Contributions of orientation and hydrogen bonding to catalysis in Asn229 mutants of thymidylate synthase

Journal of Molecular Biology

Volumn 276, Issue 1, 1998, Pages 113-129

  Finer Moore, Janet S ^a   Liu, Lu ^a   Birdsall, David L ^a   Brem, Rachel ^a   Apfeld, Javier ^a   Santi, Daniel V ^a   Stroud, Robert M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2' deoxyuridine 5' monophosphate; 5,10 methylene tetrahydrofolate; Kinetics; Methylase; X ray crystallography

Indexed keywords

5,10 METHYLENE 5,6,7,8 TETRAHYDROFOLATE; ASPARAGINE; DEOXYURIDINE DERIVATIVE; DEOXYURIDINE PHOSPHATE; FOLIC ACID DERIVATIVE; MUTANT PROTEIN; PYRIMIDINE DERIVATIVE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME CONFORMATION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME STRUCTURE; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR MODEL; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

FELIS CATUS;

EID: 0032512806     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1006/jmbi.1997.1495     Document Type: Article

References (33)

1. Agarwalla, S., LaPorte, S., Liu, L., Finer-Moore J., Stroud, R. M., Santi D.V. A novel dCMP methylase by engineering thymidylate synthase. Biochemistry, in the press
2. Birdsall D.L., Finer-Moore J., Stroud R.M. Entropy in bi-substrate enzymes proposed role of an alternate site in chaperoning substrate into, and products out of, thymidylate synthase. J. Mol. Biol. 255:1996;522-535
3. Brünger A.T., Kuriyan J., Karplus M. Crystallographic R-factor refinement by molecular dynamics. Science. 235:1987;458-460
4. Carreras C.W., Santi D.V. The catalytic mechanism and structure of thymidylate synthase. Annu. Rev. Biochem. 64:1995;721-762
5. Chambers J.L., Stroud R.M. The accuracy of refined protein structures comparison of two independently refined models of bovine trypsin. Acta Crystallog. sect. B. 35:1979;1861-1874
6. Climie S., Santi D.V. Chemical synthesis of the thymidylate synthase gene. Proc. Natl Acad. Sci. USA. 87:1990;633-637
7. Climie S.C., Carreras C.W., Santi D.V. A complete replacement set of amino acids at the C-terminus of thymidylate synthase quantitative structure-activity relationships of mutants of an enzyme. Biochemistry. 31:1992;6032-6038
8. Dev I.K., Yates B.B., Atashi J., Dallas W.S. Catalytic role of histidine 147 in Escherichia coli thymidylate synthase. J. Biol. Chem. 264:1989;19132-19137
9. Fauman E.B., Rutenber E.E., Maley G.F., Maley F., Stroud R.M. Water-mediated substrate/product discrimination the product complex of thymidylate synthase at 1.83 Å Biochemistry. 33:1994;1502-1511
10. Finer-Moore J.S., Montfort W.R., Stroud R.M. Pairwise specificity and sequential binding in enzyme catalysis thymidylate synthase. Biochemistry. 29:1990;6977-6986
11. Finer-Moore J., Fauman E.B., Foster P.G., Perry K.M., Santi D.V., Stroud R.M. Refined structures of substrate-bound and phosphate-bound thymidylate synthase from Lactobacillus casei. J. Mol. Biol. 232:1993;1101-1116
12. Garret C., Wataya Y., Santi D.V. Catalysis of dehalogenation of 5-bromo- and 5-iodo-2′-deoxyuridylate. Biochemistry. 18:1979;2798-2804
13. Hardy L.W., Nalivaika E. Asn177 in Escherichia coli thymidylate synthase is a major determinant of pyrimidine specificity. Proc. Natl Acad. Sci. USA. 89:1992;9725-9729
14. Hardy L.W., Graves K.L., Nalivaika E. Electrostatic guidance of catalysis by a conserved glutamic acid in Escherichia coli dTMP synthase and bacteriophage T4 dCMP hydroxymethylase. Biochemistry. 34:1995;8422-8432
15. Higashi T. Auto-indexing of oscillation images. J. Appl. Crystallog. 23:1990;253-257
16. Huang W., Santi D.V. Isolation of a covalent steady-state intermediate in glutamate 60 mutants of thymidylate synthase. J. Biol. Chem. 269:1994;31327-31329
17. Jones T.A. Diffraction methods for biological macromolecules. Interactive computer graphics FRODO. Methods Enzymol. 115:1985;157-171
18. Jones T.R., Calvert A.H., Jackman A.L., Brown S.J., Jones M., Harrap K.R. A potent antitumor quinazoline inhibitor of thymidylate synthase synthesis, biological properties and therapeutic results in mice. Eur. J. Cancer. 17:1981;11-19
19. Kealey J.T., Santi D.V. Purification methods for recombinant Lactobacillus casei thymidylate synthase and mutants a general, automated procedure. Protein Express. Purificat. 3:1992;380-385
20. Kraulis P.J. MOLSCRIPT a program to produce both detailed and schematic plots of protein structures. J. Appl. Crystallog. 24:1991;946-950
21. Liu L., Santi D.V. Mutation of asparagine 229 to aspartate in thymidylate synthase converts the enzyme to a deoxycytidylate methylase. Biochemistry. 31:1992;5100-5104
22. Liu L., Santi D.V. Asparagine 229 in thymidylate synthase contributes to, but is not essential for, catalysis. Proc. Natl Acad. Sci. USA. 90:1993;8604-8608
23. Liu L., Santi D.V. Exclusion of 2′-deoxycytidine 5′-monophosphate by asparagine 229 of thymidylate synthase. Biochemistry. 32:1993;9263-9267
24. Matthews D.A., Villafranca J.E., Janson C.A., Smith W.W., Welsh K., Freer S. Stereochemical mechanism of action for thymidylate synthase based on the X-ray structure of the covalent inhibitory ternary complex with 5-fluoro-2′-deoxyuridylate and 5,10-methylenetetrahydrofolate. J. Mol. Biol. 214:1990;937-948
25. Montfort W.R., Perry K.M., Fauman E.B., Finer-Moore J.S., Maley G.F., Hardy L., Maley F., Stroud R.M. Structure, multiple site binding, and segmental accommodation in thymidylate synthase on binding dUMP and an anti-folate. Biochemistry. 29:1990;6964-6977. (Published erratum appears in Biochemistry (1990) 29, 10864.)
26. Perry K.M., Fauman E.B., Finer-Moore J.S., Montfort W.R., Maley G.F., Maley F., Stroud R.M. Plastic adaptation toward mutations in proteins structural comparison of thymidylate synthases. Proteins: Struct. Funct. Genet. 8:1990;315-333
27. Perry K.M., Carreras C.W., Chang L.C., Santi D.V., Stroud R.M. Structures of thymidylate synthase with a C-terminal deletion role of the C-terminus in alignment of 2′-deoxyuridine 5′-monophosphate and 5,10-methylenetetrahydrofolate. Biochemistry. 32:1993;7116-7125
28. Sack J.S. CHAIN a crystallographic modelling program. J. Mol. Graph. 6:1988;244-245
29. Santi D.V., Pinter K., Kealey J., Davisson V.J. Site-directed mutagenesis of arginine 179 of thymidylate synthase. A nonessential substrate-binding residue. J. Biol. Chem. 265:1990;6770-6775
30. Santi D.V., Ouyang T.M., Tan A.K., Gregory D.F., Scanlon T., Carreras C.W. Interaction of TS with PLP as studied by uv/vis difference spectroscopy and molecular modeling. Biochemistry. 32:1993;11819-11824
31. Sato M., Yamamoto M., Imada K., Katsube Y., Tanaka N., Higashi T. A high-speed data-collection system for large-unit-cell crystals using an imaging plate as a detector. J. Appl. Crystallog. 25:1992;348-357
32. Stroud R.M., Fauman E.B. Significance of structural changes in proteins expected errors in refined protein structures. Protein Sci. 4:1995;2392-2404
33. Zapf J.W., Weir M.S., Emerick V., Villafranca J.E., Dunlap R.B. Substitution of glutamine for glutamic acid-58 in Escherichia coli thymidylate synthase results in pronounced decreases in catalytic activity and ligand binding. Biochemistry. 32:1993;9274-9281