Synthesis of the First Stable Phosphonamide Transition State Analogue

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8424-8430

  De Medina, P ^a   Ingrassia, L S ^a   Mulliez, M E ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TRANSITION STATES;

ACYLATION; ELECTRON ENERGY LEVELS; PH EFFECTS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALANINE DERIVATIVE; AMIDE; AMINE; AMINO ACID; ANTIINFECTIVE AGENT; BETA FLUOROAMINOPHOSPHONIC ACID; ESTER; FLUORINE; GAMMA GLUTAMYLTRANSFERASE; ORGANOPHOSPHORUS COMPOUND; PEPTIDE HYDROLASE; PHOSPHITE; PHOSPHONAMIDE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMISTRY; CONFORMATION; DRUG DESIGN; ELIMINATION REACTION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STEREOISOMERISM; SYNTHESIS;

ACYLATION; AMIDES; AMINES; AMINO ACIDS; ANTI-BACTERIAL AGENTS; DRUG DESIGN; ESTERS; FLUORINE; MOLECULAR CONFORMATION; ORGANOPHOSPHORUS COMPOUNDS; PEPTIDE HYDROLASES; PHOSPHONIC ACIDS; STEREOISOMERISM;

EID: 0142196879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034229j     Document Type: Article

References (46)

1. See inter alia: Rich, D. H. Peptidases Inhibitors In Comprehensive Medicinal Chemistry; Sammes P. G., Ed.; Pergamon Press: Oxford, 1990; Vol. II. This has been verified particularly with metallo-proteases but not so much with serine- or cysteine-proteases.
2. For example, Cbz-NHCH2PO(OH)Phe, one of the most stable, potent inhibitors of carboxypeptidase A displays a half-life of 4 h at pH 6.2 (8 days at pH 7.5): Jacobsen, N. E.; Bartlett, P. A. J Am. Chem. Soc. 1981, 103, 654.
3. See inter alia: Benkovic, S. J.; Benkovic, P. A. J. Am. Chem. Soc. 1967, 89, 4714.
4. Mulliez, M. Tetrahedron 1981, 37, 2027.
5. See for example Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984.
6. In light of the known activiy of D-Ala-D-Ala analogues, as penicillins or alaphosphaline. See inter alia: Neuhaus, F. C.; Hammes, W. P. Pharma. Ther. 1981, 14, 265.
7. Sinitsa, A. D.; Onysko, P. P.; Kim, T. V.; Kiseleva, E. I.; Pirozhenko, V. V. J. Gen. Chem. U.S.S.R. 1986, 52, 2372.
8. Flynn, G. A.; Beight, D. W.; Bohme, E. H. W.; Metcalf, B. W. Tetrahedron Lett. 1985, 26, 285.
9. Vaubaillon, D.; Giraud, V.; Rabiller, C.; Gruss, U.; Haas, A.; Hägele, G. Phosphorus, Sulfur Silicon 1997, 126, 177.
10. Seebach, D.; Charczuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401.
11. Corcoran, R.; Green, J. Tetrahedron Lett. 1990, 31, 6827.
12. Ingrassia, L.; Mulliez, M. Synthesis 1999, 10, 1731.
13. Vo Quang, Y.; Carniato, D.; Vo Quang, L.; Le Goffic, F. Synthesis 1985, 62.
14. Albrecht, R.; Kresze, G.; Mlakar, B. Chem. Ber. 1964, 97, 483.
15. Weygand, F.; Steglich, W.; Lengyel, I.; Fraunberger, F.; Oettmeier, W. Chem. Ber. 1966, 99, 1944.
16. Steglich, W.; Burger, K.; Durr, M.; Burgis, E. Chem. Ber. 1974, 107, 1488.
17. See inter alia: Redmore, D. In Topics in Phosphorus Chemistry; Griffith, E. J., Grayson, M., Eds.; Interscience: New York, 1976; Vol. 8, p 515.
18. With the exception of the N-sulfonyl protected hemiaminals: see ref 12.
19. Einhorn, A. Justus Liebigs Ann. Chem. 1905, 343, 27.
20. Ivanov, B. E.; Gorin, Y. A.; Krokhina, Bull. Acad. Sci. S.S.S.R., Ser. Chim. 1970, 11, 2627.
21. Scharf, D. J. J. Org. Chem. 1976, 41, 28.
22. In particular with RNHP(OR′)Cl compounds, if R is a peptide chain, its N-terminal elongation was allowed.
23. No use for phosphonic esters is indicated in the two misleading following reviews: Siling, M. I.; Laricheva, T. N. Russ. Chem. Rev. 1996, 65, 279. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
24. No use for phosphonic esters is indicated in the two misleading following reviews: Siling, M. I.; Laricheva, T. N. Russ. Chem. Rev. 1996, 65, 279. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999.
25. Weygand, F.; Steglich, W.; Maierhofer, A.; Fraunberger, F. Chem. Ber. 1967, 100, 3838.
26. Weygand, F.; Steglich, W.; Oettmeier, W. Chem. Ber. 1970, 103, 1655.
27. Afarinkia, K.; Rees, C. W.; Cadogan, J. I. G. Tetrahedron 1990, 46, 7175.
28. See for example: Mulliez, M. Bull. Soc. Chim. Fr. 1985, 1211.
29. See for example: Jackson, A. E.; Johnstone, A. W. Synthesis 1976, 685.
30. Zervas, L.; Dilaris, I. J. Am. Chem. Soc. 1955, 77, 5354.
31. See for example: Hirschmann, R.; Yager, K. M.; Taylor, C. M.; Witherington, J.; Sprengeler, P. A.; Philips, B. W.; Moore, W.; Smith, A. B. J. Am. Chem. Soc. 1997, 119, 8177.
32. Musiol, H. J.; Grams, F.; Rudolph-Böhner, S.; Moroder, L. J. Org. Chem. 1994, 59, 6144.
33. Theoretically, two additional more simple one-pot syntheses of 5 (i.e. 20) may be envisaged using the P-H compound 4i: first by electrophilic amination and the second one after silylation with bissilylacetamide (BSA) according to the literature (see, for example: Hata, T.; Yamamoto, I.; Sekine, M. Chem. Lett. 1976, 601). The silylated phosphorous intermediate compound formed should react in a Staudinger reaction with amyl azide and eventually lead, after hydrolysis, to 5. In fact, the initial Staudinger reaction is followed by a cyclization expelling the N-silylated amylamine. This was not unexpected in light of the known participation of the amide group in the hydrolysis of N-acyl α-amino phosphonic monoesters: Rahil, J.; Pratt, R. F. J. Chem. Soc., Perkin Trans. 2 1991, 947. Moreover, the heterocycles formed, as for phosphorous heterocycles in general and in particular the related phosphoxazolones (ref 30), remain resistant to aminolysis.
34. Theoretically, two additional more simple one-pot syntheses of 5 (i.e. 20) may be envisaged using the P-H compound 4i: first by electrophilic amination and the second one after silylation with bissilylacetamide (BSA) according to the literature (see, for example: Hata, T.; Yamamoto, I.; Sekine, M. Chem. Lett. 1976, 601). The silylated phosphorous intermediate compound formed should react in a Staudinger reaction with amyl azide and eventually lead, after hydrolysis, to 5. In fact, the initial Staudinger reaction is followed by a cyclization expelling the N-silylated amylamine. This was not unexpected in light of the known participation of the amide group in the hydrolysis of N-acyl α-amino phosphonic monoesters: Rahil, J.; Pratt, R. F. J. Chem. Soc., Perkin Trans. 2 1991, 947. Moreover, the heterocycles formed, as for phosphorous heterocycles in general and in particular the related phosphoxazolones (ref 30), remain resistant to aminolysis.
35. a of comparable phosphonamidic acids are rather conflicting from ∼7 (Crunden, E. W.; Hudson, R. F. Chem. Ind. (London) 1962, 613) to ∼3 (Suarez, A. I.; Lin, J; Thompson, C. M. Tetrahedron 1996, 52, 6117).
36. a of comparable phosphonamidic acids are rather conflicting from ∼7 (Crunden, E. W.; Hudson, R. F. Chem. Ind. (London) 1962, 613) to ∼3 (Suarez, A. I.; Lin, J; Thompson, C. M. Tetrahedron 1996, 52, 6117).
37. Wang, E. A.; Walsh, C. Biochemistry 1981, 20, 7539.
38. Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassal, C. H., Holmes, S. W. ; Lambert, R. W.; Nisbet, L. L.; Ringrose, P. S. Nature 1978, 272, 56.
39. Hassal, C. H. Actual. Chim. Ther. 1985, 12, 193.
40. Wulf, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812.
41. More details are available in L.S.I.'s thesis, Toulouse, Dec 2000.
42. Chen, S. T.; Wu, S. H.; Wang, K. T. Synthesis 1989, 37.
43. 31P Nuclear Magnetic Resonance In Topics in Phosphorus Chemistry; Crutchfield, M. M., Dungan, C. H., Mark, V., Van Wazer, J., Graysson, M., Griffith, J., Eds.; J. Wiley, New York: 1967; p 673.
44. Issleib, K.; Mögelin, W.; Balzuweit, A. Z. Anorg. Allg. Chem. 1985, 530, 16.
45. Boyd, E. A.; Ragan A. C.; James, K. Tetrahedron Lett. 1992, 33, 813.
46. Shapiro, G.; Marzi, M. J. Org. Chem. 1997, 62, 7096.