Facilitation of enzyme-catalyzed reactions by partial proton transfer: Application to coenzyme-B12-dependent methylmalonyl-CoA mutase [3]

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1383-1384

  Smith, David M ^a   Golding, Bernard T ^b   Radom, Leo ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBAMAMIDE; METHYLMALONYL COENZYME A MUTASE; PROTON;

CATALYSIS; CHEMICAL REACTION; HYDROGEN BOND; LETTER; PROTON TRANSPORT;

EID: 0033576991     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983512a     Document Type: Letter

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25. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
26. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
27. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
28. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970-6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
29. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
30. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
31. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259-267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
32. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
33. See, for example: (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887-1890. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927-1930. (d) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-103. (e) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970- 6975. (f) Guthrie, J. P. Chem. Biol. 1996, 3, 163-170. (g) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670. (h) Gerlt, J. A.; Kreevoy, M. M.; Cleland, W.; Frey, P. A. Chem. Biol. 1997, 5, 259- 267. (i) Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511- 544. (j) Pan, Y.; McAllister, M. J. Am. Chem. Soc. 1998, 120, 166-169.
34. 19 of methylmalonyl-CoA mutase has shown that the active site is deeply buried and largely inaccessible to solvent, suggesting that partial proton transfer should be quite efficient in this protein.
35. 24
36. Smith, D. M.; Golding, B. T.; Radom, L. To be published.