High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide

Organic Letters

Volumn 3, Issue 1, 2001, Pages 9-12

  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; PHOSPHOROTHIOIC ACID DERIVATIVE; PROTEIN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AZIDES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOTHIOPHOSPHORUS COMPOUNDS; PROTEINS;

EID: 0035843279     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006739v     Document Type: Article

References (47)

1. Wieland, T.; Bokelmann, E.; Bauer, L.; Lang, H. U.; Lau, H. Liebigs Ann. Chem. 1953, 583, 129-149.
2. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
3. For recent reviews of peptide ligation methods, see: (a) Tam, J. P.; Yu, Q.; Miao, Z. Biopolymers 1999, 51, 311-332.
4. (b) Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
5. Borgia, J. A.; Fields, G. B. Trends Biotechnol. 2000, 18, 243-251.
6. (a) Muir, T. W.; Sondhi, D.; Cole, P. A. Proc. Natl. Acad. Sci. U.S.A. 1998, 9, 6705-6710. For reviews, see:
7. (b) Holford, M.; Muir, T. W. Structure 1998, 15, 951-956.
8. Cotton, G. J.; Muir, T. W. Chem. Biol. 1999, 6, R247-R256.
9. Evans, T. C., Jr.; Xu, M.-Q. Biopolymers 2000, 51, 333-342.
10. Only tryptophan (1.3%) is less common. McCaldon, P.; Argos, P. Proteins 1988, 4, 99-122.
11. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646. For comprehensive reviews, see:
12. (b) Gololobov, Yu. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472.
13. Gololobov, Yu. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
14. For examples, see: (a) Garcia, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1984, 25, 4841-4844.
15. (b) Garcia, J.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 639-640.
16. (c) Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1986, 27, 4623-4624.
17. Bosch, I.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett 1993, 34, 4671-4674.
18. (e) Inazu, T.; Kobayashi, K. Synlett. 1993, 869-870.
19. (f) Molina, P.; Vilaplana, M. J. Synthesis-Stuttgart 1994, 1197-1218.
20. (g) Bosch, I.; Urpí, F.; Vilarrasa, J. J. Chem. Soc., Chem. Commun. 1995, 91-92.
21. (h) Shalev, D. E.; Chiacchiera, S. M.; Radkowsky, A. E.; Kosower, E. M. J. Org. Chem. 1996, 61, 1689-1701.
22. Bosch, I.; Gonzalez, A.; Urpí, F.; Vilarrasa, J. J. Org. Chem. 1996, 61, 5638-5643.
23. (j) Maunier, V.; Boullanger, P.; Lafont, D. J. Carbohydr. Res. 1997, 16, 231-235.
24. (k) Afonso, C. A. M. Synth. Commun. 1998, 28, 261-276.
25. (l) Tang, Z.; Pelletier, J. C. Tetrahedron Lett. 1998, 39, 4773-4776.
26. (m) Ariza X.; Urpí, F.; Viladomat, C.; Vilarrasa J. Tetrahedron Lett. 1998, 39, 9101-9102.
27. (n) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis-Stuttgart 1999, 162-165.
28. (o) Mizuno, M.; Haneda, K.; Iguchi, R.; Muramoto, I.; Kawakami, T.; Aimoto, S.; Yamamoto, K.; Inazu, T. J. Am. Chem. Soc. 1999, 121, 284-290.
29. (p) Boullanger P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106.
30. (q) Velasco, M. D.; Molma, P.; Fresneda, P. M.; Sanz, M. A. Tetrahedron 2000, 56, 4079-4084.
31. (r) Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
32. (a) Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007-2010.
33. (b) Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1941.
34. (c) Saxon, E.; Armstrong, J. I.; Bertozzi, C. R. Org. Lett. 2000, 2, 2141-2143.
35. (a) Lamoureux, G. V.; Whitesides, G. M. J. Org. Chem. 1993, 58, 633-641.
36. (b) Woycechowsky, K. J.; Wittrup, K. D.; Raines, R. T. Chem. Biol. 1999, 6, 871-879.
37. Charrier, C.; Mathey, F. Tetrahedron Lett. 1978, 27, 2407-2410.
38. Hydrolysis under acidic conditions was unsuccessful.
39. 2OH. The basis for the antipodal reactivity of thioesters and esters is unclear.
40. For examples of the "reactive rotamer effect", see: (a) Bruice, T. C.; Pandit, U. K. J. Am. Chem. Soc. 1960, 82, 5858-5865.
41. (b) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
42. Janssen, M. J. The Chemistry of Carboxylic Adds and Esters; Patai, S., Ed.; Interscience Publishers: New York, 1969; pp 730-736.
43. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374.
44. (b) 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.
45. Swinnen, D.; Hilvert, D. Org. Lett. 2000, 2, 2439-2442.
46. Zaloom, J.; Roberts, D. C. J. Org. Chem. 1981, 46, 5173-5176.
47. Meldal, M.; Juliano, M. A.; Jansson, A. M. Tetrahedron Lett. 1997, 38, 2531-2534.