Selective enzymatic removal of protecting groups: The phenylacetamide as amino protecting group in phosphopeptide synthesis

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8725-8728

  Waldmann, Herbert ^a   Heuser, Axel ^a   Schulze, Sonja ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; AMIDASE; PHOSPHOPEPTIDE;

ARTICLE; CHEMICAL REACTION; ENZYME MECHANISM; PROTEIN MODIFICATION;

EID: 0030602202     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02041-2     Document Type: Article

References (45)

1. 1) a) Protein Phosphorylation (F. Marks, ed.), VCH, Weinheim 1996;
2. b) T. Hunter, M. Karin, Cell 1992, 70, 375-387;
3. c) E. G. Krebs, Angew. Chem. 1993, 105, 1173-1180; Angew. Chem. Int. Ed. Engl. 1993, 32, 1122;
4. c) E. G. Krebs, Angew. Chem. 1993, 105, 1173-1180; Angew. Chem. Int. Ed. Engl. 1993, 32, 1122;
5. d) E. H. Fischer, Angew. Chem. 1993, 105, 1181-1188; Angew. Chem. Int. Ed. Engl. 1993, 105, 1130;
6. d) E. H. Fischer, Angew. Chem. 1993, 105, 1181-1188; Angew. Chem. Int. Ed. Engl. 1993, 105, 1130;
7. e) D. O. Morgan, Nature 1995, 374, 131-134;
8. f) P. Cohen, TIBS 1992, 17, 408-413.
9. 2) a) G. M: Cooper Oncogenes, 2nd ed. Jones and Bartlett, Boston 1995;
10. b) A. Levitzki, A. Gazit, Science 1995, 267, 1782-1788;
11. c) A. Levitzki, Eur. J. Biochem. 1994, 226, 1-13;
12. d) A. J. Bridges, CHEMTRACTS - ORGANIC CHEMISTRY 1995 , 8, 73-107;
13. e) M. L. Gishitzky, Ann. Rep. Med. Chem. 1995, 30, 247-253.
14. 3) For recent applications of phosphopeptides in biological studies see for instance: a) M. J. Eck, S. K. Atwell, S. E. Shoelson, S. C. Harrison, Nature 1994, 368, 764-769;
15. b) T. Tagawa, T. Kuroki, P. K. Vogt, K. Chida, J. Cell. Biol. 1995, 130, 255-263;
16. c) J. W. Perich, F. Meggio, L. A. Pinna, Bioorg. Med. Chem. 1996, 4, 143-150;
17. d) S. F. Arnold, A. C. Notides, Proc. Natl. Acad. Sci. USA 1995, 92, 7475-7479;
18. e) G. Waksman, S. E. Shoelson, N. Pant, D. Cowburn, J. Kuriyan, Cell 1993, 72, 779-790;
19. f) S. Sugimoto, T. J. Wandless, S. E. Shoelson, B. G. Neel, C. T. Walsh, J. Biol. Chem. 1994, 269, 13614-13622;
20. g) G. Shapiro, D. Büchler, C. Daloit, P. Frey, M. d. Carmen Fernandez, B. Gomez-Lor, E. Pombo-Villar, U. Stauss, R. Swoboda, C. Warichl, Bioorg. Med. Chem. 1996, in press; and ref. given therein;
21. h) R. L. Stone, J. E. Dixon, J. Biol. Chem. 1994, 269, 31323-31326;
22. i) H. Hall, E. J. Williams, S. E. Moore, F. S. Walsh, A. Prochianz, P. Doherty, Current Biology 1996, 6, 580-587 and refs. given therein.
23. 4) Review: J. W. Perich, In Peptides and Protein Phosphorylation (B. E. Kemp, ed.) CRC Press, Boca Raton 1990, p. 289. For some recent developments see 3c), 3g), 5) and 6) and the references given therein.
24. 5) a) T. Wakamiya, K. Saruta, J. Yasuoka, S. Kusumoto, Chem. Lett. 1994, 1099;
25. b) T. Wakamiya, T. Nichida, R. Togashi, K. Saruta, J. Yasuoka, S. Kusumoto, Bull. Chem. Soc. Jpn. 1996, 69, 465;
26. c) T. Wakamiya, R. Togashi, T. Nishida, K. Saruta, J. Yasuoka, S. Kusumoto, S. Aimoto, K. Yoshizawa Kumogaye, K. Nakajima, K. Nagata, Bioorg. Med. Chem. 1996, in print.
27. 6) a) G. Shapiro, R. Swoboda, U. Stauss, Tetrahedron Lett. 1994, 35, 869;
28. b) G. Shapiro, D. Büchler, Tetrahedron Lett. 1994, 35, 5421;
29. c) G. Shapiro, D. Büchler, C. Dalvit, M. del Carmen Fernandez, B. Gomez-Lor, E. Pombo-Villar, U. Strauss, R. Swoboda, Bioorg. Med. Chem. Lett. 1996, 6, 409;
30. d) D. B. A. de Bout, W. J. Moore, J. H. van Boom, R. M. J. Liskamp, J. Org. Chem. 1993, 58, 1309.
31. 7) Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996,108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056;
32. 7) Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996,108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056;
33. b) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911-937.
34. 8) a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
35. 8) a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
36. b) 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.
37. b) 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.
38. 9) a) P. Braun, H. Waldmann, H. Kunz, Bioorg. Med. Chem. 1993, 1, 197-207;
39. b) T. Pohl, H. Waldmann, Angew. Chem. 1996, 108, 1829-1832; Angew. Chem. Int. Ed. Engl. 1996, 35, 1720-1723.
40. b) T. Pohl, H. Waldmann, Angew. Chem. 1996, 108, 1829-1832; Angew. Chem. Int. Ed. Engl. 1996, 35, 1720-1723.
41. 10) Use of the PhAc group for the deprotection of peptides carbohydrates and nucleosides: a) H. Waldmann, Liebigs Ann. Chem. 1988, 1175-1180 and references therein;
42. b) H. Waldmann, A. Heuser, A. Reidel, Synlett 1994, 65-67;
43. c) M. A. Dineva, B. Galunsky, V. Kasche, D. D. Petkov, Bioorg. Med. Chem. Lett. 1993, 3, 2781-2784.
44. 11) W. Bannwarth, E. Küng, Tetrahedron Lett. 1989, 30, 4219.
45. 23= -31,8 (c=1, CH3OH).