Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2951-2953

  Brask, Jesper ^a,b,c   Albericio, Fernando ^c   Jensen, Knud J ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; PEPTIDE; PROTEIN; THIOESTER;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PHASE TRANSITION;

EID: 0141520480     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351044     Document Type: Article

References (26)

1. Kochendoerfer, G. G.; Kent, S. B. H. Curr. Opin. Chem. Biol. 1999, 3, 665-671.
2. (a) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779.
3. (b) Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325-4329.
4. For early applications of peptide thioesters in segment couplings, see: (a) Blake, J.; Li, C. H. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4055-4058. (b) Blake, J. Int. J. Pept. Protein Res. 1981, 17, 273-274.
5. For early applications of peptide thioesters in segment couplings, see: (a) Blake, J.; Li, C. H. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4055-4058. (b) Blake, J. Int. J. Pept. Protein Res. 1981, 17, 273-274.
6. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. Chem. Commun. 1971, 636-637.
7. Biancalana, S.; Hudson, D.; Songster, M. F.; Thompson, S. A. Lett. Pept. Sci. 2001, 7, 291-297.
8. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374. (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.
9. Ingenito, R.; Bianchi, E.; Fattori, D.; Pessi, A. J. Am. Chem. Soc. 1999, 121, 11369-11374. (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.
10. Li, X.; Kawakami, T.; Aimoto, S. Tetrahedron Lett. 1998, 39, 8669-8672.
11. Futaki, S.; Sogawa, K.;. Maruyama, J.; Asahara, T.; Niwa, M. Tetrahedron Lett. 1997, 38, 6237-6240.
12. (a) Jensen, K. J.; Alsina, J.; Songster, M. F.; Vágner, J.; Albericio, F.; Barany, G. J. Am. Chem. Soc. 1998, 120, 5441-5452.
13. (b) Guillaumie, F.; Kappel, J. C.; Kelly, N. M.; Barany, G.; Jensen, K. J. Tetrahedron Lett. 2000, 41, 6131-6135.
14. (c) For a review see: Alsina, J.; Jensen, K. J.; Albericio, F.; Barany, G. Chem. Eur. J. 1999, 5, 2787-2795.
15. Abbreviations: o-BAL, ortho-backbone amide linker; DKP, diketopiperazine; MTBE, methyl tert-butyl ether; o-PALdehyde, 5-(2-formyl-3,5-dimethoxy-phenoxy)pentanoic acid; SPPS, solid-phase peptide synthesis; TG, tentagel; TFA, trifluoroacetic acid. Amino acid symbols denote the L-configuration unless stated otherwise.
16. Alsina, J.; Yokum, T. S.; Albericio, F.; Barany, G. J. Org. Chem. 1999, 64, 8761-8769.
17. (a) Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1973, 95, 5829-5831.
18. (b) Corey, E. J.; Kozikowski, A. P. Tetrahedron Lett. 1975, 925-928.
19. (a) Swinnen, D.; Hilvert, D. Org. Lett. 2000, 2, 2439-2442.
20. (b) Sewing, A.; Hilvert, D. Angew. Chem., Int. Ed. 2001, 40, 3395-3396.
21. Boas, U.; Brask, J.; Christensen, J. B.; Jensen, K. J. J. Comb. Chem. 2002, 4, 223-228.
22. The tert-butyl ester was chosen here for solubility reasons.
23. Vázquez, J.; Albericio, F. Tetrahedron Lett. 2001, 42, 6691-6693.
24. (a) Albericio, F.; Barany, G. Int. J. Pept. Protein Res. 1987, 30, 206-216.
25. (b) Albericio, F.; Barany, G. Int. J. Pept. Protein Res. 1993, 41, 307-312.
26. Sole, N. A.; Barany, G. J. Org. Chem. 1992, 57, 5399-5403.