Factors controlling relative stability of anomers and hydroxymethyl conformers of glucopyranose

Journal of Computational Chemistry

Volumn 19, Issue 10, 1998, Pages 1111-1129

  Barrows, Susan E ^a   Storer, Joey W ^a   Cramer, Christopher J ^a   French, Alfred D ^b   Truhlar, Donald G ^b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Anomer; Conformational analysis; Glucose; Molecular modeling; Molecular orbital theory; Quantum mechanics; Solvation; Stereoelectronic effects; Sugars

Indexed keywords

EID: 0000287183     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(19980730)19:10<1111::AID-JCC1>3.0.CO;2-P     Document Type: Article

References (91)

1. S. J. Angyal, Aust. J. Chem. 21, 2737 (1968).
2. S. N. Ha, A. Giammona, M. Field, and J. W. Brady, Carbohydr. Res., 180, 207 (1988).
3. J. W. Brady, J. Am. Chem. Soc., 111, 5155 (1989).
4. L. M. J. Kroon-Batenburg and J. Kroon, Biopolymers, 29, 1243 (1990).
5. B. P. van Eijck L. M. J. Kroon-Batenburg, and J. Kroon, J. Mol. Struct., 237, 315 (1990).
6. S. J. Angyal, Adv. Carbohydr. Chem. Biochem., 49, 19 (1991).
7. S. Ha, J. Gao, B. Tidor, J. W. Brady, and M. Karplus, J. Am. Chem. Soc., 113, 1553 (1991).
8. R. G. Zhbankov, J. Mol. Struct., 275, 645 (1992).
9. P. L. Polavarapu and C. S. Ewig, J. Comput. Chem., 13, 1255 (1992).
10. C. J. Cramer and D. G. Truhlar, J. Am. Chem. Soc., 115, 5745 (1993).
11. B. P. van Eijck, R. W. W. Hooft and J. Kroon, J. Phys. Chem., 97, 12093 (1993).
12. S. J. Angyal, Carbohydr. Res., 263, 1 (1994).
13. T. M. Glennon, Y. J. Zheng, S. M. Le Grand, B. A. Shutzberg, and K. M. Merz, J. Comput. Chem., 15, 1019 (1994).
14. M. K. Dowd, A. D. French, and P. J. Reilly, Carbohydr. Res., 264, 1 (1994).
15. F. Zuccarello and G. Buemi, Carbohydr. Res., 273, 129 (1995).
16. S. E. Barrows, F. J. Dulles, C. J. Cramer, D. G. Truhlar, and A. D. French, Carbohydr. Res., 276, 219 (1995).
17. G. I. Csonka, K. Éliás, and I. G. Csizmadia, Chem. Phys. Lett., 257, 49 (1996).
18. J. W. Brown and B. D. Wladkowski, J. Am. Chem. Soc., 118, 1190 (1996).
19. H. Senderowitz, C. Parish, and W. C. Still, J. Am. Chem. Soc., 118, 2078 (1996).
20. K. H. Ott and B. Meyer, J. Comput. Chem., 17, 1068 (1996).
21. C. J. Cramer, D. G. Truhlar, and A. D. French, Carbohydr. Res., 298, 1 (1997).
22. H. Senderowitz and W. C. Still, J. Org. Chem., 62, 1427 (1997).
23. W. Damm, A. Frontera, J. Tirado-Rives, and W. L. Jorgensen, manuscript in preparation.
24. N. L. Allinger and L. Yan, J. Am. Chem. Soc., 115, 11918 (1993).
25. N. L. Allinger, X. F. Zhou, and J. Bergsma, J. Mol. Struct. (Theochem), 118, 69 (1994).
26. I. J. -H. Lii and N. L. Allinger, J. Phys. Org. Chem., 7, 591 (1994).
27. J. W. Storer, D. J. Giesen, G. D. Hawkins, G. C. Lynch, C. J. Cramer, D. G. Truhlar, and D. A. Liotard, In Structure and Reactivity in Aqueous Solution, C. J. Cramer and D. G. Truhlar, Eds., American Chemical Society, Washington, DC, 1994, p. 24.
28. D. J. Giesen, J. W. Storer, C. J. Cramer, and D. G. Truhlar, J. Am. Chem. Soc., 117, 1057 (1995).
29. D. J. Giesen, C. J. Cramer, and D. G. Truhlar, J. Phys. Chem., 99, 7137 (1995).
30. C. C. Chambers, G. D. Hawkins, C. J. Cramer, and D. G. Truhlar, J. Phys. Chem., 100, 16385 (1996).
31. C. J. Cramer and D. G. Truhlar, Science, 256, 213 (1992).
32. C. J. Cramer and D. G. Truhlar, J. Comput. Chem., 13, 1089 (1992).
33. C. J. Cramer and D. G. Truhlar, J. Comput.-Aid. Mol. Des., 6, 629 (1992).
34. J. W. Storer, D. J. Giesen, C. J. Cramer, and D. G. Truhlar, J. Comput.-Aid. Mol. Des., 9, 87 (1995).
35. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
36. J. J. P. Stewart, J. Comput. Chem., 10, 221 (1989).
37. W. J. Hehre, L. Radom, P. v. R. Schleyer, and J. A. Pople, Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York, 1986.
38. K. -H. Ott and B. Meyer, J. Comput. Chem., 17, 1068 (1996).
39. S. J. Angyal, Angew. Chem. Int. Ed. Engl., 8, 157 (1969).
40. A. J. de Hoog, Org. Magnet. Res., 6, 233 (1974).
41. C. L. Jungius, Z. Phys. Chem., 52, 97 (1905).
42. J. T. Edward, Chem. Ind. (London), 1102 (1955).
43. R. U. Lemieux, In Molecular Rearrangements, P. de Mayo, Ed., Interscience, New York, 1964, p. 709.
44. A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, Berlin, 1983.
45. E. Juaristi and G. Cuevas, Tetrahedron, 48, 5019 (1992).
46. G. R. J. Thatcher, Ed., The Anomeric Effect and Associated Stereoelectronic Effects, American Chemical Society, Washington, DC, 1993.
47. P. P. Gracryk and M. Mikolajczyk, In Topics in Stereochemistry, Vol. 21, E. L. Eliel and S. H. Wilen, Eds., John Wiley & Sons, New York, 1994, p. 159.
48. E. S. Marcos, R. R. Pappalardo, J. L. Chiara, M. C. Domene, J. M. Martínez, and R. M. Parrondo, J. Mol. Struct. (Theochem), 371, 245 (1996).
49. D. J. Giesen, C. C. Chambers, G. D. Hawkins, C. J. Cramer, and D. G. Truhlar, In Computational Thermochemistry: Prediction and Estimation of Molecular Thermodynamics, K. Irikura and D. J. Frurip, Eds., American Chemical Society, Washington, DC (in press).
50. Y. Nishida, H. Ohrui, and H. Meguro, Tetrahed. Lett., 25, 1575 (1984).
51. B. R. Leefland, J. F. G. Vliegenthart, L. M. J. Kroon-Batenburg, B. P. van Eijck, and J. Kroon, Carbohydr. Res., 230, 41 (1992).
52. L. Poppe and H. Van Halbeek, J. Am. Chem. Soc., 114, 1092 (1992).
53. B. Adams and L. Lerner, J. Am. Chem. Soc., 114, 4827 (1992).
54. S. A. Stortz and A. S. Cerezo, J. Carbohydr. Chem., 13, 235 (1994).
55. N. L. Allinger and I. J. -H. Lii (personal communication). These parameters have been optimized based on comparison to various model systems calculated at the B3LYP/6-31G* level. We thank Prof. Allinger for communicating these new values to us - previous versions of the MM3 force field have taken all three parameters to be zero.
56. A. D. French, L. Schäfer, and S. Q. Newton, Carbohydr. Res., 239, 51 (1993).
57. A. D. French and M. K. Dowd, J. Comput. Chem., 15, 561 (1994).
58. C. Van Alsenoy, A. D. French, M. Cao, S. Q. Newton, and L. Schäfer, J. Am. Chem. Soc., 116, 9590 (1994).
59. The MM3 program is available to commercial users from Tripos Associates, 1699 South Hartley Rd., St. Louis, MO 63144, and to academic users from QCPE, Indiana University, Bloomington, IN 47405.
60. T. H. Dunning, J. Chem. Phys., 90, 1007 (1989).
61. J. Cizek, Adv. Chem. Phys., 14, 35 (1969).
62. G. D. Purvis and R. J. Bartlett, J. Chem. Phys., 76, 1910 (1982).
63. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, GAUSSIAN-94, Rev. D.1, Gaussian, Inc., Pittsburgh, PA, 1995.
64. G. D. Hawkins, D. J. Giesen, G. C. Lynch, C. C. Chambers, I. Rossi, J. W. Storer, D. Rinaldi, D. A. Liotard, C. J. Cramer, and D. G. Truhlar, AMSOL, Version 6.1.1, Oxford Molecular Group, London, 1997.
65. C. J. Cramer and D. G. Truhlar, J. Am. Chem. Soc., 113, 8305 (1991).
66. C. J. Cramer and D. G. Truhlar, In Reviews in Computational Chemistry, Vol. 6, K. B. Lipkowitz and D. B. Boyd, Eds., VCH, New York, 1995, p. 1.
67. C. J. Cramer and D. G. Truhlar, In Quantitative Treatments of Solute/Solvent Interactions, Vol. 1, P. Politzer and J. S. Murray, Eds., Elsevier, Amsterdam, 1994, p. 9.
68. C. J. Cramer and D. G. Truhlar, In Solvent Effects and Chemical Reactivity, O. Tapia and J. Bertrán, Eds., Kluwer, Dordrecht, 1996, p. 1.
69. B. Lee and F. M. Richards, J. Mol. Biol. 55, 379 (1971).
70. R. B. Hermann, J. Phys. Chem., 76, 2754 (1972).
71. K. B. Wiberg and M. A. Murcko, J. Am. Chem. Soc., 111, 4821 (1489).
72. M. C. Krol, C. J. M. Huige, and C. Altona, J. Comput. Chem., 11, 765 (1990).
73. C. J. Cramer, J. Org. Chem., 57, 7034 (1992).
74. U. Salzner and P. v. R. Schleyer, J. Org. Chem. 59, 2138 (1994).
75. M. L. C. E. Konwijzer, B. P. van Eijck, and J. Kroon, Acta Cryst., B51, 209 (1995).
76. E. Hough, S. Neidle, D. Rogers, and P. G. H. Troughton, Acta Cryst., B29, 365 (1973).
77. G. M. Brown and H. A. Levy, Acta Crystallogr., B35, 656 (1979).
78. S. Raymond, A. Heyraud, D. T. Qui, A. Kvick, and H. Chanzy, Macromolecules, 28, 2096 (1995).
79. M. N. Ramos and B. d. B. Neto, Chem. Phys., Lett., 199, 482 (1992).
80. C. Alemán, F. J. Luque, and M. Orozco, J. Comput. Chem., 14, 799 (1993).
81. G. Rauhut and T. Clark, J. Comput. Chem., 14, 503 (1993).
82. G. P. Ford and B. Wang, J. Comput. Chem., 14, 1101 (1993).
83. B. Wang and G. P. Ford, J. Comput. Chem., 15, 200 (1994).
84. I. Tvaroska and J. P. Carver, J. Phys. Chem. 98, 9477 (1994).
85. S. J. Weiner, P. A. Kollman, D. T. Nguyen, and D. A. Case, J. Comput. Chem. 7, 230 (1986).
86. T. A. Halgren, J. Comput. Chem., 17, 490 (1996).
87. W. D. Cornell, P. Cieplak, C. L. Bayly, I. R. Gould, K. M. Merz, D. M. Ferguson, D. C. Spellmeyer, T. Fox, J. W. Caldwell, and P. A. Kollman, J. Am. Chem. Soc., 117, 5179 (1995).
88. C. Simmerling and P. A. Kollman, manuscript in preparation.
89. CHEM-X, Chemical Design, Ltd., London, United Kingdom, 1994.
90. B. Ma, H. F. Schaefer III, and N. L. Allinger, manuscript in preparation.
91. G. D. Rockwell and T. B. Grindley, Aust. J. Chem., 49, 379 (1996).