4-methoxybenzyloxymethyl group, a racemization-resistant protecting group for cysteine in fmoc solid phase peptide synthesis

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1926-1929

  Hibino, Hajime ^a   Nishiuchi, Yuji ^a,b  

^a Peptide Institute Inc   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; FLUORENE DERIVATIVE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYSTEINE; FLUORENES; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM;

EID: 84859568134     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300592w     Document Type: Article

References (28)

1. Dawson, P.; Muir, T.; Clark-Lewis, I.; Kent, S. Science 1994, 266, 776
2. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923
3. Hackenberger, C. P. R; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030
4. Isidro-Llobet, A.; álvarez, M.; Albericio, F. Chem. Rev. 2009, 109, 2455
5. Otaka, A.; Morimoto, H.; Fujii, N.; Koide, T.; Funakoshi, S.; Yajima, H. Chem. Pharm. Bull. 1989, 37, 526
6. Garcia, O.; Bofill, J.; Nicolas, E.; Albercio, F. Eur. J. Org. Chem. 2010, 3631
7. Shen, F.; Zhang, Z.; Li, J.; Lin, Y.; Liu, L. Org. Lett. 2011, 13, 568
8. Kaiser, E. T.; Nicholson, G. J.; Kohlbau, H. J.; Voelter, W. Tetrahedron Lett. 1996, 37, 1187
9. Angell, Y. M.; Alsina, J.; Albericio, F.; Barany, G. J. Pept. Res. 2002, 60, 292-299
10. Han, Y.; Albercio, F.; Barany, G. J. Org. Chem. 1997, 62, 4307
11. Atherton, E.; Hardy, P.; Harris, D.; Matthews, B. Racemization of C-terminal cysteine during peptide assembly. In Peptides 1990, Proceeding of the Twenty-First European Peptide Symposium 1990; Giralt, E.; Andreu, D., Eds.; ESCOM Science Publishers B.V.: 1991; p 243.
12. Fujiwara, Y.; Akaji, K.; Kiso, Y. Chem. Pharm. Bull. 1994, 42, 724
13. Branderhorst, H.; Liskamp, R.; Pieters, R. Tetrahedron 2007, 63, 4290
14. Hibino, H.; Nishiuchi, Y. Tetrahedron Lett. 2011, 52, 4947
15. Mitchell, M. A.; Runge, T. A.; Mathews, W. R.; Ichhpurani, A. K.; Harn, N. K.; Dobrowolski, P. J.; Eckenrode, F. M. Int. J. Pept. Protein Res. 1990, 36, 350
16. Yoshizawa-Kumagaye, K.; Inui, T.; Nakajima, K.; Kimura, T.; Sakakibara, S. Pept. Res. 1991, 4, 84
17. Yoshizawa-Kumagaye, K.; Ishizu, T.; Isaka, S.; Tamura, M.; Ohkihara, R.; Nishiuchi, Y.; Kimura, T. Protein Pept. Lett. 2005, 12, 579
18. Taichi, M.; Kimura, T.; Nishiuchi, Y. Int. J. Pept. Res. Ther. 2009, 15, 247
19. Mergler, M.; Dick, F.; Sax, B.; Schwindling, J.; Vorherr, T. J. Pept. Sci. 2001, 7, 502
20. in-carbamic acid compound to prevent such electrophilic attacks during TFA treatment. See: Fields, C. G.; Fields, G. B. Tetrahedron Lett. 1993, 34, 6661
21. Palasek, S. A.; Cox, Z. J.; Collins, J. M. J. Pept. Sci. 2007, 13, 143
22. Barber, M.; Jones, J.; Witty, M. J. Chem. Soc., Perkin Trans. 1 1979, 10, 2425
23. Williams, S.; Albercio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: New York, 1997.
24. Turton, M.; O'Shea, D.; Gunn, I.; Beak, S.; Edwards, C.; Meeran, K.; Chol, S.; Taylor, G.; Heath, M.; Lambert, P.; Wilding, J.; Smith, D.; Ghatel, M.; Herbert, J.; Bloom, S. Nature 1996, 361, 362
25. Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526
26. Wan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 9248
27. Haase, C.; Rohde, H.; Seitz, O. Angew. Chem., Int. Ed. 2008, 47, 6807
28. Rohde, H.; Seitz, O. Peptide Sci. 2010, 94, 551