"Customizable" units in Di- and tripeptides: Selective conversion into substituted dehydroamino acids

Organic Letters

Volumn 14, Issue 14, 2012, Pages 3788-3791

  Saavedra, Carlos J ^a   Boto, Alicia ^a   Hernández, Rosendo ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DIPEPTIDE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOSPHORYLATION; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; DIPEPTIDES; MOLECULAR STRUCTURE; PEPTIDES; PHOSPHORYLATION; STEREOISOMERISM;

EID: 84864151610     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301676z     Document Type: Article

References (50)

1. Nandy, J. P.; Prakesch, M.; Khadem, S.; Reddy, P. T.; Sharma, U.; Arya, P. Chem. Rev. 2009, 109, 1999-2060
2. Jimenez, J. C.; Chavarria, B.; Lopez-Macia, A.; Royo, M.; Giralt, E.; Albericio, F. Org. Lett. 2003, 5, 2115
3. Loiseau, N.; Cavelier, F.; Noel, J. P.; Gomis, J. M. J. Peptide Sci. 2002, 8, 335-346
4. Chatterjee, C.; Paul, M.; Xie, L.; van der Donk, W. A. Chem. Rev. 2005, 105, 633-683
5. van der Donk, W. A. J. Org. Chem. 2006, 71, 9561-9571
6. Okeley, N. M.; Zhu, Y.; van der Donk, W. A. Org. Lett. 2000, 2, 3603-3609
7. Zhang, X.; Ni, W.; van der Donk, W. A. Org. Lett. 2007, 9, 3343-3346
8. Bowers, A. A.; Acker, M. G.; Koglin, A.; Walsh, C. T. J. Am. Chem. Soc. 2010, 132, 7519-7527
9. Zhang, C.; Occi, J.; Masurekar, P.; Barrett, J. F.; Zink, D. L.; Smith, S.; Onishi, R.; Ha, S. H.; Salazar, O.; Genilloud, O.; Basilio, A.; Vicente, F.; Gill, C.; Hickey, E. J.; Dorso, K.; Motyl, M.; Singh, S. B. J. Am. Chem. Soc. 2008, 130, 12102-12110
10. Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301-3313
11. Liao, R.; Liu, W. J. Am. Chem. Soc. 2011, 133, 2852-2855
12. Hamada, Y.; Shioiri, T. Chem. Rev. 2005, 105, 4441-4482
13. Cruz, L. J.; Luque-Ortega, J. R.; Rivas, L.; Albericio, F. Mol. Pharmac. 2009, 6, 813-824
14. Ueoka, R.; Ise, Y.; Ohtsuka, S.; Okada, S.; Yamori, T.; Matsunaga, S. J. Am. Chem. Soc. 2010, 132, 17692-17694
15. Freidinger, R. M. J. Med. Chem. 2003, 46, 5554-5566
16. Sun, X.; Rodriguez, M.; Zeckner, D.; Sachs, B.; Current, W.; Boyer, R.; Paschal, J.; McMillian, C.; Chen, S.-H. J. Med. Chem. 2001, 44, 2671-2674
17. Gupta, M.; Chauhan, V. S. Biopolymers 2010, 95, 161-173
18. Jain, R.; Chauhan, V. S. Biopolymers (Pept. Sci.) 1996, 40, 105-119
19. Yamada, K.; Shinoda, S.; Oku, H.; Komagoe, K.; Katsu, T.; Katakai, R. J. Med. Chem. 2006, 49, 7592-7595
20. Torino, D.; Mollica, A.; Pinnen, F.; Feliciani, F.; Lucente, G.; Fabrizi, G.; Portalone, G.; Davis, P.; Lai, J.; Ma, S. W.; Porreca, F.; Hruby, V. J. J. Med. Chem. 2010, 53, 4550-4554
21. Chen, H.; Luzy, J. P.; Gresh, N.; Garbay, C. Eur. J. Org. Chem. 2006, 2329-2335
22. Baldisserotto, A.; Marastoni, M.; Lazzari, I.; Trapella, C.; Gavioli, R.; Tomatis, R. Eur. J. Med. Chem. 2008, 43, 1403-1411
23. Jones, M. C.; Marsden, S. P. Org. Lett. 2008, 10, 4125-4128
24. van den Broek, S. M. A. W.; Rensen, P. G. W.; van Delft, F. L.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2010, 5906-5912
25. Wang, C. J.; Xu, Z. P.; Wang, X.; Teng, H. L. Tetrahedron 2010, 66, 3702-3706
26. Ramapanicker, R.; Mishra, R.; Chandrasekaran, S. J. Pept. Sci. 2010, 16, 123-125
27. Ebran, J. P.; Jensen, C. M.; Johannesen, S. A.; Karaffa, J.; Lindsay, K. B.; Taaning, R.; Skrydstrup, T. Org. Biomol. Chem. 2006, 4, 3553-3564
28. Antos, J. M.; Francis, M. B. Curr. Opin. Chem. Biol. 2006, 10, 253-262
29. Qi, D.; Tann, C. M.; Distefano, M. D. Chem. Rev. 2001, 101, 3081-3112
30. Seebach, D.; Bech, A. K.; Studer, A. Modern Synthetic Methods; Ernst, B.; Leumann, C., Eds.; VCH: Weinheim, 1995;, Vol. 7.
31. Datta, S.; Kazmaier, U. Org. Biomol. Chem. 2011, 9, 872-880
32. Deska, J.; Kazmaier, U. Chem.-Eur. J. 2007, 13, 6204-6211
33. Franz, N.; Menin, L.; Klok, H. A. Org. Biomol. Chem. 2009, 7, 5207-5218
34. Ricci, M.; Madariaga, L.; Skrydstrup, T. Angew. Chem., Int. Ed. 2000, 39, 242-245
35. For other interesting approaches, see: Chapman, C. J.; Hargrave, J. D.; Bish, G.; Frost, C. G. Tetrahedron 2008, 64, 9528-9539
36. Wan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 9248-9252
37. Dialer, H.; Steglich, W.; Beck, W. Tetrahedron 2001, 57, 4855-4861
38. Schuemann, S.; Zeitler, K.; Jäger, M.; Polborn, K.; Steglich, W. Tetrahedron 2000, 56, 4187-4195
39. Boto, A.; Gallardo, J. A.; Hernández, R.; Saavedra, C. J. Tetrahedron Lett. 2005, 46, 7807-7811
40. In other complex substrates, such as carbohydrates, the H -abstraction often predominates over the scission: Boto, A.; Hernández, D.; Hernández, R.; Suárez, E. J. Org. Chem. 2006, 71, 1938-1948
41. For other work on scission-addition processes, see: Saavedra, C.; Boto, A.; Hernandez, R. Org. Biomol. Chem. 2012, 10, 4448-4461
42. Boto, A.; Romero-Estudillo, I. Org. Lett. 2011, 13, 3426-3429
43. Saavedra, C.; Hernandez, R.; Boto, A.; Alvarez, E. J. Org. Chem. 2009, 74, 4655-4665
44. Boto, A.; Gallardo, J. A.; Hernández, D.; Hernández, R. J. Org. Chem. 2007, 72, 7260-7269
45. Boto, A; Hernández, D.; Hernández, R. Eur. J. Org. Chem. 2010, 3847-3857 and references cited therein
46. Buck, R. T.; Clarke, P. A.; Coe, D. M.; Drysdale, M. J.; Ferris, L.; Haigh, D.; Moody, C. J.; Pearson, N. D.; Swann, E. Chem.-Eur. J. 2000, 6, 2160-2167
47. See also: Alexander, P. A.; Marsden, S. P.; Muñoz-Subtil, D. M.; Reade, J. C. Org. Lett. 2004, 6, 1433-1436
48. Falorni, M.; Giacomelli, G.; Satta, M.; Cossu, S. Synthesis 1994, 391-395
49. Falorni, M.; Satta, M.; Conti, S.; Giacomelli, G. Tetrahedron: Asymmetry 1993, 4, 2389-2398
50. Nandel, F. S.; Jaswal, R. Biomacromolecules 2007, 8, 3093-3101