DOI QR코드

DOI QR Code

$\beta$ -Lactam Derivatives as Inhibitors for Carboxypeptidase A. Enzyme Inhibitor Design, Part 17


Abstract

2-(Azetidin-2-one-1-yl)-3-phenylpropionic acid and 2-(azetidin-2-thione-1-yl)-3-phenylpropionic acid were designed as potential active site directed inactivators for carboxypeptidase A, but shown to be they are competitive reversible inhibitors for the enzyme. The observation was somewhat surprising, but is not unexpected considering the recent report of Page who questioned the validity of the generally believed notion that $\beta-lactam$ ring is highly unstable.

Keywords

References

  1. Comprehensive Medicinal Chemistry Newall, C. E.;Hallam, P. D.;Hansch, C.(ed.);Sammes, P. G.(ed.);Taylor, J. B.(ed.)
  2. Acc. Chem. Res. v.17 Page, M. I.
  3. Pharmaceu. Res. Fink, A. L.
  4. Acc. Chem. Res. v.18 Knowles, J. R.
  5. Nature v.322 Doherty, J. B.;Ashe, B. M.;Argenbright, L. W.;Barker, P. L.;Bonney, R. J.;Chandler, G. O.;Dahlgren, M. E.;Dorn, C. P. Jr.;Finke, P. E.;Firestone, R. A.;Fletcher, D.;Hagmann, W. K.;Mumford, R.;O'Grady, L.;Maycock, A. L.;Pisano, J. K.;Shah, S. K.;Thompson, K. R.;Zimmerman, M.
  6. Bioorg. Med. Chem. Lett. v.3 Rizzo, V.;Borghi, D.;Sacchi, N.;Alpegiani, M.;Perrone, E.
  7. J. Med. Chem. v.37 Alpegiani, M.;Bissolino, P.;Corigli, R.;Del Nero, S.;Perrone, E.;Rizzo, V.;Sacchi, N.;Cassinelli, G.;Franceschi, G.
  8. Drugs Exp. Clin. Res. v.18 Rebound-Ravaux, M.;Vergely, I.;Maillard, J.;Favreau, C.;Kobaiter, R.;Joyeau, R.;Wakselman, M.
  9. FEBS Lett. v.189 Ambler, R. P.;Daniel, M.;Fleming, J.;Hermoso, J.-M.;Pang, C.;Waley, S. G.
  10. J. Bacteriol. v.164 Hussain, M.;Carlino, A.;Madonna, M. J.;Lampen, J. O.
  11. Biochem. J. v.233 Little, C.;Emanuel, E. L.;Gagnon, J.;Waley, S. G.
  12. Biochem. J. v.248 Sutton, B. J.;Artymiuk, P. J.;Cordero-Barboa, A. E.;Little, C.
  13. Acc. Chem. Res. v.22 Christianson, D. W.;Lipscomb, W. N.
  14. J. Am. Chem. Soc. v.113 Kim, D. H.;Kim, K. B.
  15. J. Am. Chem. Soc. v.114 Yun, M.;Park, C.;Kim, S.;Nam, D.;Kim, S. C.;Kim, D. H.
  16. J. Bioorg. Med. Chem. Lett. v.3 Kim, D. H.;Kim, Y.
  17. Pure Appl. Chem. v.66 Kim, D. H.;Kim, Y. M.;Li. Z.-H.;Kim, K. B.;Choi, S. Y.
  18. J. Chem. Soc. Perkin Trans. Lee, S.-S.;Li, Z.-H.;Lee, D. H.;Kim, D. H.
  19. Bioorg. Med. Chem. Lett. v.5 Kim, D. H.;Chung, S. J.
  20. J. Med. Chem. v.29 Sofia, M. J.;Katzenellenbogen, J. A.
  21. J. Biol. Chem. v.266 Reed, P. E.;Katzenellenbogen, J. A.
  22. J. Am. Chem. Soc. v.114 Bemis, G. W.;Carlson-Golab, G.;Katzenellenbogen, J. A.
  23. Biochemistry v.29 Baek, D.-J.;Reed, P. E.;Daniels, S. B.;Katzenellenbogen, J. A.
  24. J. Med. Chem. v.29 Gelb, M. H.;Abeles, R. H.
  25. Biochemistry v.24 Harper, J. W.;Hemmi, K.;Powers, J. C.
  26. J. Bioorg. Med. Chem. Lett. v.5 Kim, D. H.;Ryoo, J.
  27. J. Chem. Soc. Perkin Trans.Ⅱ Laws, A. P.;Page, M. I.
  28. Pure Appl. Chem. v.67 Page, M. I.;Laws, A. P.;Slater, M. J.;Stone, J. R.
  29. Biochemistry v.21 Bartlett, P. A.;Spear, K. L.;Jacobsen, N. E.
  30. Tetrahedron Lett. Wasserman, H. H.;Hlasta, D. J.
  31. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology v.6 Silverman, R. B.
  32. Biochem. J. v.55 Dixon, M.
  33. J. Am. Chem. Soc. v.117 Mustafi, D.;Makinen, M. W.
  34. J. Am. Chem. Soc. v.103 Jacobsen, N. E.;Bartlett, P. A.
  35. Acta Cryst. v.C43 Yang, Q.-C.;Seiler, P.;Dunitz, J. D.
  36. J. Chem. Soc. Perkin Trans.Ⅱ Fujiwara, H.;Varley, R. L.;Van der Veen, J. M.
  37. Biochemistry(2nd ed.) v.19 Stryer, L.
  38. Principles of Biochemistry(2nd ed.) Lehminger, A. L.;Nelson, D. L.;Cox, M. M.
  39. J. Am. Chem. Soc. v.115 Abbound, J.-L.;Mo, O;de Paz, L. G.;Yanez, M.;Esseffar, M.;Bouab, W.;El-Mouhtadi, M.;Mokhlisse, R.;Ballesteros, E.;Herreros, M.;Homan, H.;Lopez-Mardomingo, C.;Notario, R.