Exploring the scope of the 29G12 antibody catalyzed 1,3-dipolar cycloaddition reaction

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 7810-7815

  Toker, Jonathan D ^a   Tremblay, Martin R ^a   Yli Kauhaluoma, Jari ^a   Wentworth, Anita D ^a   Zhou, Bin ^a   Wentworth Jr , Paul ^a,b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BIOCATALYSTS; CATALYSIS; HYDROPHOBICITY; PROTEINS; SUBSTRATES; THERMAL EFFECTS;

CYCLOADDITION REACTION; ENANTIOSELECTIVE REACTION; MURINE MONOCLONAL ANTIBODY; STEREOCHEMICAL CONTROL;

ANTIBODIES;

4 ACETAMIDOBENZONITRILE N OXIDE; BENZONITRILE; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 29G12; N,N DIMETHYLACRYLAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; CATALYST; CYCLOADDITION; DIPOLE; DRUG STRUCTURE; ENANTIOSELECTIVITY; ENTHALPY; ENTROPY; ENZYME SPECIFICITY; HYDROPHOBICITY; PARAMETER; REACTION ANALYSIS; STEADY STATE; STEREOSPECIFICITY; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

ACRYLAMIDES; AMINO ACID SUBSTITUTION; ANIMALS; ANTIBODIES, MONOCLONAL; CYCLIZATION; ISOXAZOLES; MICE; STEREOISOMERISM; THERMODYNAMICS;

EID: 25444493936     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050410b     Document Type: Article

References (32)

1. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley and Sons: New York, 1984; Vol. 1, p 1.
2. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984.
3. Curtius, T. Ber. Dtsch. Chem. Ges. 1883, 16, 2230.
4. Buchner, E. Ber. Dtsch. Chem. Ges. 1888, 21, 2637.
5. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633.
6. Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
7. Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
8. Wentworth, P., Jr. Science 2002, 296, 2247.
9. Blackburn, G. M.; Datta, A.; Denham, H.; Wentworth, P. In Adv. Phys. Org. Chem. 1998, 31, 249.
10. Wentworth, P.; Janda, K. D. Cell Biochem. Biophys. 2001, 35, 63.
11. Toker, J. D.; Wentworth, P., Jr.; Hu, Y.; Houk, K. N.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 3244.
12. Firestone, R. A. J. Org. Chem. 1968, 33, 2285.
13. Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
14. Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033.
15. Morao, I.; Cossío, F. P. J. Org. Chem. 1999, 64, 1868.
16. Houk, K. N.; Yamaguchi, K. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley and Sons: New York, 1984; Vol. 2, p 407.
17. Sauer, J. Angew. Chem., Int. Ed. Engl. 1966, 5, 211.
18. Janda, K. D.; Lerner, R. A.; Tramontano, A. J. Am. Chem. Soc. 1988, 110, 4835.
19. Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841.
20. Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1988, 110, 5593.
21. Hilvert, D.; Hill, K. W.; Nared, K. D.; Auditor, M.-T. M. J. Am. Chem. Soc. 1989, 111, 9261.
22. Taniguchi, T.; Yokoama, Y.; Miyashita, T. Macromolecules 1997, 30, 3646.
23. Liu, K.; Shelton, B.; Howe, R. K. J. Org. Chem. 1980, 45, 3916.
24. Tanaka, F.; Kinoshita, K.; Tanimura, R.; Fujii, I. J. Am. Chem. Soc. 1996, 118, 2332.
25. Segel, I. H. Enzyme Kinetics; John Wiley and Sons: New York, 1975.
26. Cleland, W. W. Biochim. Biophys. Acta 1963, 67, 104.
27. Cleland, W. W. In The Enzymes; Boyer, P. D., Ed.; Academic Press: New York, 1970; Vol. 2, p 1.
28. Wolfenden, R. Acc. Chem. Res. 1972, 5, 10.
29. Kobayashi, M.; Kannan, M. R.; Feng, J.; Roberts, M. F.; Lomasney, J. W. Biochemistry 2004, 43, 7522.
30. Bohm, H.-J.; Stahl, M. Med. Chem. Res. 1999, 9, 445.
31. Hsieh, L. C.; Stephans, J. C.; Schultz, P. G. J. Am. Chem. Soc. 1994, 116, 2167.
32. Grate, J. W.; McGill, R. A.; Hilvert, D. J. Am. Chem. Soc. 1993, 115, 8577.