Quantum mechanical analysis of an α-carboxylate-substituted oxocarbenium ion. Isotope effects for formation of the sialyl cation and the origin of an unusually large secondary 14C isotope effect

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 1101-1107

  Horenstein, Benjamin A ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 14; DEUTERIUM;

ARTICLE; CALCULATION; CARBOHYDRATE ANALYSIS; DRUG STRUCTURE; IONIZATION; ISOTOPE LABELING; MOLECULAR DYNAMICS; QUANTUM MECHANICS;

EID: 0031029301     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963079+     Document Type: Article

References (48)

1. Comb, D. G.; Watson, D. R.; Roseman, S. J. Biol. Chem. 1966, 241, 5637-5642.
2. Harduin-Lepers, A.; Recchi, M.-A.; Delannoy, P. Glycobiology 1995, 5, 741-758.
3. Varki, A. Glycobiology 1992, 2, 25-40. Reglero, A.; Rodriguez-Aparicio, L. B.; Luengo, J. M. Int. J. Biochem. 1993, 11, 1517-1527. Hayes, B. K.; Varki, A. J. Biol. Chem. 1993, 268, 16155-16169.
4. Varki, A. Glycobiology 1992, 2, 25-40. Reglero, A.; Rodriguez-Aparicio, L. B.; Luengo, J. M. Int. J. Biochem. 1993, 11, 1517-1527. Hayes, B. K.; Varki, A. J. Biol. Chem. 1993, 268, 16155-16169.
5. Varki, A. Glycobiology 1992, 2, 25-40. Reglero, A.; Rodriguez-Aparicio, L. B.; Luengo, J. M. Int. J. Biochem. 1993, 11, 1517-1527. Hayes, B. K.; Varki, A. J. Biol. Chem. 1993, 268, 16155-16169.
6. (a) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
7. (b) Schramm, V. L. In Enzyme Mechanism from Isotope Effects; Cook, P. F., Ed.; CRC Press: Boca Raton, FL, 1991.
8. Withers, S. G. Pure Appl. Chem. 1995, 67, 1673-1682.
9. Horenstein, B. A.; Bruner, M. J. Am. Chem. Soc. 1996, 118, 10371-10379.
10. Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Kreiger: Malabar, FL, 1980; Chapter 6.
11. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
12. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
13. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
14. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
15. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
16. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
17. Richard, J. P. Tetrahedron 1995, 51, 1535-1573. El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 8023-8027. Woods, R. J.; Andrews, C. W.; Bowen, J. P. J. Am. Chem. Soc. 1992, 114, 850-858. Allen, A. D.; Tidwell, T. T. Adv. Carbocation Chem. 1989, 1, 1-44. Creary, X.; Hopkinson, A. C.; Lee-Ruff, E. Ibid. 1989, 1, 45-92. Richard, J. P. Ibid. 1989, 1, 121-170. Schleyer, P. v. R. Pure Appl. Chem. 1987, 59, 1647-1660.
18. Chong, A. K. J.; Pegg, M. S.; Taylor, N. R.; von Itzstein, M. Eur. J. Biochem. 1992, 207, 335-343.
19. Baasov, T.; Kohen, A. J. Am. Chem. Soc. 1995, 117, 6165-6174.
20. Kim, D. H.; Lees, W. J.; Haley, T. M.; Walsh, C. T. J. Am. Chem. Soc. 1995, 117, 1494-1502.
21. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
22. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
23. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
24. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
25. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
26. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
27. Koshland, D. E. Biol. Rev. 1953, 28, 416-420. Phillips, D. C. Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 484-495. Dahlquist, F. W.; Rand-Meir, T.; Raftery M. A. Biochemistry 1969, 8, 4214-4221. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424. Kuroki, R.; Weaver, L. H.; Matthews, B. W. Science 1993, 262, 2030-2033. Matsumura, I.; Kirsch, J. F. Biochemistry 1996, 35, 1881-1889. Hashimoto, Y.; Yamada, K.; Motoshima, H.; Omura, T.; Yamada, H.; Yasukochi, T.; Miki, T.; Ueda, T.; Imoto, T. J. Biochem. 1996, 119, 145-150.
28. Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Kreiger: Malabar, FL, 1980; Chapter 8.
29. Gaussian 94, Revision C.3: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
32. QCPE #455. QCPE, Creative Arts Bldg. 181, Indiana University, Bloomington, IN 47405.
33. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899-4907.
34. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776-4782.
35. Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989-8994.
36. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098-16104. Keith, T. A.; Foresman, J. B.; Frisch, M. J.; Wiberg, K. B. Manuscript in preparation.
37. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098-16104. Keith, T. A.; Foresman, J. B.; Frisch, M. J.; Wiberg, K. B. Manuscript in preparation.
38. Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 8293-8298.
39. Stern, M. J.; Wolfsberg, M. J. Chem. Phys. 1966, 45, 2618-2629.
40. See Supporting Information.
41. 2 and methylene, and the twist conformer collapsed without barrier to the α-lactone. Antolovic, D.; Shiner, V. J.; Davidson, E. R. J. Am. Chem. Soc. 1988, 110, 1375-1381.
42. Richard, J. P.; Amyes, T. L.; Jagannadham, V.; Lee, Y.-L.; Rice, D. J. J. Am. Chem. Soc. 1995, 117, 5198-5205.
43. Creary, X.; Wang, Y.-X.; Jiang, Z. J. Am. Chem. Soc. 1995, 117, 3044-3053.
44. 26 for a formylcarbenium ion.
45. A similar observation has recently been reported for solvation effects on vibrational frequencies: Williams, R. W.; Cheh, J. L.; Lowrey, A. H.; Weir, A. F. J. Phys. Chem. 1995, 99, 5299-5307.
46. Ashwell, M.; Guo, X.; Sinnott, M. L. J. Am. Chem. Soc. 1992, 114, 10158-10166.
47. Bayles, J. W.; Bron, J.; Paul, S. O. J. Chem. Soc., Faraday Trans. 1 1976, 7, 1546-1542.
48. 14C isotope effect shown in Table 2.