Eliminations in the reactions catalyzed by UDP-N-acetylglucosamine 2-epimerase

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10269-10277

  Morgan, Paul M ^a   Sala, Rafael F ^a   Tanner, Martin E ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EPIMERASE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE N ACETYLGLUCOSAMINE 2 EPIMERASE;

ARTICLE; ENZYME ACTIVITY; IN VITRO STUDY; ISOTOPE LABELING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030700684     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971718q     Document Type: Article

References (69)

1. Adams, E. Adv. Enzymol. Relat. Areas Mol. Biol. 1976, 44, 69-138.
2. Gerlt, J. A.; Kenyon, G. L.; Kozarich, J. W.; Neidhart, D. J.; Petsko, G. A.; Powers, V. M. Curr. Opin. Struct. Biol. 1992, 2, 736-742.
3. Thoden, J. B.; Frey, P. A.; Holden, H. M. Biochemistry 1996, 35, 2557-2566.
4. Liu, Y. J.; Vanhooke, J. L.; Frey, P. A. Biochemistry 1996, 35, 7615-7620.
5. Thoden, J. B.; Frey, P. A.; Holden, H. M. Biochemistry 1996, 35, 5137-5144.
6. Vanhooke, J. L.; Frey, P. A. J. Biol. Chem. 1994, 269, 31496-31504.
7. Burke, J. R.; Frey, P. A. Biochemistry 1993, 32, 13220-13230.
8. Frey, P. A. In Pyridine Nucleotide Coenzymes; Dolphin, D., Poulson, R., Avramovic, O., Eds.; Wiley: New York, 1987; Vol. 2B, pp 461-477.
9. The epimerase acts at the C-2″ position of UDP-GlcNAc (the C-2 position of the GlcNAc moiety). Throughout the remainder of this text the notation C-X″ or H-X″ will be employed in reference to atoms in the GlcNAc or ManNAc portions of the sugar nucleotides.
10. Kawamura, T.; Ishimoto, N.; Ito, E. Methods Enzymol. 1982, 83, 515-519.
11. Kawamura, T.; Ishimoto, N.; Ito, E. J. Biol. Chem. 1979, 254, 8457-8465.
12. Kawamura, T.; Kimura, M.; Yamamori, S.; Ito, E. J. Biol. Chem. 1978, 253, 3595-3601.
13. A preliminary communication describing portions of this work has appeared: Sala, R. F.; Morgan, P. M.; Tanner, M. E. J. Am. Chem. Soc. 1996, 118, 3033-3034.
14. Yokoyama, K.; Mizuguchi, H.; Araki, Y.; Kaya, S.; Ito, E. J. Bacteriol. 1989, 171, 940-946.
15. Yokoyama, K.; Miyashita, T.; Araki, Y.; Ito, E. Eur. J. Biochem. 1986, 161, 479-489.
16. Harrinaton, C. R.; Baddiley, J. Eur. J. Biochem. 1985, 153, 639-645.
17. Yoneyama, T.; Koike, Y.; Arakawa, H.; Yokoyama, K.; Sasaki, Y.; Kawamura, T.; Araki, Y.; Ito, E.; Takao, S. J. Bacteriol. 1982, 149, 15-21.
18. Heptinstall, S.; Archibald, A. R.; Baddiley, J. Nature 1970, 225, 519-521.
19. Baddiley, J. Acc. Chem. Res. 1970, 3, 98-105.
20. Kuhn, H.-M.; Meier-Dieter, U.; Mayer, H. FEMS Microbiol. Rev. 1988, 54, 195-222.
21. Meier-Dieter, U.; Barr, K.; Starman, R.; Hatch, L.; Rick, P. D. J. Biol. Chem. 1992, 267, 746-753.
22. Meier-Dieter, U.; Starman, R.; Barr, K.; Mayer, H.; Rick, P. D. J. Biol. Chem. 1990, 265, 13490-13497.
23. Lew, H. C.; Nikaido, H.; Mäkelä, H. J. Bacteriol. 1978, 136, 227-233.
24. Lee, C.-J.; Banks, S. D.; Li, J. P. Crit. Rev. Microbiol. 1991, 18, 89-114.
25. Jann, B.; Jann, K. Curr. Top. Microbiol. Immunol. 1990, 150, 19-42.
26. Moxon, E. R.; Kroll, J. S. Curr. Top. Microbiol. Immunol. 1990, 150, 65-86.
27. Lee, C.-J.; Fraser, B. A. J. Biol. Chem. 1980, 255, 6847-6851.
28. Morona, J. K.; Morona, R.; Paton, J. C. Mol. Microbiol. 1997, 23, 751-763.
29. Sommar, K. M.; Ellis, D. B. Biochim. Biophys. Acta 1972, 268, 590-595.
30. Sommar, K. M.; Ellis, D. B. Biochim. Biophys. Acta 1972, 268, 581-589.
31. Salo, W. L.; Fletcher, H. G. Biochemistry 1970, 9, 882-885.
32. Spivak, C. T.; Roseman, S. Methods Enymol. 1966, 9, 612-615.
33. Glaser, L. Biochim. Biophys. Acta 1960, 41, 534-536.
34. Salo, W. Biochim. Biophys. Acta 1976, 452, 625-628.
35. Salo, W. L.; Fletcher, H. G., Jr. Biochemistry 1970, 9, 878-881.
36. Yamazaki, T.; Warren, C. D.; Herscovics, A.; Jeanloz, R. W. Can. J. Chem. 1981, 59, 2247-2252.
37. Srivastava, G.; Alton, G.; Hindsgaul, O. Carbohydr. Res. 1990, 207, 259-276.
38. See Supporting Information.
39. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254.
40. Kiino, D. R.; Licudine, R.; Wilt, K.; Yana, D. H. C.; Rothman-Denes, L. B. J. Bacteriol. 1993, 175, 7074-7080.
41. Lai, E. C. K.; Withers, S. G. Biochemistry 1994, 33, 14743-14749.
42. Meynial, I.; Paquet, V.; Combes, D. Anal. Chem. 1995, 67, 1627-1631.
43. Sebesan, S.; Neira, S. Carbohydr. Res. 1992, 223, 169-185.
44. Sim, M. M.; Kondo, H.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 2260-2267.
45. Daniels, D. L.; Plunkett, G., III; Burland, V.; Blattner, F. R. Science 1992, 257, 771-777.
46. Marolda, C. L.; Valvano, M. A. J. Bacteriol. 1995, 177, 5539-5546.
47. Kiino, D. R.; Rothman-Denes, L. B. J. Bacteriol. 1989, 171, 4595-4602.
48. 40 indicates that it contains 420 codons. Full details will be reported elsewhere (Morgan, P. M., Tanner, M. E., manuscript in preparation).
49. Klinman, J. P. In Transition States of Biochemical Processes; Gandour, R. D., Schowen, R. L., Eds.; Plenum Press: New York, 1978; pp 165-200.
50. Raushel, F. M.; Villafranca, J. J. CRC Crit. Rev. Biochem. 1988, 23, 1-26.
51. Hester, L. S.; Raushel, F. M. Biochemistry 1987, 26, 6465-6471.
52. Cohn, M.; Hu, A. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 200-203.
53. Pravdic, N.; Fletcher, H. G., Jr. J. Org. Chem. 1967, 32, 1806-1810.
54. Bender, S. L.; Widlanski, T.; Knowles, J. R. Biochemistry 1989, 28, 7560-7572.
55. Palmer, J. L.; Abeles, R. H. J. Biol. Chem. 1979, 254, 1217-1226.
56. I = 1 mM.
57. Wierenga, R. K.; Terpstra, P.; Hol, W. G. J. J. Mol Biol. 1986, 187, 101-107.
58. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 349-357 and references therein.
59. Smar, M.; Short, S. A.; Wolfenden, R. Biochemistry 1991, 30, 7908-7912.
60. Kaila, N.; Blumenstein, M.; Bielawska, H.; Franck, R. W. J. Org. Chem. 1992, 57, 4576-4578.
61. Anderson, V. E. In Enzyme Mechanism from Isotope Effects; Cook, P. F., Ed.; CRC Press: Cleveland, OH, 1991; pp 389-417.
62. Creighton, D. J.; Murthy, N. S. R. K. In The Enzymes; Sigman, D. S., Boyer, P. D., Eds.; Academic Press: San Diego, CA, 1990; Vol. 19, pp 397-403.
63. Bahnson, B. J.; Anderson, V. E. Biochemistry 1991, 30, 5894-5906.
64. Yang, S.-Y.; Elzinga, M. J. Biol. Chem. 1993, 268, 6588-6592.
65. Smeland, T. E.; Cuebas, D.; Schulz, H. J. Biol. Chem. 1991, 266, 23904-23908.
66. Hiltunen, J. K.; Palosaari, P. M.; Kunau, W.-H. J. Biol. Chem. 1989, 264, 13536-13540.
67. Parker, A. R.; Moore, J. A.; Schwab, J. M.; Davisson, V. J. J. Am. Chem. Soc. 1995, 117, 10605-10613.
68. Collins, P.; Ferrier, R. Monosaccharides; Wiley: Chichester, 1995; pp 236-237.
69. Knapp, S.; Vocadlo, D.; Gao, Z.; Kirk, B.; Lou, J.; Withers, S. G. J. Am. Chem. Soc. 1996, 118, 6804-6805.