Incorporation of α-substituted serine analog into peptide via a novel O,N-migration

Synlett

Volumn , Issue 6, 1998, Pages 609-610

  Horikawa, M ^a   Nakajima, T ^c   Ohfune, Y ^b  

^a SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^b Osaka Prefecture University   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001502832     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1748     Document Type: Article

References (10)

1. Davies, J. S. Amino Acids, Peptides and Proteins; The Royal Society of Chemistry 1997;28:166-232 and references cited therein.
2. (a) Moon, S.-H.; Ohfune, Y. J. Am. Chem. Soc. 1994, 116, 7405-7406.
3. (b) Horikawa, M.; Nakajima, T.; Ohfune, Y. Synlett 1997, 253-254.
4. (c) Ohfune, Y.; Horikawa, M. J. Syn. Org. Chem. Jpn. 1997, 55, 982-993.
5. Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266 and literatures cited therein.
6. (a) Fujino, M.; Wakimasu, M.; Shinagawa, S.; Kitada, C.; Yajima, H. Chem. Pharm. Bull. 1978, 26, 539-548.
7. (d) Swerdloff, M. D.; Anderson, S. B.; Sedgwick, R. D.; Gabriel, M. K.; Brambilla, R. J.; Hindelang, D. M.; Williams, J. I. Int. J. Peptide Protein Res. 1989, 33, 318-327.
8. 3) δ 0.96 (3 H, d, J = 6.8 Hz), 1.01 (3 H, d, J = 6.8 Hz), 1.25-1.88 (7 H, m), 2.20 (1 H, dsep, J = 6.8, 6.4 Hz), 2.43 (1 H, brd, J = 13.6 Hz), 3, 47 (1 H, brs), 3.73 (3 H, s), 3.91 (1 H, m), 4.01 (1 H, dd, J = 6.4, 8.0 Hz), 5.10 (1 H, d, J = 12.0 Hz), 5.15 (1 H, d, J = 12.0 Hz), 5.29 (1 H, m), 6.33 (1 H, s), 7.31-7.37 (5 H, m).
9. 2 at room temperature.
10. Biological activity of 5 and 7 to the opioid receptors is currently under investigation.