Thiazolium-dependent catalytic antibodies produced using a covalent modification strategy

Chemical Communications

Volumn , Issue 15, 1999, Pages 1383-1384

  Tanaka, Fujie ^a   Lerner, Richard A ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; CATALYTIC ANTIBODY; THIAZOLIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENZYME ACTIVE SITE; IMMUNIZATION;

EID: 0033533131     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902337b     Document Type: Article

References (25)

1. C. Walsh, Enzymatic Reaction Mechanisms, ed. A. C. Bartlett and L. W. McCombs, W. H. Freeman and Company, New York, 1979.
2. For the introduction of cofactors into antibodies using cleavable affinity labels, see S. J. Pollack, G. R. Nakayama and P. G. Schultz, Science, 1988, 242, 1038.
3. For cofactor dependent catalytic antibodies, see P. G. Schultz and R. A. Lerner, Science, 1995,269,1835;
4. F. Tanaka, M. Oda and I. Fujii, Tetrahedron Lett., 1998,39,5057;
5. S. I. Gramatikova and P. Christen, Biol. Client., 1996, 271, 30583.
6. (a) J. Wagner, R. A. Lerner and C. F. Barbas III, Science, 1995, 270, 1797;
7. (b) C. F. Barbas III, A. Heine, G. Zhong, T. Hoffmann, S. Gramatikova, R. Bjornestedt, B. List, J. Anderson, E. A. Stura, I. A. Wilson and R. A. Lemer, Science. 1997, 278, 2085;
8. G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky and C. F. Barbas III, J. Am. Client. Soc., 1997, 119, 8131;
9. T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lernerand C. F. Barbas III, J. Am. Client. Soc.,1998,120, 2768;
10. (e) G. Zhong, D. Shabat, B. List, J. Anderson, S. C. Sinha, R. A. Lerner and C. F. Barbas lll.Angeu: Client., Int. Ed., 1998, 110,2609.
11. Reactions of amines with benzylpenicillin have been reported: J. J. Morris and M. I. Page, J. Client. Soc., Perkin Trans. 2, 1980, 212.
12. Covalent bond formation has been reported in the time-dependent inactivation of a catalytic antibody: B. Gigant, J.-B. Charbonnier, B. Golinelli-Pimpaneau, R. R. Zemel, Z. Eshhar, B. S. Green and M. Knossow, Etir. J. Biocliem., 1997, 246, 471.
13. The range of extinction coefficients of the known dyes possessing the dimethylaminophenylazopyridinium group was used: M. Takeuchi, M. Taguchi, H. Shinmori and S. Shinkai, Bull. Client. Soc. Jpn., 1996, 69, 2613;
14. P. Schindler and G. Huber, Enzyme Inhibitors, Proc. Meet.; (Brodbeck, Urs,eds),
15. Weinheim, Fed. Rep. Ger., Verlag Chem., 1980, 169.
16. The observed order of the reactivity was: 3 > 11-13 > 2, 9, 10,14 > 8> 7. In studies of 3, 90% of the active site was modified after 3 h whereas with 8, 29% of the active site was modified after 40 h.
17. R. Kluger, Client. Rev., 1987, 87, 863.
18. J. Hong, S. Sun, T. Derrick, C. Larive, K. B. Schowen and R. L. Schowen, Biocliim. Biophys. Ada, 1998,1385,187;
19. S. Sun, G. S. Smith, M. H. O'Leary and R. L. Schowen, J. Am. Client. Soc., 1997,119, 1507 and references cited therein.
20. Aldehyde generation from the reaction intermediate in the decarboxylation has been reported to be a difficult process in the model reaction: see réf. 8 and Y. Chen, G. L. Barletta, K. Haghjoo, J. T. Cheng and F. Jodan, J. Org. Client., 1994, 59, 7714.
21. However, atmospheric oxygen reacts with the intermediate and the hydrolysis gives the acid as the relatively easier process: A. I. Vovk and I. V. Murav'eva, RUSS. J. Gen. Client., 1995, 65, 119;
22. A. I. Vovk and I.V. Murav'eva, KUSS. J. Gen. Client., 1989,59, 1048;
23. L. J. Dirmaier, G. A. Garcia, J. W. Kozarich and G. L. Kenyan, J. Ant. Client. Soc., 1986,108, 3149.
24. J. Crosby and G. E. Lienhard, J. Am. Client. Soc.. 1970, 92, 5707.
25. D. R. Burton and C. F. Barbas III, Adv. Immitnol., 1994, 57, 191.