Staudinger ligation: A peptide from a thioester and azide

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1939-1941

  Nilsson, Bradley L ^a   Kiessling, Laura L ^a   Raines, Ronald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CYSTEINE; ESTER; PEPTIDE;

ARTICLE; BIOCHEMISTRY; CHEMISTRY; METHODOLOGY; SYNTHESIS;

AZIDES; BIOCHEMISTRY; CYSTEINE; ESTERS; PEPTIDES;

EID: 0034729576     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060174     Document Type: Article

References (52)

1. For historical references, see: (a) Merrifield, R. B. Science 1984, 252, 341-347.
2. (b) Kent, S. B. Annu. Rev. Biochem. 1988, 57, 957-989.
3. (c) Kaiser, E. T. Acc. Chem. Res. 1989, 22, 47-54.
4. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. Science 1994, 266, 776-779.
5. For important precedents, see: (a) Wieland, T.; Bokelmann, E.; Bauer, L.; Lang, H. U.; Lau, H. Liebigs Ann. Chem. 1953, 583, 129-149.
6. (b) Kemp, D. S.; Galakatos, N. G. J. Org. Chem. 1986, 51, 1821-1829.
7. For reviews, see: (c) Muir, T. W.; Dawson, P. E.; Kent, S. B. H. Methods Enzymol. 1997, 289, 266-298.
8. (d) Wilken, J.; Kent, S. B. H. Curr. Opin. Biotechnol. 1998, 9, 412-426.
9. (e) Kochendoerfer, G. G.; Kent, S. B. H. Curr. Opin. Chem. Biol. 1999, 3, 665-671.
10. (a) Muir, T. W.; Sondhi, D.; Cole, P. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 9, 6705-6710.
11. (b) Evans, T. C., Jr.; Benner, J.; Xu, M.-Q. Protein Sci. 1998, 7, 2256-2264.
12. (c) Ayers, B.; Blaschke, U. K.; Camarero, J. A.; Cotton, G. J.; Holford, M.; Muir, T. W. Biopolymers 2000, 51, 343-354.
13. For reviews, see: (d) Holford, M.; Muir, T. W. Structure 1998, 15, 951-956.
14. (e) Cotton, G. J.; Muir, T. W. Chem. Biol. 1999, 6, R247-R256.
15. (f) Evans, T. C., Jr.; Xu, M.-Q. Biopolymers 2000, 51, 333-342.
16. For a few specific ligation reactions, this restriction has been overcome by using the native conformation of the protein to guide the regioselective coupling of an activated ester and amine. For examples, see: (a) Homandberg, G. A.; Laskowski, M. Biochemistry 1979, 18, 586-592.
17. (b) Wuttke, D. S.; Gray, H. B.; Fisher, S. L.; Imperiali, B. J. Am. Chem. Soc. 1993, 113, 8455-8456.
18. (c) Vogel, K.; Chmielewski, J. J. Am. Chem. Soc. 1994, 116, 11163-11164.
19. (d) Beligere G. S.; Dawson, P. E. J. Am. Chem. Soc. 1999, 121, 6332-6333.
20. McCaldon, P.; Argos, P. Proteins 1988, 4, 99-122.
21. (a) Schneider, C. H.; de Weck, A. L. Biochim. Biophys. Acta 1965, 168, 27-35.
22. (b) Raines, R. T. Nat. Struct. Biol. 1997, 4, 424-427.
23. Friedman, M. Adv. Exp. Med. Biol. 1999, 459, 145-159.
24. Offer, J.; Dawson, P. E. Org. Lett. 2000, 2, 23-26.
25. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646.
26. For reviews, see: (a) Gololobov, Yu. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472.
27. (b) Gololobov, Yu. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
28. For examples, see: (a) Bosch, I.; Romea, P.; Urpf, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674.
29. (b) Bosch I.; Urpi F.; Vilarrasa J. J. Chem. Soc., Chem. Commun. 1995, 91-92.
30. (c) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701.
31. (d) Bosch, I.; Gonzalez, A.; Urpi, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643.
32. (e) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776.
33. (f) Ariza X.; Urpi, F.; Viladomat, C.; Vilarrasa J. Tetrahedron Lett. 1998, 39, 9101-9102.
34. Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007-2010.
35. Amide formation by intramolecular acyl transfer from an N-acyl imidazole to an iminophosphorane nitrogen is also traceless and effective (Bertozzi, C. R. Presented at the 218th National Meeting of the American Chemical Society, New Orleans, LA, August 1999; Paper ORGN 233).
36. Dawson, P. E.; Churchill, M.; Ghadiri, M. R.; Kent, S. G. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
37. o-(Diphenylphosphino)benzenethiol (2) was prepared by reaction of chlorodiphenylphosphine and ortholithiated thiophenol, as described by Block, E.; Ofori-Okai, G.; Zubieta, J. J. Am. Chem. Soc. 1989, 111, 2327-2329.
38. 4-o-SH)C(O)R), followed by intramolecular P-to S-acyl migration.
39. The other major product was GlyNHBn, which can derive from the Staudinger reaction (ref 9).
40. 2O (3:1).
41. A peptide or protein with a C-terminal thioester can be produced from Fmoc-based solid-phase synthesis (Ingenito, R.; Blanchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374. Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689) or rDNA techniques (ref 3).
42. A peptide or protein with a C-terminal thioester can be produced from Fmoc-based solid-phase synthesis (Ingenito, R.; Blanchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374. Shin, Y.; Winans, K. A.; Backes, B. J.; Kent, S. B. H.; Ellman, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 1999, 121, 11684-11689) or rDNA techniques (ref 3).
43. 3 (Zaloom, J.; Roberts, D. C. J. Org. Chem. 1981, 46, 5173-5176).
44. (a) Tam, J. P.; Lu, Y. A.; Chuan-Fa, L.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489.
45. (b) Tam, J. P.; Yu, Q.; Miao, Z. Biopolymers 2000, 51, 311-332.
46. For recent reviews, see: (a) Katz, L. Chem. Rev. 1997, 97, 2557-2575.
47. (b) Khosla, C. Chem. Rev. 1997, 97, 2577-2590.
48. (c) Marahiel, M. A.; Stachelhaus, T.; Mootz, H. D. Chem. Rev. 1997, 97, 2651-2673.
49. (d) von Döhren, H.; Keller, U.; Vater, J.; Zocher, R. Chem. Rev. 1997, 97, 2675-2705.
50. (e) Cane, D. E.; Walsh, C. T. Khosla, C. Science 1998, 282, 63-68.
51. (f) Konz, D.; Marahiel, M. A. Chem. Biol. 1999, 6, R39-R48.
52. (g) Keating, T. A.; Walsh, C. T. Curr. Opin. Chem. Biol. 1999, 3, 598-606.