Synthesis of an external beta-turn based on the GLDV motif of cell adhesion proteins

Tetrahedron

Volumn 61, Issue 1, 2005, Pages 301-312

  Davies, David E ^a   Doyle, Paul M ^b   Hill, Richard D ^c   Young, Douglas W ^c  

^a GLAXOSMITHKLINE   (United Kingdom)

^b BioFocus DPI   (United Kingdom)

^c UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

Bicyclic lactam; Eschenmoser olefination; Integrin

Indexed keywords

CARBOXYL GROUP; CELL PROTEIN; CYCLOPEPTIDE; INTEGRIN; LACTAM;

ARTICLE; CELL ADHESION; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN MOTIF; PROTEIN SYNTHESIS; STEREOCHEMISTRY;

EID: 9644272352     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.037     Document Type: Article

References (24)

1. Part of this work has been published as a preliminary communication in: D.E. Davies, P.M. Doyle, R.D. Farrant, R.D. Hill, P.B. Hitchcock, P.N. Sanderson, and D.W. Young Tetrahedron Lett. 44 2003 8887 8891
2. G.D. Rose, L.M. Gierasch, and J.A. Smith Adv. Protein Chem. 37 1985 1 109
3. J.A. Smith, and L.G. Pease CRC Crit. Rev. Biochem. 8 1980 315 399
4. U. Nagai, and K. Sato Tetrahedron Lett. 26 1985 647 650
5. K. Sato, and U. Nagai J. Chem. Soc., Perkin Trans. 1 1986 1231 1234
6. U. Nagai, K. Sato, R. Nakamura, and R. Kato Tetrahedron 49 1993 3577 3592
7. F.M. Wisskirchen, P.M. Doyle, S.L. Gough, C.J. Harris, and I. Marshall Br. J. Pharm. 126 1999 1163 1170
8. Y.T. Osano, U. Nagai, and T. Matsuzaki Anal. Sci. 5 1989 625 626 The data are available from the Cambridge Crystallographic Data Centre, Cambridge, code number SEYZUR
9. P.M. Doyle, C.J. Harris, C.M. Moody, P.J. Sadler, M. Sims, J.M. Thornton, J. Uppenbrink, and J.H. Viles Int. J. Peptide Protein Res. 47 1996 427 436
10. Berry, J. M.; Doyle, P. M.; Young, D. W. Tetrahedron 2004, 60, preceding paper. doi:10.1016/j.tet.2004.09.036.
11. J.A. Robl, M.P. Cimarusti, L.M. Simpkins, B. Brown, D.E. Ryono, J.E. Bird, M.M. Asaad, T.R. Schaeffer, and N.C. Trippodo J. Med. Chem. 39 1996 494 502
12. L. Belvisi, A. Bernardi, A. Checchia, L. Manzoni, D. Potenza, C. Scolastico, M. Castorina, A. Cupelli, G. Giannini, P. Carminati, and C. Pisano Org. Lett. 3 2001 1001 1004
13. F. Cornille, U. Slomczynska, M.L. Smythe, D.D. Beusen, K.D. Moeller, and G.R. Marshall J. Am. Chem. Soc. 117 1995 909 917
14. R. Haubner, D. Finsinger, and H. Kessler Angew. Chem. Int. Ed. 36 1997 1374 1389
15. F. Weygand, P. Klinke, and I. Eigen Chem. Ber. 90 1957 1896 1905
16. D. Gani, and D.W. Young J. Chem. Soc., Perkin Trans. 1 1983 2393 2398
17. First prepared by August, R. A. D. Phil Thesis, Sussex, 1987.
18. T.P. Andersen, P.B. Rasmussen, I. Thomsen, S.-O. Lawesson, P. Jørgensen, and P. Lindhardt Annalen 1986 269 279
19. Shiosaki, K. In Heathcock, C. H., Ed.; Comprehensive Organic Synthesis, Trost, B.; Fleming, I., Series Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 865-892.
20. J.S. Petersen, G. Fels, and H. Rapoport J. Am. Chem. Soc. 106 1984 4539 4547
21. T. Kolasa, and M.J. Miller J. Org. Chem. 55 1990 1711 1721
22. C.M. Wilmot, and J.M. Thornton J. Mol. Biol. 203 1998 221 232
23. I. Takishi Tetrahedron 59 2003 3527 3536
24. Smith, L. I.; Howard, K. L. In Organic Syntheses; Horning E. C., Ed.; Wiley: New York, 1955; Collect. Vol. III, p 135.