Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thioester

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4465-4468

  Nagaike, Fumihiro ^a   Onuma, Yuko ^a   Kanazawa, Chie ^a   Hojo, Hironobu ^a   Ueki, Akiharu ^a   Nakahara, Yuko ^a   Nakahara, Yoshiaki ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 MERCAPTOPROPIONIC ACID; ESTER; PEPTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROWAVE RADIATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

3-MERCAPTOPROPIONIC ACID; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GLYCOSYLATION; MICROWAVES; OXIDATION-REDUCTION; PEPTIDES; SULFHYDRYL COMPOUNDS;

EID: 33750040284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0616034     Document Type: Article

References (34)

1. Hojo, H.; Aimoto, S. Bull Chem. Soc. Jpn. 1991, 64, 111-117.
2. Aimoto, S. Biopolymer (Pept. Sci.) 1999, 51, 247-265.
3. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
4. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923-960.
5. Futaki, S.; Sogawa, K.; Maruyama, J.; Asahara, T.; Niwa, M.; Hojo, H. Tetrahedron Lett. 1997, 38, 6237-6240.
6. Li, X.; Kawakami, T.; Aimoto, S. Tetrahedron Lett. 1998, 39, 8669-8672.
7. 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.
8. Alsina, J.; Yokumu, T. S.; Albericio, F.; Barany, G. J. Org. Chem. 1999, 64, 8761-8769.
9. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374.
10. Clippingdale, A. B.; Barrow, C. J.; Wade, J. D. J. Pept. Sci. 2000, 6, 225-234.
11. Swinnen, D.; Hilvert, D. Org. Lett. 2000, 2, 2439-2442.
12. Mezo, A. R.; Cheng, R. P.; Imperiali, B. J. Am. Chem. Soc. 2001, 123, 3885-3891.
13. Flavell, R. R.; Huse, M.; Goger, M.; Trester-Zedlitz, M.; Kuriyan, J.; Muir, T. W. Org. Lett. 2002, 4, 165-168.
14. Brask, J.; Albericio, F.; Jensen, K. Org. Lett. 2003, 5, 2951-2953.
15. Camarero, J. A.; Hackel, B. J.; de Yoreo, J. J.; Mitchell, A. R. J. Org. Chem. 2004, 69, 4145-4151.
16. Warren, J. D.; Miller, J. S.; Keding, S. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6576-6578.
17. Botti, P.; Villain, M.; Manganiello, S.; Gaertner, H. Org. Lett. 2004, 6, 4861-4864.
18. Kawakami, T.; Sumida, M.; Nakamura, K.; Vorherr, T.; Aimoto, S. Tetrahedron Lett. 2005, 46, 8805-8807.
19. Ollivier, N.; Behr, J.-B.; El-Mahdi, O.; Blanpain, A.; Melnyk, O. Org. Lett. 2005, 7, 2647-2650.
20. Ohta, Y.; Itoh, S.; Shigenaga, A.; Shintaku, S.; Fujii, N.; Otaka, A. Org. Lett. 2006, 8, 467-470.
21. Macmillan, D.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2004, 43, 1355-1359.
22. Hojo, H.; Haginoya, E.; Matsumoto, Y.; Nakahara, Y.; Nabeshima, K.; Toole, B. P.; Watanabe, Y. Tetrahedron Lett. 2003, 44, 2961-2964.
23. Hojo, H.; Matsumoto, Y.; Nakahara, Y.; Ito, E.; Suzuki, Y.; Suzuki, M.; Suzuki, A.; Nakahara, Y. J. Am. Chem. Soc. 2005, 127, 13720-13725.
24. Mezzato, S.; Schaffrath, M.; Unverzagt, C. Angew. Chem., Int. Ed. 2005, 44, 1650-1654.
25. Wu, B.; Warren, J. D.; Chen, J.; Chen, G.; Hua, Z.; Danishefsky, S. J. Tetrahedron Lett. 2006, 47, 5219-5223.
26. Wu, B.; Chen, J.; Warren, J. D.; Chen, G.; Hua, Z.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 4116-4125.
27. Yamamoto, N.; Takayanagi, A.; Yoshino, A.; Sakakibara, T.; Kajihara, Y. Chem.-Eur. J. 2006, in press.
28. Kajihara, Y.; Yoshihara, A.; Hirano, K.; Yamamato, N. Carbohydr. Res. 2006, 341, 1333-1340.
29. Chiesa, M. V.; Manzoni, L.; Scolastico, C. Synlett 1996, 441-443.
30. King, D. S.; Fields, C. G.; Fields, G. B. Int. J. Pept. Protein Res. 1990, 36, 255-266.
31. Matsushita, T.; Hinou, H.; Kurogochi, M.; Shimizu, H.; Nishimura, S.-I. Org. Lett. 2005, 7, 877-880.
32. Murray, J. K.; Farooqi, B.; Sadowsky, J. D.; Scalf, M.; Freund, W. A.; Smith, L. M.; Chen, J.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 13271-13280.
33. Tam, J. P.; Heath, W. F.; Merrifield, B. R. J. Am. Chem. Soc. 1986, 108, 5242-5251.
34. Takano, Y.; Habiro, M.; Someya, M.; Hojo, H.; Nakahara, Y. Tetrahedron Lett. 2002, 43, 8395-8399.