Chemtracts: Org. Chem. 1995, 8, 73.
11. (a) Hart, G. W.; Haltiwanger, R. S.; Holt, G. D; Kelly, W. G. Ann. Rev. Biochem. 1989, 58, 841.
12. (b) Hart, G. W.; Kelly, W. G.; Blomberg, M. A.; Roquemore, E. P.; Dong, L.-Y.; Kreppel, L.; Chou, T.-Y.; Snow, D.; Greis, K. Glyco- and Cellbiology, 44; Colloquium Mosbach 1993; Springer-Verlag: Berlin, Heidelberg, 1994.
13. (a) Jackson, S. P.; Tjian, R. Cell 1988, 55, 125.
14. (b) Lichtsteiner, S.; Schibler, U. Cell 1989, 57, 1179.
15. (c) Reason, A.; Dell, A.; Morris, H. R.; Panico, M.; Treisman, R.; Marais, R.; Hart, G. W.; Haltiwanger, R. S. Glycoconjugate J. 1991, 8, 211.
16. (a) Privalsky, M. L. J. Virol. 1990, 64, 463.
17. (b) Chou, T.-Y.; Hart, G. W.; Dang, C. V. J. Biol. Chem. 1995, 270, 18961.
18. (a) Datta, B.; Ray, M. K.; Chakrabarti, D.; Wylie, D. E.; Gupta, N. K. J. Biol. Chem. 1989, 264, 20620.
19. (b) Maikrantz, W.; Smith, D. M.; Sladicka, M. M.; Schlegel, R. A. J. Cell. Sci. 1991, 98, 303.
20. (a) Mullis, K. G.; Haltiwanger, R. S.; Hart, G. W.; Marchase, R. B.; Engler, J. A. J. Virol. 1990, 64, 5317.
21. (b) Whitford, M.; Faulkner, P. J. Virol. 1992, 66, 3324.
22. (c) Gonzalez, S. A.; Burrone, O. R. Virology 1992, 182, 8.
23. Haltiwanger, R. S.; Kelly, W. G.; Roquemore, E. P.; Blomberg, M. A.; Dong, L.-Y. D.; Kreppel, L.; Chou, T.-Y.; Greis, K.; Hart, G. W. Biochem. Soc. Trans. 1992, 20, 264.
24. Kelly, W. G.; Dahmus, M. E.; Hart, G. W. J. Biol. Chem. 1993, 268, 10416.
25. (a) Perich, J. W. Peptides and Protein Phosphorylation; Kemp, B. E., Ed.; CRC Press: Boca Raton, FL, 1990.
26. (b) Shapiro, G.; Buechler, D. Tetrahedron Lett. 1994, 35, 5421.
27. (a) Kunz, H. Angew. Chem. 1987, 99, 297; Angew. Chem., Int. Ed. Engl. 1987, 26, 294.
28. (a) Kunz, H. Angew. Chem. 1987, 99, 297; Angew. Chem., Int. Ed. Engl. 1987, 26, 294.
29. (b) Garg, H.; Jeanloz, R. W. Adv. Carbohydr. Chem. Biochem. 1985, 43, 135.
30. For reviews, see: (a) Pohl, T.; Nägele, E.; Waldmann, H. Catal. Today 1994, 22, 407. (b) Drauz, K.; Waldmann, H. Enzymes in Organic Synthesis - A Comprehensive Handbook; VCH: Weinheim, 1995. (c) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
31. For reviews, see: (a) Pohl, T.; Nägele, E.; Waldmann, H. Catal. Today 1994, 22, 407. (b) Drauz, K.; Waldmann, H. Enzymes in Organic Synthesis - A Comprehensive Handbook; VCH: Weinheim, 1995. (c) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
32. For reviews, see: (a) Pohl, T.; Nägele, E.; Waldmann, H. Catal. Today 1994, 22, 407. (b) Drauz, K.; Waldmann, H. Enzymes in Organic Synthesis - A Comprehensive Handbook; VCH: Weinheim, 1995. (c) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
33. (a) Waldmann, H.; Nägele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259.
34. (a) Waldmann, H.; Nägele, E. Angew. Chem. 1995, 107, 2425; Angew. Chem., Int. Ed. Engl. 1995, 34, 2259.
35. (b) Schelhaas, M.; Glomsda, S.; Häusler, M.; Jakubke, H.-D. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106.
36. (b) Schelhaas, M.; Glomsda, S.; Häusler, M.; Jakubke, H.-D. Angew. Chem. 1996, 108, 82; Angew. Chem., Int. Ed. Engl. 1996, 35, 106.
37. (c) Waldmann, H.; Nägele, E.; Schelhaas, M. Bioorg. Med. Chem. 1996, 5, 75.
38. Braun, D.; Waldmann, H.; Kunz, H. Bioorg. Med. Chem. 1993, 1, 197.
39. (a) Waldmann, H.; Heuser, A.; Schulze, S. Tetrahedron Lett. 1996, 37, 8725.
40. (b) Sebastian, D.; Waldmann, H. Tetrahedron Lett. 1997, 38, 2927.
41. Gabold, S.; Waldmann, H. Submitted for publication.
42. Part of this work was published in preliminary form, see: Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720.
43. Part of this work was published in preliminary form, see: Pohl, T.; Waldmann, H. Angew. Chem. 1996, 108, 1829; Angew. Chem., Int. Ed. Engl. 1996, 35, 1720.
44. Schultheiss-Reimann, P.; Kunz, H. Angew. Chem. 1983, 95, 64; Angew. Chem., Int. Ed. Engl. 1983, 22, 62.
45. Schultheiss-Reimann, P.; Kunz, H. Angew. Chem. 1983, 95, 64; Angew. Chem., Int. Ed. Engl. 1983, 22, 62.
46. (a) Waldmann, H.; Heuser, A.; Reidel, A. Synlett 1994, 65.
47. (b) Waldmann, H.; Heuser, A. Bioorg. Med. Chem. 1994, 2, 477.
48. (a) Pohl, T.; Waldmann, H. Tetrahedron Lett. 1995, 36, 2963 and references given therein.
49. (b) Cole, M. Biochem. J. 1969, 115, 741, 747.
50. Bolin, D. R.; Sytwu, I. I.; Humiec, F.; Meienhofer, J. Int. J. Pept. Protein Res. 1989, 33, 353 and references therein.
51. Le Corré, G.; Guibé-Jampel, E.; Wakselman, M. Tetrahedron 1978, 34, 3105.
52. Friedrich-Bochnitschek, S.; Waldmann, H.; Kunz, H. J. Org. Chem. 1989, 54, 751.
53. For a synthesis of a glycosylated analog to 2, see: Meinjohanns, E.; Vargas-Berenguel, A.; Meldal, M.; Paulsen, H.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1995, 2165.
54. Arsequell, G.; Krippner, L.; Dwek, R. A.; Wong, S. Y. C. J. Chem. Soc., Chem. Commun. 1994, 2383.
55. Mathias, L. Synthesis 1979, 561.
56. Waldmann, H. Liebigs Ann. Chem. 1988, 1179 and references given therein.
57. Hayakawa, Y.; Kato, H.; Uchiyama, M.; Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2402.