Phosphorodithioates: Synthesis and evaluation of new haptens for the generation of antibody acyl transferases

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7307-7310

  Brümmer, Oliver ^a   Wentworth Jr , Paul ^a   Weiner, David P ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Antibodies; Bisaryl carbonate hydrolysis; Catalysis; Phosphorodithioate; Transition state analogues

Indexed keywords

48F10; ACYLTRANSFERASE; BOVINE SERUM ALBUMIN; CARBONIC ACID DERIVATIVE; HAPTEN; KEYHOLE LIMPET HEMOCYANIN; MONOCLONAL ANTIBODY; PHOSPHOROTHIOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CATTLE; HYDROLYSIS; MICHAELIS MENTEN KINETICS; MOLLUSC; MOUSE; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0033536684     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01501-4     Document Type: Article

References (24)

1. 1. (a) Tramontano, A.; Janda, K. D.; Lerner, R. A. Science 1986, 234, 1566;
2. (b) Pollack, S. J.; Jacobs, J. W.; Schulz, P. G. Science 1986, 234, 1570.
3. 2. (a) Teraishi, K.; Saito, M.; Fujii, I.; Nakamura, H. Tetrahedron Lett. 1992, 7153;
4. (b) Tantillo, D. J.; Houk, K. N. J. Org. Chem. 1999, 64, 3066.
5. 3. For recent reviews, see: (a) Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth Jr., P. In Advances in Physical Organic Chemistry, Vol. 3; Bethell, D., Ed.; Academic Press: London, 1998; pp. 249-393;
6. (b) Wentworth Jr., P.; Janda, K. D. Curr. Opin. Chem. Biol. 1998, 2, 138.
7. 4. Li, T.; Hilton, S.; Janda, K. D. J. Am. Chem. Soc. 1995, 117, 2133, and references cited therein.
8. 5. (a) Wilmore, B. H.; Iverson, B. L. J. Am. Chem. Soc. 1994, 116, 2181.
9. (b) Janda, K. D.; Schloeder, D.; Benkovic, S. J.; Lerner, R. A. Science, 1988, 241, 1188.
10. 6. Benedetti, F; Berti, F.; Colombatti, A.; Ebert, C.; Linda, P.; Tonizzo, F. J. Chem. Soc., Chem. Commun. 1996, 1417.
11. 7. Shokat, K. M.; Ko, K. M.; Scanlan, T. S.; Kochesperger, L.; Yonkovich, S.; Thaisirvongs, S.; Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1990, 29, 1296.
12. 8. Kitazume, T.; Tsukamoto, T.; Yoshimura, K. J. Chem. Soc. Chem. Commun. 1994, 1355.
13. 9. Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97, 1281.
14. 10. Handbook of Chemistry and Physics, 73rd edition; Lide, D. R., Ed.; CRC Press: Boca Raton; 1992-1993.
15. 11. Martin, S. F.; Wagman, A. S. J. Org. Chem. 1996, 61, 8016, and references cited therein.
16. 12. Porritt, G. M.; Reese, C. B. Tetrahedron Lett. 1990, 31, 1319.
17. 13. (a) Köhler, G.; Milstein, C. Nature 1975, 256, 495;
18. (b) Enguall, E. Methods Enzymol. 1980, 70, 419.
19. -1, respectively, and were determined by the method of initial rates using the buffer system vide supra.
20. 15. (a) Shokat, K. M.; Ko, M. K.; Scanlan, T. S.; Kochersperger, L.; Yonkovich, S.; Thaisirvongs, S.; Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1990, 29, 1296;
21. (b) Jacobs, J.; Schultz, P. G.; Sugasawara, R.; Powell, M. J. Am. Chem. Soc. 1987, 109, 2174;
22. (c) Pollack, S. J.; Jacobs, J. W.; Schultz, P. G. Science 1986, 234, 1570;
23. (d) Wallace, M. B.; Iverson, B. L. J. Am. Chem. Soc. 1996, 118, 251.
24. i values of tight-binding inhibitors.