Turnover Is rate-limited by deglycosylation for micromonospora viridifaciens sialidase-catalyzed hydrolyses: Conformational implications for the Michaelis complex

Journal of the American Chemical Society

Volumn 133, Issue 9, 2011, Pages 2989-2997

  Chan, Jefferson ^a   Lu, April ^a   Bennet, Andrew J ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDO; ANOMERIC CARBON; BOAT CONFORMATIONS; CHARGE DELOCALIZATION; CORE STRUCTURE; DEGLYCOSYLATION; GENERAL BASE; KINETIC ISOTOPE EFFECTS; LEAVING GROUPS; MICHAELIS COMPLEX; NATURAL SUBSTRATES; OXYGEN ATOM; RATE-LIMITING STEPS; SIALIDASES; SIALOSIDE; TRANSITION STATE; TYROSINE RESIDUES;

AMINO ACIDS; CARBOHYDRATES; CATALYSIS; HYDROLASES; HYDROLYSIS; OXYGEN; PROTONS; SOLVENTS;

DEUTERIUM;

CARBON; COUMARIN DERIVATIVE; DEUTERIUM; OXYGEN; SIALIDASE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; DEGLYCOSYLATION; ENZYME CONFORMATION; ENZYME METABOLISM; HYDROLYSIS; MICHAELIS MENTEN KINETICS; MICROMONOSPORA; MICROMONOSPORA VIRIDIFACIENS; NONHUMAN; PROTON TRANSPORT;

GLYCOSYLATION; KINETICS; MICROMONOSPORA; NEURAMINIDASE; SUBSTRATE SPECIFICITY;

EID: 79952260308     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109199p     Document Type: Article

References (47)

1. Miyagi, T.; Kato, K.; Ueno, S.; Wada, T. Trends Glycosci. Glycotechnol. 2004, 16, 371-381
2. Schauer, R. Trends Biochem. Sci. 1985, 10, 357-360
3. Corfield, T. Glycobiology 1992, 2, 509-521
4. Taylor, G. Curr. Opin. Struct. Biol. 1996, 6, 830-837
5. Davies, G.; Sinnott, M. L.; Withers, S. G. In Comprehensive Biological Catalysis, 1 st ed.; Sinnott, M. L., Ed.; Academic Press: San Diego, CA, 1998; pp 119 - 209.
6. Watson, J. N.; Dookhun, V.; Borgford, T. J.; Bennet, A. J. Biochemistry 2003, 42, 12682-12690
7. Watson, J. N.; Newstead, S.; Dookhun, V.; Taylor, G.; Bennet, A. J. FEBS Lett. 2004, 577, 265-269
8. Watson, J. N.; Newstead, S.; Narine, A.; Taylor, G.; Bennet, A. J. ChemBioChem 2005, 6, 1999-2004
9. Newstead, S.; Watson, J. N.; Knoll, T. L.; Bennet, A. J.; Taylor, G. Biochemistry 2005, 44, 9117-9122
10. Watts, A. G.; Damager, I.; Amaya, M. L.; Buschiazzo, A.; Alzari, P.; Frasch, A. C.; Withers, S. G. J. Am. Chem. Soc. 2003, 125, 7532-7533
11. Watts, A. G.; Oppezzo, P.; Withers, S. G.; Alzari, P. M.; Buschiazzo, A. J. Biol. Chem. 2006, 281, 4149-4155
12. Chan, J.; Lewis, A. R.; Gilbert, M.; Karwaski, M. F.; Bennet, A. J. Nat. Chem. Biol. 2010, 6, 405-407
13. Chong, A. K. J.; Pegg, M. S.; Taylor, N. R.; von Itzstein, M. Eur. J. Biochem. 1992, 207, 335-343
14. Narine, A. A.; Watson, J. N.; Bennet, A. J. Biochemistry 2006, 45, 9319-9326
15. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3 rd ed.; Harper & Row: New York, 1987.
16. Guo, X.; Laver, W. G.; Vimr, E.; Sinnott, M. L. J. Am. Chem. Soc. 1994, 116, 5572-5578
17. Guo, X.; Sinnott, M. L. Biochem. J. 1993, 294, 653-656
18. Sinnott, M. L.; Guo, X. M.; Li, S. C.; Li, Y. T. J. Am. Chem. Soc. 1993, 115, 3334-3335
19. Indurugalla, D.; Watson, J. N.; Bennet, A. J. Org. Biomol. Chem. 2006, 4, 4453-4459
20. Karwaski, M. F.; Wakarchuk, W. W.; Gilbert, M. Protein Expression Purif. 2002, 25, 237-240
21. Ashwell, M.; Guo, X.; Sinnott, M. L. J. Am. Chem. Soc. 1992, 114, 10158-10166
22. Indurugalla, D.; Bennet, A. J. Can. J. Chem. 2008, 86, 1005-1009
23. Bergson, G.; Matsson, O.; Sjoberg, S. Chem. Scr. 1977, 11, 25-31
24. Cook, P. F.; Cleland, W. W. Enzyme Kinetics and Mechanism; Garland Science: London; New York, 2007.
25. Melander, L. C. S.; Saunders, W. H. J. Reaction Rates of Isotopic Molecules; Wiley: New York, 1980.
26. Cook, P. F.; Cleland, W. W. Biochemistry 1981, 20, 1790-1796
27. Northrop, D. B. Biochemistry 1975, 14, 2644-2651
28. Xue, H.; Wu, X. W.; Huskey, W. P. J. Am. Chem. Soc. 1996, 118, 5804-5805
29. Zhou, X.; Toney, M. D. J. Am. Chem. Soc. 1998, 120, 13282-13283
30. Alon, R.; Bayer, E. A.; Wilchek, M. J. Biochem. Biophys. Methods 1991, 22, 23-33
31. Ziegler, D. W.; Hutchinson, H. D. Appl. Microbiol. 1972, 23, 1060-1066
32. Segel, I. H. Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady State Enzyme Systems; Wiley: New York, 1975.
33. Sun, W. C.; Gee, K. R.; Haugland, R. P. Bioorg. Med. Chem. Lett. 1998, 8, 3107-3110
34. Bennet, A. J.; Sinnott, M. L. J. Am. Chem. Soc. 1986, 108, 7287-7294
35. Bennet, A. J.; Sinnott, M. L.; Wijesundera, W. S. S. J. Chem. Soc., Perkin Trans. 2 1985, 1233-1236
36. Bennet, A. J.; Davis, A. J.; Hosie, L.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1987, 581-584
37. Kresge, A. J.; Weeks, D. P. J. Am. Chem. Soc. 1984, 106, 7140-7143
38. Tanaka, Y.; Tao, W.; Blanchard, J. S.; Hehre, E. J. J. Biol. Chem. 1994, 269, 32306-32312
39. Buncel, E.; Lee, C. C. Secondary and Solvent Isotope Effects; Elsevier: Amsterdam; New York, 1987.
40. Vocadlo, D. J.; Davies, G. J. Curr. Opin. Chem. Biol. 2008, 12, 539-555
41. Sinnott, M. Carbohydrate Chemistry and Biochemistry: Structure and Mechanism; RSC Publishing: Cambridge, 2007.
42. Berti, P. J.; Blanke, S. R.; Schramm, V. L. J. Am. Chem. Soc. 1997, 119, 12079-12088
43. Berti, P. J.; Tanaka, K. S. E. Adv. Phys. Org. Chem. 2002, 37, 239-314
44. Chen, X.-Y.; Berti, P. J.; Schramm, V. L. J. Am. Chem. Soc. 2000, 122, 6527-6534
45. Ghanem, M.; Murkin, A. S.; Schramm, V. L. Chem. Biol. 2009, 16, 971-979
46. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1373-1383
47. Taylor, J. R. An Introduction to Error Analysis: The Study of Uncertainties in Physical Measurements; University Science Books: Mill Valley, CA, 1982.