Bulletin of the Korean Chemical Society

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Synthesis of Peptide Amides on Safety-catch Resin with Microwave Irradiation

  • Park, Jun-won (Bioorganic Chemistry Lab., Department of Chemistry, Inha University) ;
  • Lee, Keun-Hyeung (Bioorganic Chemistry Lab., Department of Chemistry, Inha University)
  • Published : 2009.10.20
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References

  1. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1971, 636.
  2. Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055. https://doi.org/10.1021/ja9535165
  3. Backes, B. J.; Ellman, J. A. J. Org. Chem. 1999, 64, 2322. https://doi.org/10.1021/jo981990y
  4. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 1369.
  5. Huse, M.; Holford, M. N.; Kuriyan, J.; Muir, T. W. J. Am. Chem. Soc. 2000, 122, 8337. https://doi.org/10.1021/ja001763p
  6. Gieselman, M. D.; Xie, L.; van der Donk, W. A. Org. Lett. 2001, 3, 1331. https://doi.org/10.1021/ol015712o
  7. Quaderer, R.; Hilvert, D. Org. Lett. 2001, 3, 3181. https://doi.org/10.1021/ol016492h
  8. Wehofsky,N.; Koglin, N.; Thust, S.; Bordusa, F. J. Am. Chem. Soc. 2003, 125, 6126. https://doi.org/10.1021/ja0344213
  9. Yang, L.; Morriello, G. Tetrahedron Lett. 1999, 40, 8197. https://doi.org/10.1016/S0040-4039(99)01701-3
  10. Li, Q.; Moutiez, M.; Charbonnier, J.-B.; Vaudry, K.; Me´nez, A.; Quéméneur, E.; Dugave, C. J. Med. Chem. 2000, 43, 1770. https://doi.org/10.1021/jm9903139
  11. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496. https://doi.org/10.1021/ja0108584
  12. Maclean, D.; Hale, R.; Chen, M. Org. Lett. 2001, 3, 2977. https://doi.org/10.1021/ol0163124
  13. Heidler, P.; Link, A. Bioorg. Med. Chem. 2005, 13, 585. https://doi.org/10.1016/j.bmc.2004.10.045
  14. Fattori, D.; Kinzel, O.; Ingallinella, P.; Bianchi, E.; Pessi, A. Bioorg. Med. Chem. Lett. 2002, 12, 1143. https://doi.org/10.1016/S0960-894X(02)00122-1
  15. Díaz-Moscoso, A.; Benito, J. M.; Mellet, C. O.; Fernandez, J. M. J. Comb. Chem. 2007, 9, 339. https://doi.org/10.1021/cc070025v
  16. Kessler, B. M.; Tortorella, D.; Altun, M.; Kisselev, A. F.; Fiebiger, E.; Hekking, B. G.; Ploegh, H. L.; Overkleeft, H. S. Chem. Biol. 2001, 8, 913. https://doi.org/10.1016/S1074-5521(01)00069-2
  17. Ding, Y.; Qin, C.; Guo, Z.; Niu, W.; Zhang, R.; Li, Y. Chem. Biodivers. 2007, 4, 2827. https://doi.org/10.1002/cbdv.200790232
  18. Sabatino, G.; Papini, A. M. Curr. Opin. Drug. Discov. Devel. 2008, 11, 762.
  19. Cemazar, M.; Craik, D. J. J. Pept. Sci. 2008, 14, 683. https://doi.org/10.1002/psc.972
  20. Bacsa, B.; Horvati, K.; Bosze, S.; Andreae, F.; Kappe, C. O. J. Org. Chem. 2008, 73, 7532. https://doi.org/10.1021/jo8013897
  21. Basca, B.; Kappe, C. O. Nat. Protoc. 2007, 2, 2222. https://doi.org/10.1038/nprot.2007.300
  22. Mario, A.; Fara.; Díaz-Mochon, J. J.; Bradley, M. Tetrahedron Lett. 2006, 47, 1011. https://doi.org/10.1016/j.tetlet.2005.11.127
  23. Park, M. S.; Oh, H. S.; Cho, H. G.; Lee, K. H. Tetrahedron Lett. 2007, 48, 1053. https://doi.org/10.1016/j.tetlet.2006.11.151
  24. Joshi, B. P.; Park, J. W.; Kim, J. M.; Lohani, C. R.; Cho, H. J.; Lee, K. H. Tetrahedron Lett. 2008, 49, 98. https://doi.org/10.1016/j.tetlet.2007.11.004
  25. Murray, J. K.; Gellman, S. H. Nature Protoc. 2007, 2, 624. https://doi.org/10.1038/nprot.2007.23
  26. Bunin, B. A. The Combinatorial Index; Academic Press: San Diego, 1998; pp 213-236.

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