PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Synthesis of 2,6-Diaminopimelic Acid (DAP) and Its Analogues

Autorzy
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
This article reviews synthesis of 2,6-diaminopimelic acid, an important amino acid biosynthesized by bacteria and higher plants. Anumber of peptidoglycan fragments containing the diaminopimelic acid (DAP) residue exhibit antitumor and/or immunostimulant activity. DAP is a versatile building block of many natural and synthetic compounds with a number of potentialmedicinal applications. The synthesis of immunostimulants FK-156 and FK-565 is also presented.
Rocznik
Strony
455--473
Opis fizyczny
Bibliogr. 54 poz., rys.
Twórcy
  • Department of Organic Chemistry, Gdansk University of Technology, 11/12 G. Narutowicza Street, 80-952 Gdansk, Poland, kd@chem.pg.gda.pl
Bibliografia
  • 1. Arakawa Y., Goto T., Kawase K. and Yoshifuji S., Chem. Pharm. Bull., 43, 535 (1995).
  • 2. Sturn P.A. and Henry D.W., J. Med. Chem., 17,481 (1974).
  • 3. Zeitler K. and Steglich W., J. Org. Chem., 69, 6134 (2004).
  • 4. Cox R.J., Nat. Prod. Rep., 13, 29 (1996).
  • 5. Holcomb R.C., Schow S., Kaloustian S.A. and Powell D., Tetrahedron Lett., 35, 7005 (1994).
  • 6. Gottschalk G., Bacterial Metabolism; Springer-Verlag: New York, 1979.
  • 7. Avenoza A., CativielaC., PeregrinaJ.M. andZurbanoM.M, Tetrahedron: Asymmetry,7,1555 (1996).
  • 8. Tanaka K. and Sawanishi H., Tetrahedron: Asymmetry, 11, 3837 (2000).
  • 9. Hiebl J., Kollmann H., Rovenszky F. and Winkler K., J. Org. Chem., 64, 1947 (1999).
  • 10. Ferreira P.M.T., Maia H.L.S. and Monteiro L.S., Tetrahedron Lett., 44, 2137 (2003).
  • 11. Jurgens A.R., Tetrahedron Lett., 33, 4727 (1992).
  • 12. Bold G., Duthaler R.O. and Riediker M., Angew. Chem. Int. Ed. Engl, 28, 497 (1989).
  • 13. Gelb M.H., Lin Y, Pickard M.A., Song Y. and Vederas J.C., J. Am. Chem. Soc., 112,4932 (1990).
  • 14. Williams R.M., Im M.N. and Cao J., J. Am. Chem. Soc., 113, 6976 (1991).
  • 15. Williams R.M. and Yuan C.G., J. Org. Chem., 57, 6519 (1992).
  • 16. Williams R.M. and Yuan C.G., J. Org. Chem., 59, 6190 (1994).
  • 17. Paradisi F., Porzi G. and Sandri S., Tetrahedron: Asymmetry, 12, 3319 (2001).
  • 18. Wang W, Xiong C.Y., Yang J.Q. and Hruby V.J., Synthesis, 94 (2002).
  • 19. Collier P.N., Patel I. and Taylor R.J.K., Tetrahedron Lett., 42, 5953 (2001).
  • 20. Collier P.N., Campbell A.D., Patel I. and Taylor R.J.K., Tetrahedron, 58, 6117 (2002).
  • 21. Sutherland A. and Yederas J.C., Chem. Commun., 224 (2002).
  • 22. Gao Y, Lane-Bell P. and Yederas J.C., J. Org. Chem., 63, 2133 (1998).
  • 23. Davis F.A. and Srirajan V., J. Org. Chem., 65, 3248 (2000).
  • 24. Hernandez N. and Martin V.S., J. Org. Chem., 66,4934 (2001).
  • 25. Roberts J.L. and Chan C., Tetrahedron Lett., 43, 7679 (2002).
  • 26. Sutherland A., Caplan J.F. and Yederas J.C., Chem. Commun., 555 (1999).
  • 27. Kubasch N. and Schmidt R.R., Eur. J. Org. Chem., 2710 (2002).
  • 28. CollierP.N., Campbell A.D., Patel L, RaynhamT.M. and Taylor R. J.K.,.7. Org. Chem., 67,1802 (2002).
  • 29. Galeazzi R., Garavelli M., Grandi A., Monari M., Porzi G. and Sandri S., Tetrahedron: Asymmetry, 14, 2639 (2003).
  • 30. Buli S.D., Davies S.G., ParkinR.M. and Sanchez-SanchoF.,J. Chem. Soc. Perkin Trans. I, 2313 (1998).
  • 31. Del Valle J.R. and Goodman M., J. Org. Chem., 69, 8946 (2004).
  • 32. Williams R.M. and Liu J.W., J. Org. Chem., 63, 2130 (1998).
  • 33. Gotoh T., Nakahara K., Nishiura T., Hashimoto S., Kino T. and Kuroda V, J. Antibiotics, 35, 1286 (1982).
  • 34. Kawai Y, Nakamura K., Gotoh T., Uchida L, Tanaka H. and Imanaka H., J. Antibiotics, 35,1293 (1982).
  • 35. Mine Y, Watanabe Y, Tawara S., Yokota Y, Nishida N., Goto S. and Kuwahara S., J. Antibiotics, 30, 1059(1983).
  • 36. Okada S., Takeno H., Hemmi K., Kitaura Y. and Hashimoto M., Chem. Pharm. Bull., 33, 889 (1985).
  • 37. Talmadge J.E., Lenz B., Schneider M., Phillips H. and Long C., Cancer Immunol. Immunother., 28, 93 (1989).
  • 38. Li W.Y, Kapłan S., Whiteside T. and Herberman R.H., Immunopharmacology, 18, 213 (1989).
  • 39. Imamura N., Nakahara K., Kino T., Gotoh T., Kawamura L, Aoki H., Imanaka H. and Sone S., J. Biol. Response Modif., 41, 408 (1985).
  • 40. Bouchaudon J., Dutruc-Rosset G., Farge D. and James C., J. Chem. Soc. Perkin Trans. I, 695 (1989).
  • 41. Kołodziejczyk A.M., Kołodziejczyk A.S. and Stoev S., Int. J. Peptide Protein Res., 39, 382 (1992).
  • 42. Wodecki Z., Dzierzbicka K. and Kołodziejczyk A.M., (1995) XIII Polish Peptide Symposium, Nadole, Poland, Peptydy 95, Abstract P7.
  • 43. Balducci D., Porzi G. and Sandri S., Tetrahedron: Asymmetry, 15, 1085 (2004).
  • 44. Chowdhury A.R. and Boons G.J., Tetrahedron Lett., 46, 1675 (2005).
  • 45. Cox R.J., Durston J. and Roper D.I., J. Chem. Soc. Perkin Trans. J., 1029 (2002).
  • 46. Cirilli M., Zheng R.J., Scapin G. and Blanchard J.S., Biochemistry, 37, 16452 (1998).
  • 47. Lloyd A.J., Huyton T., Turkenburg J. and Roper D.I., Acta Crystallogr., D60, 397 (2004).
  • 48. Diaper C.M., Sutherland A., Pillai B., James M.N.G., Semchuk P., Blanchard J.S. and Vederas J.C., Org. Biomol. Chem., 3, 4402 (2005).
  • 49. Koo C.W., Sutherland A., Vederas J.C. and Blanchard J.S., J. Am. Chem. Soc., 122, 6122 (2000).
  • 50. Koch A.L., Clin. Microbiol. Rev., 16, 673 (2003).
  • 51. Weidenmaier C., Kristian S.A. and Peschel A., Curr. Drug Targets, 4, 643 (2003).
  • 52. Nolen E.G., Fedorka C.J. and Blicher B., Synthetw Commun., 36, 1707 (2006).
  • 53. Uehara A., Fujimoto Y, Kawasaki A., Kusumoto S., Fukase K. and Takada H., J. Immunol., 111,1796 (2006).
  • 54. Tada H., Aiba S., Shibata K.I., Ohteki T. and Takada H., Infect. Immun., 73, 7967 (2005).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0009-0001
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.