Kinetics of the micellar nucleophilic cleavage of diastereomeric phosphotriesters

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 965-968

  Moss, Robert A ^a   Bose, Susmita ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE PESTICIDE;

ARTICLE; CATALYSIS; HYDROLYSIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031562043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02491-4     Document Type: Article

References (23)

1. (1) Yang, Y-C. Chem. Ind.(London) 1995 (1 May), 334; Yang, Y-C.; Baker, J.A.; Ward, J.R. Chem. Rev. 1992, 92, 1729.
2. (1) Yang, Y-C. Chem. Ind.(London) 1995 (1 May), 334; Yang, Y-C.; Baker, J.A.; Ward, J.R. Chem. Rev. 1992, 92, 1729.
3. (2) Ember, L. Chem. Eng. News 1995 (27 March), 6.
4. (3) Moss, R.A.; Alwis, K.W.; Bizzigotti, G.O. J. Am. Chem. Soc. 1983, 105, 681; Moss, R.A.; Alwis, K.W.; Shin, J-S. Ibid. 1984, 106, 2651.
5. (3) Moss, R.A.; Alwis, K.W.; Bizzigotti, G.O. J. Am. Chem. Soc. 1983, 105, 681; Moss, R.A.; Alwis, K.W.; Shin, J-S. Ibid. 1984, 106, 2651.
6. (4) Hammond, P.S.; Forster, J.S.; Lieske, C.N.; Durst, H.D. J. Am. Chem. Soc. 1989, 111, 7860.
7. (5) Vanhooke, J.L.; Benning, M.M.; Raushel, F.M.; Holden, H.M. Biochemistry 1996, 35, 6020;
8. Benning, M.M.; Kuo, J.M.; Raushel, F.M.; Holden, H.M. Ibid. 1994, 33, 15001; and references therein.
9. (6) For leading references to the production and properties of catalytic antibodies, see Yli-Kauhaluoma, J.T.; Ashley, J.A.; Lo, G-H.; Tucker, L.; Wolfe, M.M.; Janda, K.D. J. Am. Chem. Soc. 1995, 117, 7041; Koch, T.; Reymond, J-L.; Lerner, R.A. Ibid. 1995, 117, 9383; Hilvert, D. Acc. Chem. Res. 1993, 26, 552; Schultz, P.G.; Lerner, R.A. Ibid. 1993, 26, 391; Schultz, P.G. Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
10. (6) For leading references to the production and properties of catalytic antibodies, see Yli-Kauhaluoma, J.T.; Ashley, J.A.; Lo, G-H.; Tucker, L.; Wolfe, M.M.; Janda, K.D. J. Am. Chem. Soc. 1995, 117, 7041; Koch, T.; Reymond, J-L.; Lerner, R.A. Ibid. 1995, 117, 9383; Hilvert, D. Acc. Chem. Res. 1993, 26, 552; Schultz, P.G.; Lerner, R.A. Ibid. 1993, 26, 391; Schultz, P.G. Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
11. (6) For leading references to the production and properties of catalytic antibodies, see Yli-Kauhaluoma, J.T.; Ashley, J.A.; Lo, G-H.; Tucker, L.; Wolfe, M.M.; Janda, K.D. J. Am. Chem. Soc. 1995, 117, 7041; Koch, T.; Reymond, J-L.; Lerner, R.A. Ibid. 1995, 117, 9383; Hilvert, D. Acc. Chem. Res. 1993, 26, 552; Schultz, P.G.; Lerner, R.A. Ibid. 1993, 26, 391; Schultz, P.G. Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
12. (6) For leading references to the production and properties of catalytic antibodies, see Yli-Kauhaluoma, J.T.; Ashley, J.A.; Lo, G-H.; Tucker, L.; Wolfe, M.M.; Janda, K.D. J. Am. Chem. Soc. 1995, 117, 7041; Koch, T.; Reymond, J-L.; Lerner, R.A. Ibid. 1995, 117, 9383; Hilvert, D. Acc. Chem. Res. 1993, 26, 552; Schultz, P.G.; Lerner, R.A. Ibid. 1993, 26, 391; Schultz, P.G. Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
13. (6) For leading references to the production and properties of catalytic antibodies, see Yli-Kauhaluoma, J.T.; Ashley, J.A.; Lo, G-H.; Tucker, L.; Wolfe, M.M.; Janda, K.D. J. Am. Chem. Soc. 1995, 117, 7041; Koch, T.; Reymond, J-L.; Lerner, R.A. Ibid. 1995, 117, 9383; Hilvert, D. Acc. Chem. Res. 1993, 26, 552; Schultz, P.G.; Lerner, R.A. Ibid. 1993, 26, 391; Schultz, P.G. Angew. Chem. Int. Ed. Engl. 1989, 28, 1283.
14. (7) Rosenblum, J.S.; Lo, L-C.; Li, T.; Janda, K.D.; Lerner, R.A. Angew. Chem. Int. Ed. Engl. 1995, 34, 2275.
15. (8) Moss, R.A.; Kim, K-Y; Swarup, S. J. Am. Chem. Soc. 1986, 108, 788.
16. (9) Moss, R.A.; Kotchevar, A.T.; Park, B.D.; Scrimin, S. Langmuir 1996, 12, 2200.
17. (10) Moss, R.A.; Zhang, H.; Chatterjee, S.; Krogh-Jespersen, K. Tetrahedron Lett. 1993, 34, 1729.
18. (11) Toullec, J.; Moukawin, M. Chem. Commun. 1996, 221.
19. (12) Kirby, A.J. "The Anomeric Effect and Related Stereoelectronic Effects at Oxygen," Springer-Verlag, Berlin, 1983, pp 78f, 126f.
20. (13) Thatcher, G.R.J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99, esp. pp. 171f.
21. 9 so that substrates 1 and 2 are (respectively) -0.9 and 2.8 (IBA), or 2.7 and 7.6 times (INA) as reactive as 3. These results probably reflect better binding of the more hydrophobic 1 and 2 to the CTACl micellar phase where the cleavage reactions occur.
22. (15) The high reactivity of hydroperoxide toward phosphotriesters is well known; see Bunton, C.A.; Foroudian, H.J. Langmuir 1993, 9, 2832, and references therein.
23. 9