Phosphonate and α-fluorophosphonate analogue probes of the ionization state of pyridoxal 5′-phosphate (PLP) in glycogen phosphorylase

Biochemistry

Volumn 35, Issue 47, 1996, Pages 15057-15064

  Stirtan, William G ^a   Withers, Stephen G ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

5 DEOXYPYRIDOXAL 5 METHYLENEPHOSPHONIC ACID; 5' DEOXYPYRIDOXAL 5' DIFLUOROMETHYLENEPHOSPHONIC ACID; GLYCOGEN PHOSPHORYLASE; PHOSPHONIC ACID DERIVATIVE; PYRIDOXAL 5 PHOSPHATE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATALYSIS; ENZYME ACTIVITY; IONIZATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RABBIT; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MUSCLES; PHOSPHONIC ACIDS; PHOSPHORYLASES; PYRIDOXAL; PYRIDOXAL PHOSPHATE; RABBITS;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0030446436     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9606004     Document Type: Article

References (59)

1. Ashwell, G. (1957) Methods Enzymol. 3, 73
2. Barford, D., Hu, S.-H., & Johnson, L. N. (1991) J. Mol. Biol. 218, 233.
3. Bergstrom, D. E., & Shum, P. W. (1988) J. Org. Chem. 53, 3953.
4. Bigge, C. F., Drummond, J. T., & Johnson, G. (1989) Tetrahedron Lett. 30, 7013.
5. Blackburn, G. M., Brown, D., Martin, S. J., & Parratt, M. J. (1987) J. Chem. Soc. Perkin Trans. 1, 181.
6. Brocklehurst, K. (1994) Protein Eng. 7, 292-299.
7. Bue, M. H., & Buc, H. (1968) Regul. Enzyme Act. Allosteric Interact., Proc. Meet Fed. Eur. Biochem. Soc., 4th, 1967, 109.
8. Challoner, R., McDowell, C. A., Stirtan, W,. & Withers, S. G. (1993) Biophys. J. 64, 484.
9. Chang, Y.-C., McCalmont, T., & Graves, D. J. (1983) Biochemistry 22, 4987.
10. Chang, Y.-C., Scott, R. D., & Graves, D. J. (1986) Biochemistry 25, 1932.
11. Chang, Y.-C., Scott, R. D., & Graves, D. J. (1987) Biochemistry 26, 360.
12. Corey, E. J., & Volante, R. P. (1976) J. Am. Chem. Soc. 98, 1291.
13. Engers, H. D., Shechosky, S., & Madsen, N. B. (1970) Can. J. Biochem. 48, 746.
14. Feldmann, K., & Hull, W. E. (1977) Proc. Natll. Acad. Sci. U.S.A. 74, 856.
15. Feldmann, K., & Helmreich, E. J. M. (1976) Biochemistry 15, 2394.
16. Fischer, E. H., & Krebs, E. G. (1962) Methods Enzymol. 5, 369.
17. Gerig, J. T. (1989) Methods Enzymol. 177, 3.
18. Gorenstein, D. (1975) J. Am. Chem. Soc. 97, 898.
19. Helmreich, E. J. M. (1992) BioFactors 3, 159.
20. Hullar, T. L. (1969) J. Med. Chem. 12, 58.
21. Jencks, W. P. (1975) Adv. Enzymol. Relat. Areas Mol. Bid. 43, 219-410.
22. Johnson, L. N., Acharya, K. R., Jordan, M. D., & McLaughlin, P. J. (1990) J. Mol. Biol. 211, 645.
23. Kallen, R. G., Korpela, T., Martell, A. E., Malsushima, Y., Metzler, C. M., Morozov, Y. V., Ralston, I. M., Savin, F. A., Torchinsky, Y. M., & Ueno, H. (1985) in Transaminases (Christen, P., & Metzler, D. E., Eds.) p 37, John Wiley & Sons, New York.
24. Kasvinsky, P. J., & Meyer, W. L. (1977) Arch. Biochem. Biophys. 181, 616.
25. Klein, H. W., Palm, D., & Helmreich, E. J. M. (1982) Biochemistry 22, 6675.
26. Klein, H. W., Im, M.-J., Palm, D., & Helmreich, E. J. M. (1984) Biochemistry 23, 5853.
27. Knowles, J. R. (1976) CRC Crit. Rev. Biochem. 165.
28. Korytnyk, W., & Ikawa, M. (1970) Methods Enzymol. 18A, 524.
29. Leatherbarrow, R. J. (1990) GraFit Version 2.0, Erithacus Software Ltd., Staines, U.K.
30. 6 Catalysis (Evangelopoulos, A. E., Ed.) Part A, p 117, A. R. Liss, Inc., New York.
31. 6 Pyridoxal Phosphate: Chemical, Biochemical, and Medical Aspects (Dolphin, D., Poulson, R., & Avramovic, O., Eds.) Part B. p 355, John Wiley & Sons, Inc., New York.
32. Martin, J. L., Johnson, L. N., & Withers, S. G. (1990) Biochemistry 29, 10745.
33. Mitchell, E. P., Withers, S. G., Ermert, P., Vasella, A. T., Garman, E. F., Oikonomakos, N., & Johnson, L. N. (1996) Biochemistry 35, 7341.
34. Miura, R., Metzler, C. M., & Metzler, D. E. (1989) Arch. Biochem. Biophys. 270, 526.
35. Obayashi, M., Ito, E., Matsui, K., & Kondo, K. (1982) Tetrahedron Lett. 23, 2323.
36. O'Connor, J. V., Nunez, H. A., & Barker, R. (1979) Biochemistry 18, 500.
37. Oikonomakos, N. G., Johnson, L. N., Acharya, K. R., Stuart, D. I., Barford, D., Hadju, J., Varvill, K. M., Melpidou, A. E., Papageorgiou, T., Graves, D. J., & Palm, D. (1987) Biochemistry 26, 8381.
38. Palm, D., Klein, H. W., Schinzel, R., Buehner, M., & Helmreich, E. J. M. (1990) Biochemistry 29, 1099.
39. Parrish, R. F., Uring, R. J., & Graves, D. J. (1977) Biochemistry 16, 4824.
40. Percival, M. D., & Withers, S. G. (1992) Biochemistry 31, 505.
41. Schinzel, R., Palm, D., & Schnackerz, K. D. (1992) Biochemistry 31, 4128.
42. Schnackerz, K. D., & Feldmann, K. (1980) Biochem. Biophys. Res. Commun. 95, 1832.
43. 6 Pyridoxal Phosphate: Chemical, Biochemical and Medical Aspects (Dolphin, D., Poulson, R., & Avramovic, O., Eds.) Part A, p 245, John Wiley & Sons, Inc., New York.
44. Schnackerz, K. D., Wahler, G., Vincent, M. G., & Jansonius, J. N. (1989) Eur. J. Biochem. 185, 525.
45. Sprang, S. R., & Fletterick, R. J. (1979) J. Mol. Biol. 131, 523.
46. Sprang, S. R., Withers, S. G., Goldsmith, E. J., Fletterick, R. J., & Madsen, N. B. (1991) Science 254, 1367.
47. Sprang, S. R., Madsen, N. B., & Withers, S. G. (1992) Protein Sci. 1, 1100.
48. Street, I. P., & Withers, S. G. (1995) Biochem. J. 308, 1017.
49. Sykes, B. D., & Hull, W. E. (1978) Methods Enzymol. 49, 270.
50. Taguchi, J. E., Heyes, S. J., Barford, D., Johnson, L. N., & Dobson, C. M. (1993) Biophys. J. 64, 492-501.
51. Uhing, R. J., Lentz, S. R., & Graves, D. J. (1981) Biochemistry 20, 2537.
52. Vidgoff, J. M., Pocker, A., Hullar, T. L., & Fischer, E. H. (1974) Biochem. Biophys. Res. Commun. 57, 1166.
53. Vogel, H. J., & Bridger, W. A. (1982) Biochemistry 21, 394.
54. Withers, S. G., Sykes, B. D., Madsen, N. B., & Kasvinsky, P. J. (1979) Biochemistry 18, 5342.
55. Withers, S. G., Madsen, N. B., & Sykes, B. D. (1981) Biochemistry 20, 1748.
56. Withers, S. G., Shechosky, S., & Madsen, N. B. (1982a) Biochem. Biophys. Res. Comm. 108, 322.
57. Withers, S. G., Madsen, N. B., Sprang, S. R., & Fletterick, R. J. (1982b) Biochemistry 21, 5372.
58. Withers, S. G., Street, I. P., & Percival, M. D. (1988) in Fluorinated Carbohydrates: Chemical and Biological Aspects (Taylor, N. F., Ed.) American Chemical Society Symposium Series 374, p 59, American Chemical Society, Washington DC.
59. Zographos, S. E., Oikonomakos, N. G., Dixon, H. B. F., Griffin, W. G., Johnson, L. J., & Leonidas, D. D. (1995) Biochem. J. 310, 565.