Synthesis of an orthogonally-protected bifunctional amino acid for conformationally constrained peptides

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3063-3066

  Andrews, Martin J I ^a   Tabor, Alethea B ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE;

ARTICLE; CHIRALITY; IN VITRO STUDY; METHODOLOGY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0030970263     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00545-5     Document Type: Article

References (19)

1. Hruby, V. J.; Bonner, G. G.; in Methods in Molecular Biology, Vol. 35: Peptide Synthesis Protocols, Pennington, M. W.; Dunn, B. M. Eds; Humana Press, New Jersey, 1994; pp. 201.
2. Ösapay, G.; Taylor, J. W.; J. Am. Chem. Soc., 1990, 112, 6046.
3. Ruan, F.; Chen, Y.; Itoh, K.; Sazaki, T.; Hopkins, P. B; J. Org. Chem., 1991, 56, 4347.
4. Marqusee, S.; Baldwin, R. L.; Proc. Natl. Acad. Sci. U. S. A., 1987, 84, 8898.
5. Jackson, D. Y.; King, D. S.; Chmielewski, J., Singh, S.; Schultz, P. G.; J. Am. Chem. Soc., 1991, 113, 9391.
6. Campbell, R. M.; Bongers, J.; Felix, A. M.; Biopolymers, 1995, 37, 67.
7. Polinsky, A.; Cooney, M. G.; Toy-Palmer, A.; Ösapay, G.; Goodman, M.; J Med. Chem., 1992, 35, 4185.
8. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F.; Tetrahedron Lett., 1993, 34, 1549.
9. For a recent paper describing the stereoselective synthesis and differential protection of the related diaminopimelic acid, see: Williams, R. M.; Yuan, C.; J. Org. Chem., 1992, 57, 6519.
10. Schöllkopf, U.; Top. Curr. Chem., 1983, 109, 65; Schöllkopf, U.; Groth, U.; Deng, C.; Angew. Chem., Int. Ed. Engl., 1981, 20, 798.
11. Schöllkopf, U.; Top. Curr. Chem., 1983, 109, 65; Schöllkopf, U.; Groth, U.; Deng, C.; Angew. Chem., Int. Ed. Engl., 1981, 20, 798.
12. Baldwin, J. E.; Adlington, R. M.; Mitchell., M. B; Tetrahedron, 1995, 51, 5193.
13. Satisfactory analytical and spectral data were obtained for all compounds.
14. Evans, D. A.; Britton, T. C.; J. Am. Chem. Soc., 1987, 109, 6881.
15. The reaction was quenched by the addition of glacial acetic acid: saturated potassium acetate (1:3.5 v/v), allowed to warm to room temperature and stirred for 12 hours. The THF was then removed in vacuo, and theproduct taken up in ethyl acetate and washed with water.
16. 3, c=3.1 mg/ml)
17. Heerding, D.; Bhatnager, P.; Hartmann, M.; Kremminger, P.; LoCastro, S.; Tetrahedron: Asymmetry, 1996, 7, 237.
18. Seebach, D.; Thaler, A.; Blaser, D.; Ko, S. Y.; Helv. Chim. Acta., 1991, 74, 1102.
19. Carpino, L. A.; Han, G. Y.; J. Org. Chem., 1972, 37, 3404.