The Chemistry of Phosphapeptides: Formation of Functionalized Phosphonochloridates under Mild Conditions and Their Reaction with Alcohols and Amines

Journal of Organic Chemistry

Volumn 59, Issue 25, 1994, Pages 7616-7624

  Malachowski, William P ^a   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0028561861     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00104a016     Document Type: Article

References (50)

1. Sandler, M., Smith, H. J., Eds. Design of Enzyme Inhibitors as Drugs; Oxford University Press: Oxford, 1989.
2. Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Mamada, M. J. Antibiot. 1970, 23, 259.
3. Morishima, H.; Takita, T.; Umezawa, H. J. Antibiot. 1973, 26, 115.
4. Rich, D. H. J. Med. Chem. 1985, 28, 263.
5. Capon, B.; Dosunmu, M. I.; de Matos Sanchez, M. D.; Adv. Phys. Org. Chem. 1985, 21, 37.
6. Wlodawer, A.; Erickson, J. W. Annu. Rev. Biochem. 1993, 62, 543.
7. Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760.
8. Wolfenden, R.; Kati, W. M. Acc. Chem. Res. 1991, 24, 209
9. Suda, H.; Aoyagi, T.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1973, 26, 621.
10. Hanson, J. E.; Kaplan, A. P.; Bartlett, P. A. Biochemistry 1989, 28, 6294
11. Bartlett, P. A.; Marlowe, C. K. Biochemistry 1983, 22, 4618.
12. Karanewsky, D. S.; Badia, M. C.; Cushman, D. W.; DeForrest, J. M.; Dejneka, T.; Loots, M. J.; Perrie, M. G.; Petrillo, E. W., Jr.; Powell, J. R. J. Med. Chem. 1988, 31, 204.
13. Colanduoni, J. A.; Villafranca, J. J. Bioorg. Chem. 1986, 14, 163
14. Logusch, E. W.; Walker, D. M.; McDonald, J. F.; Franz, J. E. Biochemistry 1989, 28, 3043.
15. Duncan, K.; Walsh, C. T. Biochemistry 1988, 27, 3709.
16. Parsons, W. H.; Patchett, A. A.; Bull, H. G.; Schoen, W. R.; Taub, D.; Davidson, J.; Combs, P. L.; Springer, J. P.; Gadebusch, H.; Weissberger, B.; Valiant, M. E.; Mellin, T. N.; Busch, R. D. J. Med. Chem. 1988, 31, 1772.
17. Chen, Y.-C.J.; Danon, T.; Sastry, L.; Mubaraki, M.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 357
18. Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659.
19. Bertenshaw, S. R.; Rogers, R. S.; Stern, M. K.; Norman, B. H.; Moore, W. M.; Jerome, G. M.; Branson, L. M.; McDonald, J. F.; McMahon, E. G.; Palomo, M. A. J. Med. Chem. 1993, 36, 173
20. Rahil, J.; Pratt, R. F. Biochemistry 1992, 31, 5869.
21. Morgan, B. P.; Scholtz, J. M.; Ballinger, M. D.; Zipkin, I. D.; Bartlett, P. A. J. Am. Chem. Soc. 1991, 113, 297
22. Lienhard, G. E. Science 1973, 180, 149.
23. Wolfenden, R.; Frick, L. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987; pp 97.
24. Malachowski, W. P.; Coward, J. K. J. Org. Chem.
25. Walsh, C.; Bradley, M.; Nadeau, K. TIBS 1991, 16, 305.
26. Smith, K.; Nadeau, K.; Bradley, M.; Walsh, C.; Fairlamb, A. H. Protein Sci. 1992, 1, 874
27. Sampson, N. S.; Bartlett, P. A. J. Org. Chem. 1988, 53, 4500.
28. Maier, L.; Rist, G. Phosphorus Sulfur 1983, 17, 21
29. Petrov, K. A.; Maklyaev, F. L.; Korshunov, M. A. Zh. Obshch. Khim. 1959, 29, 304.
30. Elliott, R. L.; Marks, N.; Berg, M. J.; Portoghese, P. S. J. Med. Chem. 1985, 28, 1208.
31. Yamauchi, K.; Kinoshita, M.; Imoto, M. Bull. Chem. Soc. Jpn. 1972, 45, 2528.
32. Hariharan, M.; Chaberek, S.; Martell, A. E. Synth. Commun. 1973, 3, 375
33. Razumov, A. I.; Mukjacheva, O. A.; Markovich, E. A. Zh. Obshch. Khim. 1957, 27, 2450.
34. Lakanen, J. R. Ph.D. Thesis, The University of Michigan, Ann Arbor, MI, Jan 1994
35. de Roos, A. M.; Toet, H. J. Recl. Trav. Chim. Pavs-Bas 1959, 78, 59.
36. Coe, D. G.; Perry, B. J.; Brown, R. K. J. Chem. Soc. 1957, 3604.
37. Pelchowicz, Z. J. Chem. Soc. 1961, 238.
38. Maier, L. Phosphorus, Sulfur Silicon 1990, 47, 465.
39. Bartlett, P. A.; Hanson, J. E.; Giannousis, P. P. J. Org. Chem. 1990, 55, 6268.
40. Giannousis, P. P.; Bartlett, P. A. J. Med. Chem. 1987, 30, 1603
41. Bartlett, P. A.; Lamden, L. A. Bioorg. Chem. 1986, 14, 356.
42. Jacobsen, N. E.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 654.
43. Robl, J. A.; Duncan, L. A.; Pluscec, J.; Karanewsky, D. S.; Gordon, E. M.; Ciosek, C. P., Jr.; Rich, L. C.; Dehmel, V. C.; Slusarchyk, D. A.; Harrity, T. W.; Obrien, K. A. J. Med. Chem. 1991, 34, 2804
44. Gray, M. D. M.; Smith, D. J. H. Tetrahedron Lett. 1980, 21, 859
45. Biller, S. A.; Forster, C. Tetrahedron 1990, 46, 6645
46. Malachowski, W. P. Ph.D. Thesis, The University of Michigan, Ann Arbor, MI, May 1993
47. Campbell, D. A. J. Org. Chem. 1992, 57, 6331
48. Yamauchi, K.; Ohtsuki, S.; Kinoshita, M. J. Org. Chem. 1984, 49, 1158
49. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923
50. Sasse, K. In Methoden der Organischen Chemie (Houben-Weyl); Muller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1963; Vol. XII; pp 416