The controlled introduction of multiple negative charge at single amino acid sites in subtilisin Bacillus lentus

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 11, 1999, Pages 2293-2301

  Davis, Benjamin G ^a   Shang, Xiao ^a   DeSantis, Grace ^a   Bott, Richard R ^b   Jones, J Bryan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b GENENCOR INTERNATIONAL INC   (United States)

Author keywords

Electrostatic effects; Enzymes and enzyme reactions; Kinetics; Mutagenesis

Indexed keywords

AMINO ACID; ANION; SUBTILISIN; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; EGGERTHELLA LENTA; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SPECIFICITY; NONHUMAN; SITE DIRECTED MUTAGENESIS; SYNTHESIS;

AMINO ACIDS; BACILLUS; CATALYSIS; ELECTROCHEMISTRY; KINETICS; MUTAGENESIS, SITE-DIRECTED; SUBTILISIN; SULFHYDRYL REAGENTS; THIOSULFONIC ACIDS;

BACILLUS LENTUS; BACTERIA (MICROORGANISMS); EGGERTHELLA LENTA; FELIS CATUS;

EID: 0033491620     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00167-4     Document Type: Article

References (64)

1. Hermes J.D., Blacklow S.C., Knowles J.R. Proc. Natl. Acad. Sci. USA. 87:1990;696.
2. El Hawrani A.S., Sessions R.B., Moreton K.M., Holbrook J.J. J. Mol. Biol. 264:1996;97.
3. Arnold F. Acc. Chem. Res. 31:1998;125.
4. Wells J.A., Powers D.B., Bott R.R., Graycar T.P., Estell D.A. Proc. Natl. Acad. Sci. USA. 84:1987;1219.
5. Sternberg M.J.E., Hayes F.R.F., Russell A.J., Thomas P.G., Fersht A.R. Nature. 330:1987;86.
6. Cronin C.N., Kirsch J.F. Biochemistry. 27:1988;4572.
7. Blacklow S.C., Liu K.D., Knowles J.R. Biochemistry. 30:1991;8470.
8. Beaumont A., Barbe B., Le Moual H., Boileau G., Crine P., Fournié-Zaluski M.-C., Roques B.P. J. Biol. Chem. 267:1992;2138.
9. Bocanegra J.A., Scrutton N.S., Perham R.N. Biochemistry. 32:1993;2737.
10. Steinicke H.R., Mortensen U.H., Christenssen U., Remington S.J., Breddam K. Protein Eng. 7:1994;911.
11. Hogan J.K., Pittol C.A., Jones J.B., Gold M. Biochemistry. 34:1995;4225.
12. Ballinger M.D., Tom J., Wells J.A. Biochemistry. 34:1995;13312.
13. Buchbinder J.L., Luong C.B.H., Browner M.F., Fletterick R.J. Biochemistry. 36:1997;8039.
14. Ballinger M.D., Tom J., Wells J.A. Biochemistry. 35:1996;13579.
15. Mansour S.J., Candia J.M., Matsuura J.E., Manning M.C., Ahn N.G. Biochemistry. 35:1996;15529.
16. Kurth T., Ullmann D., Jakubke H.-D., Hedstrom L. Biochemistry. 36:1997;10098.
17. Tougu V., Tiivel T., Talts P., Sikanis V., Pogarkova S., Kesvatera T., Aaaviksaar A. Eur. J. Biochemistry. 222:1994;475.
18. Silvestrini M.C., Tordi M.G., Citro G., Vecchini P., Brunori M. J. Inorg. Biochemistry. 57:1995;168.
19. Lundblad, R. L. Techniques in Protein Modification; CRC: Boca Raton, FL, 1995.
20. Cornish V.W., Mendel D., Schultz P.G. Angew. Chem., Intl. Ed. Engl. 34:1995;621.
21. Karginov V.A., Mameav S.V., An H., van Cleve M.D., Hecht S.M., Komatsoulis G.A., Abelson J.N. J. Am. Chem. Soc. 119:1997;8166.
22. Park Y., Luo J., Schultz P.G., Kirsch J.F. Biochemistry. 36:1997;10517.
23. Bech L.M., Breddam K. Carlsberg Res. Commun. 53:1988;381.
24. Smith H.B., Hartman F.C. J. Biol. Chem. 263:1988;4921.
25. Grøn H., Bech L.M., Branner S., Breddam K. Eur. J. Biochemistry. 194:1990;897.
26. Wynn R., Richards F.M. Protein Sci. 2:1993;395.
27. Gloss L.M., Kirsch J.F. Biochemistry. 34:1995;12323.
28. Wynn R., Harkins P.C., Richards F.M., Fox R.O. Protein Sci. 5:1996;1026.
29. Kenyon G.L., Bruice T.W. Methods Enzymol. 47:1977;407.
30. Wynn R., Richards F.M. Methods Enzymol. 251:1995;351.
31. Berglund P., DeSantis G., Stabile M.R., Shang X., Gold M., Bott R.R., Graycar T.P., Lau T.H., Mitchinson C., Jones J.B. J. Am. Chem. Soc. 119:1997;5265.
32. Stabile M.R., Lai W.G., DeSantis G., Gold M., Jones J.B., Mitchinson C., Bott R.R., Graycar T.P., Liu C.-C. Bioorg. Med. Chem. Lett. 6:1996;2501.
33. DeSantis G., Berglund P., Stabile M.R., Gold M., Jones J.B. Biochemistry. 37:1998;5968.
34. The coordinates of SBL have been deposited at the Protein Databank at Brookhaven under the code 1JEA.
35. Nomenclature of Schechter I., Berger A. Biochemistry Biophys. Res. Commun. 27:1967;157.
36. Douglass I.B., Farah B.S. J. Org. Chem. 24:1959;973.
37. Levitt L.S., Levitt B.W. J. Org. Chem. 37:1972;332.
38. Weidner J.P., Block S.S. J. Med. Chem. 15:1972;564.
39. Palumbo G., Caputo R. Synthesis. 888:1981.
40. Block E., Zhao S.H. J. Org. Chem. 57:1992;5815.
41. Billard T., Langlois B.R., Large S., Anker D., Roidot N., Roure P. J. Org. Chem. 61:1996;7545.
42. Baldwin, T. O.; Holzmann, T. F.; Satoh, P. S.; Yein, F. S. US Patent 4879249, 1989.
43. Arnett E.M., Maroldo S.G., Schilling S.L., Harrelson J.A. Jr. J. Am. Chem. Soc. 106:1984;6759.
44. Arnett E.M., Harrelson J.A. Jr. J. Am. Chem. Soc. 109:1987;809.
45. Direct alkylation of 5a with 1,2-dibromoethane led only to the formation of a spirocyclopropane derivative, the product of intramolecular cyclization, in low yield. For a recent analysis of the high propensity of the anion of 5a to form cyclic products with α,ω-dihalides see Ridvan L.; Závada J. Tetrahedron 1997, 53, 14793.
46. Ellman G.L., Courtney K.D., Andres V., Featherstone R.M. Biochemistry Pharmacol. 7:1961;88.
47. Hsia C.Y., Ganshaw G., Paech C., Murray C.J. Anal. Biochemistry. 242:1996;221.
48. M value determined (1.52 ± 0.06 mM) is not concentration dependent.
49. -1.
50. Jackson S.E., Fersht A.R. Biochemistry. 32:1993;13919.
51. Estell D.A., Graycar T.P., Miller J.V., Powers D.B., Burnier J.P., Ng P.G., Wells J.A. Science. 233:1986;659.
52. 1 pocket contains four less amino acid residues.
53. Akabas M.H., Stauffer D.A., Xu M., Karlin A. Science. 258:1992;307.
54. Akabas M.H., Kaufman C., Archdeacon P., Karlin A. Neuron. 13:1994;919.
55. Akabas M.H., Kaufman C., Cook T.A., Archdeacon P. J. Biol. Chem. 269:1994;14865.
56. Cheung M., Akabas M.H. J. Gen. Physiol. 109:1997;289.
57. Stauffer D.A., Karlin A. Biochemistry. 33:1994;6840.
58. Yang N., George A.L. Jr., Horn R. Neuron. 16:1996;113.
59. Holmgren M., Liu Y., Xu Y., Yellen G. Neuropharmacol. 35:1996;797.
60. Huynh P.D., Cui C., Zhan H.J., Oh K.J., Collier R.J., Finklestein A. J. Gen. Physiol. 110:1997;229.
61. Rassendren F., Buell G., Newbolt A., North R.A., Surprenant A. EMBO J. 16:1997;3446.
62. Fittig R., von Furtenbach E. Justus Liebigs Anal. Chem. 147:1868;292.
63. Bonneau P.R., Graycar T.P., Estell D.A., Jones J.B. J. Am. Chem. Soc. 119:1991;1026.
64. Grøn H., Bech L.M., Branner S., Breddam K. Eur. J. Biochemistry. 194:1990;897.