Molecular mechanism of enantioselective proton transfer to carbon in catalytic antibody 14D9

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 10, 2004, Pages 3387-3392

  Zheng, Lei ^a   Baumann, Ulrich ^a   Reymond, Jean Louis ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ASPARTIC ACID; CARBON; CATALYTIC ANTIBODY; CATALYTIC ANTIBODY 14D9; CATALYTIC ANTIBODY 19C9; CHIMERIC ANTIBODY; ENOL ETHER; ETHER; IMMUNOGLOBULIN F(AB) FRAGMENT; ION; OXOCARBONIUM ION; OXYGEN; PHENYLALANINE; THREONINE; TYROSINE; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CATALYSIS; COVALENT BOND; CRYSTAL STRUCTURE; DOUBLE BOND; ENANTIOSELECTIVITY; ESCHERICHIA COLI; GENE EXPRESSION; HYDROGEN BOND; LIGAND BINDING; MOLECULAR CLONING; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY;

AMINO ACID SEQUENCE; ANIMALS; ANTIBODIES, CATALYTIC; BASE SEQUENCE; BINDING SITES; CARBON; CRYSTALLOGRAPHY, X-RAY; DNA, RECOMBINANT; ESCHERICHIA COLI; HUMANS; HYDROGEN BONDING; IMMUNOGLOBULIN FAB FRAGMENTS; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; PROTONS; RECOMBINANT FUSION PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM;

ESCHERICHIA COLI;

EID: 1542409023     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0400263101     Document Type: Article

References (35)

1. Kemp, D. S. (1995) Nature 373, 196-197.
2. Mitra, B., Kallarakal, A. T., Kozarich, J. W., Gerlt, J. A., Clifton, J. G., Petsko, G. A. & Kenyon, G. L. (1995) Biochemistry 34, 2777-2787.
3. Davenport, R. C., Bash, P. A., Seaton, B. A., Karplus, M., Petsko, G. A. & Ringe, D. (1991) Biochemistry 30, 5821-5826.
4. Stevenson, J. D. & Thomas, N. R. (2000) Nat. Prod. Rep. 17, 535-537.
5. Shokat, K. M., Leumann, C. J., Sugasawara, R. & Schultz, P. G. (1989) Nature 338, 269-271.
6. Uno, T. & Schultz, P. G. (1992) J. Am. Chem. Soc. 114, 6573-6574.
7. Shokat, K., Uno, T. & Schultz, P. G. (1994) J. Am. Chem. Soc. 116, 2261-2262.
8. Cravatt, B. F., Ashley, J. A., Janda, K. D., Boger, D. L. & Lerner R. A. (1994) J. Am. Chem. Soc. 116, 6013-6014.
9. Koch, T., Reymond, J.-L. & Lerner, R. A. (1995) J. Am. Chem. Soc. 117, 9383-9387.
10. Thorn, S. N., Daniels, R. G. & Auditor, M.-T. M. Hilvert, D. (1995) Nature 373, 228-230.
11. Gigant, B., Charbonnier, J. B., Eshhar, Z., Green, B. S. & Knossow, M. (1997) Proc. Natl. Acad. Sci. USA 94, 7857-7861.
12. Fujii, L. Lerner, R. A. & Janda, K. D. (1991) J. Am. Chem. Soc. 113, 9528-8529.
13. Reymond, J.-L., Janda, K. D. & Lerner, R. A., (1992) J. Am. Chem. Soc. 114, 2257-2258.
14. Reymond, J.-L., Reber, R. A. & Lerner, R. A. (1994) Angew. Chem. Int. Ed. 33, 475-478.
15. Reymond, J.-L., Janda, K. D. & Lerner, R. A. (1991) Angew. Chem. Int. Ed. 30, 1711-1714.
16. Huse, W. D., Sastry, L., Iverson, S. A., Kang, A. S., Alting-Mees, M., Burton, D. R., Benkovic, S. J. & Lerner, R. A. (1989) Science 246, 1250-1251.
17. Barbas, C. F., Kang, A. S., Lerner, R. A. & Benkovic, S. J. (1991) Proc. Natl. Acad. Sci. USA 88, 7978-7982.
18. Kang, A. S., Barbas, C. F., Janda, K. D., Benkovic, S. J. & Lerner, R. A. (1991) Proc. Natl. Acad. Sci. USA 88, 4363-4366.
19. Ulrich, H. D., Patten, P. A., Yang, P. L., Romesberg, F. E. & Schultz, P. G. (1995) Proc. Natl. Acad. Sci. USA 92, 11907-11911.
20. Yin, J., Mundorff, E. C., Yang, P. L., Wendt, K. U., Hanway, D., Stevens, R. C. & Schultz, P. G. (2001) Biochemistry 40, 10764-10773.
21. Harlow, E. & Lane, D. (1988) Antibodies: A Laboratory Manual (Cold Spring Harbor Lab. Press, Plainview, NY)
22. Sinha, S. C. & Keinan, E. (1995) J. Am. Chem. Soc. 117, 3653-3654.
23. Collaborative Computational Project Number 4. (1994) Acta Crystallogr. D 50, 760-763.
24. Mundorff, E. C., Hanson, M. A., Varvak, A., Ulrich, H., Schultz, P. G. & Stevens, R. C. (2000) Biochemistry 39, 627-632.
25. Jones, T. A., Zou, J. Y., Cowan, S. W. & Kjeldgaard, M. (1991) Acta Crystallogr. A 47, 110-119.
26. Murshudov, G. N., Vagin, A. A. & Dodson, E. J. (1997) Acta Crystallogr. D 53, 240-255.
27. Jahangiri, G. K., Reymond, J.-L. & Lerner, R. A. (1994) J. Am. Chem. Soc. 116, 11264-11274.
28. Reymond, J.-L., Jahanghiri, G. K., Stoudt, C. & Lerner, R. A. (1993) J. Am. Chem. Soc. 115, 3909-3917.
29. Kang A. S., Jones T. M. & Burton D. R. (1991) Proc. Natl. Acad. Sci. USA 88, 11120-11123.
30. Miller, G. P., Posner, B. A. & Benkovic, S. J. (1997) Bioorg. Med. Chem. 5, 581-590.
31. Sinha, S. C., Keinan, E. & Reymond, J.-L., (1993) J. Am. Chem. Soc. 115, 4893-4894.
32. Shabat D., Itzhaky, H., Reymond, J.-L. & Keinan, E. (1995) Nature 374, 143-145.
33. Sinha, S. C., Keinan, E. & Reymond, J.-L. (1993) Proc. Natl. Acad. Sci. USA 90, 11910-11913.
34. Shabat, D., Sinha, S. C., Reymond, J.-L. & Keinan, E. (1996) Angew. Chem. Int. Ed. 35, 2628-2631.
35. Shabat, D., Shulman, H., Itzhaky, H., Reymond, J.-L. & Keinan, E. (1998) Chem. Commun. 1759-1760.