Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Aminophosphonopeptides Containing Carbapenem

  • Ik Joong Kang (Department of Chemical Engineering, Kyungwon University) ;
  • Kyu Wan Lee (Korea Research Institute of Chemical Technology) ;
  • Wan Joo Kim (Korea Research Institute of Chemical Technology) ;
  • Yong Joon Kim (Department of Chemical Engineering, Korea University)
  • Published : 1994.09.20
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Abstract

A new kind of aminophosphonopeptides containing carbapenem, allyl-(5R,6S)-3-(2-carbobenzyloxyamino-3-dialkylph osphonopropionyl-2-amino)ethanthio-6-{(1'R)-hydro xyethyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-carb oxylate 1a-1d, have been synthesized. 2-Carbobenzyloxyamino-3-dialkylphosphonopropion yl-2-amino-ethanethiol 7a-7d, aminophosphonopeptides, were produced starting from N-carbobenzyloxyserine methyl ester (2) and 2-amino-3-dialkyl-phosphonopropionate(4) by way of methyl 2-carbobenzyloxyamino-3-dialkylphosphonopropion ate 5a-5d. The coupling of amino-phosphonopeptides 7a-7d and allyl-(5R,6S)-6-{(1'R)-hydroxyethyl}-1-aza-3,7-dio xobicyclo[3.2.0]-heptane-2-carboxylate yielded aminophosphonopeptides containing carbapenem 1a-1d.

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References

  1. Nature v.184 Horiguchi, M.;Kandatsu, M.
  2. Agri. Bio. Chem. v.29 Kandatsu, M.;Horiguchi, M.
  3. Nature v.207 Shimizu, H.;Kakimodo, Y.;Nagagima, T.;Danaza, A.;Sano, A.
  4. J. Biochem. v.9 Aldadelff, J. A.;Davis, G. D.
  5. J. Biochem. Biophy. Acta v.244 Alhadelff, J. A.;Davis, G. D.
  6. Tetrahedron Lett. v.24 Ogita, K.;Gungi, H.;Fugazawa, Y.;Terahara, A.;Kinoshita, T.;Nagai, H.
  7. Abstracts of annual meeting of Agric. Chem. Soc. Jpn. Gungi, H.;Beppu, T.
  8. Abstracts of annual Meeting of Agric. Chem. Soc. Jpn. Ogita, K.;Fugazawa, Y.;Terahara, A.;Kinoshita, T.;Nagai, H.;Beppu, T.
  9. Chemical Abstract v.104 Kleinrok, T.;Stirling, I.
  10. Res. Commun. Chem. Pathol. Pharmacol. v.57 Shimada, M.;Kabuto, H.;Yokoi, I.
  11. J. Bio. Chem. v.248 Korn, E. D.;Dearborn, D. G.;Fales, H. M.;Sokoloski, E. A.
  12. Tetrahedron Lett. v.22 Reider, P. J.;Grabowski,;Edward, J. J.
  13. Tetrahedron Lett. v.23 Tanaka, T.;Hashimoto(et al.)
  14. J. Chem. Soc. Perking Trans. Stirling, I.;Clarke, B. P.
  15. J. Am. Chem. Soc. v.105 Okano, K.;Kyotani, Y.
  16. J. Antibiot. v.36 Basker, M. J.;Boon, R. J.
  17. Chem. Pharm. Bull. v.35 Tamura, N.;Natsugar, H.
  18. Jpn. Kokai Tokkyo Koho JP 63 v.170 Shimizu, H.;Kumagai, T.
  19. Tetrahedron Lett. v.29 Ohta, T.;Sato,N.
  20. European patent v.103 Atherton, F. R.;Hal. M. J.
  21. J. Am. Chem. Soc. v.103 Jacobson, N. E.;Bartlett, P. A.
  22. J. Med. Chem. v.28 Elliott, R. L.;Marks, N.;Berg, M. J.
  23. Natue v.272 Alen, J. S.;Atherton, F. R.
  24. Ger. Offen. v.22 Niida, T.;Tsuruoka, T.
  25. Helv. Chim. Acta. v.55 Bayer, E.;Gugel, K. H.
  26. Tetrahedron Lett. v.21 Sletzinger, M.;Liu, T.;Reamer, R. A.;SinKai, I.
  27. J. Am. Chem. Soc. v.102 Salzmann, T. N.;Ratcliff, R.;Christensen, B. G.;Bouffard, F. A.
  28. J. Korean Chem. Soc. v.34 Chun, Y. J.;Oh, G. M.;Cho, S. K.;Kim, Y. J.
  29. Tetrahedron Lett. v.30 Deziel, R.;Favreau, D.
  30. Biochemistry v.3 Kitridge, J. S.;Huges, R. R.
  31. J. Org. Chem. v.32 Spencer, E. Y.;Todd, A. R.;Webb, R. F.
  32. Tetrahedron v.32 Majoral, J. P.
  33. J. Am. Chem. Soc. v.75 Vaughan, Jr. I. R.;Eichler, J. A.
  34. J. Am. Chem. soc. v.78 Hofmann, K.;Peckhan, W. D.;Heiner, A. R.
  35. J. Med. Chem. v.28 Elliot, R. L.;Marks, N.;Berg, M. J.;Portoghess, P. S.
  36. Bull. Korean Chem. Soc. v.12 Kang, I. J.;Hong, S. I.;Kim, Y. J.
  37. Bull. Korean Chem. Soc. v.12 Kang, I. J.;Hong, S. I.;Kim, Y. J.
  38. The chemistry of C-P compounds having biophysiological activity Kim, Y. J.;Kang, I. J.