Conformational behavior of C-glycosyl analogues of sialyl-α-(2 → 3)- galactose

European Journal of Organic Chemistry

Volumn , Issue 9, 2000, Pages 1805-1813

  Poveda, Ana ^a   Asensio, Juan Luis ^b   Polat, Tülay ^c   Bazin, Hélèn ^c   Linhardt, Robert J ^c   Jiménez Barbero, Jesús ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c E11 SSH   (United States)

Author keywords

C Glycosides; Conformational analysis; Molecular dynamics; Selectins

Indexed keywords

GALACTOSE; GLYCOSIDASE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL BINDING; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034026344     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200005)2000:9<1805::AID-EJOC1805>3.0.CO;2-A     Document Type: Article

References (62)

1. H. J. Gabius, S. Gabius (Eds.), Glycosciences: Status and Perspectives, Chapman Hall, London, 1997.
2. [2a] J. M. Rini, Ann. Rev. Biophys. Biomol. Struct. 1993, 24, 551-577. -
3. [2b] H.-J. Gabius, Eur. J. Biochem. 1997, 243, 543-576. -
4. [2c] J. Hirabayashi, Trends Glycosci. Glycotechnol. 1997, 9, 1-190. -
5. [2d] H. Kaltner, B. Stiersdorfer, Acta Anat. 1998, 161, 162-179. -
6. [2e] J. Kopitz, C. von Reitzenstein, M. Burchert, M. Cantz, H. J. Gabius, J. Biol. Chem. 1998, 273, 11205-11211. -
7. [2f] N. L. Perillo, M. E. Marcus, L. G. Baum, J. Mol. Med. 1998, 76, 402-412. -
8. [2g] M. L. Philips, E. Nudelman, F. C. A. Gaeta, M. Perez, K. Singhal, S. Hakomori, J. C. Paulson, Science 1990, 250, 1132.
9. [3a] M. D. H. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. -
10. [3b] W. Levy, D. Chang (Eds.), Chemistry of C-Glycosides, Elsevier, Cambridge, 1995. -
11. [3c] B. A. Johns, Y. T. Pan, A. D. Elbein, C. R. Johnson, J. Am. Chem. Soc. 1997, 119, 4856-4865.
12. Y. Du, R. J. Linhardt, I. R. Vlahov, Tetrahedron 1998, 54, 9913-9959.
13. [5a] R. V. Weatherman, L. L. Kiessling, J. Org. Chem. 1996, 61, 534 -
14. [5b] R. V. Weatherman, K. H. Mortell, M. Chervenak, L. L. Kiessling, Biochemistry 1996, 35, 3619.
15. K. N. Houk, J. E. Eksterowicz, Y. Wu, C. D. Fuglesang, D. R. Mitchell, J. Am. Chem. Soc. 1993, 115, 4170-4177.
16. [7a] J. F. Espinosa, F. J. Cañada, J. L. Asensio, M. Martín-Pastor, H. Dietrich, M. Martín-Lomas, R. R. Schmidt, J. Jiménez-Barbero, J. Am. Chem. Soc. 1996, 118, 10862-10871. -
17. [7b] G. Rubinstenn, P. Sinay, P. Berthault, J. Phys. Chem. A 1997, 101, 2536. -
18. [7c] J. L. Asensio, A. Garcia, F. J. Cañada, M. T. Murillo, A. Fernández-Mayoralas, B. A. Johns, J. Kozak, Z. Zhu, C. R. Johnson, J. Jiménez-Barbero, J. Am. Chem. Soc., in press.
19. [8a] R. U. Lemieux, S. Koto, D. Voisin, Am. Chem. Soc. Symp. Ser. 1979, 87, 17-29. -
20. [8b] G. R. J. Thatcher, The Anomeric Effect and Associated Stereoelectronic Effects, American Chemical Society, Washington DC, 1993. -
21. [8c] A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer-Verlag, Heidelberg, Germany, 1983. -
22. [8d] H. Thogersen, R. U. Lemieux, K. Bock, B. Meyer, Can. J. Chem. 1982, 60, 44-65. -
23. [8e] I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-103. -
24. [8f] K. B. Wiberg, M. A. Murcko, J. Am. Chem. Soc. 1989, 111, 4821-4827. -
25. [8g] I. Tvaroska, J. P. Carver, J. Phys. Chem. 1995, 99, 6234-6241.
26. M. Martín-Pastor, J. F. Espinosa, J. L. Asensio, J. Jimenez-Barbero, Carbohydr. Res. 1997, 298, 15-47.
27. [10a] A. Wei, K. M. Boy, Y. Kishi, J. Am. Chem. Soc. 1995, 117, 9432-9437. -
28. [10b] Y. Wang, P. G. Goekjian, D. V. Ryckman, W. H. Miller, S. A. Babirad, Y. Kishi, J. Org. Chem. 1992, 57, 482-489. -
29. [10c] T. Wu, P. G. Goekjian, Y. Kishi, J. Org. Chem. 1987, 52, 4819-4823. -
30. A. Wei, Y. Kishi, J. Org. Chem. 1994, 118, 88-96, and references therein.
31. R. Ravishankar, A. Surolia, M. Vijayan, S. Lim, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 11297-11303.
32. J. F. Espinosa, M. Bruix, O. Jarreton, T. Skrydstrup, J.-M. Beau, J. Jiménez-Barbero, Chem. Eur. J. 1999, 442-448.
33. [13a] J. Breg, L. M. Kroon-Batenburg, G. Strecker, J. Montreuil, J. F. G. Vliegenthart, Eur. J. Biochem. 1989, 178, 727-739. -
34. [13b] Y. Ichikawa, Y. C. Lin, D. P. Dumas, G. J. Shen, E. Garcia-Junceda, M. A. Williams, R. Bayer, C. Ketcham, L. E. Walker, J. C. Paulson, C. H. Wong, J. Am. Chem. Soc. 1992, 114, 9283-9285. -
35. [13c] T. J. Rutherford, D. G. Spackman, P. J. Simpson, S. W. Homans, Glycobiology 1994, 5, 59-65. -
36. [13d] C. Mukhopadhyay, C. A. Bush, Biopolymers 1993, 34, 15-23.
37. [14a] S. Sabesan, J. Duus, T. Fukunaga, K. Bock, S. Ludvigsen, J. Am. Chem. Soc. 1991, 113, 3236-3241. -
38. [14b] H. C. Siebert, G. Reuter, R. Schauer, C. W. von der Lieth, J. Dabrowski, Biochemistry 1992, 31, 6962-6967. -
39. [14c] L. Poppe, J. Dabrowski, C. W. von der Lieth, K. Koike, T. Ogawa, Eur J. Biochem. 1990, 189, 313-317.
40. [15a] J. M. Coteron, K. Singh, J. L. Asensio, M. Dominguez-Dalda, A. Fernandez-Mayoralas, J. Jimenez-Barbero, M. Martin-Lomas, J. Abad-Rodriguez, M. Nieto-Sampedro, J. Org. Chem. 1995, 60, 1502-1519. -
41. [15b] K. Scheffler, B. Ernst, A. Katopodis, J. L. Magnani, W. T. Wang, R. Weisemann, T. Peters. Angew. Chem. Int. Ed. Engl. 1995, 34, 1841-1844.
42. [16a] R. Harris, G. R. Kiddle, R. A. Field, M. J. Milton, B. Ernst, J. L. Magnani, S. W. Homans, J. Am. Chem. Soc. 1999, 121, 2546-2551. -
43. [16b] L. Poppe, G. S. Brown, J. S. Philo, P. V. Nikrad, B. H. Shah, J. Am. Chem. Soc. 1997, 119, 1727-1730.
44. [17a] A. E. Torda, R. M. Scheek, W. F. van Gunsteren, J. Mol. Biol. 1990, 214, 223-235. -
45. [17b] D. A. Pearlman, J. Biomol. NMR 1994, 4, 1-16. -
46. [17c] A. E. Torda, R. M. Scheek, W. F. van Gunsteren, Chem. Phys. Lett. 1989, 157, 289-294.
47. [18a] D. A. Pearlman, D. A. Case, J. W. Caldwell, W. S. Ross, T. E. Cheatham, S. DeBolt, D. Ferguson, G. Siebal, P. Kollman, Comp. Phys. Commun. 1995, 91, 1-41. -
48. [18b] D. A. Pearlman, P. A. Kollman, J. Mol. Biol. 1991, 220, 457-479.
49. H. G. Bazin, Y. Du, T. Polat, R. L. Linhardt, J. Org. Chem. 1999, 64, 7254.
50. A general survey of conformation of carbohydrates is presented in: A. D. French, J. W. Brady, Computer Modelling of Carbohydrate Molecules, American Chemical Society, 1990.
51. [21a] B. Meyer, Topics Curr. Chem. 1990, 154, 141. -
52. [21b] K. Bock, Pure Appl. Chem. 1983, 55, 605.
53. [22a] A. Imberty, Curr. Opin. Struct. Biol. 1997, 7, 617-623. -
54. [22b] T. Peters, B. M. Pinto, Curr. Opin. Struct. Biol. 1996, 6, 710-720.
55. For the relation between H/H couplings and conformation, see: C. A. G. Haasnoot, F. A. A. M. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783.
56. D. Neuhaus, M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, VCH Publishers, New York, 1989.
57. J. F. Espinosa, F. J. Cañada, J. L. Asensio, H. Dietrich, M. Martín-Lomas, R. R. Schmidt, J. Jiménez-Barbero, Angew. Chem. Int. Ed. Engl. 1996, 35, 303-306.
58. J. F. Espinosa, E. Montera, A. Vian, J. Garcia, H. Dietrich, M. Martín-Lomas, R. R. Schmidt, A. Imberty, F. J. Cañada, J. Jiménez-Barbero, J. Am. Chem. Soc. 1998, 120, 10862-10871.
59. J. L. Asensio, J. F. Espinosa, S. Andre, H. Dietrich, M. Martín-Lomas, R. R. Schmidt, F. J. Cañada, H.-J. Gabius, J. Jiménez-Barbero, J. Am. Chem. Soc. 1999, 121, 8995-9000.
60. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
61. C. E. A. F. Schafmeister, W. S. Ross, V. Romanovski, LEAP, University of California, San Francisco, 1995.
62. K. Stott, J. Stonehouse, J. Keeler, T.-L. Hwang, A. J. Shaka, J. Am. Chem. Soc. 1995, 117, 4199.