N(in)-cyclohexyloxycarbonyl group as a new protecting group for tryptophan

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7529-7532

  Nishiuchi, Yuji ^a   Nishio, Hideki ^a   Inui, Tatsuya ^a   Kimura, Terutoshi ^a   Sakakibara, Shumpei ^a  

^a Protein Research Foundation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TRYPTOPHAN DERIVATIVE;

ARTICLE; DERIVATIZATION; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030583510     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01691-7     Document Type: Article

References (12)

1. 1. K. Hashizume and Y. Shimonishi, Bull. Chem. Soc. Jpn., 54, 3806-3810 (1981); M. Taniguchi and T. Hino, Tetrahedron, 37, 1487-1494 (1981).
2. K. Hashizume and Y. Shimonishi, Bull. Chem. Soc. Jpn., 54, 3806-3810 (1981); M. Taniguchi and T. Hino, Tetrahedron, 37, 1487-1494 (1981).
3. 2. G. R. Matsueda, Int. J. Pept. Protein Res., 20, 26-34 (1982).
4. 3. J. P. Tam, W. F. Heath and R. B. Merrifield, J. Am. Chem. Soc., 105, 6442-6455 (1983).
5. 4. N. Fujii, S. Futaki, K. Yasumura and H. Yajima, Chem. Pharm. Bull., 32, 2660-2665 (1984); Y. S. Klausner and M. Chorev, J. Chem. Soc. Perkin 1, 627-631 (1977).
6. N. Fujii, S. Futaki, K. Yasumura and H. Yajima, Chem. Pharm. Bull., 32, 2660-2665 (1984); Y. S. Klausner and M. Chorev, J. Chem. Soc. Perkin 1, 627-631 (1977).
7. 5. Y. Kiso, M. Inai, K. Kitagawa and T. Akita, Chem. Lett., 739-742 (1983).
8. 6 64.85 7.26 6.30 64.33 7.29 6.25
9. 7. C. Haskell-Luevano, L.W. Boteju and V.J. Hruby, Letters in Peptide Science, 1, 163-170 (1994).
10. 8. H. Tamamura, A. Otaka, W. Takada, Y. Terakawa, H. Yoshizawa, M. Masuda, T. Ibuka, T. Murakami, H. Nakashima, M. Waki, A. Matsumoto, N. Yamamoto and N. Fujii, Chem. Pharm. Bull., 43, 12-18 (1995).
11. 2. The peptide was synthesized with an automatic synthesizer (ABI 433A) using the Boc strategy on MBHA resin. The following side-chain-protected amino acids, which are cleavable by treatment with 1 M TMSOTf-thioanisole/TFA, were employed: Cys(MBzl), Lys(Z), Arg(Mts), Tyr(BrZ) and Trp(Mts) or Trp(Hoc).
12. 3]-T22 was 120 higher than that of T-22 by PD-MS. This mass difference is attributed to the MBzl group.