Embodying a stable α-helical protein structure through efficient chemical ligation via thioether formation

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 9, 1997, Pages 1883-1891

  Futaki, Shiroh ^a   Ishikawa, Tomoko ^a   Niwa, Mineo ^a   Kitagawa, Kouki ^b   Yagami, Takeshi ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

^c NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE;

ALPHA HELIX; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL MODIFICATION; LIGATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN STABILITY; PROTEIN STRUCTURE;

AMINO ACID SEQUENCE; CHROMATOGRAPHY, GEL; CIRCULAR DICHROISM; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION; PROTEINS; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFIDES;

EID: 0030794881     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00119-3     Document Type: Article

References (33)

1. (a) Blake, J. Int. J. Peptide Protein Res. 1981, 17, 273.
2. (b) Blake, J. Int. J. Peptide Protein Res. 1986, 27, 191.
3. (c) Hojo, H.; Aimoto, S. Bull. Chem. Soc. Jpn 1991, 64, 111.
4. (d) Hojo, H.; Kwon, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn 1993, 66, 2700.
5. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776.
6. Zhang, L.; Tam, J. P. Tetrahedron Lett. 1997, 38, 3.
7. (a) Lindner, W.; Robey, F. A. Int. J. Peptide Protein Res. 1987, 30, 794.
8. (b) Robey, F. A.; Fields, R. L. Anal. Biochem. 1989, 177, 373.
9. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221.
10. Baca, M.; Muir, T. W.; Schn̂lzer, M.; Kent, S. B. H. J. Am. Chem. Soc. 1995, 117, 1881.
11. (a) Liu, C-F.; Tam, J. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6584.
12. (b) Liu, C.-F.; Rao, C.; Tam, J. P. J. Am. Chem. Soc. 1996, 118, 307.
13. Rao, C.; Tam, J. P. J. Am. Chem. Soc. 1994, 116, 6975.
14. Lu, Y.-A.; Clavijo, P.; Galantino, M.; Shen, Z.-Y.; Liu, W.; Tam, J. P. Molecular Immunol. 1991, 28, 623.
15. (a) Bryson, J. W.; Betz, S. F.; Lu, H. S.; Suich, D. J.; Zhou, H. X.; O'Neil, K. T.; DeGrado, W. F. Science 1995, 270, 935.
16. (b) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169.
17. (c) Tuchscherer, G.; Mutter, M. J. Peptide Sci. 1995, 1, 3.
18. (a) Futaki, S.; Kitagawa, K. Tetrahedron Lett. 1994, 35, 1267.
19. (b) Futaki, S.; Ishikawa, T.; Niwa, M.; Yagami, T.; Kitagawa, K. Tetrahedron Lett. 1996, 37, 201.
20. (c) Futaki, S.; Kitagawa, K. Tetrahedron, 1997, 53, 7479.
21. Futaki, S.; Ishikawa, T.; Niwa, M.; Kitagawa, K.; Yagami, T. Tetrahedron Lett. 1995, 36, 5203.
22. (a) Atherton, E.; Sheppard, R. C. In Solid Phase Peptide Synthesis, A Practical Approach; IRL: Oxford, 1989.
23. (b) Futaki, S.; Taike, T.; Akita, T.; Kitagawa, K. Tetrahedron 1992, 48, 8899.
24. Regan, L.; DeGrado, W. F. Science 1988, 241, 976.
25. Fujii, N.; Otaka, A.; Watanabe, T.; Okamachi, A.; Tamamura, H.; Yajima, H.; Inagaki, Y.; Nomizu, M.; Asano, K. J. Chem. Soc., Chem. Commun. 1989, 283.
26. Fujii, N.; Otaka, A.; Funakoshi, S.; Yajima, H.; Nishimura, O.; Fujino, M. Chem. Pharm. Bull. 1986, 34, 869.
27. Fujii, N.; Otaka, A.; Sugiyama, N.; Hatano, M.; Yajima, H. Chem. Pharm. Bull. 1987, 35, 3880.
28. Yajima, H.; Fujii, N. J. Am. Chem. Soc. 1981, 103, 5867.
29. O'Shea, E. K.; Rutkowski, R.; Stafford III, W. F.; Kim, P. S. Science 1989, 245, 646.
30. Zhou, N. E.; Kay, C. M.; Hodges, R. S. J. Biol. Chem. 1992, 267, 2664.
31. (a) Chou, K.-C.; Maggiora, G. M.; Scheraga, H. A. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 7315.
32. (b) Suzuki, N.; Fujii, I. In Peptide Chemistry 1996; Kitada, C. Ed.; Protein Research Foundation: Osaka, 1997; pp 437-440.
33. Rink, H. Tetrahedron Lett. 1987, 28, 3787.