Site-selective conjugation of thiols with aziridine-2-carboxylic acid-containing peptides

Journal of the American Chemical Society

Volumn 126, Issue 40, 2004, Pages 12712-12713

  Galonić, Danica P ^a   Van Der Donk, Wilfred A ^a   Gin, David Y ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE 2 CARBOXYLIC ACID; AZIRIDINE DERIVATIVE; CARBOXYLIC ACID; PEPTIDE; POLYMER; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DEACYLATION; DEPROTECTION REACTION; PEPTIDE SYNTHESIS; PROTEIN PROCESSING; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID; STEREOCHEMISTRY;

EID: 5644259534     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046793x     Document Type: Article

References (31)

1. (a) Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370-2376.
2. (b) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357-2364.
3. (c) Seitz, O.; Heinemann, I.; Mattes, A.; Waldmann, H. Tetrahedron 2001, 57, 2247-2277.
4. (a) Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Science 1997, 276, 1125-1128.
5. (b) Melnyk, O.; Fehrentz, J.-A.; Martinez, J.; Gras-Masse, H. Biopolymers 2000, 55, 165-186.
6. (c) Deiters, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 725, 11782-11783 and references therein.
7. (a) Okawa, K.; Nakajima, K. Biopolymers 1981, 20, 1811-1821.
8. (b) Wakamiya, T.; Shimbo, K.; Shiba, T.; Nakajima, K.; Neya, M.; Okawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 3878-3881.
9. (c) Nakajima, K.; Oda, H.; Okawa, K. Bull. Chem. Soc. Jpn. 1983, 56, 520-522.
10. (d) Kuyl-Yeheskiely, E.; Dreef-Tromp, C. M.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1989, 108, 314-316.
11. (e) Korn, A.; Rudolph-Böhner, S.: Moroder, L. Tetrahedron 1994, 50, 1717-1730.
12. (f) Tam, J. P.; Xu, J.; Eom, K. D. Biopolymers 2001, 60, 194-205.
13. Shao, H.; Jiang, X.; Gantzel, P.; Goodman, M. Chem. Biol. 1994, 1, 231-234.
14. 3N (0.2 equiv), see: Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730.
15. 2 product was obtained as a single diastereomer, assumed to result from inversion (absolute configuration not determined).
16. For approaches to the preparation of glycopeptide mimetics, see: (a) Recent review: Peri, F.; Nicotra, F. Chem. Commun. 2004, 623-627.
17. (b) Zhao, Y.; Kent, S. B. H.; Chait, B. T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1629-1633.
18. (c) Rodriguez, E. C.; Winans, K. A.; King, D. S.; Bertozzi, C. R. J. Am. Chem. Soc. 1997, 119, 9905-9906.
19. (d) Zhu, Y., van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192.
20. (e) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534-2543.
21. (f) Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 725, 1702-1703.
22. (g) Watt, G. M.; Lund, J.; Levens, M.; Kolli, V. S. K.: Jefferis, R.; Boons, G.-J. Chem. Biol. 2003, 10, 807-814.
23. (h) Galonić, D. P.; van der Donk, W. A.; Gin, D. Y. Chem. Eur. J. 2003, 9, 5997-6006.
24. (i) Zhu, X.; Schmidt, R. R. Chem. Eur. J. 2004, 10, 875-887.
25. (j) Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem., Int. Ed. 2004, 43, 828-833.
26. For ligation approaches to the preparation of native linkages, see, for example: (k) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431-434.
27. Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. J. Chem. Soc., Chem. Commun. 1994, 2559-2560.
28. For the preparation of FmocAzyOH, see Supporting Information.
29. Wade, J. D.; Bedford, J.; Sheppard, R. C.; Tregear, G. W. Pept. Res. 1991, 4, 194-199.
30. 1H NMR) to be 80-90% pure prior to ligation.
31. Moroder, L.; Musiol, H.-J.; Scharf, R. FEBS Lett. 1992, 299, 51-53.