A model for hydride transfer in thymidylate synthase based on unnatural amino acid mutagenesis [18]

Journal of the American Chemical Society

Volumn 121, Issue 34, 1999, Pages 7965-7966

  Barrett, J E ^a   Lucero, C M ^a   Schultz, P G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [5 [[(1,2 DIHYDRO 3 METHYL 1 OXOBENZO[F]QUINAZOLIN 9 YL)METHYL]AMINO] 1 OXO 2 ISOINDOLINYL]GLUTARIC ACID; AMINO ACID; FOLIC ACID DERIVATIVE; MERCAPTOETHANOL; SODIUM; THYMIDYLATE SYNTHASE; URIDINE PHOSPHATE;

AMINO ACID ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ENZYME ACTIVITY; KINETICS; LETTER; MODEL; MUTAGENESIS;

EID: 0033198698     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991040+     Document Type: Letter

References (21)

1. Carreras, C. W.; Santi, D. V. Ann. Rev. Biochem. 1995, 64, 721-62.
2. Barrett, J. E.; Maltby, D. A.; Santi, D. V.; Schultz, P. G. J. Am. Chem. Soc. 1998, 120, 449-450.
3. Spencer, H. T.; Villafranca, J. E.; Appleman, J. R. Biochemistry 1997, 36, 4212-4222.
4. Ellman, J.; Mendel, D.; Anthony-Cahill, S.; Noren, C. J.; Schultz, P. G. Biosynthetic Method for Introducing Unnatural Amino Acid Site-Specifically into Proteins; 1992; Vol. 202, pp 301-336.
5. Saks, M. E.; Sampson, J. R.; Nowak, M. W.; Kearney, P. C.; Du, F. Y.; Abelson, J. N.; Lester, H. A.; Dougherty, D. A. J. Biol. Chem. 1996, 271, 23169-23175.
6. 35S methionine. Protein concentration was determined by using the known concentration of cold methionine, the number of methionines present in thymidylate synthase, and the concentration and activity of the labeled methionine used in the protein synthesis reaction. All of the amino acids were commercially available.
7. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525-616.
8. Sangster, J. J. Phys. Chem. Ref. Data 1989, 18, 1111-1229.
9. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
10. Zhong, W. G.; Gallivan, J. P.; Zhang, Y. N.; Li, L. T.; Lester, H. A.; Dougherty, D. A. Proc. Nat. Acad. Sci. U.S.A. 1998, 95, 12088-12093.
11. Hyatt, D. C.; Maley, F.; Montfort, W. R. Biochemistry 1997, 36, 4585-4594.
12. Stout, T. J.; Stroud, R. M. Structure 1996, 4, 67-77.
13. Additional support for the importance of the proposed second catalytic pocket can be gleaned from the crystal structure of another potent TS inhibitor, CB3717, which has a propargyl group on N10 that lies in the proposed second catalytic pocket. (Monfort, W. R.; Perry, K. M.; Fauman, E. B.; Finer-Moore, J. S.; Maley, G. F.; Hardy, L.; Maley, F.; Stroud, R M. Biochemistry 1990, 29, 6964-6977.).
14. Slieker, L. J.; Benkovic, S. J. J. Am. Chem. Soc. 1984, 106, 1833-1838.
15. Meissner, J. W. G.; Pandit, U. K. Tetrahedron Lett. 1992, 33, 2999-3002.
16. Kunitani, M. G.; Santi, D. V. Biochemistry 1980, 19, 1271-1275, Schellenberger, U.; Livi, L. L.; Santi, D. V. Protein Expression Purif. 1995, 6, 423-430, Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 13049- 13056, Butler, M. M.; Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 10521-10526.
17. Kunitani, M. G.; Santi, D. V. Biochemistry 1980, 19, 1271-1275, Schellenberger, U.; Livi, L. L.; Santi, D. V. Protein Expression Purif. 1995, 6, 423-430, Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 13049- 13056, Butler, M. M.; Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 10521-10526.
18. Kunitani, M. G.; Santi, D. V. Biochemistry 1980, 19, 1271-1275, Schellenberger, U.; Livi, L. L.; Santi, D. V. Protein Expression Purif. 1995, 6, 423-430, Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 13049-13056, Butler, M. M.; Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 10521-10526.
19. Kunitani, M. G.; Santi, D. V. Biochemistry 1980, 19, 1271-1275, Schellenberger, U.; Livi, L. L.; Santi, D. V. Protein Expression Purif. 1995, 6, 423-430, Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 13049- 13056, Butler, M. M.; Graves, K. L.; Hardy, L. W. Biochemistry 1994, 33, 10521-10526.
20. Song, H. K.; Sohn, S. H.; Suh, S. W. EMBO J. 1999, 18, 1104-13.
21. Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308.