A comparison of the geometry and of the energy results obtained by application of different molecular mechanics force fields to methyl α-lactoside and the C-analogue of lactose

Carbohydrate Research

Volumn 298, Issue 1-2, 1997, Pages 15-49

  Martín Pastor, Manuel ^a   Espinosa, Juan Félix ^a   Asensio, Juan Luis ^a   Jiménez Barbero, Jesús ^a  

^a CSIC   (Spain)

Author keywords

Coupling constants; Methyl lactoside; Molecular mechanics; NMR; NOESY; ROESY

Indexed keywords

CARBOHYDRATE; LACTOSE;

ARTICLE; CALCULATION; CARBOHYDRATE ANALYSIS; CONFORMATION; ENERGY; GEOMETRY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; X RAY;

EID: 0038771789     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(96)00225-X     Document Type: Article

References (54)

1. (a) K.G. Rice, P. Wu, L. Brand, and Y.C. Lee, Curr. Opin. Struct. Biol, 3 (1993) 669-674
2. (b) R.J. Woods, Curr. Opin. Struct. Biol., 5 (1995) 591-598.
3. (a) K. Gessler, N. Krauss, T. Steiner, C. Betzel, C. Sandmann, and W. Saenger, Science, 266 (1994) 1027-1029
4. (b) T. Steiner and W. Saenger, Carbohydr. Res., 259 (1994) 1-12.
5. (a) C.A. Bush, Curr. Opin. Struct. Biol., 2 (1992) 655-660
6. (b) M. Hricovini, R.N. Shah, and J.P. Carver, Biochemistry, 31 (1992) 10018-10023
7. P.J. Hajduk, D.A. Horita, and L. Lerner, J. Am. Chem. Soc., 115 (1993) 9196-9201
8. S.W. Homans, Glycobiology, 3 (1993) 551-555.
9. (a) Lommerse et al., J. Biomol. NMR, 5 (1995) 79-94. H. van Halbeek, Curr. Opin. Struct. Biol., 4 (1994) 697-709
10. (a) Lommerse et al., J. Biomol. NMR, 5 (1995) 79-94. H. van Halbeek, Curr. Opin. Struct. Biol., 4 (1994) 697-709
11. (b) S. Perez, Curr. Opin. Struct. Biol., 3 (1993) 675-680
12. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still, J. Comput. Chem., 11 (1990) 440-467.
13. A.D. French and J.W. Brady (Eds.), Computer Modeling Carbohyds. Molecules ACS, 430 (1990).
14. T.M. Glennon, Y.J. Zheng, S.M. Le Grand Bashutzberg, and K.M. Merz Jr., J. Comput. Chem., 15 (1994) 1019-1040.
15. M.K. Dowd, A.D. French, and P.J. Reilly, J. Carbohydr. Chem., 14 (1995) 589-600.
16. R.U. Lemieux and S. Koto, Tetrahedron, 30 (1974) 1933-1944.
17. (a) A.J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983
18. (b) I. Tvaroska and T. Bleha, Adv. Carbohydr. Chem. Biochem., 47 (1989) 45-123.
19. J.L. Asensio and J. Jiménez-Barbero, Biopolymers, 35 (1995) 55-73.
20. (a) J.L. Asensio, M. Martín-Pastor, and J. Jiménez-Barbero, Int. J. Biol. Macromol., 17 (1995) 137-148
21. (b) J.L. Asensio, M. Martín-Pastor, and J. Jiménez-Barbero, J. Mol. Struct. THEOCHEM, in press.
22. K. Hirotsu and A. Shamada, Bull. Chem. Soc. Jpn., 47 (1974) 1872-1879.
23. (a) D.A. Cumming and J.P. Carver, Biochemistry, 26 (1987) 6664-6676
24. (b) J.P. Carver, S.W. Michnick, A. Imberty, and D.A. Cumming, Carbohydrate Recognition in Cellular Function, Wiley, New York, 1989, CIBA Foundation Symp. 145, pp 6-26;
25. J.P. Carver, Pure Appl. Chem., 65 (1993) 763-770.
26. D. Neuhaus and M.P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH Publishers, New York, 1989.
27. M. Eberstadt, G. Gemmecker, D.F. Mierke, and H. Kessler, Angewandte Chem. Int. Ed. Engl., 34 (1995) 1671-1695.
28. S. Perez, A. Imberty, and J.P. Carver, Adv. Comp. Biol., 1 (1994) 147-202.
29. J.F. Espinosa, M. Martín-Pastor, J.L. Asensio, H. Dietrich, M. Martín-Lomas, R.R. Schmidt, and J. Jiménez-Barbero, Tetrahedron. Lett., 35 (1995) 6329-6332.
30. S.W. Homans, Biochemistry, 29 (1990) 9110-9118.
31. A.T. Hagler, P. Lifson, and P. Dauber, J. Am. Chem. Soc., 101 (1979) 5122-5130.
32. J. Maple, U. Dinur, and A.T. Hagler, Prot. Nat. Acad. Sci. USA, 85 (1988) 5350-5354.
33. N.L. Allinger, Y.H. Yuh, and J.H. Lu, J. Am. Chem. Soc, 111 (1989) 8551-8559.
34. Extensible Systematic Force Field, Biosym Technol. Inc., San Diego, USA, 1994.
35. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still, J. Comput. Chem., 11 (1990) 440-467.
36. K. Bock and J.O. Duus, J. Carbohydr. Chem., 13 (1994) 513-543.
37. W.C. Still, A. Tempczyk, R.C. Hawley, and T. Hendrickson, J. Am. Chem. Soc., 112 (1990) 6127-6129.
38. M.J.S. Dewar, E.G. Zoebisch, E.F. Haly, and J.J.P. Steward, J. Am. Chem. Soc., 107 (1985) 3902-3909.
39. M.J.S. Dewar and W. Tiuel, J. Am. Chem. Soc., 99 (1977) 4899-4906.
40. M. Khahl, R.J. Woods, D.F. Weaver, and V.H. Smith Jr., J. Comput. Chem., 12 (1991) 584-593.
41. C.J. Cramer and D.G. Truhlar, Science, 256 (1992) 213-219.
42. J.H. Noggle and R.E. Schirmer, The Nuclear Overhauser Effect: Chemical Applications, Academic, New York, 1971, pp 90-93,
43. P. Cagas and C.A. Bush, Biopolymers, 30 (1990) 1123-1138.
44. M. Bernabé, A. Fernández-Mayoralas, J. Jiménez-Barbero, M. Martín-Lomas, and A. Rivera, J. Chem. Soc., Perkin Trans. 2., (1989) 1867-1873.
45. (a) Y. Bourne, P. Rouge, and C. Cambilleau, J. Biol. Chem., 267 (1992) 197-203
46. (b) A. Imberty, Y. Bourne, C. Cambilleau, P. Rouge, and S. Perez, Adv. Biophys. Chem., 3 (1993) 71-118.
47. M.K. Dowd, A.D. French, and P.J. Reilly, Carbohydr. Res., 233 (1992) 15-36.
48. S.B. Engelsen, S. Perez, I. Bracani, and C. Herve du Penhoat, J. Comput. Chem., 16 (1995) 1096-1119.
49. J.L. Asensio, F.J. Cañada, and J. Jiménez-Barbero, Eur. J. Biochem., 233 (1995) 618-630.
50. K. Bock and S. Refn, Acta Chem. Scand., Sect. B, 41 (1987) 469-472.
51. K.N. Houk, J.E. Ekstrowicz, Y.D. Wu, C.D. Fuglevang, and D.B. Mitchell, J. Am. Chem. Soc, 115 (1993) 4170-4177.
52. A. Wei, A. Handrechy, C. Audin, J. Hyuk-Sang, N. Handrechy-Bretel, and Y. Kishi, J. Org. Chem., 57 (1992) 482-489.
53. J.F. Espinosa, F.J. Cañada, J.L. Asensio, H. Dietrich, R.R. Schmidt, and J. Jiménez-Barbero, Angewandte Chem. Int. Ed. Engl., 35 (1996) 303-306.
54. V.L. Bevilacqua, D.S. Thomson, and J.H. Prestegard, Biochemistry, 29 (1990) 5529-5537.